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

Delta, Southwest, 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 July 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.

$105 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 July 2026. The most frequent departure day is Mon, with 30% 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.

12:11 pm - 11:05 pm

MDW

MIA

9h 54m

1 stop

11:19 am - 10:03 pm

MIA

MDW

11h 44m

1 stop

$230Frontier

Tue, Jul 28 - Wed, Jul 29

2:40 pm - 6:40 pm

MDW

MIA

3h 00mnonstop

11:45 am - 5:10 pm

MIA

MDW

6h 25m

1 stop

$231Southwest

Sat, Jul 25 - Wed, Jul 29

6:05 am - 4:21 pm

MDW

MIA

9h 16m

1 stop

6:45 am - 10:58 am

MIA

MDW

5h 13m

1 stop

$232Frontier

Tue, Sep 8 - Mon, Sep 14

8:15 am - 4:25 pm

MDW

MIA

7h 10m

2 stops

7:00 am - 2:05 pm

MIA

MDW

8h 05m

2 stops

$233Southwest

Thu, Aug 27 - Mon, Aug 31

6:05 am - 1:53 pm

MDW

MIA

6h 48m

1 stop

5:28 pm - 10:03 pm

MIA

MDW

5h 35m

1 stop

$234Frontier

Sat, Aug 1 - Tue, Aug 4

9:25 am - 1:25 pm

MDW

MIA

3h 00mnonstop

11:50 am - 6:45 pm

MIA

MDW

7h 55m

1 stop

$235Southwest

Tue, Aug 18 - Tue, Aug 25

2:40 pm - 6:40 pm

MDW

MIA

3h 00mnonstop

11:25 am - 7:05 pm

MIA

MDW

8h 40m

2 stops

$236Southwest

Sat, Jul 25 - Tue, Jul 28

6:05 am - 1:53 pm

MDW

MIA

6h 48m

1 stop

10:50 am - 10:03 pm

MIA

MDW

12h 13m

1 stop

$237Frontier

Mon, Aug 3 - Wed, Aug 12

10:54 am - 5:20 pm

MDW

EYW

5h 26m

1 stop

11:48 am - 4:15 pm

EYW

MDW

5h 27m

1 stop

$329Delta

Fri, Aug 14 - Tue, Aug 18

10:35 am - 5:11 pm

MDW

EYW

5h 36m

1 stop

6:00 pm - 10:10 pm

EYW

MDW

5h 10m

1 stop

$354Delta

Sat, Dec 5 - Thu, Dec 10

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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

Jul 28

MDW12:11 pmChicago Midway

9h 54m

1 stop

MIA11:05 pmMiami

Jul 29

MIA11:19 amMiami

11h 44m

1 stop

MDW10:03 pmChicago Midway

$230

Frontier

Sep 8

MDW6:05 amChicago Midway

9h 16m

1 stop

MIA4:21 pmMiami

Sep 14

MIA6:45 amMiami

5h 13m

1 stop

MDW10:58 amChicago Midway

$232

Frontier

Aug 1

MDW6:05 amChicago Midway

6h 48m

1 stop

MIA1:53 pmMiami

Aug 4

MIA5:28 pmMiami

5h 35m

1 stop

MDW10:03 pmChicago Midway

$234

Southwest flights from Chicago Midway Airport to Florida Keys

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

Southwest

Jul 25

MDW2:40 pmChicago Midway

3h 00m

MIA6:40 pmMiami

Jul 29

MIA11:45 amMiami

6h 25m

1 stop

MDW5:10 pmChicago Midway

$231

Southwest

Aug 27

MDW8:15 amChicago Midway

7h 10m

2 stops

MIA4:25 pmMiami

Aug 31

MIA7:00 amMiami

8h 05m

2 stops

MDW2:05 pmChicago Midway

$233

Southwest

Aug 18

MDW9:25 amChicago Midway

3h 00m

MIA1:25 pmMiami

Aug 25

MIA11:50 amMiami

7h 55m

1 stop

MDW6:45 pmChicago Midway

$235

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

Tue 7/28

12:11 pm-11:05 pm

1 stop9h 54m

Miami

Wed 7/29

11:19 am-10:03 pm

1 stop11h 44m

$230

Quickest round-trip

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 7/25

2:40 pm-6:40 pm

Nonstop3h 00m

Miami

Wed 7/29

11:45 am-5:10 pm

1 stop6h 25m

$231

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 9/8

6:05 am-4:21 pm

1 stop9h 16m

Miami

Mon 9/14

6:45 am-10:58 am

1 stop5h 13m

$232

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 8/27

8:15 am-4:25 pm

2 stops7h 10m

Miami

Mon 8/31

7:00 am-2:05 pm

2 stops8h 05m

$233

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 8/1

6:05 am-1:53 pm

1 stop6h 48m

Miami

Tue 8/4

5:28 pm-10:03 pm

1 stop5h 35m

$234

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 8/18

9:25 am-1:25 pm

Nonstop3h 00m

Miami

Tue 8/25

11:50 am-6:45 pm

1 stop7h 55m

$235

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 7/25

2:40 pm-6:40 pm

Nonstop3h 00m

Miami

Tue 7/28

11:25 am-7:05 pm

2 stops8h 40m

$236

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 8/3

6:05 am-1:53 pm

1 stop6h 48m

Miami

Wed 8/12

10:50 am-10:03 pm

1 stop12h 13m

$237

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 8/14

10:54 am-5:20 pm

1 stop5h 26m

Key West

Tue 8/18

11:48 am-4:15 pm

1 stop5h 27m

$329

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 12/5

10:35 am-5:11 pm

1 stop5h 36m

Key West

Thu 12/10

6:00 pm-10:10 pm

1 stop5h 10m

$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 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 Thursday when prices can be found for as low as $226. 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 $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 evening are often more expensive with an average ticket price of $332.

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 $216 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	3h 00m
Direct flights	Mon, Wed, Thu, Fri, Sat and Sun
Airports in Florida Keys	3 airports

The fastest flight from Chicago Midway Airport to Florida Keys takes 3h 00m

Direct flights go from Chicago Midway Airport to Florida Keys on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

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 4 operators available for flights from Chicago Midway Airport to Florida Keys as of July 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 16.96% of all bookings. The subsequent popular models are Boeing 737-800 at 12.44%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.95%, and Airbus A320-100/200 at 9.62%.

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 8,451 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.