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

Prices for flights from Key West Airport to Chicago Midway Airport were last updated today.

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

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 Key West Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$147 Cheap Flights from Key West to Chicago Midway Airport in 2025/26

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Find the cheapest flights from Key West to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:59 am - 12:30 amEYW-MDW

14h 31m1 stop

5:30 pm - 8:15 amMDW-EYW

13h 45m1 stop

$298Multiple Airlines

Find Deal

Sun, Nov 16 - Sun, Nov 23

6:10 pm - 11:47 pmEYW-MDW

6h 37m1 stop

12:45 pm - 9:34 pmMDW-EYW

7h 49m1 stop

$362Delta

Find Deal

Fri, Dec 19 - Mon, Dec 22

6:00 pm - 9:45 pmEYW-MDW

4h 45m1 stop

6:00 am - 1:10 pmMDW-EYW

6h 10m1 stop

$402Delta

Find Deal

Fri, May 1 - Sun, May 3

6:00 pm - 9:46 pmEYW-MDW

4h 46m1 stop

10:35 am - 5:12 pmMDW-EYW

5h 37m1 stop

$414Delta

Find Deal

Thu, Apr 9 - Mon, Apr 13

7:00 am - 12:01 pmEYW-MDW

6h 01m1 stop

10:35 am - 5:12 pmMDW-EYW

5h 37m1 stop

$454Delta

Find Deal

Thu, Apr 9 - Mon, Apr 13

6:18 pm - 11:40 pmEYW-MDW

6h 22m1 stop

6:00 am - 11:31 amMDW-EYW

4h 31m1 stop

$504Delta

Find Deal

Mon, Nov 24 - Sat, Nov 29

6:00 pm - 9:46 pmEYW-MDW

4h 46m1 stop

10:35 am - 5:13 pmMDW-EYW

5h 38m1 stop

$527Delta

Find Deal

Tue, Mar 10 - Wed, Mar 11

6:18 pm - 11:40 pmEYW-MDW

6h 22m1 stop

6:00 am - 11:31 amMDW-EYW

4h 31m1 stop

$529Delta

Find Deal

Mon, Nov 24 - Sat, Nov 29

11:45 am - 8:50 amEYW-MDW

22h 05m2 stops

1:05 pm - 7:44 pmMDW-EYW

5h 39m1 stop

$629Delta

Find Deal

Tue, Mar 10 - Wed, Mar 11

6:18 pm - 11:40 pmEYW-MDW

6h 22m1 stop

6:00 am - 2:03 pmMDW-EYW

7h 03m1 stop

$659Delta

Find Deal

Mon, Nov 24 - Sat, Nov 29

Delta flights from Key West to Chicago Midway Airport

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

Delta

Dec 19

EYW6:10 pmKey West

6h 37m

1 stop

MDW11:47 pmChicago Midway

Dec 22

MDW12:45 pmChicago Midway

7h 49m

1 stop

EYW9:34 pmKey West

$362

Find similar

Delta

May 1

EYW6:00 pmKey West

4h 45m

1 stop

MDW9:45 pmChicago Midway

May 3

MDW6:00 amChicago Midway

6h 10m

1 stop

EYW1:10 pmKey West

$402

Find similar

Delta

Apr 9

EYW6:00 pmKey West

4h 46m

1 stop

MDW9:46 pmChicago Midway

Apr 13

MDW10:35 amChicago Midway

5h 37m

1 stop

EYW5:12 pmKey West

$414

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 11/16

10:59 am-12:30 am

1 stop14h 31m

Chicago Midway

Sun 11/23

5:30 pm-8:15 am

1 stop13h 45m

$298

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 12/19

6:10 pm-11:47 pm

1 stop6h 37m

Chicago Midway

Mon 12/22

12:45 pm-9:34 pm

1 stop7h 49m

$362

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 5/1

6:00 pm-9:45 pm

1 stop4h 45m

Chicago Midway

Sun 5/3

6:00 am-1:10 pm

1 stop6h 10m

$402

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Mon 4/13

10:35 am-5:12 pm

1 stop5h 37m

$414

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

7:00 am-12:01 pm

1 stop6h 01m

Chicago Midway

Mon 4/13

10:35 am-5:12 pm

1 stop5h 37m

$454

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:18 pm-11:40 pm

1 stop6h 22m

Chicago Midway

Sat 11/29

6:00 am-11:31 am

1 stop4h 31m

$504

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 3/10

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Wed 3/11

10:35 am-5:13 pm

1 stop5h 38m

$527

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:18 pm-11:40 pm

1 stop6h 22m

Chicago Midway

Sat 11/29

6:00 am-11:31 am

1 stop4h 31m

$529

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 3/10

11:45 am-8:50 am

2 stops22h 05m

Chicago Midway

Wed 3/11

1:05 pm-7:44 pm

1 stop5h 39m

$629

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:18 pm-11:40 pm

1 stop6h 22m

Chicago Midway

Sat 11/29

6:00 am-2:03 pm

1 stop7h 03m

$659

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 Key West to Chicago Midway Airport

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 airline that flies from Key West to Chicago Midway?

Delta is the most popular carrier operating from Key West to Chicago Midway

When to book flights from Key West to Chicago Midway Airport

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

Estimated round-trip price

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

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

Direct flights	None

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

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How far is Key West to Chicago Midway by plane?
There are 1237.6 mi between Key West and Chicago Midway. A reasonable flight in good conditions will take 4h 45m.
When did momondo last update prices for flights from Key West Airport to Chicago Midway Airport?
Prices for flights from Key West Airport to Chicago Midway Airport were last updated today.
How old do you have to be to fly from Key West Airport to Chicago Midway Airport?
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 Key West Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Key West to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Key West to Chicago flights to just show those with flexible booking policies.

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

Once all potential Key West to Chicago 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 Key West to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Key West to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.