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.

$128 Cheap Flights from Key West to Chicago Midway Airport in 2026

Find the cheapest flights from Key West to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:19 pm - 10:44 pmEYW Key West-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

6:05 am - 12:53 pmMDW Chicago Midway-EYW Key West

5h 48m1 stop Atlanta Hartsfield-Jackson

$339Delta

Fri, Sep 11 - Mon, Sep 14

6:19 pm - 10:44 pmEYW Key West-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

6:05 am - 12:53 pmMDW Chicago Midway-EYW Key West

5h 48m1 stop Atlanta Hartsfield-Jackson

$359Delta

Sat, Oct 3 - Mon, Oct 5

6:19 pm - 10:44 pmEYW Key West-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

11:33 am - 8:01 pmMDW Chicago Midway-EYW Key West

7h 28m1 stop Atlanta Hartsfield-Jackson

$366Delta

Mon, Oct 5 - Sat, Oct 10

6:19 pm - 10:44 pmEYW Key West-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

6:05 am - 12:53 pmMDW Chicago Midway-EYW Key West

5h 48m1 stop Atlanta Hartsfield-Jackson

$369Delta

Fri, Sep 11 - Mon, Sep 14

6:15 pm - 10:36 pmEYW Key West-MDW Chicago Midway

5h 21m1 stop Atlanta Hartsfield-Jackson

10:54 am - 5:20 pmMDW Chicago Midway-EYW Key West

5h 26m1 stop Atlanta Hartsfield-Jackson

$393Delta

Fri, Aug 28 - Tue, Sep 1

6:15 pm - 10:36 pmEYW Key West-MDW Chicago Midway

5h 21m1 stop Atlanta Hartsfield-Jackson

6:05 am - 1:00 pmMDW Chicago Midway-EYW Key West

5h 55m1 stop Atlanta Hartsfield-Jackson

$399Delta

Wed, Aug 26 - Sun, Aug 30

7:40 am - 6:00 pmEYW Key West-MDW Chicago Midway

11h 20m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

6:04 am - 12:53 pmMDW Chicago Midway-EYW Key West

5h 49m1 stop Atlanta Hartsfield-Jackson

$407Delta

Tue, Oct 6 - Tue, Oct 13

7:40 am - 6:00 pmEYW Key West-MDW Chicago Midway

11h 20m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

12:45 pm - 8:01 pmMDW Chicago Midway-EYW Key West

6h 16m1 stop Atlanta Hartsfield-Jackson

$410Delta

Tue, Oct 6 - Thu, Oct 15

6:11 pm - 10:33 pmEYW Key West-MDW Chicago Midway

5h 22m1 stop Atlanta Hartsfield-Jackson

6:04 am - 12:53 pmMDW Chicago Midway-EYW Key West

5h 49m1 stop Atlanta Hartsfield-Jackson

$426Delta

Sat, Oct 10 - Tue, Oct 13

6:11 pm - 10:33 pmEYW Key West-MDW Chicago Midway

5h 22m1 stop Atlanta Hartsfield-Jackson

12:45 pm - 8:01 pmMDW Chicago Midway-EYW Key West

6h 16m1 stop Atlanta Hartsfield-Jackson

$429Delta

Sat, Oct 10 - Thu, Oct 15

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Delta flights from Key West to Chicago Midway Airport

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

Delta

Sep 11

EYW6:19 pmKey West

5h 25m

1 stop

MDW10:44 pmChicago Midway

Sep 14

MDW6:05 amChicago Midway

5h 48m

1 stop

EYW12:53 pmKey West

$339

Delta

Oct 3

EYW6:19 pmKey West

5h 25m

1 stop

MDW10:44 pmChicago Midway

Oct 5

MDW6:05 amChicago Midway

5h 48m

1 stop

EYW12:53 pmKey West

$359

Delta

Oct 5

EYW6:19 pmKey West

5h 25m

1 stop

MDW10:44 pmChicago Midway

Oct 13

MDW6:04 amChicago Midway

5h 49m

1 stop

EYW12:53 pmKey West

$366

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

Cheapest round-trip

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 9/11

6:19 pm-10:44 pm

1 stop5h 25m

Chicago Midway

Mon 9/14

6:05 am-12:53 pm

1 stop5h 48m

$339

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sat 10/3

6:19 pm-10:44 pm

1 stop5h 25m

Chicago Midway

Mon 10/5

6:05 am-12:53 pm

1 stop5h 48m

$359

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Mon 10/5

6:19 pm-10:44 pm

1 stop5h 25m

Chicago Midway

Sat 10/10

11:33 am-8:01 pm

1 stop7h 28m

$366

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 9/11

6:19 pm-10:44 pm

1 stop5h 25m

Chicago Midway

Mon 9/14

6:05 am-12:53 pm

1 stop5h 48m

$369

Quickest round-trip

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 8/28

6:15 pm-10:36 pm

1 stop5h 21m

Chicago Midway

Tue 9/1

10:54 am-5:20 pm

1 stop5h 26m

$393

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Wed 8/26

6:15 pm-10:36 pm

1 stop5h 21m

Chicago Midway

Sun 8/30

6:05 am-1:00 pm

1 stop5h 55m

$399

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Tue 10/6

7:40 am-6:00 pm

2 stops11h 20m

Chicago Midway

Tue 10/13

6:04 am-12:53 pm

1 stop5h 49m

$407

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Tue 10/6

7:40 am-6:00 pm

2 stops11h 20m

Chicago Midway

Thu 10/15

12:45 pm-8:01 pm

1 stop6h 16m

$410

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sat 10/10

6:11 pm-10:33 pm

1 stop5h 22m

Chicago Midway

Tue 10/13

6:04 am-12:53 pm

1 stop5h 49m

$426

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sat 10/10

6:11 pm-10:33 pm

1 stop5h 22m

Chicago Midway

Thu 10/15

12:45 pm-8:01 pm

1 stop6h 16m

$429

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

Fastest flight time	5h 10m
Direct flights	None

The fastest flight from Key West to Chicago Midway Airport takes 5h 10m

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.

Search flight deals

Frequently asked questions about flying from Key West to Chicago Midway Airport

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 5h 10m.
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.