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

Southwest, Delta, and Allegiant Air 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 4 operators available for flights from Chicago Midway Airport to Florida Keys as of August 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.

$87 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 5 per week as of August 2026. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.

Discover deals from 900+ travel sites with momondo.

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.

6:25 am - 4:29 pmMDW Chicago Midway-MIA Miami

9h 04m1 stop Atlanta Hartsfield-Jackson

5:32 am - 5:51 pmMIA Miami-MDW Chicago Midway

13h 19m1 stop Atlanta Hartsfield-Jackson

$176Frontier

Mon, Sep 14 - Wed, Sep 16

12:54 pm - 10:00 pmMDW Chicago Midway-MIA Miami

8h 06m1 stop Dallas/Fort Worth

5:34 pm - 11:44 pmMIA Miami-MDW Chicago Midway

7h 10m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Fri, Sep 11 - Mon, Sep 21

12:03 pm - 6:12 pmMDW Chicago Midway-MIA Miami

5h 09m1 stop Atlanta Hartsfield-Jackson

6:45 am - 10:58 amMIA Miami-MDW Chicago Midway

5h 13m1 stop Atlanta Hartsfield-Jackson

$177Frontier

Sat, Oct 31 - Fri, Nov 6

7:40 am - 3:30 pmMDW Chicago Midway-MIA Miami

6h 50m1 stop Nashville Intl

12:35 pm - 2:40 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$181Southwest

Wed, Sep 30 - Wed, Oct 7

8:00 am - 12:10 pmMDW Chicago Midway-MIA Miami

3h 10mnonstop

4:00 pm - 6:05 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$181Southwest

Thu, Sep 17 - Tue, Sep 22

8:00 am - 12:10 pmMDW Chicago Midway-MIA Miami

3h 10mnonstop

4:00 pm - 6:05 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$181Southwest

Thu, Sep 17 - Wed, Sep 23

4:19 pm - 11:32 pmMDW Chicago Midway-MIA Miami

6h 13m1 stop Atlanta Hartsfield-Jackson

8:00 am - 12:35 pmMIA Miami-MDW Chicago Midway

5h 35m1 stop Detroit Metropolitan Wayne County

$217Delta

Thu, Nov 26 - Tue, Dec 1

1:00 pm - 9:38 pmMDW Chicago Midway-MIA Miami

7h 38m1 stop Detroit Metropolitan Wayne County

8:00 am - 12:33 pmMIA Miami-MDW Chicago Midway

5h 33m1 stop Detroit Metropolitan Wayne County

$217Delta

Tue, Feb 16 - Thu, Feb 18

6:15 am - 9:24 amMDW Chicago Midway-EYW Key West

26h 09m2 stops Atlanta Hartsfield-Jackson Tampa

10:14 am - 3:40 pmEYW Key West-MDW Chicago Midway

6h 26m1 stop Knoxville McGhee Tyson

$289Multiple Airlines

Tue, Oct 13 - Fri, Oct 16

6:15 am - 9:24 amMDW Chicago Midway-EYW Key West

26h 09m2 stops Atlanta Hartsfield-Jackson Tampa

10:14 am - 3:40 pmEYW Key West-MDW Chicago Midway

6h 26m1 stop Knoxville McGhee Tyson

$289Multiple Airlines

Tue, Oct 13 - Fri, Oct 16

Cheap last minute flights

Enter your travel dates to find the best prices.

6:05 am - 4:21 pmMDW Chicago Midway-MIA Miami

9h 16m1 stop Atlanta Hartsfield-Jackson

5:28 pm - 10:47 pmMIA Miami-MDW Chicago Midway

6h 19m1 stop Atlanta Hartsfield-Jackson

$320Frontier

Tue, Aug 25 - Tue, Sep 1

11:50 am - 11:05 pmMDW Chicago Midway-MIA Miami

10h 15m1 stop Atlanta Hartsfield-Jackson

5:28 pm - 10:47 pmMIA Miami-MDW Chicago Midway

6h 19m1 stop Atlanta Hartsfield-Jackson

$320Frontier

Mon, Aug 24 - Tue, Sep 1

6:05 am - 1:32 pmMDW Chicago Midway-MIA Miami

6h 27m1 stop Atlanta Hartsfield-Jackson

5:28 pm - 10:47 pmMIA Miami-MDW Chicago Midway

6h 19m1 stop Atlanta Hartsfield-Jackson

$322Frontier

Sat, Aug 22 - Tue, Sep 1

6:05 am - 1:32 pmMDW Chicago Midway-MIA Miami

6h 27m1 stop Atlanta Hartsfield-Jackson

5:28 pm - 10:47 pmMIA Miami-MDW Chicago Midway

6h 19m1 stop Atlanta Hartsfield-Jackson

$327Frontier

Sun, Aug 23 - Thu, Sep 3

6:11 am - 2:52 pmMDW Chicago Midway-EYW Key West

7h 41m1 stop Atlanta Hartsfield-Jackson

11:48 am - 4:15 pmEYW Key West-MDW Chicago Midway

5h 27m1 stop Atlanta Hartsfield-Jackson

$490Delta

Sat, Aug 22 - Fri, Aug 28

9:25 am - 1:25 pmMDW Chicago Midway-MIA Miami

3h 00mnonstop

4:00 pm - 6:05 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$493Southwest

Tue, Aug 25 - Wed, Aug 26

11:20 am - 3:20 pmMDW Chicago Midway-MIA Miami

3h 00mnonstop

4:00 pm - 6:05 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$493Southwest

Sat, Aug 22 - Wed, Aug 26

11:20 am - 3:20 pmMDW Chicago Midway-MIA Miami

3h 00mnonstop

2:45 pm - 4:50 pmMIA Miami-MDW Chicago Midway

3h 05mnonstop

$493Southwest

Sat, Aug 22 - Sat, Aug 29

12:46 pm - 6:42 pmMDW Chicago Midway-MIA Miami

4h 56m1 stop Atlanta Hartsfield-Jackson

6:00 am - 9:59 amMIA Miami-MDW Chicago Midway

4h 59m1 stop Atlanta Hartsfield-Jackson

$548Delta

Tue, Aug 25 - Mon, Aug 31

4:39 pm - 12:47 amMDW Chicago Midway-MIA Miami

7h 08m1 stop Atlanta Hartsfield-Jackson

6:00 am - 9:59 amMIA Miami-MDW Chicago Midway

4h 59m1 stop Atlanta Hartsfield-Jackson

$548Delta

Sat, Aug 22 - Mon, Aug 31

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Frontier flights from Chicago Midway Airport to Florida Keys

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

Frontier

Sep 14

MDW6:25 amChicago Midway

9h 04m

1 stop

MIA4:29 pmMiami

Sep 16

MIA5:32 amMiami

13h 19m

1 stop

MDW5:51 pmChicago Midway

$176

Frontier

Sep 11

MDW12:54 pmChicago Midway

8h 06m

1 stop

MIA10:00 pmMiami

Sep 21

MIA5:34 pmMiami

7h 10m

1 stop

MDW11:44 pmChicago Midway

$177

Frontier

Sep 14

MDW6:25 amChicago Midway

9h 04m

1 stop

MIA4:29 pmMiami

Sep 17

MIA4:30 pmMiami

8h 14m

1 stop

MDW11:44 pmChicago Midway

$178

Southwest flights from Chicago Midway Airport to Florida Keys

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

Southwest

Sep 12

MDW11:20 amChicago Midway

3h 00m

MIA3:20 pmMiami

Sep 14

MIA7:15 amMiami

3h 05m

MDW9:20 amChicago Midway

$181

Southwest

Sep 30

MDW10:10 amChicago Midway

8h 55m

2 stops

MIA8:05 pmMiami

Oct 7

MIA12:35 pmMiami

3h 05m

MDW2:40 pmChicago Midway

$186

Southwest

Sep 8

MDW9:25 amChicago Midway

3h 00m

MIA1:25 pmMiami

Sep 12

MIA7:45 amMiami

9h 25m

1 stop

MDW4:10 pmChicago Midway

$187

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 Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Mon 9/14

6:25 am-4:29 pm

1 stop9h 04m

Miami

Wed 9/16

5:32 am-5:51 pm

1 stop13h 19m

$176

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Fri 9/11

12:54 pm-10:00 pm

1 stop8h 06m

Miami

Mon 9/21

5:34 pm-11:44 pm

1 stop7h 10m

$177

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Sat 10/31

12:03 pm-6:12 pm

1 stop5h 09m

Miami

Fri 11/6

6:45 am-10:58 am

1 stop5h 13m

$177

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Wed 9/30

7:40 am-3:30 pm

1 stop6h 50m

Miami

Wed 10/7

12:35 pm-2:40 pm

Nonstop3h 05m

$181

Quickest round-trip

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Thu 9/17

8:00 am-12:10 pm

Nonstop3h 10m

Miami

Tue 9/22

4:00 pm-6:05 pm

Nonstop3h 05m

$181

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Thu 9/17

8:00 am-12:10 pm

Nonstop3h 10m

Miami

Wed 9/23

4:00 pm-6:05 pm

Nonstop3h 05m

$181

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Thu 11/26

4:19 pm-11:32 pm

1 stop6h 13m

Miami

Tue 12/1

8:00 am-12:35 pm

1 stop5h 35m

$217

ChicagoMiami

MDW Chicago Midway - MIA Miami

MDWMIA

Chicago Midway

Tue 2/16

1:00 pm-9:38 pm

1 stop7h 38m

Miami

Thu 2/18

8:00 am-12:33 pm

1 stop5h 33m

$217

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 10/13

6:15 am-9:24 am

2 stops26h 09m

Key West

Fri 10/16

10:14 am-3:40 pm

1 stop6h 26m

$289

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 10/13

6:15 am-9:24 am

2 stops26h 09m

Key West

Fri 10/16

10:14 am-3:40 pm

1 stop6h 26m

$289

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 January is another great option to travel to Florida Keys, with average flight prices from Chicago Midway Airport averaging around $268.

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 Thursday when prices can be found for as low as $235. The most expensive day to fly to Florida Keys is Saturday, with ticket prices averaging around $319.

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 $146. 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 evening are often more expensive with an average ticket price of $435.

How far in advance should I book a flight from Chicago Midway Airport 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 $329 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 $210 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	$87
Fastest flight time	2h 55m
Direct flights	Every day
Airports in Florida Keys	3 airports

The best one-way flight to Florida Keys from Chicago Midway Airport in the past 72 hours is $87. The best round-trip flight deal from Chicago Midway Airport to Florida Keys found on momondo in the last 72 hours is $176.

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

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 4 operators available for flights from Chicago Midway Airport to Florida Keys as of August 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 17.07% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 11.48%, Boeing 737-800 at 11.43%, and Airbus A320-100/200 at 10.14%.

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 $294	Free Cancellation	Rating 7.8 8,505 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.