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 5 operators available for flights from Chicago Midway Airport to Florida Keys as of May 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.

$76 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 14 per week as of May 2026. The most frequent departure day is Mon, with 29% 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.

6:00 am - 11:05 pm

MDW

MIA

16h 05m

1 stop

8:10 am - 10:11 pm

MIA

MDW

15h 01m

1 stop

$156Frontier

Mon, Aug 17 - Wed, Aug 19

6:00 am - 4:31 pm

MDW

MIA

9h 31m

1 stop

8:30 am - 10:11 pm

MIA

MDW

14h 41m

1 stop

$158Frontier

Tue, Jun 9 - Wed, Jun 10

6:00 am - 4:31 pm

MDW

MIA

9h 31m

1 stop

5:26 pm - 10:11 pm

MIA

MDW

5h 45m

1 stop

$183Frontier

Tue, Jun 9 - Wed, Jun 17

12:11 pm - 11:05 pm

MDW

MIA

9h 54m

1 stop

5:28 pm - 10:08 pm

MIA

MDW

5h 40m

1 stop

$184Frontier

Tue, Aug 4 - Tue, Aug 11

6:00 am - 1:53 pm

MDW

MIA

6h 53m

1 stop

5:28 pm - 10:08 pm

MIA

MDW

5h 40m

1 stop

$185Frontier

Wed, Jul 29 - Wed, Jul 29

6:00 am - 1:53 pm

MDW

MIA

6h 53m

1 stop

5:28 pm - 10:08 pm

MIA

MDW

5h 40m

1 stop

$189Frontier

Tue, Jul 7 - Tue, Jul 14

6:00 am - 1:28 pm

MDW

EYW

6h 28m

1 stop

6:24 pm - 10:17 pm

EYW

MDW

4h 53m

1 stop

$329Delta

Tue, Jun 9 - Tue, Jun 16

2:46 pm - 9:41 am

MDW

EYW

17h 55m

1 stop

1:14 pm - 10:11 pm

EYW

MDW

9h 57m

2 stops

$332Multiple Airlines

Thu, Jun 11 - Tue, Jun 23

6:00 am - 1:28 pm

MDW

EYW

6h 28m

1 stop

6:24 pm - 10:17 pm

EYW

MDW

4h 53m

1 stop

$354Delta

Wed, Jun 10 - Thu, Jun 25

10:59 am - 5:23 pm

MDW

EYW

5h 24m

1 stop

6:24 pm - 10:17 pm

EYW

MDW

4h 53m

1 stop

$359Delta

Tue, Jun 2 - Tue, Jun 9

Frontier flights from Chicago Midway Airport to Florida Keys

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

Frontier

Aug 17

MDW6:00 amChicago Midway

16h 05m

1 stop

MIA11:05 pmMiami

Aug 19

MIA8:10 amMiami

15h 01m

1 stop

MDW10:11 pmChicago Midway

$156

Frontier

Jun 9

MDW6:00 amChicago Midway

9h 31m

1 stop

MIA4:31 pmMiami

Jun 10

MIA8:30 amMiami

14h 41m

1 stop

MDW10:11 pmChicago Midway

$158

Frontier

Jun 9

MDW6:00 amChicago Midway

9h 31m

1 stop

MIA4:31 pmMiami

Jun 17

MIA5:26 pmMiami

5h 45m

1 stop

MDW10:11 pmChicago Midway

$183

Southwest flights from Chicago Midway Airport to Florida Keys

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

Southwest

Sep 16

MDW9:25 amChicago Midway

3h 00m

MIA1:25 pmMiami

Sep 23

MIA4:00 pmMiami

3h 05m

MDW6:05 pmChicago Midway

$201

Southwest

Jul 8

MDW11:45 amChicago Midway

3h 00m

MIA3:45 pmMiami

Jul 14

MIA4:00 pmMiami

3h 10m

MDW6:10 pmChicago Midway

$219

Southwest

Sep 16

MDW6:15 amChicago Midway

4h 35m

1 stop

MIA11:50 amMiami

Sep 23

MIA4:00 pmMiami

3h 05m

MDW6:05 pmChicago Midway

$220

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 8/17

6:00 am-11:05 pm

1 stop16h 05m

Miami

Wed 8/19

8:10 am-10:11 pm

1 stop15h 01m

$156

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 6/9

6:00 am-4:31 pm

1 stop9h 31m

Miami

Wed 6/10

8:30 am-10:11 pm

1 stop14h 41m

$158

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 6/9

6:00 am-4:31 pm

1 stop9h 31m

Miami

Wed 6/17

5:26 pm-10:11 pm

1 stop5h 45m

$183

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 8/4

12:11 pm-11:05 pm

1 stop9h 54m

Miami

Tue 8/11

5:28 pm-10:08 pm

1 stop5h 40m

$184

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 7/29

6:00 am-1:53 pm

1 stop6h 53m

Miami

Wed 7/29

5:28 pm-10:08 pm

1 stop5h 40m

$185

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 7/7

6:00 am-1:53 pm

1 stop6h 53m

Miami

Tue 7/14

5:28 pm-10:08 pm

1 stop5h 40m

$189

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 6/9

6:00 am-1:28 pm

1 stop6h 28m

Key West

Tue 6/16

6:24 pm-10:17 pm

1 stop4h 53m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 6/11

2:46 pm-9:41 am

1 stop17h 55m

Key West

Tue 6/23

1:14 pm-10:11 pm

2 stops9h 57m

$332

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 6/10

6:00 am-1:28 pm

1 stop6h 28m

Key West

Thu 6/25

6:24 pm-10:17 pm

1 stop4h 53m

$354

Quickest round-trip

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 6/2

10:59 am-5:23 pm

1 stop5h 24m

Key West

Tue 6/9

6:24 pm-10:17 pm

1 stop4h 53m

$359

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 December is another great option to travel to Florida Keys, with average flight prices from Chicago Midway Airport averaging around $50.

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 $217. 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 at noon. momondo users have found flights departing from Chicago Midway Airport to Florida Keys at noon for as low as $137. 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 $277.

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 $321 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 $211 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 5 operators available for flights from Chicago Midway Airport to Florida Keys as of May 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 16.72% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 12.23%, Boeing 737-800 at 11.96%, and Airbus A321neo at 9.35%.

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 8,444 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.