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Cheap flights from Chicago Midway Airport to Florida Keys from $40

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 3/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$84Frontier
Sun, Mar 1 - Fri, Mar 6
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
$86Frontier
Sun, Feb 22 - Thu, Feb 26
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$87Frontier
Sun, Mar 1 - Fri, Mar 6
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$89Frontier
Thu, Feb 26 - Sat, Mar 7
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
$93Frontier
Sun, Feb 22 - Thu, Feb 26
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
$94Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$95Frontier
Thu, Feb 26 - Fri, Mar 6
Multiple Airlines Logo
2:19 pm - 12:16 pm
MDW
-
MIA
20h 57m
1 stop
Multiple Airlines Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$100Multiple Airlines
Mon, Mar 2 - Fri, Mar 6
Delta Logo
10:43 am - 5:23 pm
MDW
-
EYW
5h 40m
1 stop
Delta Logo
6:19 pm - 10:28 pm
EYW
-
MDW
5h 09m
1 stop
$318Delta
Sun, Apr 19 - Thu, Apr 30
Delta Logo
10:45 am - 5:30 pm
MDW
-
EYW
5h 45m
1 stop
Delta Logo
7:33 am - 12:07 pm
EYW
-
MDW
5h 34m
1 stop
$319Delta
Wed, Apr 8 - Tue, Apr 14

Southwest flights from Chicago Midway Airport to Florida Keys

Our best Southwest deals on Chicago Midway Airport to Florida Keys flight tickets
Southwest
Mar 10
MDW7:40 amChicago Midway
3h 00m
MIA11:40 amMiami
Mar 17
MIA6:30 amMiami
3h 15m
MDW8:45 amChicago Midway
$131
Southwest
Mar 8
MDW6:45 pmChicago Midway
3h 00m
MIA10:45 pmMiami
Mar 13
MIA6:40 amMiami
3h 15m
MDW8:55 amChicago Midway
$147

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets
Frontier
Feb 22
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
Feb 26
MIA11:28 amMiami
3h 28m
MDW1:56 pmChicago Midway
$86
Frontier
Mar 1
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
Mar 6
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
$87
Frontier
Feb 15
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
Feb 19
MIA11:28 amMiami
3h 28m
MDW1:56 pmChicago Midway
$89

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 February 9, 2026.
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

Sun 3/1

6:15 am-10:28 am

Nonstop3h 13m

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

$84

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/22

6:15 am-10:28 am

Nonstop3h 13m

Miami

Thu 2/26

11:28 am-1:56 pm

Nonstop3h 28m

$86

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 3/1

6:15 am-10:28 am

Nonstop3h 13m

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

$87

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 2/26

6:15 am-10:28 am

Nonstop3h 13m

Miami

Sat 3/7

11:13 am-1:41 pm

Nonstop3h 28m

$89

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/22

6:15 am-10:28 am

Nonstop3h 13m

Miami

Thu 2/26

11:28 am-1:56 pm

Nonstop3h 28m

$93

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 2/19

6:15 am-10:28 am

Nonstop3h 13m

Miami

Thu 2/26

11:28 am-1:56 pm

Nonstop3h 28m

$94

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 2/26

6:15 am-10:28 am

Nonstop3h 13m

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

$95

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 3/2

2:19 pm-12:16 pm

1 stop20h 57m

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

$100

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 4/19

10:43 am-5:23 pm

1 stop5h 40m

Key West

Thu 4/30

6:19 pm-10:28 pm

1 stop5h 09m

$318

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 4/8

10:45 am-5:30 pm

1 stop5h 45m

Key West

Tue 4/14

7:33 am-12:07 pm

1 stop5h 34m

$319

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 $229.

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 $196. The most expensive day to fly to Florida Keys is Friday, with ticket prices averaging around $337.

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 at noon. momondo users have found flights departing from Chicago Midway Airport to Florida Keys at noon for as low as $187. 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 $293.

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 $313 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 $202 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

3 airports
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 are 3 airports in Florida Keys. From Chicago Midway Airport there are direct flights to 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 $268Free CancellationRating
7.9
8,176 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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