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Cheap flights from Chicago Midway Airport to Florida Keys from $58

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 12/22. 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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0 bags

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Find the cheapest flights from Chicago Midway Airport to Florida Keys

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:57 pm - 10:03 pmMDW-MIA
3h 06mnonstop
Frontier Logo
9:38 am - 1:59 pmMIA-MDW
5h 21m1 stop
$119Frontier
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Sat, Nov 29 - Sat, Dec 6
Multiple Airlines Logo
2:59 pm - 7:09 pmMDW-MIA
3h 10mnonstop
Multiple Airlines Logo
6:05 am - 6:12 pmMIA-MDW
13h 07m1 stop
$120Multiple Airlines
Find Deal
Sat, Dec 13 - Sun, Dec 14
Frontier Logo
9:58 pm - 5:10 amMDW-MIA
30h 12m1 stop
Frontier Logo
2:44 pm - 4:57 pmMIA-MDW
3h 13mnonstop
$121Frontier
Find Deal
Sat, Nov 22 - Wed, Nov 26
Frontier Logo
8:42 pm - 8:33 amMDW-MIA
10h 51m1 stop
Frontier Logo
6:59 am - 9:19 amMIA-MDW
3h 20mnonstop
$122Frontier
Find Deal
Fri, Dec 12 - Sat, Dec 20
Frontier Logo
6:15 am - 10:32 amMDW-MIA
3h 17mnonstop
Frontier Logo
11:42 am - 2:05 pmMIA-MDW
3h 23mnonstop
$123Frontier
Find Deal
Mon, Dec 22 - Mon, Dec 29
Frontier Logo
12:25 pm - 8:51 pmMDW-MIA
7h 26m1 stop
Frontier Logo
6:00 am - 9:44 pmMIA-MDW
16h 44m1 stop
$124Frontier
Find Deal
Wed, Jan 14 - Sun, Jan 18
Multiple Airlines Logo
2:16 pm - 6:26 pmMDW-MIA
3h 10mnonstop
Multiple Airlines Logo
9:59 pm - 10:18 pmMIA-MDW
25h 19m1 stop
$125Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Southwest Logo
9:40 am - 1:45 pmMDW-MIA
3h 05mnonstop
Southwest Logo
6:55 am - 11:15 amMIA-MDW
5h 20m1 stop
$167Southwest
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Mon, Jan 19 - Thu, Jan 22
Delta Logo
10:49 am - 5:15 pmMDW-EYW
5h 26m1 stop
Delta Logo
6:10 pm - 11:47 pmEYW-MDW
6h 37m1 stop
$294Delta
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Tue, Dec 2 - Tue, Dec 9
Delta Logo
10:46 am - 5:13 pmMDW-EYW
5h 27m1 stop
Delta Logo
6:08 pm - 10:26 pmEYW-MDW
5h 18m1 stop
$324Delta
Find Deal
Sat, Jan 31 - Sat, Feb 7

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets
Frontier
Nov 29
MDW5:57 pmChicago Midway
3h 06m
MIA10:03 pmMiami
Dec 6
MIA9:38 amMiami
5h 21m
1 stop
MDW1:59 pmChicago Midway
$119
Find similar
Frontier
Nov 22
MDW9:58 pmChicago Midway
30h 12m
1 stop
MIA5:10 amMiami
Nov 26
MIA2:44 pmMiami
3h 13m
MDW4:57 pmChicago Midway
$121
Find similar
Frontier
Dec 12
MDW8:42 pmChicago Midway
10h 51m
1 stop
MIA8:33 amMiami
Dec 20
MIA6:59 amMiami
3h 20m
MDW9:19 amChicago Midway
$122
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
Jan 19
MDW9:40 amChicago Midway
3h 05m
MIA1:45 pmMiami
Jan 22
MIA6:55 amMiami
5h 20m
1 stop
MDW11:15 amChicago Midway
$167
Find similar
Southwest
Nov 11
MDW9:00 amChicago Midway
3h 05m
MIA1:05 pmMiami
Nov 18
MIA1:05 pmMiami
3h 15m
MDW3:20 pmChicago Midway
$292
Find similar
Southwest
Nov 11
MDW12:55 pmChicago Midway
6h 50m
1 stop
MIA8:45 pmMiami
Nov 18
MIA1:05 pmMiami
3h 15m
MDW3:20 pmChicago Midway
$302
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 November 6, 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

Sat 11/29

5:57 pm-10:03 pm

Nonstop3h 06m

Miami

Sat 12/6

9:38 am-1:59 pm

1 stop5h 21m

$119

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 12/13

2:59 pm-7:09 pm

Nonstop3h 10m

Miami

Sun 12/14

6:05 am-6:12 pm

1 stop13h 07m

$120

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 11/22

9:58 pm-5:10 am

1 stop30h 12m

Miami

Wed 11/26

2:44 pm-4:57 pm

Nonstop3h 13m

$121

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 12/12

8:42 pm-8:33 am

1 stop10h 51m

Miami

Sat 12/20

6:59 am-9:19 am

Nonstop3h 20m

$122

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 12/22

6:15 am-10:32 am

Nonstop3h 17m

Miami

Mon 12/29

11:42 am-2:05 pm

Nonstop3h 23m

$123

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 1/14

12:25 pm-8:51 pm

1 stop7h 26m

Miami

Sun 1/18

6:00 am-9:44 pm

1 stop16h 44m

$124

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 12/4

2:16 pm-6:26 pm

Nonstop3h 10m

Miami

Sun 12/7

9:59 pm-10:18 pm

1 stop25h 19m

$125

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 1/19

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Thu 1/22

6:55 am-11:15 am

1 stop5h 20m

$167

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 12/2

10:49 am-5:15 pm

1 stop5h 26m

Key West

Tue 12/9

6:10 pm-11:47 pm

1 stop6h 37m

$294

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 1/31

10:46 am-5:13 pm

1 stop5h 27m

Key West

Sat 2/7

6:08 pm-10:26 pm

1 stop5h 18m

$324

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 October is another great option to travel to Florida Keys, with average flight prices from Chicago Midway Airport averaging around $205.

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 Tuesday when prices can be found for as low as $215. The most expensive day to fly to Florida Keys is Saturday, with ticket prices averaging around $301.

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 $220. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the afternoon are often more expensive with an average ticket price of $295.

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 $310 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 $182 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

Fastest flight time

3h 00m

Direct flights

Every day

Airports in Florida Keys

1 airport
The fastest flight from Chicago Midway Airport to Florida Keys takes 3h 00m
Direct flights go from Chicago Midway Airport to Florida Keys every day.
There is 1 airport near Florida Keys: 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 $262Free CancellationRating
7.9
8,004 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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Sat 12/6
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