$71 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 10/1. 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
1 adult, Economy

KAYAK searches 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
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Cheap Flights from Midway to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miaminonstop$114
Key West
Key West1 stop$244
Miami
Miaminonstop$114
Key West
Key West1 stop$244

Book Cheap Midway to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Florida Keys that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Florida Keys

Fri, Oct 24 - Sat, Oct 25
Frontier Logo
12:18 pm - 4:19 pmMDW-MIA
3h 01mnonstop
Frontier Logo
10:34 am - 5:13 pmMIA-MDW
7h 39m1 stop
$114Frontier
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Mon, Oct 20 - Fri, Oct 24
Frontier Logo
10:33 am - 2:33 pmMDW-MIA
3h 00mnonstop
Frontier Logo
5:22 pm - 11:20 pmMIA-MDW
6h 58m1 stop
$120Frontier
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Thu, Oct 9 - Fri, Oct 17
Frontier Logo
8:25 am - 7:54 pmMDW-MIA
10h 29m1 stop
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
$121Frontier
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Wed, Nov 12 - Tue, Nov 18
Southwest Logo
9:00 am - 1:05 pmMDW-MIA
3h 05mnonstop
Southwest Logo
1:05 pm - 3:20 pmMIA-MDW
3h 15mnonstop
$157Southwest
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Wed, Oct 22 - Wed, Oct 29
Multiple Airlines Logo
8:05 am - 2:33 pmMDW-MIA
5h 28m1 stop
Multiple Airlines Logo
7:23 pm - 12:37 pmMIA-MDW
18h 14m1 stop
$174Multiple Airlines
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Sat, Oct 11 - Sun, Oct 12
Multiple Airlines Logo
5:20 pm - 8:54 amMDW-MIA
14h 34m1 stop
Multiple Airlines Logo
5:46 pm - 12:36 amMIA-MDW
7h 50m1 stop
$180Multiple Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Southwest Logo
9:20 am - 4:10 pmMDW-MIA
5h 50m1 stop
Southwest Logo
1:05 pm - 3:20 pmMIA-MDW
3h 15mnonstop
$187Southwest
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Tue, Feb 24 - Thu, Mar 5
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
Delta Logo
6:00 pm - 9:46 pmEYW-MDW
4h 46m1 stop
$269Delta
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Wed, Oct 15 - Wed, Oct 22
Delta Logo
12:48 pm - 8:06 pmMDW-EYW
6h 18m1 stop
Delta Logo
12:22 pm - 4:09 pmEYW-MDW
4h 47m1 stop
$289Delta
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Fri, Oct 24 - Sun, Oct 26
Allegiant Air Logo
2:45 pm - 8:55 pmMDW-EYW
5h 10m1 stop
Allegiant Air Logo
3:30 pm - 5:04 pmEYW-MDW
26h 34m2 stops
$465Allegiant Air
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Booking Insights

KAYAK's insights & trends for Midway to Florida Keys flights

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

Can I save money by flying with a layover from Chicago Midway Airport to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $321, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Florida Keys, 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 from Chicago Midway Airport to Florida Keys is February, when tickets cost $173 (return) on average. On the other hand, the most expensive months are June and September, when the average cost of round-trip tickets is $439 and $379 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Florida Keys?

The average price of all round-trip flights from Chicago Midway Airport to Florida Keys clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Florida Keys, look for departures on Wednesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Florida Keys, Friday is the cheapest day to fly and Sunday is the most expensive.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Florida Keys, you should book around 2 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$71
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 6% increase in price.
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 from Chicago Midway Airport to 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 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 from Chicago Midway Airport to Florida Keys 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 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 from Chicago Midway Airport to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida Keys?

    The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $214 on average. Morning departures are around 12% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $317.

Reviews of the 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.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Everything you need to know for your flight to Florida Keys

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