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 December 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.

$130 Cheap Flights from Chicago Midway Airport to Key West in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Key West

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:16 pm - 8:15 am

MDW

EYW

16h 59m1 stop

12:20 pm - 10:17 pm

EYW

MDW

10h 57m2 stops

$286Multiple Airlines

Sat, Jan 3 - Tue, Jan 6

6:15 pm - 9:06 am

MDW

EYW

13h 51m1 stop

12:15 pm - 11:25 pm

EYW

MDW

12h 10m2 stops

$288Multiple Airlines

Sat, Feb 14 - Thu, Feb 19

2:49 pm - 2:34 pm

MDW

EYW

22h 45m2 stops

8:55 am - 9:04 pm

EYW

MDW

13h 09m1 stop

$290Multiple Airlines

Wed, Dec 17 - Sun, Dec 21

3:10 pm - 8:15 am

MDW

EYW

16h 05m1 stop

12:20 pm - 10:17 pm

EYW

MDW

34h 57m2 stops

$293Multiple Airlines

Wed, Dec 31 - Tue, Jan 6

11:21 am - 7:40 pm

MDW

EYW

7h 19m1 stop

6:06 pm - 10:22 pm

EYW

MDW

5h 16m1 stop

$294Delta

Sat, Jan 17 - Thu, Jan 22

7:00 am - 12:21 pm

MDW

EYW

28h 21m2 stops

1:06 pm - 7:50 pm

EYW

MDW

7h 44m1 stop

$295Multiple Airlines

Mon, Feb 23 - Fri, Feb 27

3:10 pm - 2:24 pm

MDW

EYW

22h 14m1 stop

12:20 pm - 10:17 pm

EYW

MDW

10h 57m2 stops

$313Multiple Airlines

Fri, Jan 2 - Tue, Jan 6

3:10 pm - 8:15 am

MDW

EYW

16h 05m1 stop

12:20 pm - 10:17 pm

EYW

MDW

10h 57m2 stops

$314Multiple Airlines

Wed, Dec 31 - Tue, Jan 6

6:00 am - 12:26 pm

MDW

EYW

29h 26m2 stops

1:06 pm - 7:50 pm

EYW

MDW

7h 44m1 stop

$317Multiple Airlines

Thu, Feb 19 - Mon, Feb 23

10:46 am - 5:11 pm

MDW

EYW

5h 25m1 stop

6:06 pm - 10:22 pm

EYW

MDW

5h 16m1 stop

$319Delta

Sat, Jan 31 - Sat, Feb 7

Delta flights from Chicago Midway Airport to Key West

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

Delta

Jan 17

MDW11:21 amChicago Midway

7h 19m

1 stop

EYW7:40 pmKey West

Jan 22

EYW6:06 pmKey West

5h 16m

1 stop

MDW10:22 pmChicago Midway

$294

Find similar

Delta

Jan 31

MDW10:46 amChicago Midway

5h 25m

1 stop

EYW5:11 pmKey West

Feb 7

EYW6:06 pmKey West

5h 16m

1 stop

MDW10:22 pmChicago Midway

$319

Find similar

Delta

Jan 24

MDW10:46 amChicago Midway

5h 25m

1 stop

EYW5:11 pmKey West

Jan 30

EYW6:06 pmKey West

5h 16m

1 stop

MDW10:22 pmChicago Midway

$324

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

Sat 1/3

2:16 pm-8:15 am

1 stop16h 59m

Key West

Tue 1/6

12:20 pm-10:17 pm

2 stops10h 57m

$286

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 2/14

6:15 pm-9:06 am

1 stop13h 51m

Key West

Thu 2/19

12:15 pm-11:25 pm

2 stops12h 10m

$288

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 12/17

2:49 pm-2:34 pm

2 stops22h 45m

Key West

Sun 12/21

8:55 am-9:04 pm

1 stop13h 09m

$290

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 12/31

3:10 pm-8:15 am

1 stop16h 05m

Key West

Tue 1/6

12:20 pm-10:17 pm

2 stops34h 57m

$293

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 1/17

11:21 am-7:40 pm

1 stop7h 19m

Key West

Thu 1/22

6:06 pm-10:22 pm

1 stop5h 16m

$294

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 2/23

7:00 am-12:21 pm

2 stops28h 21m

Key West

Fri 2/27

1:06 pm-7:50 pm

1 stop7h 44m

$295

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 1/2

3:10 pm-2:24 pm

1 stop22h 14m

Key West

Tue 1/6

12:20 pm-10:17 pm

2 stops10h 57m

$313

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 12/31

3:10 pm-8:15 am

1 stop16h 05m

Key West

Tue 1/6

12:20 pm-10:17 pm

2 stops10h 57m

$314

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 2/19

6:00 am-12:26 pm

2 stops29h 26m

Key West

Mon 2/23

1:06 pm-7:50 pm

1 stop7h 44m

$317

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 1/31

10:46 am-5:11 pm

1 stop5h 25m

Key West

Sat 2/7

6:06 pm-10:22 pm

1 stop5h 16m

$319

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

What is the cheapest month to fly to Key West?

In general, January 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 $306. If you are unable to visit Key West during the month of January, 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 $376. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Key West for around $540.

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 afternoon. momondo users have found flights departing from Chicago Midway Airport to Key West in the afternoon for as low as $454. 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

Fastest flight time	5h 19m
Direct flights	None

The fastest flight from Chicago Midway Airport to Key West takes 5h 19m

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 5h 19m 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 December 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 $262	Free Cancellation	Rating 7.9 8,007 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.