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.

$183 Cheap Flights from Key West to Chicago Midway Airport (EYW-MDW) in 2025

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0 bags

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

Round-trip

One-way

Last minute

Cheap round-trip flights

7:00 am - 11:48 amEYW-MDW

5h 48m1 stop

12:43 pm - 8:07 pmMDW-EYW

6h 24m1 stop

$384Delta

Find Deal

Tue, Sep 16 - Tue, Sep 23

6:00 pm - 9:44 pmEYW-MDW

4h 44m1 stop

1:05 pm - 7:44 pmMDW-EYW

5h 39m1 stop

$405Delta

Find Deal

Sat, Nov 15 - Sun, Nov 16

6:00 pm - 9:44 pmEYW-MDW

4h 44m1 stop

1:05 pm - 7:44 pmMDW-EYW

5h 39m1 stop

$519Delta

Find Deal

Mon, Nov 24 - Sat, Nov 29

6:00 pm - 9:44 pmEYW-MDW

4h 44m1 stop

1:05 pm - 7:44 pmMDW-EYW

5h 39m1 stop

$599Delta

Find Deal

Mon, Nov 24 - Sat, Nov 29

11:50 am - 6:35 pmEYW-MDW

7h 45m2 stops

12:43 pm - 8:07 pmMDW-EYW

6h 24m1 stop

$741Delta

Find Deal

Tue, Sep 16 - Tue, Sep 23

11:52 am - 6:37 pmEYW-MDW

7h 45m2 stops

6:00 am - 1:05 pmMDW-EYW

6h 05m1 stop

$756Delta

Find Deal

Fri, Sep 5 - Tue, Sep 9

11:52 am - 3:42 pmEYW-MDW

4h 50m1 stop

10:31 am - 5:25 pmMDW-EYW

5h 54m1 stop

$789Delta

Find Deal

Fri, Aug 29 - Sun, Aug 31

7:00 am - 1:36 pmEYW-MDW

7h 36m1 stop

6:00 am - 1:05 pmMDW-EYW

6h 05m1 stop

$898Delta

Find Deal

Mon, Sep 1 - Fri, Sep 5

6:00 pm - 9:44 pmEYW-MDW

4h 44m1 stop

9:30 am - 7:44 pmMDW-EYW

9h 14m2 stops

$956Delta

Find Deal

Mon, Nov 24 - Sat, Nov 29

11:52 am - 6:37 pmEYW-MDW

7h 45m2 stops

6:00 am - 1:05 pmMDW-EYW

6h 05m1 stop

$989Delta

Find Deal

Fri, Aug 29 - Sun, Aug 31

Delta flights from Key West to Chicago Midway Airport

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

Delta

Sep 16

EYW7:00 amKey West

5h 48m

1 stop

MDW11:48 amChicago Midway

Sep 23

MDW12:43 pmChicago Midway

6h 24m

1 stop

EYW8:07 pmKey West

$384

Find similar

Delta

Nov 15

EYW6:00 pmKey West

4h 44m

1 stop

MDW9:44 pmChicago Midway

Nov 16

MDW1:05 pmChicago Midway

5h 39m

1 stop

EYW7:44 pmKey West

$405

Find similar

Delta

Aug 22

EYW2:00 pmKey West

4h 47m

1 stop

MDW5:47 pmChicago Midway

Aug 25

MDW6:00 amChicago Midway

6h 05m

1 stop

EYW1:05 pmKey West

$433

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

Tue 9/16

7:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 9/23

12:43 pm-8:07 pm

1 stop6h 24m

$384

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 11/15

6:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Sun 11/16

1:05 pm-7:44 pm

1 stop5h 39m

$405

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Sat 11/29

1:05 pm-7:44 pm

1 stop5h 39m

$519

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Sat 11/29

1:05 pm-7:44 pm

1 stop5h 39m

$599

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 9/16

11:50 am-6:35 pm

2 stops7h 45m

Chicago Midway

Tue 9/23

12:43 pm-8:07 pm

1 stop6h 24m

$741

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 9/5

11:52 am-6:37 pm

2 stops7h 45m

Chicago Midway

Tue 9/9

6:00 am-1:05 pm

1 stop6h 05m

$756

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 8/29

11:52 am-3:42 pm

1 stop4h 50m

Chicago Midway

Sun 8/31

10:31 am-5:25 pm

1 stop5h 54m

$789

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 9/1

7:00 am-1:36 pm

1 stop7h 36m

Chicago Midway

Fri 9/5

6:00 am-1:05 pm

1 stop6h 05m

$898

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:00 pm-9:44 pm

1 stop4h 44m

Chicago Midway

Sat 11/29

9:30 am-7:44 pm

2 stops9h 14m

$956

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 8/29

11:52 am-6:37 pm

2 stops7h 45m

Chicago Midway

Sun 8/31

6:00 am-1:05 pm

1 stop6h 05m

$989

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

Best Price Found	$183
Fastest flight time	4h 44m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Key West in the past 72 hours is $183. The best round-trip flight deal from Key West to Chicago Midway Airport found on momondo in the last 72 hours is $384.

The fastest flight from Key West to Chicago Midway Airport takes 4h 44m

There are no direct flights from Key West to Chicago Midway Airport. Popular non-direct route for this connection is Key West Airport - Chicago Midway Airport.

Search flight deals

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 44m.
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.