Find cheap flights from Florida to Chicago Midway Airport

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Find cheap flights from Florida to Chicago Midway Airport

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Boston (BOS)
Chicago Midway
Thu 12/3
Thu 12/10
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Good to know

Low season

August Best time to beat the crowds with an average 5% drop in price.

High season

April Most popular time to fly with an average 18% increase in price.

Average price round-trip

$297 (avg. price over the last 2 weeks)

Good deal round-trip

$159 or less

Good deal one-way

$72 or less

FAQs for booking Florida to Chicago Midway Airport flights

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Top airlines flying Florida to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,803 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "A 7+ hour delay!"

Pros: "Not too bad once we got on the plane"
Cons: "They make up this lame excuse about a slight delay on the plane arriving and having no flight attendants to get on the plane on time. This delayed our flight by two hours. They need to staff their flights !"

Pros: "No lines at the baggage drop off. No lines at TSA. Efficient and organized boarding. Seat area was clean. No delay, friendly energetic flight attendants."
Cons: "Lots of turbulence on the last 20 minutes of the flight. Captain had warned us. Nothing they can control though."

Pros: "Very nice and courteous crew."
Cons: "Lady at the gate was a bit standoff Ish and the delays were an annoyance."

Pros: "Seats. Service. Timing"

Pros: "Cody was such a great flight attendant. We weren’t seated with our kids and he helped us switch seats. He was so help and just sincerely nice. Really great person to represent your brand."

Cons: "No tv screen"

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: "Friendly, efficient"
Cons: "n/a"

Cons: "All went well"

Cons: "By mistake I booked my ticket for the wrong date Called to change it, wait time was over 2hrs went to the delta app and it cost me $200 to do it. Get to airport and ask for an up grade not possible but if I paid $200 when rebooking the flight I could have gotten one. Snacks were horrible and I have a delta card and was charged $29 to get in plus a charge for my extra suitcase. It’s ridiculous given the amount of money I spend on m card on the monthly basis. Very disappointing"

Pros: "short flight not much to say all was smooth crew was efficent"
Cons: "not a delta thing but passengers drag all these pieces of luggage on making boarding longer clogging up aisles ect. gate agents need to be more strict with people past the allowed limit"

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: "They gave me extra pretzels and 2 cans of soda"
Cons: "The seats were awful.. Miniscule"

Pros: "Very professional cabin crew"

Pros: "Thank God I was able to get a refund"

Pros: "very punctual and nice aircraft"
Cons: "timming of the flight"

Pros: "Finally got upgraded!"
Cons: "delayed"

Pros: "Delta graciously rebooked us on a different flight."
Cons: "Late delayed notification after we reached airport and kept delaying for several hours"

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: "Loved the new aircrafts, the flight attendants were friendly and attentive. We landed 40 mins earlier than expected, the captain really sped the whole way and I didn't feel a thing!! The landing didn't even feel as though we were speeding...one of the best flights I've ever had (Jessica England) thank you!"
Cons: "Food options, early morning flights I get you're not going to have real food, but can there be an option to purchase a bagel with cream cheese or croissant, something other than a snack box. I understand the flight is under 3 hours so certain foods aren't available but Delta you upgraded everything else. I enjoy the Tapas box for those that are vegan, kosher, gluten free, etc....PS-the bathrooms are smaller"

Pros: "Exit row seat with no seat in front. Was able to stretch legs."

Pros: "Efficient boarding and unloading. Friendly staff. Good movies/tv shows."
Cons: "There was a storm so we flew in circles for over an hour. I didn't see headphones for the tvs (mine are bluetooth so they didn't work)."

Pros: "Pretty much nothing"
Cons: "Delta. They just hate their passengers"

Pros: "They had good entertainment for free. There were movies, tv shows, and games."
Cons: "The plane was delayed for 5 hours and the ride was longer than expected."

Cons: "No electronic check-in; No seat assignment; will be avoiding flying Delta"

Cons: "Food and entertainment as always."

Pros: "I got home. That's the highlight. We didn't have any incidents."
Cons: "Took off late because the bus to transport flight attendants were late. Backed up once into New York. Had to circle several times. Once landed we waited in a queue behind 10 aircraft."

Pros: "Crew was nice"
Cons: "Always a delay with Delta"

Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."

Pros: "People were nice."
Cons: "I didn't like having my seat assigned at the gate. I booked this flight months ago, but yet somehow I got the very last row of the plan. Which is the noisiest location with the least amount of room. On the flight back they put me in the second to last row, even though there were about 10 seats empty scattered throughout the plan. Made no sense to me."

Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Pros: "The crew were wonderful, efficient, and professional."
Cons: "On this Delta flight operated by Virgin Atlantic one of us was unable to check in or change our seats. You think you are getting Delta but everything must be done through VA. VA bag weights are less than Delta and the seat was incredibly cramped. We both had to sit with our legs bowed to the side as the seat ahead was so close. For nine hours we were cramped and could not sleep due to only be able to squeeze into one position. To get into the seat I put on leg in and then sat on the armrest and then brought my other leg up and then lowered my but into the seat. I am not even 6 feet tall and had this issue. So due to the difficult online check-in and seat selection and to the cramped seats we will never fly Virgin Atlantic again."

Pros: "Upgraded to first class so had more room, nicer seats. No lines at TSA, had the first gate past security so a short walk. Nice shopping and food choices."
Cons: "No meal served on flight, only drinks and cookies / popcorn. No entertainment at all. You have to provide your own device. There was wifi but not free, it was so slow I couldn't download the entertainment app, so I gave up and slept. No access to Delta lounge with domestic first class WTF?"

Pros: "Comfortable seats and great flight attendants."
Cons: "The boarding. Having to wait for people to place their carry ons."

Pros: "Planes were nice and updated, screens, wi-fi, easy to board, on time! FA were nice and friendly. Delta terminal at Mia was easier to navigate than AA. Liked that they didn't charge for middle seat towards the front. I feel claustrophobic in the back but hate paying extra for seats up front. A long time AA Gold Member, looking forward to more Delta flights."

Pros: "Always have great experience with Delta flight attendants and staff. The entertainment on mobile phone was a really nice add-on, I had never seen before."
Cons: "Flight was delayed in taking off, waiting for connecting passengers. Plane was old, which is most Delta planes, but this one showed it. The tray table looked like it was from the 70s or 80s. Flying into Midway instead of O'hare was anticlimactic."

Cons: "Only food available was pretzels. Not even peanuts or cookies."

Cons: "I booked with Delta who doesnt give you limits of weight for the carryon...why since the flight was operated from Airfrance they gave me limits of weight of 12 kg??? one ticket one law pls again, the hostess in my row was very nice, even the steward who was working with her very snob...it's not his job"

Pros: "The hotel I had to stay I. Because of a delayed flight was nice"
Cons: "Delay, delay, delay, delay, no show on the crew so cancelled, delay, delay, delay only to arrive in a different city from my original place of arrival just to go home."

Pros: "Wonderful"

Pros: "That the flight ran on time"
Cons: "Everything is an added charge. No food option. No TVs. No friendliness. We were consistently inconvenienced as the flight attendant was seated next to us and interrupted us consistently with no apologies."

Pros: "Short flight"
Cons: "Delayed"

Cons: "Too cramped"

Pros: "Fast board in. And take off time. Everything was managed efficiently."
Cons: "This flight went extremely well. No complaints or suggestions at this time."

Pros: "Arrived early and luggage on time."
Cons: "No entertainment"

Pros: "The pilot did a good job flying considering the conditions."
Cons: "Delta and Midway airport did not handle the weather conditions as well as they could have. Communications we terrible and no one adapted quickly to handle things properly. Of course the winter weather alert was mostly to blame, but what could be done to smooth things out didn't happen."

Pros: "Very easy going"

Cons: "Great crew and smooth ride"

Cons: "Give complimentary water"

Pros: "Price"
Cons: "Communication is always my #1 complaint with Allegiant. They delay flights regularly but there’s never any additional information...they just send you a text or email saying your flight is delayed, never tell you why, but they want you at the gate at the regular time...so you sit there for hours with No further communication and the gate agents never come to the gate to let you know what’s going on or what to expect because corporate has gotten stingy with regard to compensating folks even when THEY are to blame for the delay. Two trips in a row, two weeks apart, they’ve done the same thing to us. I appreciate the low fares, but I’ve just about decided I’d rather pay more for good customer service because theirs just sucks."

Cons: "Major delays, no communication from airline"

Cons: "I love the changes that have taken place. I last flew with them 5 years ago and vowed too never fly with them again. Times have changed and they are a great Airline!!!"

Cons: "The ticket lady was rude just nasty and upset for no reason."

Cons: "$50 bag fee for small carry on is punative."

Pros: "Crew was nice"
Cons: "Leg room"

Pros: "Arrived safely"
Cons: "Almost two hours late."

Pros: "Crew was friendly, boarding process was easy, spacious aisles"
Cons: "The seats do not recline and are not very comfortable. Drinks and snacks are not complimentary"

Pros: "Late"
Cons: "Be on time"

Cons: "2 hour weather delay. Flight didnt arrive in Tampa until 1:30am. Hard time finding transportation from airport that late"

Cons: "Seats were not comfortable"

Pros: "When you land at Concord you are right near the parking lot!!!"

Pros: "Crew was very pleasant and professional"

Pros: "Ticket prices are always the best. Even though The flight was delayed by 30 minutes we were only 15 minutes later into the terminal"
Cons: "The flight was delayed by 30 minutes but we were only 15 minutes later into the terminal"

Pros: "Crew was really nice! Flight was quick and easy"

Pros: "the staff was nice."
Cons: "the soda can was 2$ and for a rum and coke 20$, the plane was uncomfortable"

Pros: "Timing and ease of travel"
Cons: "Nothing"

Cons: "It was to uncomfortable to sit there in the plane for so long. I also noticed one of the flight attendants with the long brunette hair kept over looking me but would be in all the guys faces instead. Pretty sure it was a jelouse thing. The shorter brunette girl was really pleasant"

Pros: "The price!"
Cons: "Flights in both directions were late."

Pros: "somehow after waiting on tamarac for half hour, we still got to Asheville, destination, on time."
Cons: "boarding in the rain, areas to check your bag and check in were so crowded you couldn't even find a proper line calling out names, some of the voices couldn't be heard no one available to answer questions what line a person should get in.som"

Pros: "Made it home safely."
Cons: "Waited on tarmac 2.5 hrs. Then plane delayed 10 hours. Then waited on tarmac 2 more hours. Horrible first experience flying with Allegiant."

Pros: "Flight crew were friendly and courteous and even added some humor. Flight was on time for departure and 20 min early on arrival. Couldn’t beat the fare. Only airline to fly direct non stop to my location."
Cons: "Had to pay for drinks or snacks. Seats did not recline. Fortunately only a little over a 2 hour flight."

Pros: "That we made it once we were in the air"
Cons: "The 3 hour delay that should have been announced but we had to get alerts on line not from the airline but Kayak"

Cons: "4 hours late. No explanation. I have flown Allegiant 3 times. Late twice."

Pros: "Friendly staff!!"
Cons: "Hour delay on flight"

Pros: "People in my row."

Pros: "It was exceervice"

Cons: "Allegiant Crew were very snotty and sassy... bossy even, like they were all having a bad day. The flight itself felt like we were falling out of the sky the entire time. Up and down up and down. Seat back tray tables were extremely small."

Pros: "My kids and I had great experiences with Allegiant Air, thanks in large part to some excellent flight attendants. This was the first flight for both of my children (5, 7) and they had a blast. On our initial flight from Indianapolis to Ft. Lauderdale the attendants even gave each of them their own set of pin-on wings since it was their first time. The kids loved this!"

Pros: "Great price on airfare"
Cons: "Long line for baggage check in"

Cons: "Ground crew at ticket very slow and inefficient. Two groups missed their flight because of it."

Pros: "After the delay, we were treated to complimentary soft drinks and snack mix. This was after sitting in the plane for over an hour, though."
Cons: "We spent two hours of the delay in the airport and then eventually boarded. However, another problem with the plane developed and we waited for at least an hour more in the incredibly cramped plane. The seats are bearable for a short flight, but they’re hard to endure with multiple delays. The boarding was also disorganized. There were two announcements: one for people who needed extra time to board and another for the final call. Nothing in between."

Pros: "It got us there and back for a descent price. The flight was fine but the seats are not comfortable and do not recline. I wouldn't suggest Allegiant for anything more than 2 hours and that was even pushing it."
Cons: "We arrived 3.5 hours early and the line was very long. They must have had a system glitch but didn't communicate to anyone in the line as to what was going on. When it did come time to board, they told everyone in the line that was going to Cincinnati that we couldn't check in until 2 hours before the departure time. Apparently there were some other flights that left before us. If they had told us to keep our place in line and to let other people through, that wouldn't have been a problem. But, they didn't. Their own website says you should check baggage at least 2 hours before your flight and no more than 4 hours before. They took it upon themselves to change the rules on people who arrive early. Then, once they no longer had anyone else to check in, they changed their rules again and start checking in people for Cincinnati about 2.5 hours ahead of time. A little communication and brain power from the staff would have gone a long way. After all that mess, the flight was delayed leaving about 15 minutes without any updates from Allegiant either."

Pros: "I fly this airline airline quite a bit because I have family in the mountains of North Carolina. I have never had a problem with them, I fly out of Fort Lauderdale to Asheville, it's a quick one and a half hour flight. The flight crew is always professional and courteous."

Cons: "Sent email out asking for volunteers to reschedule her flight. Got on the plane our seats were not the same as selected. And we paid more to select our seats. Friend of ours seat was switched also and instead of him sitting next to his wife he sat next to a person who did not have an assigned seat he was extremely large and he was hanging off The seat into the aisle I noticed an empty seat and had to ask the stewardess if he could switch seats instead of the stewardess offering on her own. The flight out was delayed approximately one hour various mechanics coming on and off plane until finally we were able to leave."

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: "No much"
Cons: "The flight was over 5 hours late. We were supposed to leave at 6:06 PM and didn't leave until about 11:10 PM. We were supposed to get into Asheville at about 8:00 PM, but finally arrived about 1:00 AM. I fly this route frequently and Allegiant has a terrible problem with on-time flights and communications with passengers waiting for their flights. I am not certain what the problem is, but it is a significant issue with them. Captain was "bubbly" and upbeat without properly managing the passengers' expectations. Bad public relations."

Pros: "The price and the nonstop flight."
Cons: "6+ hour delays Plane looked to be in sad shape, paint peeling, looked bolted together from spare parts. Strange Air Conditioning issues mid-flight that turned the plane into a walk-in freezer. upon landing our entire flights bags were abandoned and there wasn't a single Allegiant representative in the airport to communicate with the airport baggage people. After 1.5 hour wait our bags were finally offloaded onto the baggage claim by an airport employee not normally tasked with the job. Allegiant was paged over and over with no response. I will NEVER fly Allegiant again."

Cons: "Seats were very uncomfortable"

Pros: "Flight attendant Lisa was great."

Pros: "It's like taking the public bus during rush hour. Organized chaos. But I guess you literally get what you pay for so, yeah. The crew was awesome though. No qualms there."
Cons: "Disorganized boarding. Even the extra room seats are cramped. Bathrooms are a step up from a porta potty. DO NOT SIT NEAR THEM unless you plan on holding your breath the while flight."

Pros: "Easy boarding"
Cons: "Slow to get luggage. Seats not comfortable"

Pros: "The flight crew was nice."
Cons: "The staff at Ft Lauderdale airport was not customer focused. They were disorganized and rude. My friend paid $5 for his ticket to be printed and, at the very least, they should refund that. I'll never fly Allegiant again."

Pros: "Everything"
Cons: "Paying for my carry on bag."

Cons: "Not clean"

Pros: "Plane was roomy and comfortable."
Cons: "The Plane WAS NOT CLEAN! The turn around of the plane was so short that you guys did not take the time to vacuum the interior of the plane. My seat and other seats in my row was full of cookie crumbs and sticky food from the previous passengers. It was totally disgusting. Yuck !!"

Pros: "flight attendants"
Cons: "flight was delayed 4 hrs"

Pros: "When you add all the separate costs to the initial ticket price your better off flying a "more expensive " airline. Additional costs are for seat selection, unless you want to take a chance of getting stuck in a middle seat, carry on and checked bags and paying for bottled water and soda. Also the seats don't recline so carry ibuprofen if you fly on Alegient."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Florida to Chicago Midway

Airlines flying from Florida to Chicago Midway 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 Florida to Chicago Midway

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Florida to Chicago Midway

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Florida to Chicago Midway

Book cheap flights from Florida to Chicago Midway Airport

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