MDW
Find cheap flights from Florida to Chicago Midway Airport from $44
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 6/14. 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.Round-trip
1 adult
Economy
Sun 7/2
Sun 7/9
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Good to know
Low season | January |
|---|---|
High season | April |
Cheapest flight | $44 |
Average price round-trip | $178 |
Good deal round-trip | $81 |
Good deal one-way | $45 |
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Miami to Chicago Midway Airport
(avg. price over the last 2 weeks)
or less
or less
FAQs for booking Florida to Chicago Midway Airport flights
Top 5 airlines serving from Florida to Midway
Scores according to KAYAK customer reviews8.4
SouthwestOverall score based on 13953 reviews
80entertainment
87boarding
86overall
84comfort
90crew
78food
Airline reviews
Cons: "The service wasn’t great and it was not a great experience"
Cons: "The service wasn’t great and it was not a great experience"
Cons: "I was able to connect to internet and watch movie Thank you"
Cons: "Nothing. Smooth flight, friendly crew, and early arrival. Can’t be beat!"
Cons: "I was supposed to go to a wedding in Chicago, and leave on thursday. They cancelled my thursday flight and did not get me to Chicago until Saturday, so I missed the wedding. They strung the whole thing out by scheduling me on new flights, only to cancel those later. Total mess!"
Pros: "Arrived on time, courteous crew, smooth flight, good value ."
Cons: "Healthier snacks, real milk for the coffee, more audible announcements over the PA, provide instructions and announcements via smart phones and tablets for those who have them. One passenger clearly was hacking from a cold or flu virus. Another trashed a seat and floor with nut shells and tissues."
Pros: "Crew was good. On boarding was smooth"
Cons: "It’s a 4 hours flight. Snack has to be better."
Pros: "The crew was nice and friendly. They came around multiple times offering us drinks."
Pros: "Their sense of humor and safety first."
Cons: "My suitcase was soaked like it had been left out in the rain but my other one was dry. Delayed due to mechanical error for three hours then had to taxi back to gate for weather advisory. I was so tired that I couldn’t relax."
Pros: "Everything about this flight was better than fly American Airlines. I gave up on AA and started flying Delta a couple years ago and now I'll add Southwest to my list as long as cost makes up for the longer drive."
Cons: "Did not like the long delay but couldn't be helped. Toilets had a problem but they found us another plane, which was good."
Pros: "Not much"
Cons: "Crew kept bumping me in flight. Deplaning took too long."
Pros: "Crew was awesome!"
Cons: "The boarding did not go on time. An announcement about why would have been nice. Still made it on the flight on time."
Pros: "I wish the airlines, all airlines would keep the middle seat vacant on all flights!! Such a comfortable feeling and flight. I’ve flown multiple times this summer during Covid, having that middle seat vacant has made traveling by air for me a very good, comfortable thing again. Don’t ever go back to packing us in like cattle car flights!!"
Cons: "The flight was delayed by 3 hours because of storms in Atlanta earlier. This caused us to miss our connection to Fairbanks in Seattle, so we had to spend the night in Seattle at our own cost."
Pros: "The crew was very nice and helpful, I had a nice spot on the plane, and it went very smoothly, especially considering the circumstances. I was supposed to be flying to Seattle later on, but I had to change my flight last minute because of the virus. The whole Delta team was very understanding and considerate and it made the process much less stressful."
Cons: "My flight was cancelled and rescheduled for a later time the day before and there was a lot of changing of gates and running around, but I understand that everything has been hectic and I don’t blame that on you, I know you’re all doing your best."
Cons: "TVs/outlets on my side and section of the plane were not working."
Pros: "The crew did a great job and I enjoyed the movies."
Cons: "Nothing"
Pros: "They did not clean with antiseptic the tray tables and tv screens between flights. Because of corona virus scare. I asked stewardess and she said no"
Cons: "Turn on the lights before landing graduallyb- noone likes bright fast - too nasty;"
Cons: "The cabin was a little cool for me during at least half of the flight"
I did not go on my trip. I requested a refund and still have not received it.
Plane had mechanic problem that was never explained. Had to bring a plane from another airport. Six hour delay. No apology for the delay. Not even an acknowledgment.
My only real issue was that when I booked this flight through Kayak, I somehow booked via BudgetAir.com (though I was on your website.) Due to this, I was unable to access boarding passes coming or going via the Kayak app, or the Allegient app. Luckily I was able to print them prior to leaving home (and the resort printed them for on the way back), but using this site is definitely something I'll have to consider for my trip. I should have been able to access boarding passes electronically via the app regardless.
Cons: "They left on time with 46 pax and took over a 2 hour delay. Then my bag did not show up."
Pros: "Easy boarding"
Cons: "Half the flight didn't wear masks, crew didn't bother to enforce."
Pros: "Crew was very nice and very competent."
Cons: "I'm trying to wrap my head around the # of flights that are delayed or cancelled, when I fly on Allegiant. Perhaps, I have just had bad luck. The flight was delayed a total of 5 times for a total delay of about 4 hours. The original scheduled flight was for 6:35 pm and we didn't actually leave the ground until almost 10:30. We kept getting pushed back. I am not certain if it was due to weather (in another area) or required flight crew rest, both of which I would understand. There was no reason posted that I saw. I have a 10 yo son who has Autism and should be in bed no later than 10 pm, preferably 9 pm. I appreciate all that Allegiant does for the military, and therefore, will continue to fly on your airline. I will NOT, however, take any more evening flights as most of the ones I've flown on have either been delayed or altogether cancelled. Again, I truly appreciate your recognition of retired and active duty military. 8/10 is a B and can be improved upon with more clarevoyance and keeping on-time flights."
Pros: "I love that they fly out of smaller airports. I feel like the crew is kind and helpful."
Cons: "The seats are not very comfortable but luckily most of the flights are not too long."
Pros: "They sat my family together and the crew was amazing."
Cons: "The seats are really uncomfortable and the flight was really packed with all this covid stuff."
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."
Pros: "The crew was amazing, super helpful, very friendly and understanding when it came to social distancing."
Cons: "The seats are not the most comfortable, but the price is right."
Pros: "The crew was very nice."
Cons: "Frontier has actually become less comfortable than Spirit. And your bag charges are outrageous."
Pros: "The cheap price of the flight."
Cons: "The flight attendant took my bag out of the overhead compartment and made me check it. It was the same bag I used flying to Florida and did not have any issues with it. She insisted it was too big. I told her it obviously fit just fine because she took it out easily and that it was regulation size and weight. I was not happy at all. I paid to sit up front and get on first to put my bag in the overhead compartment for a reason! I’ve used this bag several times with no issues. I spent an extra 35 minutes trying to get my bag and leave the airport that I didn’t have to spare. She had no regard for incredible inconvenience it caused me."
Pros: "The crew was professional and friendly."
Cons: "Both my outbound and inbound flights were 1 hour late. The tiny tray tables and lack of reclining chairs make Frontier's planes more uncomfortable than others. Being charged for a basic beverage or snack also seems "chintzy" when you've already charged me for my flight + my seat + all baggage."
Pros: "Ticket agent and crew were very friendly and professional"
Cons: "Downloaded the Frontier app, but could not get my boarding pass. Had to go to ticket agent at airport. Baggage charges confusing."
Pros: "One member of the crew was positive and energetic. The flight was short and the pilot was light-hearted and welcoming."
Cons: "Most of the crew was “blah” and one member seemed like she was having a bad day. Short with passengers. The seats are uncomfortable."
Cons: "Was the worst flight ever check in was opened late , computers were down , boarding was horrific , problems with many people and seating , flight left late ,"
Pros: "The crew was great, the prices fantastic and everything whet extremely well. We even arrived in Denver early. The flight crew did a great job of keeping turbulence down despite some conditions that were less than easy to navigate. For a no frills flight, this was fine."
Cons: "I miss the frills although they have them available all at a cost during and before the flight. If you need all the frills I would probably go to a more comfortable venue. If you bring your drink and snack and don't mind not choosing your seat, etc., this will work just fine."
Pros: "Crew was super pleasant and chipper. Passengers seemed to have a handle on how to board in a timely manner."
Cons: "Management could schedule time for maintenance software updates so as not to affect departure time. We were 20 minutes delayed."
Pros: "Great flight for the price"
Cons: "Nothing- there were delays but not due to the airline"
Cons: "Offering WiFi would make the cramped and uncomfortable seats a little less unbearable."
Cons: "Didn't have enough staff to leave when scheduled..2 1/2 hour delay, chaos, police had to come. Rinky dink airline, the WORSE..never would fly again.."
Cons: "Terminal process is awful. Customer Service is awful. Never flying Spirit Airlines again."
Cons: "The suiteress (Carol) was a bit rude. Plane was packed"
Pros: "Customers service from flight crew was very good. They work with what they have and make the best of it."
Cons: "Uncomfortable seats."
Pros: "Early arrival"
Cons: "Paid for 6th rows seats and got 22nd Flight was so expensive by the time I paid for them and bags. Will never fly Spirit again. Chairs were like the metal folding chairs for soccer games."
Pros: "Good crew members. Very personable and entertaining"
Cons: "Well the usual: have to pay for literally everything including a carry on bag"
Pros: "I traveled with my two boys (8 months and 2 year) everyone was caring , helpful and understanding of my situation. They made sure I had help and snacks to keep the boys as comfortable as possible."
Cons: "I didn’t like the snack selection. Maybe add more kid friendly drinks and snacks would be perfect for the traveling families."
Pros: "My luggage arrived in good condition in Tampa.Easy pickup.lol"
Cons: "Daughter got sick.I checked in and had to leave the airport to take care of her."
Pros: "Sheets did not decline could not eat peanuts because a kid on the plane had an allergy"
Cons: "Sheets did not decline could not eat peanuts because a kid on the plane had an allergy"
Pros: "It was $140 round trip to Seattle."
Cons: "Seats are uncomfortable. You feel vibrations from everyone in your column, not just your row."
Book cheap flights from Florida to Chicago Midway Airport
Recent round-trip flight deals
10/7Sat
nonstopFrontier
3h 11mMIA-MDW
10/11Wed
nonstopFrontier
3h 11mMDW-MIA
$91
6/20Tue
nonstopFrontier
3h 30mMIA-MDW
6/27Tue
nonstopFrontier
3h 01mMDW-MIA
$92
6/21Wed
nonstopFrontier
3h 30mMIA-MDW
6/21Wed
nonstopFrontier
3h 01mMDW-MIA
$94
6/13Tue
nonstopFrontier
3h 30mMIA-MDW
6/14Wed
nonstopFrontier
3h 01mMDW-MIA
$96
7/19Wed
nonstopFrontier
3h 30mMIA-MDW
8/1Tue
nonstopFrontier
3h 01mMDW-MIA
$97
6/21Wed
nonstopFrontier
3h 30mMIA-MDW
6/26Mon
nonstopFrontier
3h 01mMDW-MIA
$99
8/1Tue
nonstopFrontier
2h 51mTPA-MDW
8/8Tue
nonstopFrontier
2h 36mMDW-TPA
$100
6/17Sat
nonstopFrontier
3h 30mMIA-MDW
6/21Wed
nonstopFrontier
3h 01mMDW-MIA
$100
10/25Wed
nonstopFrontier
2h 52mMCO-MDW
10/31Tue
nonstopFrontier
2h 50mMDW-MCO
$100
6/13Tue
nonstopFrontier
3h 30mMIA-MDW
6/15Thu
nonstopFrontier
3h 01mMDW-MIA
$103
6/20Tue
nonstopMultiple Airlines
3h 30mMIA-MDW
6/27Tue
1 stopMultiple Airlines
6h 09mMDW-MIA
$107
6/20Tue
1 stopMultiple Airlines
26h 53mMIA-MDW
6/24Sat
nonstopMultiple Airlines
3h 01mMDW-MIA
$114
6/20Tue
nonstopMultiple Airlines
3h 30mMIA-MDW
6/29Thu
1 stopMultiple Airlines
11h 52mMDW-MIA
$123
8/23Wed
1 stopMultiple Airlines
9h 30mTPA-MDW
8/24Thu
nonstopMultiple Airlines
2h 37mMDW-TPA
$124
6/22Thu
1 stopMultiple Airlines
18h 15mTPA-MDW
6/27Tue
1 stopMultiple Airlines
11h 12mMDW-TPA
$126
6/20Tue
1 stopMultiple Airlines
6h 08mTPA-MDW
6/22Thu
2 stopsMultiple Airlines
12h 19mMDW-TPA
$148
7/5Wed
1 stopDelta
6h 59mRSW-MDW
7/8Sat
1 stopDelta
5h 10mMDW-RSW
$219
6/21Wed
1 stopDelta
6h 59mRSW-MDW
6/27Tue
1 stopDelta
5h 10mMDW-RSW
$228
7/3Mon
nonstopSouthwest
2h 20mJAX-MDW
7/6Thu
nonstopSouthwest
2h 15mMDW-JAX
$343
7/13Thu
1 stopAllegiant Air
18h 49mPBI-MDW
7/21Fri
3 stopsAllegiant Air
41h 27mMDW-PBI
$370
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Recent one-way flight deals
6/14Wed
nonstopFrontier
3h 30mMIA-MDW
$44
7/18Tue
nonstopFrontier
3h 30mMIA-MDW
$46
7/19Wed
nonstopFrontier
3h 30mMIA-MDW
$47
6/13Tue
nonstopFrontier
3h 30mMIA-MDW
$48
6/28Wed
nonstopFrontier
2h 48mMCO-MDW
$48
6/27Tue
1 stopFrontier
8h 36mFLL-MDW
$49
6/21Wed
nonstopFrontier
3h 30mMIA-MDW
$50
6/27Tue
nonstopFrontier
2h 49mTPA-MDW
$51
6/21Wed
1 stopFrontier
18h 23mFLL-MDW
$51
8/1Tue
nonstopFrontier
3h 30mMIA-MDW
$51
6/21Wed
1 stopMultiple Airlines
14h 16mMCO-MDW
$59
6/20Tue
1 stopMultiple Airlines
28h 38mMCO-MDW
$60
6/22Thu
1 stopMultiple Airlines
18h 15mTPA-MDW
$67
6/27Tue
1 stopMultiple Airlines
26h 53mMIA-MDW
$67
6/20Tue
1 stopMultiple Airlines
28h 38mMCO-MDW
$69
6/7Wed
1 stopMultiple Airlines
5h 21mMCO-MDW
$70
7/6Thu
1 stopAllegiant Air
19h 39mFLL-MDW
$97
7/4Tue
1 stopDelta
5h 00mTPA-MDW
$100
7/2Sun
2 stopsAllegiant Air
23h 42mSRQ-MDW
$105
7/3Mon
nonstopSouthwest
2h 20mJAX-MDW
$172
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Flights to Chicago Midway Airport
Destination:
Chicago Midway Airport (MDW)United States
Return flight deals:
Chicago Midway Airport - Florida
Cabin classes:
$61
Browse origins:
$257
$91
$134
$219
$355
$249
$283
$326
$91
$95
$349
$255
$284
$250
$104
$70
$293
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