What is the cheapest airline that flies from Chicago Midway to Florida Keys?

Southwest and Delta are the most popular carriers operating from Chicago Midway to Florida Keys

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?

There are 6 operators available for flights from Chicago Midway Airport to Florida Keys as of April 2026.

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.

$47 Cheap Flights from Chicago Midway Airport to Florida Keys in 2026

Q: How many flights depart from Chicago Midway Airport to Florida Keys on average per week?

The number of flights available between Chicago Midway Airport and Florida Keys is 10 per week as of April 2026. The most frequent departure day is Mon, with 30% of weekly flights leaving on this day.

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Find the cheapest flights from Chicago Midway Airport to Florida Keys

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

11:10 am - 7:31 pm

MIA

MDW

9h 21m

1 stop

$101Frontier

Mon, Apr 13 - Wed, Apr 22

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

3:54 pm - 10:14 pm

MIA

MDW

7h 20m

1 stop

$106Multiple Airlines

Mon, Apr 13 - Wed, Apr 22

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

1:10 pm - 7:31 pm

MIA

MDW

7h 21m

1 stop

$117Frontier

Mon, Apr 13 - Wed, Apr 15

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

12:26 pm - 7:31 pm

MIA

MDW

8h 05m

1 stop

$119Frontier

Mon, Apr 13 - Thu, Apr 16

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

3:54 pm - 10:26 pm

MIA

MDW

7h 32m

1 stop

$121Multiple Airlines

Mon, Apr 13 - Fri, Apr 17

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

3:54 pm - 10:26 pm

MIA

MDW

7h 32m

1 stop

$122Multiple Airlines

Mon, Apr 13 - Fri, Apr 17

6:30 am - 10:40 am

MDW

MIA

3h 10mnonstop

1:10 pm - 10:14 pm

MIA

MDW

10h 04m

1 stop

$130Frontier

Mon, Apr 13 - Wed, Apr 15

2:48 pm - 9:41 am

MDW

EYW

17h 53m

1 stop

8:48 pm - 2:38 pm

EYW

MDW

18h 50m

2 stops

$328Allegiant Air

Thu, Jul 2 - Sun, Jul 5

12:52 pm - 7:40 pm

MDW

EYW

5h 48m

1 stop

6:23 pm - 10:28 pm

EYW

MDW

5h 05m

1 stop

$329Delta

Thu, Apr 23 - Wed, Apr 29

6:00 am - 1:09 pm

MDW

EYW

6h 09m

1 stop

6:00 pm - 9:46 pm

EYW

MDW

4h 46m

1 stop

$354Delta

Mon, Sep 7 - Wed, Sep 16

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets

Frontier

Apr 13

MDW6:30 amChicago Midway

3h 10m

MIA10:40 amMiami

Apr 22

MIA11:10 amMiami

9h 21m

1 stop

MDW7:31 pmChicago Midway

$101

Frontier

Apr 6

MDW6:30 amChicago Midway

3h 10m

MIA10:40 amMiami

Apr 10

MIA11:35 amMiami

3h 26m

MDW2:01 pmChicago Midway

$107

Frontier

Apr 6

MDW6:30 amChicago Midway

3h 10m

MIA10:40 amMiami

Apr 11

MIA11:35 amMiami

3h 26m

MDW2:01 pmChicago Midway

$108

Delta flights from Chicago Midway Airport to Florida Keys

Our best Delta deals on Chicago Midway Airport to Florida Keys flight tickets

Delta

Apr 23

MDW12:52 pmChicago Midway

5h 48m

1 stop

EYW7:40 pmKey West

Apr 29

EYW6:23 pmKey West

5h 05m

1 stop

MDW10:28 pmChicago Midway

$329

Delta

Sep 7

MDW6:00 amChicago Midway

6h 09m

1 stop

EYW1:09 pmKey West

Sep 16

EYW6:00 pmKey West

4h 46m

1 stop

MDW9:46 pmChicago Midway

$354

Delta

Apr 17

MDW12:52 pmChicago Midway

5h 48m

1 stop

EYW7:40 pmKey West

Apr 21

EYW6:23 pmKey West

5h 05m

1 stop

MDW10:28 pmChicago Midway

$359

momondo Fare Finder

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

Cheapest round-trip

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Wed 4/22

11:10 am-7:31 pm

1 stop9h 21m

$101

Quickest round-trip

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Wed 4/22

3:54 pm-10:14 pm

1 stop7h 20m

$106

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Wed 4/15

1:10 pm-7:31 pm

1 stop7h 21m

$117

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Thu 4/16

12:26 pm-7:31 pm

1 stop8h 05m

$119

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Fri 4/17

3:54 pm-10:26 pm

1 stop7h 32m

$121

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Fri 4/17

3:54 pm-10:26 pm

1 stop7h 32m

$122

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

Wed 4/15

1:10 pm-10:14 pm

1 stop10h 04m

$130

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 7/2

2:48 pm-9:41 am

1 stop17h 53m

Key West

Sun 7/5

8:48 pm-2:38 pm

2 stops18h 50m

$328

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 4/23

12:52 pm-7:40 pm

1 stop5h 48m

Key West

Wed 4/29

6:23 pm-10:28 pm

1 stop5h 05m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 9/7

6:00 am-1:09 pm

1 stop6h 09m

Key West

Wed 9/16

6:00 pm-9:46 pm

1 stop4h 46m

$354

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Florida Keys?

The month of March is another great option to travel to Florida Keys, with average flight prices from Chicago Midway Airport averaging around $273.

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 Sunday when prices can be found for as low as $223. The most expensive day to fly to Florida Keys is Friday, with ticket prices averaging around $311.

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 $141. 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 $290.

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 $205 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).

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Frequently asked questions about flying from Chicago Midway Airport to Florida Keys

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?
There are 6 operators available for flights from Chicago Midway Airport to Florida Keys as of April 2026.
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?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Florida Keys is Boeing 737 MAX 8, representing 16.06% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 12.42%, Airbus A320neo at 11.34%, and Airbus A321neo at 11.01%.

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
Delta	PriceFrom $268	Free Cancellation	Rating 7.9 8,369 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.