Find cheap flights from Canada to Chicago Midway Airport

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— MDW
May 26 — Jun 21
Round-trip
1 adult
Economy
0 bags
From?
To?
Thu 5/26
Thu 6/2

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Good to know

Low season

March

High season

July

Cheapest flight

$116

Average price round-trip

$236

Good deal round-trip

$236

Good deal one-way

$129
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Montreal Pierre Elliott Trudeau Intl to Chicago Midway
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Chicago Midway Airport

  • Looking for cheap airfare to Chicago Midway Airport? 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Ottawa $129 one-way - $129 round-trip, from Québec City $236 round-trip
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be June, July and August. The cheapest month to fly from Canada is March.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

FAQs - booking Chicago Midway Airport flights

Top 4 airlines serving Canada to Chicago Midway

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 30770 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

Less crowded aircraft

Read more about Delta

Less crowded aircraft

Thanks

Pros: "Service was fast"
Cons: "Better seats"
Pros: "Nothing"
Cons: "Proper communication"
Pros: "non stop flight"
Cons: "Crowded, small plane. No air after people had boarded while fuel was being replenished (dangerous?), sitting at gate for 20minutes. This, after a 2 hour delay. Then a rough landing in Minneapolis- plane brakes sharply and suddenly, shuddered to a taxi rate of speed. simple snacks, not very good."
Pros: "Nothing"
Cons: "Worse experience ever, flight delayed, lost connection, many hours in phone trying to fixed and anyway lost the flight, spent so many time at the airport with the front desk so disappointed"
Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"
Cons: "When we booked this trip via Kayak, we thought that we were booking on Westjet. Westjet knew nothing about the flight when we tried to check in."
Cons: "Plane had to divert from Salt-Lake City due to a storm. My son 17 years old traveling alone once in Salt-Lake City should have been given priority for an overnight stay instead of sleeping on an airport bench! Dinner + Breakfast vouchers would also have been nice compared to the 15$ food voucher..."
Pros: "The on board food was amazing, nothing like I’d ever had on a plane before. I was also pleased with the choices for entertainment."
Cons: "The seat was not comfortable in economy. I could not sleep and there were no air vents. Every time I tried to rest my head on the seat in front of me the screen would turn on and get super hot. I wish there was a cover or something you could turn the screen completely off."
Pros: "The flight attendants were amazing. 12 people had a connecting flight and they brought a shuttle bus. You dont see that kind of service any more 10 stars for that"
Cons: "Super small plane."
Cons: "No food on board and we were hungry"
Pros: "Friendly crew."
Cons: "Slow boarding."
Cons: "No charging outlet."
Pros: "I liked the touch screen displays in each headrest. Seats and leg room comfortable"
Cons: "Boarding was somewhat unorganized"
Pros: "The crew"
Cons: "Timing"
Pros: "The kind staff"
Cons: "Dirty bathroom on flight from Toronto Ontario to Atlanta. Smelled like urine."
Pros: "Boarding was smooth, attendants were nice and informative, and everything was on time"
Pros: "Crew was friendly!"
Cons: "Plane wasn’t clean"
Pros: "The movie selection was good"
Cons: "Instead of a flight from Toronto to Atlanta.. it was a flight from Seattle to Atlanta, and I only had 45 mins to get to boarding because of the last minute flight changes."
Cons: "Customs massively backed up. Somewhat disorganized"
Pros: "Nothing."
Cons: "Flight left 2 hours late. Did not get adequate cabin service. Put in the back in an awful seat."
Pros: "Airline and airport staff were great"
Cons: "There was no time to eat. Nothing other than snacks. The time allotted was *barely* sufficient to get from gate to gate. We were starving when we got to our destination."
Pros: "Delta always tries to do the very best. There were no issues with Delta."
Cons: "I did not like the seat assignment. It seems that when I have booked through Kayak, I get a very bad seat. In this case, it was all the way in the back - next to the toilet. The seats didn't recline, and there was no window - because we were right next to one of the engines. I will use Kayak to price compare on future flights, but I will not book through Kayak. Not sure if this is just a coincidence - but it only happens when booking here."
Pros: "On Time. Nothing else to say,"
Pros: "Friendly, leg room, on time."
Pros: "There was nothing I liked about this flight."
Cons: "Everything from beginning to end was horrible. They messed up on our seats so I couldn't sit with my parents who are both elderly and need my assistance. The flight attendants were rude (no greeting, no smiles). My TV did not work and my tray for food was dirty."
Pros: "Delta did find us a new route to get us to our final destination after west jet booked on a flight that was already sold out ."
Cons: "We had to add on an extra connecting flight . We had to then fly from Toronto to Detroit then on yo Atlanta ."
Pros: "Flight went off pretty well. On time no complaints."
Cons: "Somewhere somehow you need to know that, although partners, Delta and West Jet do not share computer systems and that they are two completely different airlines. This affects ,sometimes, how luggage is handled especially when you land in another country and you have to manually transfer your own - and nobody tells you. You actually change airlines. Itinerary implies West Jet controls the entire thing. Not the case. Better job economic explaining what to With luggage and that, while itinerant implies 1 airline, they are only partners and should be treated separately."
Cons: "Flight delayed 2 hrs"
Pros: "After almost every airline cancelled. Delta still took me to where I needed to go with not one single problem. That pilot was amazing. I forget his name. But the plane didn't slide or anything during take off. Amazing."
Cons: "What was there not to like. We were a little bit late but I wasn't in a rush. I planned well ahead. Delta moved my flight from 10 a.m. to 6 a.m. and that was perfectly fine with me."
Pros: "The crew tried their best. The seats were average. The food ok."
Cons: "The entertainment is non-existent. Wifi wasn't even enabled. Four to five hours without ANY entertainment is totally unacceptable especially with teens and kids!!"
Pros: "Delta flew their way back into my heart this time around"
Pros: "Staff, Ease of boarding"
Cons: "Bring back in flight meals, please"
Cons: "They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac."
Cons: "Temperature was too cold"
Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"
Pros: "The food"
Cons: "No entertainment"
Cons: "Bad"
Pros: "Boarding, checking in etc. The usual stuff, nothign spectacular."
Cons: "Seats are getting too crowded!"
Cons: "West Jet gave me a "fake" ticket delta would not let me board missed the flight I had to wake up at 3am to catch. This is after I finally made it to my hotel last night at 11:30 pm. This is completely unacceptable. NEVER AGAIN IN MY LIFE WILL I EVER FLY WITH THIS COMPANY!!!!"
Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."
Pros: "The flight attendants were helpful, the flight was smooth."
Cons: "I was unable to check in online without a delta confirmation number and I had booked through west jet. The flight was delayed 40 min so I arrived later and I was removed from the flight. I got through security and customs with plenty of time and managed to get back on the flight. It was all around just annoying."
Pros: "The flight attendants were great! Super friendly and helpful with everything!"
Cons: "I'd love slightly larger snack portions."
Pros: "Staffing was great!"
Cons: "The fact is that it is illegal to pack Sardines at compact as you are packing us on your aluminum cans."
Pros: "The flight being on time, friendly staff, clean aircraft.i"
Cons: "It was a morning flight from Toronto to Omaha via Minneapolis and unfortunately coffee wasn't served. Or maybe it got over."
Pros: "My first and last time flying Delta! Everything that could have went wrong, did in fact go wrong. We were re-booked on connecting flights different then the one we originally booked and weren't even notified. They have a Delta app, but it doesn't even work right. Unless you physically go to the gate to check to see if the flight is on time, that is the only was to find out if you are re-booked onto a different flight or not. I have never flown an airline that re-books you on a different flight when they feel like it. I wouldn't recommend Delta Airlines to my worse enemy!"
Cons: "The boarding process was chaotic, half the time the staff did not use the PA system. They were not clear on who needed to do a passport check. Started to read names off then just gave up and said "a lot of you""
Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."
Pros: "Crew smiling at the end of the flight."
Cons: "Cheap coffee (although it says Starbucks, I have tried better)."

Porter is always amazing. I feel like a VIP when I fly with you!

Pros: "Nothing"
Cons: "Porter declined re-booking the flight due to weather conditions and forced us to purchase new tickets. Reservations made through anything other than Porter are treated poorly, service can be declined due to overbooking."
Pros: "Efficient check in. Liked the shuttle bus service from subway to airport."
Cons: "As expected this is a commuter flight so very stripped down in terms of amenities. Tight plane seating and those overhead bins just barely accommodate the carry on."
Pros: "Crew was very professional"
Cons: "For a quick hop boston to toronto it was ideal"
Pros: "The crew was helpful and everything was on time."
Cons: "The ride was a bit rough at the end if the flight."
Pros: "The crew is lovely"
Cons: "Porters flights out of Toronto have been significantly delayed every time I’ve flown"
Cons: "Flight was delayed"
Pros: "Same"
Cons: "Same"
Pros: "All ok"
Cons: "Not a thing"
Pros: "Fast and convenient"
Pros: "First time in 10 flights in 3 months flying with Porter in time - what a miracle!"
Pros: "Free bar nuts while delayed 10 hours"
Cons: "Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be"
Cons: "Justfly.com is awful and I wish kayak would stop sending customers to it. I will no longer use kayak because this is the second time my ticket has ended up being purchased through justfly."
Pros: "Once we got on the flight it was fine."
Cons: "Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages."
Pros: "It was hassle free. Trace and arrival times were perfect. Thank you for caring."
Pros: "Efficient, punctual, polite and reliable"
Pros: "The service is very good. In flight snacks and drinks are complimentary."
Cons: "No in flight entertainment."
Cons: "Flight was delayed by 3 hours."
Cons: "Got to Billy Bishop, only to find out flight is delayed 2 hours."
Pros: "Convenient, easy boarding, snacks and free wine on leg from toronto to chicago"
Cons: "Major delays that were poorly handled."
Cons: "Delay"
Pros: "fast"
Cons: "no TSA precheck"
Pros: "Free drinks and snacks. Staff were friendly."
Cons: "Very small overhead compartment. Boarding procedure was chaotic."
Cons: "The flights were cancelled after everyone was already waiting for a long time for their delayed flights. Then the rebooking process took way too long after the staff at the airport said it would take 20 minutes. The website is extremely confusing about which flight you are rebooked, confirmed or on standby. After waiting at the airport for five hours, I still ended up having to spend the night in Toronto. I flew back the next day after my flight was rebooked four times... I filed a claim for hotel reimbursement, but no responses after three days...."
Pros: "I liked the lounge"
Cons: "There were a lot of people and not enough outlets"
Pros: "The service both on board and in the airport was wonderful. This helped make my trip that much more enjoyable, and can't imagine picking another airline to Canada - I will always pick Porter Airlines!"
Cons: "Good"
Pros: "Nothing"
Cons: "Everything"
Pros: "Onboard crew was very nice"
Cons: "Crew didn't answer any of my questions, were snappy, and rude."
Pros: "Polite crew"
Cons: "Would like a sandwich instead of nuts"
Pros: "Efficient"
Cons: "Late flight"
Pros: "Small airport. Easy to find everything. Ferry ride fun. Staff did not seem happy to be at work nor did they smile or acknowledge me. I asked 2 staff questions and was barked at: red line! And was told to get into a line that was non existent outside of security."
Cons: "I asked if I was supposed to leave my luggage in the rack that was just outside of the plane because I saw that's what everyone was doing. I was told it was my choice but that if it didn't fit in the overhead I would have to come back out and put it on the rack. I was very dismayed when I got off the plane to see that I had to wait in the hallway for quite a while until my luggage appeared. It was a real traffic jam of people. I really wish I had put my luggage in the overhead. Also, minutes before boarding we were told to go and verify our passports. It was quite a rush to run to the other end of the room, wait in line and then get to the boarding gate. I barely made it back in time even though I had been waiting there for nearly an hour ."
Cons: "If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems."
Pros: "Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight."
Cons: "Louder than a usual commercial flight, probably due to being a turboprop aircraft."
Pros: "There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays."
Pros: "Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter."
Pros: "Breakfast, bars, etcnithin"
Cons: "Nada"
Pros: "Lounge with free drinks (soda, coffee, water) and cookies/snacks! Glass drinks glasses on the plane! And leg room!"
Cons: "I fly weekly for work, but last week I got to fly to Toronto for pleasure to see my fiancé. In all of my years of traveling, I have missed a flight maybe 5 times due to traffic, weather, or other uncontrollable factors. It happened to be that on my way to Chicago Midway, there was an accident on the road that stopped traffic dead for 40 minutes. When I arrived at the airport, I begged for people to help me out by letting me cut security lines so that I wouldn't be late, but alas...others were also rushed and the TSA agents weren't too helpful. I arrived at the gate for my flight about 3 minutes late in defeat. Oh well - it happens! What was really unpleasant was that nobody would help me out. I was charged $150 to "change" my flight instead of just getting rebooked on the next one the way any other airline would happily do. And to top it all off, I was given the runaround with 3 different Porter employees diffusing responsibility. I will be moving to Toronto after the wedding but will still work out of Chicago - which means that I could provide business to Porter Airlines for the next few decades! Because of this poor service, you have lost my business. I would rather fly with another airline where customer service is a priority. Losing years of a customer's weekly business over a $150 fee seems to me to be a rather poor business model and I am sorry that the bureaucratic rules in this case could not be bent."
Cons: "The fee for my bag was too high!"
Pros: "Not sure if this is Porter Airlines or the airport, but the lounge at Billy Bishop Airport is fantastic. Free water, coffee, and snacks - it is so home-y in there, which is amazing when you are away from home :)"
Cons: "N/A"
Pros: "I especially love the lounge in Toronto - comfortable seating (some with access to electrical outlets), a bank of Mac computers available for passengers to use, free coffee, cappuccino, espresso, cookies, soda, water, free Wi-Fi,..Flight was on time, crew was friendly."
Cons: "n/a"
Cons: "Porter lost my baggage despite such a short and easy flight for them to track. Let's see how long they take to get the luggage back to me in what condition"
Pros: "Departing from Billy Bishop is amazing. Incredibly quick and convenient. Complimentary nacks and drinks in the gate area?!"
Pros: "Porter lounge in Toronto"
Cons: "Nothing!"
Pros: "The service"
Cons: "The flight deleyed"
Pros: "Service. Location of both Toronto Island and Chicago Midway are closer to downtown than the bigger airports in each city."
Cons: "Porter was a nice, small, well-kept secret. Now they have expanded quite a bit and the lounge is always full, to the extent that people are sitting all over the ground. Flights are almost always late to take-off. I guess all good things must come to an end."
Pros: "Free alcohol and snacks! They don't skimp on drinks - you get a full water bottle, full can of soda, fairly large glass of wine, full can of beer - whatever you choose. Crew was extremely pleasant, kind and helpful."
Cons: "Planes were small propeller planes. Not a bad thing, just not my first choice."
Pros: "Excellent. Polite service, free (and tasty) food + beverages, (dry and otherwise) comfortable seats, other customers polite, bilingual announcements, fast + efficient. Really impressed! Good price too."
Cons: "Nothing, really! No in-flight entertainment besides a magazine, but all short flights anyway."

More leg room

Everything was actually very good except for the fact that they delayed the flight 3 times for a total of 4 hours when the flight was supposed to be at 8:30pm. So that made for an extremely late landing (2.5 hour flight), and if we had the wrong rental car company, we would have missed our rental checkout time.

The check-in process couldn't have been worse. Besides they have no customer service to speak of, I wasn't able to purchase a 2nd checked bag prior to the trip, the app just wouldn't let me no matter what. I spent over an hour on hold waiting for a rep who wasn't able to help me. At the airport we politely asked the rep to help since we were unable. She flatly refused to do anything. When we asked to speak to a supervisor she said she was one of the most senior people there and if "We're still not happy she can give me a number to call where I can wait on hold for over 2 hours to be told the same thing I'm telling you now." Absolutely atrocious. First and definitely LAST time flying Allegiant.

My family in Arizona didn’t have a printer to print our return flight tickets, so I took a screenshot of our tickets on my phone. Apparently, when you go through security they enlarge the QR code, which makes it blurry, so it can’t be scanned. We had to go back to the check in desk and pay $5 for each ticket to be printed. Lesson learned, print out all flight tickets before you leave.

6 hour delay! No mechanical problems, they didn’t have enough people.

Pros: "No seat not comfortable."
Cons: "No legroom."
Cons: "Give complimentary water"
Cons: "Covid travel. Had us board an hour before take off and the back half of the plane was 100% full. Every seat including middle seats. 15 min before take off they allowed passengers to take empty seats and spread out."
Cons: "Everything"
Pros: "Quick boarding, on time."
Cons: "The flight attendant checking people’s bags and boarding passes at the gate was not friendly."
Pros: "Crew, check in and access"
Cons: "Seats are getting a bit tiny and the trays are small. Comfort and baggage prices are starting to drive the price out of competitiveness."
Cons: "Reclining seats would be great!!"
Pros: "Boarding was super smooth,"
Cons: "Offer some type of entertainment, ie internet or something"
Cons: "If you dont have TSA precheck....get it...lifesaver"
Pros: "Not bad for the price, convenience beats all"
Cons: "First class"
Pros: "Cost"
Cons: "OMG, miffed and aggravated right now!! Currently on Allegiant Flight 1355. PIE to CVG A non-eating flight. These POSs MFers decide to have a friggen pizza party in the middle of the flight"
Cons: "I booked two tickets at the same time through kayak and was assigned a seat not next to my son! Because the flight was fully booked there was no ability to rearrange seats."
Pros: "On time"
Cons: "Seats could recline"
Cons: "Small seats, flight was late"
Pros: "Crew was nice."
Cons: "Not having so many extra charges and having to pay for a carry on"
Pros: "Quick direct flight that wasn't packed"
Cons: "The woman that checked my bag kept calling me "sir" and after I corrected her a second time she rolled her eyes and said "oh, I don't even look up" I am not a man. For Pete's sake pay attention."
Pros: "The actual flight was comfortable and the crew was good."
Cons: "Flight time was pushed back a few weeks ago. Slow boarding process so we landed about 30 min late."
Cons: "Unfriendly Flight attendants"
Pros: "was not able to go,"
Cons: "information in the reservation part of this app could have been better, my layover was 22 hours long. the 1st time i looked at this flight it was 30 mins long."
Pros: "Pilot was friendly"
Cons: "A little confusion about departure gate"
Pros: "I finally got home"
Cons: "We took off 3 hours late. No transparency about what the delay was or how long, they just kept stringing us along 30 minutes to an hour at a time."
Pros: "Very efficient. You cannot beat the price. All I expected is to get there."
Cons: "The plane was very clean and looked new, the seats were comfortable but did not recline. I missed that."
Pros: "Great crew and online customer service..."
Cons: "1- Flight Behind Schedule 2- Live customer service agents are truly non-existent until 1.5hrs before ‘departure’"
Pros: "To be honest nothing"
Cons: "Missed flight any no one was willing to help us pure BS"
Pros: "It was exceervice"
Pros: "I chose this flight knowing it was gonna be a little cramped and no snacks. But I loved the price, so I booked it. The unexpected bonus was the crew. They were down to earth and funny."
Pros: "Love the Military advantages. Thank you. Feels good to be honored & respected."
Pros: "The staff was nice, kind of, but also unprofessional at time."
Cons: "My flights were both fine but the flight from Fresno to Las Vegas was such a disaster! They switched planes so the majority of the people did not have a seat because the plane did not have any B seats. It would have been nice if ANYONE had made that announcement before we boarded to avoid confusion. Also, the fees are ridiculous! Your app is not user friendly at all! Who the hell charges for a carry on bag?! Are you kidding me?! The directions on the app made it sound like the $17 charge was for an additional carry on item, not the allowed one carry on item. So, when we went to check in and I was told I would have to pay $50 for my mother's carry on, it was livid! Also, are you serious with the $5 fee to print a boarding pass? I will NEVER fly with Allegiant Air again. That is absolutely unacceptable. I will say that the staff was pleasant but the airline is inept and inefficient. The reason I will never fly this airline again because of what a rip off the fees are. Allegiant Air, you should be ashamed of yourself."
Cons: "Was assigned a middle seat. I am a small woman and had absolutely no room."
Pros: "Great flight. On time. Easy on. Easy off. And amazing fares."
Cons: "Everything great"
Pros: "Very efficient service... actually a good experience."
Cons: "The airline nickel and dimes for everything."
Pros: "They offered a direct flight from Cincinnati to Austin. The price was good, even though they charge for carry on."
Cons: "They land at the Austin airport, kind of. Once we landed they took us to a Remote terminal which required waiting for a bus to fill up and then take you back to the actual airport. There was no quick way for the bus to return and it has to drive for 15 to 20 minutes to get to the main airport. I took 1 complete hour from when I landed to when I got in my car in lot D."
Pros: "The speed"
Cons: "Leg room"
Pros: "The crew was plesant and helpful."
Cons: "The flight was delayed 35 mins. Then we couldnt get luggage when we arrived because of lighting. We were told to go one place and our luggage was taken somewhere else."
Pros: "No complaints about the trip to Newqrk. Everyone was very helpful and patient since I am an unexperienced flyer."
Cons: "I didn't like thinking I was paying one price then paying another or buying insurance that would have been useless since it doesn't cover anythIntg."
Cons: "Two out of three bathrooms out of order"
Cons: "No complaints."
Pros: "The crew was very friendly"
Cons: "The flight was delayed 2 hours. The plane was freezing the entire flight. Apparently, the crew tried to get the pilot to turn down the air, but it never happened. I hate how Allegiant nickel and dimes you. Not even a cup of water is free."
Pros: "The price"
Cons: "Everything"
Pros: "The price and the fact that our flight left late but still arrived almost on time."
Cons: "The gate agent wouldn't switch our seats so we could sit beside each other. We've done this multiple times if we find ourselves not out beside each other and it's never been a problem before. He claimed he had to charge us to do this. We have never been charged before. We fly Allegiant often. The on-board flight crew were so not friendly at all. Typically Allegiant flight attendants aren't as happy as Southwest but they're at least cordial. This crew we're just unhappy, snippy, a little unprofessional (saying huh or what instead of excuse me. Pointing people to things instead of getting it for them or walking them to it) and at one point one stewardess was just rude to a passenger."
Pros: "The flight left on time. Friendly crew"
Cons: "I don't like that they charge for carry on bags and they don't have a toll free number"
Cons: "I didn't like the schedule time change. Very inconvenient missed some of my planned festivities that were prepaid."
Pros: "The flight was fast, and direct."
Cons: "The seats"
Pros: "I had a great experience with Allegiant. The airline had a great rate, professional staff, and great service. I'd recommend Allegiant to all my friends."
Pros: "I needed a one way flight last min and booked this flight the day before. Every other airline was over $300 and this one only cost me $127."
Cons: "This is an "a la carte" airline. Be prepared for hidden fees for choosing a seat, carry one bag, etc. Luckily I didn't need the ticket counter because the line was literally around the corner and out the door. they do not have any self serve kiosks at the ticket counter. Also, the plane was half empty but they didn't want us moving seats--I suppose because a lot of people had already paid an additional fee to pick their seat."
Cons: "It was all excellent."
Cons: "First plane was newer, 2nd plane was older."
Cons: "Took 45 minutes to get through Calgary security, long line ups"
Cons: "Air Canada continues to underwhelm me. We left the gate 35 minutes late despite having everyone on board. Then off to de-ice where we sat with a truck outside for ten minutes they did work. It was like they were having a coffee break. The flight and board service was exceptional. Baggage delay of a"
Cons: "They changed planes and the seats I paid for at reservation were different on the new plane. No warning!!"
Pros: "Only thing good was the brevity of the flight."
Cons: "The aircraft was dirty and ridiculously cramped. Air Canada undermines its brand by flying planes like these."
Cons: "JustFly did not release my coupon to Lufthansa or Air Canada, and so I was nearly prevented from flying."
Cons: "This leg was so late...I was waiting in Calgary almost 7 hours... they put me on a different flight so I would make my connector in Toronto to Windsor....I originally had a 2 hour window. The second plane was so late, by the time I landed in Toronto, I had 10 minutes. Needless to say, after starting out in Kamloops at 6 am, that was missed also. Last leg missed as well, and had to wait another 4 hours for the last flight out. Just an incredibly frustrating trip"
Pros: "Movies available. Food available for purchase."
Cons: "It was crowded in the back of the aircraft. Many vacant rows were available, but my advance check in and seat change / upgrade was not available on line. I would have paid to have moved up to an un-occupied section of the aircraft if I could have. My mistake. I should have got up and walked around looking for these vacant seats. Despite the captain announcing that WIFI Internet was available for purchase. There was no WIFI on this aircraft. I am a tech guy. The flight attendant said just use your credit card. NO there was no WIFI available."
Pros: "Flight was late leaving and I had a connection flight - they changed my seat so I could be at the front and get my bag easily and run to get my connecting flight. Everyone was very helpful."
Pros: "Entertainment"
Cons: "My seat was wet and i had to wait quite a while for it to be rectified. I asked to sit on a crew seat at the back of the plane and was told that i would break it. I found this rather disgusting . Seating plan is very crammed like sardines"
Pros: "First flight comfortable fast clean aircraft Second flight older plane small not as clean"
Cons: "Air canada has a problem at every arrival gate each time we landed there was no sttebdebt st the gate and so we sat on the tarmac fir a while while they awIted somebody to come and drive the Jetway to allow us to park and deplane This happened all three times"
Cons: "Cancelled one flight, then delayed another one because they were waiting for a pilot. They offered very little help, citing that they couldn’t control the weather, meanwhile WestJet is finding & paying for rooms, shuttle buses and taxis to make the delay more tolerable and less stressful. We could only watch and wish we were flying WestJet."
Pros: "Everything else was fine/standard."
Cons: "Not all ground staff are crosstrained on how to accept manual payment for extra luggage and had to wait an extra half hour for the only person who can process a debit transaction. Does not make sense..."
Cons: "I bought my ticket with Air Canadafrom Vancouver to Calgary then connected with Lufthansa from Calgary to London UK. Unknown to me I could not find the flight because it had been changed to an AC reference flight. With a very short time for the connection I did not know where to get my boarding pass as my flight with Lufthansa was nowhere referred to ! Not which gate to go . Why not put it in the ticket that Lufthansa and Air Canada work together and that both flights ref should show !! It would avoid a great deal of anxiety . Only offered 1 round if hot drinks over 9 hours ! Departure delayed by nearly 60 minutes"
Pros: "excellent service"
Cons: "flight was late"
Pros: "Nice staff"
Cons: "Uncomfortable chairs"
Cons: "The plane was late and caused me to miss my connecting flight and my very important doctor's appointment."
Pros: "Calgary airport first and foremost went above and beyond for me. The flight then after was the same, friendly attendants, great smooth flight. 5 stars for staff."
Cons: "The headphones are bad, i had my own headphones so it was fine. I did go w the air canada ones first just out of convenience, but they were fuzzy, probably would have ruined the movies."
Pros: "This was a boring flight which is a good thing, no drama, no mechanical problems, no weather problems. More leg room than an overseas flight."
Cons: "Flight late (30 minutes) as mostly with Air Canada, fortunately not cancelled this time as also common with Air Canada short distance flights Not enough space in overhead compartments for carry on. The lady at the boarding makes it sound like that is the passengers fault."
Pros: "Very good overall."
Cons: "Entertainment selection poor and dated."
Cons: "We were already running late when during take off, one of the engines malfunctioned and we had to emergency break on the runway and go back to the gate. Because it was unexpected, we had to wait even longer for a gate to become available. We then had to re go through customs and get our bags then wait in line again at the counter to schedule our flight for the next day. Thankfully we were given a hotel room and money for food. Very scary experience overall on the runway, but they tried to handle it as smoothly as possible under the unusual circumstances."
Cons: "The prop aircraft that Air Canada uses for the YYC-YEG route are old and cramped. They do nothing for the Air Canada brand."
Pros: "I didn't like anything."
Cons: "I was stuck in immigration for about an hour. The screening process at this airport is so laborious. You have to wait on a bench until they call your name and they don't care if your flight is about to be boarding. I understand that immigration is necessary but they could at least have people form a queue instead of having us wait for our names to be called. I told them that my flight would be boarding in 25 minutes and they told me "Oh, don't worry, they'll just put you on the next flight". But when I got to my airline to check in, they charged me $150. I needed that $150 to pay some bills when I got back home."
Pros: "Once again, being on time was important to me. Crew members were nice."
Cons: "I wish they would've offered free snacks on this flight given how long it was. It would've also been to nice to have been forewarned about needing to go through security again, as I had a U.S. connection from Toronto. That takes a lot of time, even with a bit of a layover."
Pros: "Good leg room in coach"
Cons: "Flight was late leaving, the boarding process was messed up and could not understand the person doing the announcements (was speaking too fast)..."
Pros: "This was the absolute worst experience of my life. Out flight from Calgary to LAX was on the complete other side of the airport than our connector to San Diego. After a delay we had a short amount of time to get to the next flight. We literally were told to just cross the parking lot. Well... that ended up being a 25 minute run across the airport to only have to go thru security again. After navigating construction and parking structures we got to our gate 10 minutes late and would not be let on the flight. There was zero communication, sympathy or help from the United Airlines staff. We were told it was not their problem because we came in through Air Canada- BUT we booked through United! All in all it was an absolute nightmare that ended in us renting a car at 12am and driving back to San Diego with zero compensation from United Airlines"
Cons: "No communication between airlines! No customer service to fix their lack of planning and communication. Just terrible all around"
Pros: "Staff were friendly"
Cons: "Seats were narrow and sitting in aisle seat you were constantly hit every time cabin crew took trolley up / down aisle. Woke up by cabin crew banging into me."
Pros: "The flight itself was good. Service at the end of the flight was the worst ever."
Cons: "They got in late to lax. Made no apparent effort to get us on alternative airlines or flights. I was rebooked on a flight 24 hours out No help finding hotels, meals or even terminal. It was a codeshare with united but neither would united help in any way because it was booked through air Canada."
Cons: "Air Canada was one hour late leaving the gate. This in fact was a great improvement as when we left Montreal on Dec.21 they were 4 hours late and in the best of xmas cheer didn't even offer us a free drink. Way to go AC."
Pros: "the seat beside me was open"
Cons: "they made us rush through customs while yellig at us nd being very condescending then we waited an hour to board because the airport door wouldn't open for the crew"
Cons: "The lady who checked us in caused a major problem with seating. The person I was traveling with was blind and I was her guide. We specifically asked to be seated together and the lady told me we were. I even confirmed with her and she told me yes again. When we boarded we found out our seats were 17 rows apart. I found out that she did this for the connecting flight as well (not as far apart but still not together) this caused a great deal of stress as I couldn't help her when I needed to."
Pros: "The seats were comfortable and the crew was friendly. We were re-booked onto another flight by the time we de-planed, which took some stress away."
Cons: "The entertainment selection needs more variety. The food choices were just okay. The flight was delayed and we missed our connection. Also, our friend received a food voucher for the delay while we did not. Boarding can be a little chaotic."
Pros: "This flight ended up arriving at the final destination a day later instead of first thing in morning last thing at night."
Pros: "Only 30 minutes late, nice landing."
Cons: "Pitch between seats, filth all over seat back and tray table, mass rush to board when zone three is called, no free snacks, limited drink choices, etc."
Pros: "Meh."
Cons: "Video display didn't accept touch input so didn't work at all."
Pros: "Nice staff. Efficient boarding."
Cons: "No basic food for free."
Pros: "Crew was friendly and courteous."
Cons: "Flight delayed as usual (for Air Canada)"
Pros: "nothing"
Cons: "everything"
Cons: "Flight was delayed making me miss my connection. Poor customer service at the airport plus the fact that my baggage got lost however, it was delivered after 24 hours."
Cons: "I had a last minute seat assignment (middle seat) in both legs of my flight. AC lost my bags and a day later only retrieved one of them. Still waiting for my second bag."
Cons: "Too many people with more than two bags. You have to force more people to put there bags in the plane storage not overhead. Two many carry-on bags and people had back packs with another bag, some computer bags. It takes too long to board the plan"
Pros: "Comfort of seats and spaciousness of the plane"
Cons: "Agent off loaded me and only me from return flight with zero reason. Second flight I was put on was delayed 2 hours. Sat for 5 hours in the airport for a 1 hour domestic flight. Customer service was terrible. Emailed Air Canada 4 days ago and have yet to recover any response."
Pros: "Linda the Air Canada check in Agent at the Priority desk in Calgary was the best Check in Agent I have ever dealt with in over 20 years of business travel. I was with my family and she even made a special effort with my two Granddaughters that they are still talking about today. She is the reason Air Canada still has ALL of my business every year"
Pros: "They had a wheelchair accessible for me and delivered me to my waiting party."
Pros: "Entertainment system might have been nice if the earphone plug worked."
Cons: "The most uncomfortable seat of all time because it was broken but the flight attendant didn't care."
Pros: "Great valve"
Cons: "Delay in boarding by about 20 minutes. Had to stand in line for about 1 hour because we were not allowed in the terminal seating area until the previous plane's passengers disembarked."
Pros: "New 787 dreamliner, live up to the hype."
Cons: "Its hard to sleep as the seat is very bench like. Air Canada's food isnt as generous as it use to be, but their fares are quite low so i guess its a tradeoff."
Pros: "The comfort of a Dash 8 was surprising. The seats have a suitable amount of leg room which I'm actually scared to mention so they don't add an extra seat to each row to take it away. Not too much, not too small, just right for a 6 foot man to not have his knees pressed against the seat in front for the whole ride. Small plane size did allow for quick retrieval of bags at final destination."
Cons: "Where to start? Dash 8's shake, rattle and roll for the whole trip. Felt like we could fall out of the sky at any time. Staff don't care. Split our group after rescheduling due to aircraft issues despite seats available on both connectors. Said to wait until next stop to fix. Next stop said nothing they can do since we checked a bag. Put 2 hours between arrivals just because they can. Blamed it on the computer."
COVID-19 information

Safety measures for airlines flying from Canada to Chicago Midway Airport

Airlines flying from Canada to Chicago Midway Airport have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Canada to Chicago Midway Airport

Mandatory masks

Masks required on board, masks provided on flights from Canada to Chicago Midway Airport

Social distancing seating

Middle seats unavailable to book on flights from Canada to Chicago Midway Airport

Pre-flight testing

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Flexible cancellations

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Canada

Cabin classes:

$187