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$109 Find cheap flights from Canada to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 8/24
Sat 8/31

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 50,552,696 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Flights to Midway - Travel Insights & Trends

Get data-powered insights and trends for flights to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago Midway Airport?

These are the best prices found by users searching on KAYAK in the last 72 hours.
The cheapest airline ticket to Chicago Midway Airport from the Canada in the last 72 hours was $109 one-way, and $182 round-trip on the route from Vancouver to Chicago Midway Airport. The most popular route is from Toronto to Chicago Midway Airport and the cheapest ticket found on this route in the last 72 hours was $208 round-trip.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where tickets can be as cheap as $229. On the other hand, the most expensive day to fly is Monday, where prices are $434 on average.

What is the cheapest month to fly to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago Midway Airport is January, where tickets cost $230 on average for one-way flights. On the other hand, the most expensive months are September and November, where the average cost of tickets from Canada is $410 and $396 respectively. For return trips, the best month to travel is March with an average price of $216.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when flights cost $228 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $301.

What is a good deal for flights to Chicago Midway Airport?

If you’re 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 Toronto Island Airport $140 one-way - $221 round-trip.

How far in advance should I book a flight to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 50 days before departure.

Which airline offers the most flights to Chicago Midway Airport?

Of the 5 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 2,618 per week, followed by Frontier with 109 flights per week.

How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montreal, which takes 2h 30m, Toronto, which takes 3h 04m, Calgary, which takes 3h 25m, and Vancouver, which takes 4h 01m.

How many direct flights to Chicago Midway Airport are there each day?

There are around 403 direct flights from within Canada to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 45% of flights departing in the morning.

How many long-haul flights are there to Chicago Midway Airport each week?

There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Chicago Midway Airport. Instead, there are 20 short-haul flights (up to 3 hour flight duration), with the most arriving from Toronto.

How many cities have direct flights to Chicago Midway Airport?

From Canada, there are direct flights to Chicago Midway Airport from 1 city. This city is Toronto and there are 20 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

$109
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Vancouver to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    The cheapest airline ticket to Chicago Midway Airport from the Canada in the last 72 hours was $109 one-way, and $182 round-trip on the route from Vancouver to Chicago Midway Airport. The most popular route is from Toronto to Chicago Midway Airport and the cheapest ticket found on this route in the last 72 hours was $208 round-trip.

  • How far is Chicago Midway Airport from central Chicago?

    You’ll need to travel 9 miles to reach the Chicago city center from Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $224. The cheapest price found on KAYAK in the last 2 weeks cost $129 and departed from Toronto Island Airport.

  • How does KAYAK find such low prices on flights to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 2,821 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Monday, with 18% of flights taking off on this day.

See more FAQs

Top tips for finding cheap flights to Chicago Midway Airport

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Prefer to fly non-stop to Chicago Midway?

Find which airlines fly direct to Chicago Midway Airport, which days they fly and book direct flights.

Nonstop departures

Canada to Chicago Midway

Monday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Tuesday

Aeromexico, Air France, Air Transat, +10 more

Aeromexico, Air France, +11 more

Wednesday

Aeromexico, Air France, Air Transat, +10 more

Aeromexico, Air France, +11 more

Thursday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Friday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Saturday

Aeromexico, Air France, Air Transat, +10 more

Aeromexico, Air France, +11 more

Sunday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

See more direct flights

Nonstop returns

Chicago Midway to Canada

Monday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Tuesday

Aeromexico, Air France, Air Transat, +10 more

Aeromexico, Air France, +11 more

Wednesday

Aeromexico, Air France, Air Transat, +10 more

Aeromexico, Air France, +11 more

Thursday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Friday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

Saturday

Aeromexico, Air France, Air Transat, +10 more

Aeromexico, Air France, +11 more

Sunday

Aeromexico, Air France, Air Transat, +12 more

Aeromexico, Air France, +13 more

See more direct flights
See more direct flights

Top airlines flying from Canada to Midway

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
Porter AirlinesOverall score based on 344 reviews
7.8Boarding
7.7Comfort
6.8Entertainment
7.6Food
8.4Crew
Airline reviews

Chaotic boarding, but mostly my issues are with Toronto airport

6.0 GoodArti, Jul 2024YYZ - YUL
Read more about Porter Airlines reviews

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Service was amazing, and the plane was comfortable even for this long haul. But they could have more movies selections. But they were still a lot to choose from.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

I was never able to depart because of an IT outage, I could not get help through Delta’s website, app, or on the concourse. I eventually (after more than three hours in the airport) got rebooked with another airline the following day and Delta didn’t offer vouchers or any assistance with finding a hotel or getting to the hotel. I need to file a claim. Just an awful experience.

I always worry about flying budget airlines but I was impressed by Westjet. The checkin agent was terrific. Seated my husband & me together w/o us asking. TSA checkin was smooth & easy. Plane was clean & comfortable. Drink & snack was unexpected. I will fly with them again.

WiFi was not working. Zero entertainment. Did not receive a discount etc to make up for this.

Calgary WJET supervisor was the most professional, and diligent official who I have experienced personally to resolve our flight issues.

Flight was canceled last minute and no re-booking was offered. Had to buy a same day flight from another carrier at double the price. I’ll never fly WestJet again.

Don’t actually know how this flight would have been since we missed it.

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Book cheap flights from Canada to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
10/16Wed
1 stop
9h 24mYVR-MDW
10/19Sat
1 stop
25h 20mMDW-YVR
$182
10/16Wed
2 stops
11h 40mYVR-MDW
10/19Sat
1 stop
13h 04mMDW-YVR
$188
9/19Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
9/23Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$208
9/3Tue
1 stopPorter Airlines
5h 52mYUL-MDW
9/7Sat
1 stopPorter Airlines
5h 13mMDW-YUL
$209
8/8Thu
nonstopAir Transat
1h 47mYTZ-MDW
8/11Sun
nonstopAir Transat
1h 42mMDW-YTZ
$242
8/16Fri
1 stopDelta
3h 38mYUL-MDW
8/20Tue
1 stopDelta
7h 50mMDW-YUL
$261
8/22Thu
nonstopAir Transat
1h 47mYTZ-MDW
9/1Sun
nonstopAir Transat
1h 42mMDW-YTZ
$263
8/15Thu
1 stopDelta
7h 42mYUL-MDW
8/21Wed
1 stopDelta
8h 37mMDW-YUL
$269
8/12Mon
1 stopWestJet
25h 06mYYZ-MDW
8/15Thu
1 stopWestJet
20h 45mMDW-YYZ
$331
9/1Sun
1 stopWestJet
13h 08mYYZ-MDW
9/7Sat
1 stopWestJet
22h 38mMDW-YYZ
$335

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
10/10Thu
1 stop
9h 24mYVR-MDW
$109
10/1Tue
1 stop
23h 34mYVR-MDW
$114
8/28Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$124
8/10Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$125
9/1Sun
2 stopsDelta
9h 38mYYC-MDW
$138
9/12Thu
1 stopDelta
7h 28mYUL-MDW
$156
8/7Wed
nonstopAir Transat
1h 47mYTZ-MDW
$164
8/8Thu
nonstopAir Transat
1h 47mYTZ-MDW
$172
8/27Tue
1 stopWestJet
4h 47mYYZ-MDW
$187
8/21Wed
1 stopWestJet
13h 08mYYZ-MDW
$189

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Last minute flights to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
7/29Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
8/8Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$345
7/27Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
8/10Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$351
7/27Sat
multi-stopPorter Airlines
4h 52mYUL-MDW
8/31Sat
multi-stopPorter Airlines
5h 33mMDW-YUL
$377
7/30Tue
multi-stopWestJet
6h 29mYYZ-MDW
8/8Thu
multi-stopWestJet
4h 59mMDW-YYZ
$448
7/30Tue
multi-stopWestJet
6h 29mYYZ-MDW
8/8Thu
multi-stopWestJet
4h 59mMDW-YYZ
$463
7/26Fri
multi-stopDelta
8h 18mYYZ-MDW
7/31Wed
multi-stopDelta
8h 28mMDW-YYZ
$487
7/27Sat
nonstopAir Transat
1h 47mYTZ-MDW
7/28Sun
nonstopAir Transat
1h 42mMDW-YTZ
$530
7/26Fri
multi-stopDelta
8h 18mYYZ-MDW
7/28Sun
multi-stopDelta
6h 35mMDW-YYZ
$531
7/27Sat
multi-stop
3h 57mYUL-MDW
7/30Tue
multi-stop
19h 30mMDW-YUL
$584
7/29Mon
multi-stop
28h 07mYOW-MDW
8/1Thu
multi-stop
19h 18mMDW-YOW
$594

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Flights to Chicago Midway Airport