What is the cheapest airline that flies from Chicago Midway to Key West?

Allegiant Air and Delta are the most popular carriers operating from Chicago Midway to Key West

When did momondo last update prices for flights from Chicago Midway Airport to Key West Airport?

Prices for flights from Chicago Midway Airport to Key West Airport refresh daily.

How many operators does momondo search for flights from Chicago Midway Airport to Key West Airport?

The number of operators available for flights from Chicago Midway Airport to Key West Airport is 1 as of August 2025.

How old do you have to be to fly from Chicago Midway Airport to Key West Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Key West Airport.

What documentation or ID do you need to fly to Key West Airport?

The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$145 Cheap Flights from Chicago Midway Airport to Key West (MDW-EYW) in 2025

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Find the cheapest flights from Chicago Midway Airport to Key West (MDW-EYW)

Round-trip

One-way

Last minute

Cheap round-trip flights

6:21 am - 4:00 pmMDW-EYW

8h 39m1 stop

9:52 am - 12:44 pmEYW-MDW

27h 52m1 stop

$219

Find Deal

Sun, Sep 21 - Sat, Sep 27

6:21 am - 4:00 pmMDW-EYW

8h 39m1 stop

9:52 am - 11:17 pmEYW-MDW

14h 25m2 stops

$245

Find Deal

Sun, Sep 21 - Sat, Sep 27

12:43 pm - 8:07 pmMDW-EYW

6h 24m1 stop

7:00 am - 11:48 amEYW-MDW

5h 48m1 stop

$269Delta

Find Deal

Tue, Sep 23 - Tue, Sep 30

6:21 am - 4:04 pmMDW-EYW

8h 43m1 stop

9:52 am - 11:25 pmEYW-MDW

14h 33m2 stops

$276

Find Deal

Sun, Oct 5 - Sat, Oct 11

12:43 pm - 8:07 pmMDW-EYW

6h 24m1 stop

6:00 pm - 9:36 pmEYW-MDW

4h 36m1 stop

$289Delta

Find Deal

Tue, Sep 23 - Mon, Sep 29

6:21 am - 4:04 pmMDW-EYW

8h 43m1 stop

9:52 am - 11:44 amEYW-MDW

26h 52m1 stop

$291

Find Deal

Sun, Oct 5 - Sat, Oct 11

6:20 am - 8:11 amMDW-EYW

24h 51m2 stops

4:47 pm - 12:30 amEYW-MDW

8h 43m1 stop

$308

Find Deal

Thu, Nov 6 - Mon, Nov 10

10:35 am - 5:12 pmMDW-EYW

5h 37m1 stop

7:00 am - 6:35 pmEYW-MDW

12h 35m2 stops

$311Delta

Find Deal

Tue, Sep 23 - Tue, Sep 30

6:00 am - 11:27 amMDW-EYW

4h 27m1 stop

7:40 am - 11:53 amEYW-MDW

5h 13m1 stop

$320Delta

Find Deal

Sat, Oct 18 - Thu, Oct 23

1:05 pm - 7:44 pmMDW-EYW

5h 39m1 stop

7:00 am - 11:55 amEYW-MDW

5h 55m1 stop

$324Delta

Find Deal

Thu, Dec 11 - Tue, Dec 16

Delta flights from Chicago Midway Airport to Key West

Our best Delta deals on Chicago Midway Airport to Key West flight tickets

Delta

Sep 23

MDW12:43 pmChicago Midway

6h 24m

1 stop

EYW8:07 pmKey West

Sep 30

EYW7:00 amKey West

5h 48m

1 stop

MDW11:48 amChicago Midway

$269

Find similar

Delta

Sep 23

MDW12:43 pmChicago Midway

6h 24m

1 stop

EYW8:07 pmKey West

Sep 29

EYW6:00 pmKey West

4h 36m

1 stop

MDW9:36 pmChicago Midway

$289

Find similar

Delta

Sep 23

MDW10:35 amChicago Midway

5h 37m

1 stop

EYW5:12 pmKey West

Sep 30

EYW7:00 amKey West

12h 35m

2 stops

MDW6:35 pmChicago Midway

$311

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 9/21

6:21 am-4:00 pm

1 stop8h 39m

Key West

Sat 9/27

9:52 am-12:44 pm

1 stop27h 52m

$219

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 9/21

6:21 am-4:00 pm

1 stop8h 39m

Key West

Sat 9/27

9:52 am-11:17 pm

2 stops14h 25m

$245

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/23

12:43 pm-8:07 pm

1 stop6h 24m

Key West

Tue 9/30

7:00 am-11:48 am

1 stop5h 48m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 10/5

6:21 am-4:04 pm

1 stop8h 43m

Key West

Sat 10/11

9:52 am-11:25 pm

2 stops14h 33m

$276

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/23

12:43 pm-8:07 pm

1 stop6h 24m

Key West

Mon 9/29

6:00 pm-9:36 pm

1 stop4h 36m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 10/5

6:21 am-4:04 pm

1 stop8h 43m

Key West

Sat 10/11

9:52 am-11:44 am

1 stop26h 52m

$291

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 11/6

6:20 am-8:11 am

2 stops24h 51m

Key West

Mon 11/10

4:47 pm-12:30 am

1 stop8h 43m

$308

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/23

10:35 am-5:12 pm

1 stop5h 37m

Key West

Tue 9/30

7:00 am-6:35 pm

2 stops12h 35m

$311

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 10/18

6:00 am-11:27 am

1 stop4h 27m

Key West

Thu 10/23

7:40 am-11:53 am

1 stop5h 13m

$320

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 12/11

1:05 pm-7:44 pm

1 stop5h 39m

Key West

Tue 12/16

7:00 am-11:55 am

1 stop5h 55m

$324

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 Key West

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

What is the cheapest month to fly to Key West?

In general, October is the cheapest month to fly from Chicago Midway Airport to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $225. If you are unable to visit Key West during the month of October, then departing from Chicago Midway Airport during the month July is also very affordable. Most momondo users find prices during this month for around $343.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $352. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Key West for around $541.

What is the cheapest time of day to depart on your flight to Key West?

According to our data, the cheapest time of day to fly to Key West is in the morning. momondo users have found flights departing from Chicago Midway Airport to Key West in the morning for as low as $465. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Key West according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Key West (MDW to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Key West

Direct flights	None

There are no direct flights from Chicago Midway Airport to Key West. There are no popular flight routes from Chicago Midway Airport to Key West.

Search flight deals

How far is Chicago Midway to Key West by plane?
The distance between Chicago Midway and Key West is about 1237.6 mi. Typically, this will take 4h 27m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to Key West Airport?
Prices for flights from Chicago Midway Airport to Key West Airport refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Key West Airport?
The number of operators available for flights from Chicago Midway Airport to Key West Airport is 1 as of August 2025.
How old do you have to be to fly from Chicago Midway Airport to Key West Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Key West Airport.
What documentation or ID do you need to fly to Key West Airport?
The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular airline from Chicago Midway Airport to Key West?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago Midway Airport to Key West is Delta (100% of total bookings).

Best airlines flying from Chicago Midway Airport to Key West

Compare and see reviews for airlines that fly from Chicago Midway Airport to Key West with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $225	Free Cancellation	Rating 7.9 7,981 reviews		Search Delta flights

Big Pine Key

Little Torch Key

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Why should I use momondo to find a flight deal from Chicago to Key West?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Key West. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Key West with flexible booking policies on momondo?

Flights from Chicago to Key West with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Key West?

Once all potential Chicago to Key West flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Key West right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Chicago and alert you when they change.