$38 Find Cheap Flights from Chicago Midway Airport to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Florida Keys departing on 12/17. 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

Search hundreds of travel sites at once for deals on flights to Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida Keys, as well as popular online travel agencies

Best Florida Keys Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Miami
Miaminonstop$96
Key West
Key West1 stop$218

Good to know

Low season

August

High season

March

Cheapest flight

$38
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago Midway Airport to Miami

FAQs - booking Florida Keys flights

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

    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 Chicago Midway Airport to Florida Keys.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Florida Keys from 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 from Chicago Midway Airport to Florida Keys?

    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 Florida Keys with an airline and back to Chicago Midway Airport with another airline.

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

    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 Florida Keys from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Miami $52 one-way - $144 round-trip

Top 5 airlines serving from Midway to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Florida Keys? 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.
8.1
SouthwestOverall score based on 5005 reviews
8.2Boarding
7.7Entertainment
8.7Crew
7.2Food
8.1Comfort
Airline reviews

Excellent experience. WiFi worked on this leg of My trip

10.0 ExcellentDONALD, Nov 2024MDW - MCO
Read more Southwest reviews

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

wifi wasn't working correctly so couldn't watch live tv

Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.

The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.

Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day

It good. Just not that plane didn’t have power outlets to charge devices etc.

Although the flight was delayed, but the crew was amazing. They did the best they could to make the time enjoyable.

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

Average, boarding was ok, the eye scanner broken mid way through boarding they ahd to do it manually. Did not eat any food, Not even water was offered for free.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

Direct 2.5 hour flight good. Free snacks and coffee, water, or soft drinks not available...bad.

Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

The flight was delayed and the announcements were hard to hear, but the crew was great

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

Really nice, flight attendants were so helpful with me and my kids. Extremely grateful, keep up the good work and spirit :)

I liked the low price. I did not like the cramped passenger seats. As a below average size person I was cramped in the seat; I can only imagine how uncomfortable an average or large size person would be. I guess that is part of the deal with low cost airlines.

It just baffled me that spirit boarding process that I was charged 2 check in fees for a person bag and carry on. I ended up lugging 3 kids under 10 with 2 bags and to find out at the boarding area that I could not get on the plane due to my lack of reading the baggage policy. I understand if that was the case but the agent also failed to understand one item was in fact a personal item such as laptop bag and charge me as if it was a carry on not personal item. And knowing it’s a horrible storm and last flight in the destination of travel. I could have very easily handed the items to my relative to keep but I didn’t learned about this enforced policy until I was about to board.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Airline changed the gate from Terminal A to Terminal D which is quite far and only sent a text message few minutes before boarding. Around 50 people missed their flight and as plane didn’t wait for them.

The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

Horrible my trip was delayed 3 hours, we already have set in the plane and they delayed the flight.

Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Book cheap flights from Chicago to Florida Keys

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to Florida Keys found on KAYAK in the last 72 hours.
12/15Sun
nonstopFrontier
3h 13mMDW-MIA
12/17Tue
nonstopFrontier
3h 30mMIA-MDW
$96
12/16Mon
nonstopFrontier
3h 08mMDW-MIA
12/19Thu
nonstopFrontier
3h 28mMIA-MDW
$97
12/16Mon
nonstopFrontier
3h 08mMDW-MIA
12/19Thu
nonstopFrontier
3h 28mMIA-MDW
$99
12/17Tue
nonstopFrontier
3h 13mMDW-MIA
12/24Tue
nonstopFrontier
3h 30mMIA-MDW
$100
12/9Mon
1 stopFrontier
6h 13mMDW-MIA
12/12Thu
nonstopFrontier
3h 30mMIA-MDW
$101
1/14Tue
nonstopSouthwest
3h 00mMDW-MIA
1/18Sat
nonstopSouthwest
3h 10mMIA-MDW
$194
2/18Tue
1 stopDelta
6h 46mMDW-MIA
2/25Tue
1 stopDelta
6h 59mMIA-MDW
$216
1/28Tue
1 stopDelta
5h 28mMDW-EYW
2/4Tue
1 stopDelta
5h 00mEYW-MDW
$218
12/9Mon
nonstopSouthwest
3h 05mMDW-MIA
12/11Wed
nonstopSouthwest
3h 10mMIA-MDW
$229
12/18Wed
1 stopDelta
6h 50mMDW-EYW
12/25Wed
1 stopDelta
7h 16mEYW-MDW
$243

Search by stops

Search by airline

Search by price

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Florida Keys found on KAYAK in the last 72 hours.
12/17Tue
nonstopFrontier
3h 13mMDW-MIA
$38
12/19Thu
nonstopFrontier
3h 13mMDW-MIA
$48
12/19Thu
nonstopFrontier
3h 13mMDW-MIA
$50
12/19Thu
nonstopFrontier
3h 13mMDW-MIA
$51
12/19Thu
nonstopFrontier
3h 13mMDW-MIA
$52
1/21Tue
nonstopSouthwest
3h 00mMDW-MIA
$79
3/4Tue
1 stopDelta
5h 19mMDW-MIA
$108
11/26Tue
1 stopDelta
6h 47mMDW-EYW
$118
1/22Wed
nonstopSouthwest
3h 00mMDW-MIA
$134
11/27Wed
2 stops
32h 33mMDW-MIA
$155

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Florida Keys

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 from Chicago to Florida Keys that are departing in the next 10 days.
11/26Tue
nonstopFrontier
3h 19mMDW-MIA
12/29Sun
nonstopFrontier
3h 28mMIA-MDW
$166
11/25Mon
nonstopFrontier
3h 19mMDW-MIA
12/4Wed
multi-stopFrontier
17h 13mMIA-MDW
$193
11/26Tue
nonstopFrontier
3h 19mMDW-MIA
11/28Thu
multi-stopFrontier
7h 52mMIA-MDW
$203
11/25Mon
nonstopFrontier
3h 19mMDW-MIA
12/7Sat
multi-stopFrontier
5h 49mMIA-MDW
$205
11/22Fri
multi-stopDelta
4h 38mMDW-EYW
11/27Wed
multi-stopDelta
5h 33mEYW-MDW
$458
11/23Sat
multi-stopDelta
4h 52mMDW-EYW
11/24Sun
multi-stopDelta
6h 21mEYW-MDW
$518
11/22Fri
nonstopSouthwest
3h 05mMDW-MIA
12/12Thu
nonstopSouthwest
3h 10mMIA-MDW
$558
11/22Fri
multi-stopSouthwest
8h 25mMDW-MIA
12/12Thu
nonstopSouthwest
3h 10mMIA-MDW
$572
11/25Mon
multi-stopSouthwest
9h 15mMDW-MIA
11/28Thu
multi-stopSouthwest
10h 10mMIA-MDW
$599
11/22Fri
multi-stopDelta
5h 16mMDW-MIA
11/27Wed
multi-stopDelta
5h 44mMIA-MDW
$646

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.