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Cheap flights from Chicago Midway Airport to Florida Keys from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Florida Keys departing on 10/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Florida Keys

Cheap round-trip flights

Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
$137Southwest
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Mon, Sep 15 - Fri, Sep 19
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
$144Frontier
Find Deal
Thu, Oct 23 - Mon, Oct 27
Southwest Logo
5:25 am - 3:15 pmMDW-MIA
8h 50m1 stop
Southwest Logo
7:30 am - 9:35 amMIA-MDW
3h 05mnonstop
$147Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
Frontier Logo
10:03 pm - 2:03 amMDW-MIA
3h 00mnonstop
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
$151Frontier
Find Deal
Thu, Oct 23 - Mon, Oct 27
Southwest Logo
2:05 pm - 8:40 pmMDW-MIA
5h 35m1 stop
Southwest Logo
5:25 pm - 9:40 pmMIA-MDW
5h 15m1 stop
$157Southwest
Find Deal
Wed, Sep 24 - Wed, Oct 1
Southwest Logo
7:55 am - 3:55 pmMDW-MIA
7h 00m1 stop
Southwest Logo
11:45 am - 7:10 pmMIA-MDW
8h 25m2 stops
$162Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 22
Frontier Logo
7:23 pm - 11:09 pmMDW-MIA
26h 46m1 stop
Frontier Logo
6:53 pm - 9:08 pmMIA-MDW
3h 15mnonstop
$166Frontier
Find Deal
Fri, Oct 24 - Sun, Oct 26
Delta Logo
10:35 am - 6:33 pmMDW-MIA
6h 58m1 stop
Delta Logo
12:20 pm - 6:25 pmMIA-MDW
7h 05m1 stop
$217Delta
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Tue, Sep 30 - Wed, Oct 8
Delta Logo
4:25 pm - 12:24 amMDW-MIA
6h 59m1 stop
Delta Logo
7:30 am - 11:48 amMIA-MDW
5h 18m1 stop
$237Delta
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Sat, Aug 16 - Tue, Aug 19
Allegiant Air Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Allegiant Air Logo
10:41 am - 3:22 pmEYW-MDW
5h 41m1 stop
$335Allegiant Air
Find Deal
Fri, Nov 14 - Mon, Nov 17

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets
Frontier
Oct 23
MDW10:03 pmChicago Midway
3h 00m
MIA2:03 amMiami
Oct 27
MIA6:53 pmMiami
3h 15m
MDW9:08 pmChicago Midway
$144
Find similar
Frontier
Oct 23
MDW10:03 pmChicago Midway
3h 00m
MIA2:03 amMiami
Oct 27
MIA6:53 pmMiami
3h 15m
MDW9:08 pmChicago Midway
$151
Find similar
Frontier
Oct 24
MDW7:23 pmChicago Midway
26h 46m
1 stop
MIA11:09 pmMiami
Oct 26
MIA6:53 pmMiami
3h 15m
MDW9:08 pmChicago Midway
$166
Find similar

Southwest flights from Chicago Midway Airport to Florida Keys

Our best Southwest deals on Chicago Midway Airport to Florida Keys flight tickets
Southwest
Sep 15
MDW2:10 pmChicago Midway
3h 00m
MIA6:10 pmMiami
Sep 19
MIA12:35 pmMiami
3h 10m
MDW2:45 pmChicago Midway
$137
Find similar
Southwest
Sep 4
MDW5:25 amChicago Midway
8h 50m
1 stop
MIA3:15 pmMiami
Sep 7
MIA7:30 amMiami
3h 05m
MDW9:35 amChicago Midway
$147
Find similar
Southwest
Sep 24
MDW2:05 pmChicago Midway
5h 35m
1 stop
MIA8:40 pmMiami
Oct 1
MIA5:25 pmMiami
5h 15m
1 stop
MDW9:40 pmChicago Midway
$157
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Florida Keys that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/15

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Fri 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$144

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/4

5:25 am-3:15 pm

1 stop8h 50m

Miami

Sun 9/7

7:30 am-9:35 am

Nonstop3h 05m

$147

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$151

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 9/24

2:05 pm-8:40 pm

1 stop5h 35m

Miami

Wed 10/1

5:25 pm-9:40 pm

1 stop5h 15m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 10/7

7:55 am-3:55 pm

1 stop7h 00m

Miami

Wed 10/22

11:45 am-7:10 pm

2 stops8h 25m

$162

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 10/24

7:23 pm-11:09 pm

1 stop26h 46m

Miami

Sun 10/26

6:53 pm-9:08 pm

Nonstop3h 15m

$166

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 9/30

10:35 am-6:33 pm

1 stop6h 58m

Miami

Wed 10/8

12:20 pm-6:25 pm

1 stop7h 05m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 8/16

4:25 pm-12:24 am

1 stop6h 59m

Miami

Tue 8/19

7:30 am-11:48 am

1 stop5h 18m

$237

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 11/14

5:35 pm-9:01 am

2 stops14h 26m

Key West

Mon 11/17

10:41 am-3:22 pm

1 stop5h 41m

$335

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Florida Keys from

How to get the cheapest flight ticket from Chicago Midway Airport to Florida Keys

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Florida Keys?

The month of February is another great option to travel to Florida Keys, with average flight prices from Chicago Midway Airport averaging around $174.

What is the cheapest day to depart on your flight to Florida Keys?

The cheapest day to depart from Chicago Midway Airport to Florida Keys is on a Wednesday when prices can be found for as low as $181. The most expensive day to fly to Florida Keys is Saturday, with ticket prices averaging around $292.

What is the cheapest time of day to depart on your flight to Florida Keys?

According to our data, the cheapest time of day to fly to Florida Keys is in the evening. momondo users have found flights departing from Chicago Midway Airport to Florida Keys in the evening for as low as $197. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights at noon are often more expensive with an average ticket price of $313.

How far in advance should I book a flight to Florida Keys?

You are more likely to see cheaper flights to Florida Keys from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $280 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Chicago Midway Airport for as low as $170 on momondo.

Can stopping save me money on Chicago Midway Airport to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Florida Keys.

Cheap Chicago Midway Airport to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Florida Keys

Best Price Found

$49

Fastest flight time

3h 00m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Florida Keys

2 airports
The best one-way flight to Florida Keys from Chicago Midway Airport in the past 72 hours is $49. The best round-trip flight deal from Chicago Midway Airport to Florida Keys found on momondo in the last 72 hours is $137.
The fastest flight from Chicago Midway Airport to Florida Keys takes 3h 00m
Direct flights go from Chicago Midway Airport to Florida Keys on Monday, Tuesday, Friday, Saturday and Sunday. Airlines offering direct flights are: Southwest and Frontier.
There are 2 airports near Florida Keys: Key West (EYW), Miami (MIA)
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Florida Keys?

    Prices for flights from Chicago Midway Airport to Florida Keys were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Florida Keys?

  • How old do you have to be to fly from Chicago Midway Airport to Florida Keys?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Florida Keys.

  • What documentation or ID do you need to fly to Florida Keys?

    The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Florida Keys?

Best airlines flying from Chicago Midway Airport to Florida Keys

Compare and see reviews for airlines that fly from Chicago Midway Airport to Florida Keys with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $225Free CancellationRating
8.0
7,981 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florida Keys?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Florida Keys for you.

Can I find flights from Chicago to Florida Keys with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Florida Keys flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Florida Keys?

momondo provides multiple filters to help you find the best flight to Florida Keys from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Florida Keys right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Florida Keys, momondo offers a useful price alert feature which will track prices for flights to Florida Keys from Chicago and alert you when they change.

An easier way to manage your Florida Keys trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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