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$36 Find cheap flights from Florida Keys 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 5/29. 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
Fri 6/14
Fri 6/21

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Good to know

Low season

January

High season

June

Cheapest flight

$36
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 6% increase in price.
Flight from Miami to Chicago Midway Airport

FAQs for booking Florida Keys to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Florida Keys 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 from Florida Keys to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida Keys 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 from Florida Keys is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Florida Keys 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 to Florida Keys with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida Keys 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 from Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Florida Keys to Chicago Midway Airport?

Find which airlines fly direct from Florida Keys to Midway, which days they fly and book direct flights.

Nonstop departures

Florida Keys to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights

Nonstop returns

Chicago Midway to Florida Keys

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 more

See more direct flights
See more direct flights

Top airlines flying from Florida Keys to Midway

 
Need help choosing which airline to fly with from Florida Keys 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.
8.0
DeltaOverall score based on 10691 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.9Comfort
7.4Food
Airline reviews

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

10.0 ExcellentGregory, May 2024MCO - JFK
Read more about Delta reviews

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

Frontier is a crappy airline nothing about it is honest

Crew members are very rude and not cooperate with passengers.

30 minute delay due to boarding and settling of a family.

I am HIGHLY unhappy with the amount of money I spent on the flight. Paid in advance only to find the flight at a discount price a week or so before the flight. I will not fly frontier again and have bad mouthed your business since to anyone I have spoken with about flying (which has been many a people). Crew was mediocre and instead of moving me to a spot where I could gain some leg room they sat their flight attendant there. Won’t be flying frontier in the future.

Well, I didn’t have food! So NA wasn’t an option. I’ll be back!

First time flying with Frontier . From buying tickets ,getting boarding pass and boarding plane was super easy. Definitely would fly again with Frontier .

Our flight was on time and unremarkable which I'm grateful for, as it is not the norm traveling these days. Frontier is a low-cost carrier and it really shows when compared to other "normal" carriers. They don't even give you water during the flight. The coach seats are decent, however it was not as clean as it should be. We had crumbs all over the floor by our seats.

They lost my baggage on my connection flight, it’s been 24 hours since I put my claim in and still no update on my bags.

they charge too much when you arrive in the air port

The flight was canceled, then delayed twice, we were moved gates twice. Short staff at the counter and check in. We waited for our flight 9 hours. Will never use Frontier ever again, or Spirit.

Book cheap flights from Florida Keys to Chicago

Recent round-trip flight deals

6/5Wed
nonstopFrontier
3h 11mMIA-MDW
6/11Tue
nonstopFrontier
3h 08mMDW-MIA
$37
6/7Fri
nonstopFrontier
3h 11mMIA-MDW
6/11Tue
nonstopFrontier
3h 08mMDW-MIA
$47
6/12Wed
nonstopFrontier
3h 11mMIA-MDW
6/18Tue
nonstopFrontier
3h 08mMDW-MIA
$49
7/16Tue
nonstopFrontier
3h 06mMIA-MDW
7/23Tue
nonstopFrontier
3h 04mMDW-MIA
$58
6/7Fri
nonstopFrontier
3h 11mMIA-MDW
6/18Tue
nonstopFrontier
3h 08mMDW-MIA
$59
6/5Wed
nonstopFrontier
3h 11mMIA-MDW
6/10Mon
nonstopFrontier
3h 07mMDW-MIA
$60
6/26Wed
nonstopFrontier
3h 11mMIA-MDW
7/16Tue
nonstopFrontier
3h 04mMDW-MIA
$61
6/12Wed
nonstopFrontier
3h 11mMIA-MDW
6/16Sun
nonstopFrontier
3h 08mMDW-MIA
$63
6/12Wed
1 stopDelta
6h 03mMIA-MDW
6/18Tue
1 stopDelta
5h 10mMDW-MIA
$216
9/27Fri
1 stopDelta
4h 39mEYW-MDW
10/1Tue
1 stopDelta
5h 28mMDW-EYW
$232

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Recent one-way flight deals

5/29Wed
nonstopFrontier
3h 15mMIA-MDW
$36
7/9Tue
nonstopFrontier
3h 06mMIA-MDW
$37
7/3Wed
nonstopFrontier
3h 11mMIA-MDW
$39
5/31Fri
nonstopFrontier
3h 15mMIA-MDW
$42
7/9Tue
1 stopDelta
5h 41mMIA-MDW
$108
6/14Fri
1 stopDelta
5h 33mMIA-MDW
$118
6/7Fri
2 stops
14h 48mMIA-MDW
$154
7/12Fri
2 stops
16h 17mMIA-MDW
$208
6/6Thu
2 stopsVolaris
17h 51mMIA-MDW
$366
10/6Sun
2 stopsVolaris
17h 51mMIA-MDW
$407

Search by stops

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Last minute flights from Florida Keys to Midway

Last minute flight, train and bus deals

5/20Mon
nonstopFrontier
3h 15mMIA-MDW
5/22Wed
nonstopFrontier
3h 11mMDW-MIA
$156
5/18Sat
multi-stopFrontier
21h 22mMIA-MDW
5/22Wed
nonstopFrontier
3h 11mMDW-MIA
$173
5/18Sat
multi-stopFrontier
21h 22mMIA-MDW
5/26Sun
nonstopFrontier
3h 11mMDW-MIA
$185
5/20Mon
multi-stopFrontier
12h 01mMIA-MDW
5/22Wed
nonstopFrontier
3h 11mMDW-MIA
$198
5/19Sun
nonstopSouthwest
3h 10mMIA-MDW
5/23Thu
nonstopSouthwest
2h 55mMDW-MIA
$545
5/19Sun
nonstopSouthwest
3h 10mMIA-MDW
5/23Thu
multi-stopSouthwest
9h 50mMDW-MIA
$554
5/19Sun
nonstopSouthwest
3h 10mMIA-MDW
5/23Thu
multi-stopSouthwest
14h 05mMDW-MIA
$559
5/20Mon
multi-stopDelta
5h 35mMIA-MDW
5/20Mon
multi-stopDelta
5h 01mMDW-MIA
$748
5/17Fri
multi-stopDelta
5h 35mMIA-MDW
5/19Sun
multi-stopDelta
6h 45mMDW-MIA
$806
5/17Fri
multi-stopDelta
5h 48mMIA-MDW
5/20Mon
multi-stopDelta
5h 28mMDW-MIA
$986

Search by stops

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Florida Keys

Cabin classes:

$408
$513
$246
$37