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Cheap flights from Chicago Midway Airport to Florida Keys from $71

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 10/1. 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

Frontier Logo
12:18 pm - 4:19 pmMDW-MIA
3h 01mnonstop
Frontier Logo
10:34 am - 5:13 pmMIA-MDW
7h 39m1 stop
$114Frontier
Find Deal
Fri, Oct 24 - Sat, Oct 25
Frontier Logo
12:13 pm - 7:59 pmMDW-MIA
6h 46m1 stop
Frontier Logo
7:20 am - 9:33 amMIA-MDW
3h 13mnonstop
$120Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
10:33 am - 2:33 pmMDW-MIA
3h 00mnonstop
Frontier Logo
6:00 am - 12:36 amMIA-MDW
19h 36m1 stop
$121Frontier
Find Deal
Fri, Oct 17 - Sun, Oct 19
Southwest Logo
9:00 am - 1:05 pmMDW-MIA
3h 05mnonstop
Southwest Logo
6:20 am - 8:35 amMIA-MDW
3h 15mnonstop
$157Southwest
Find Deal
Tue, Nov 4 - Fri, Nov 7
Logo
8:05 am - 2:33 pmMDW-MIA
5h 28m1 stop
Logo
7:23 pm - 12:37 pmMIA-MDW
18h 14m1 stop
$174
Find Deal
Wed, Oct 22 - Wed, Oct 29
Logo
5:20 pm - 8:54 amMDW-MIA
14h 34m1 stop
Logo
5:46 pm - 12:36 amMIA-MDW
7h 50m1 stop
$180
Find Deal
Sat, Oct 11 - Sun, Oct 12
Southwest Logo
9:00 am - 1:05 pmMDW-MIA
3h 05mnonstop
Southwest Logo
3:10 pm - 12:05 amMIA-MDW
9h 55m1 stop
$187Southwest
Find Deal
Wed, Dec 10 - Fri, Dec 12
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
Find Deal
Tue, Feb 24 - Thu, Mar 5
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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Wed, Oct 15 - Wed, Oct 22
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
Find Deal
Fri, Oct 24 - Sun, Oct 26

Southwest flights from Chicago Midway Airport to Florida Keys

Our best Southwest deals on Chicago Midway Airport to Florida Keys flight tickets
Southwest
Nov 4
MDW9:00 amChicago Midway
3h 05m
MIA1:05 pmMiami
Nov 7
MIA6:20 amMiami
3h 15m
MDW8:35 amChicago Midway
$157
Find similar
Southwest
Dec 10
MDW9:00 amChicago Midway
3h 05m
MIA1:05 pmMiami
Dec 12
MIA3:10 pmMiami
9h 55m
1 stop
MDW12:05 amChicago Midway
$187
Find similar
Southwest
Dec 10
MDW12:25 pmChicago Midway
8h 25m
2 stops
MIA9:50 pmMiami
Dec 12
MIA6:20 amMiami
3h 15m
MDW8:35 amChicago Midway
$192
Find similar

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets
Frontier
Oct 24
MDW12:18 pmChicago Midway
3h 01m
MIA4:19 pmMiami
Oct 25
MIA10:34 amMiami
7h 39m
1 stop
MDW5:13 pmChicago Midway
$114
Find similar
Frontier
Oct 17
MDW12:13 pmChicago Midway
6h 46m
1 stop
MIA7:59 pmMiami
Oct 20
MIA7:20 amMiami
3h 13m
MDW9:33 amChicago Midway
$120
Find similar
Frontier
Oct 17
MDW10:33 amChicago Midway
3h 00m
MIA2:33 pmMiami
Oct 19
MIA6:00 amMiami
19h 36m
1 stop
MDW12:36 amChicago Midway
$121
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 September 16, 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

Fri 10/24

12:18 pm-4:19 pm

Nonstop3h 01m

Miami

Sat 10/25

10:34 am-5:13 pm

1 stop7h 39m

$114

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 10/17

12:13 pm-7:59 pm

1 stop6h 46m

Miami

Mon 10/20

7:20 am-9:33 am

Nonstop3h 13m

$120

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 10/17

10:33 am-2:33 pm

Nonstop3h 00m

Miami

Sun 10/19

6:00 am-12:36 am

1 stop19h 36m

$121

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 11/4

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Fri 11/7

6:20 am-8:35 am

Nonstop3h 15m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 10/22

8:05 am-2:33 pm

1 stop5h 28m

Miami

Wed 10/29

7:23 pm-12:37 pm

1 stop18h 14m

$174

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 10/11

5:20 pm-8:54 am

1 stop14h 34m

Miami

Sun 10/12

5:46 pm-12:36 am

1 stop7h 50m

$180

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 12/10

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Fri 12/12

3:10 pm-12:05 am

1 stop9h 55m

$187

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/24

1:05 pm-7:44 pm

1 stop5h 39m

Key West

Thu 3/5

6:00 pm-9:46 pm

1 stop4h 46m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 10/15

12:48 pm-8:06 pm

1 stop6h 18m

Key West

Wed 10/22

12:22 pm-4:09 pm

1 stop4h 47m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 10/24

2:45 pm-8:55 pm

1 stop5h 10m

Key West

Sun 10/26

3:30 pm-5:04 pm

2 stops26h 34m

$465

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 $206.

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 $215. The most expensive day to fly to Florida Keys is Saturday, with ticket prices averaging around $297.

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 $214. 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 $317.

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 $306 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 $169 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

2h 55m

Direct flights

Every day

Airports in Florida Keys

1 airport
The fastest flight from Chicago Midway Airport to Florida Keys takes 2h 55m
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 $248Free CancellationRating
7.9
7,954 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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