How do I get Price Alerts for flights from Key West to Chicago Midway Airport?

You can take advantage of momondo’s Price Alerts by first searching for your flights to Key West from Chicago Midway Airport . Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

How can I save money on flights from Key West to Chicago Midway Airport with momondo?

By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

How does momondo find its flight prices?

We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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.

$106 Cheap Flights from Key West to Chicago Midway Airport in 2026

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Find the cheapest flights from Key West to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:23 pm - 10:28 pm

EYW

MDW

5h 05m

1 stop

10:59 am - 7:49 pm

MDW

EYW

7h 50m

1 stop

$329Delta

Fri, May 1 - Fri, May 8

11:46 am - 10:11 pm

EYW

MDW

11h 25m

2 stops

2:48 pm - 9:41 am

MDW

EYW

17h 53m

1 stop

$353Multiple Airlines

Wed, Jul 1 - Sun, Jul 5

11:56 am - 4:15 pm

EYW

MDW

5h 19m

1 stop

11:05 am - 7:51 pm

MDW

EYW

7h 46m

1 stop

$384Delta

Wed, Jul 15 - Wed, Aug 5

6:23 pm - 10:28 pm

EYW

MDW

5h 05m

1 stop

6:00 am - 1:44 pm

MDW

EYW

6h 44m

1 stop

$444Delta

Wed, Apr 15 - Sun, Apr 19

6:23 pm - 10:28 pm

EYW

MDW

5h 05m

1 stop

6:00 am - 1:44 pm

MDW

EYW

6h 44m

1 stop

$504Delta

Tue, Apr 14 - Sat, Apr 18

6:18 pm - 10:15 pm

EYW

MDW

4h 57m

1 stop

11:05 am - 5:23 pm

MDW

EYW

5h 18m

1 stop

$509Delta

Wed, Jul 29 - Mon, Aug 3

6:24 pm - 10:17 pm

EYW

MDW

4h 53m

1 stop

6:05 am - 12:23 pm

MDW

EYW

5h 18m

1 stop

$544Delta

Wed, Jul 1 - Sun, Jul 5

6:23 pm - 10:28 pm

EYW

MDW

5h 05m

1 stop

12:52 pm - 7:40 pm

MDW

EYW

5h 48m

1 stop

$587Delta

Tue, Apr 28 - Wed, Apr 29

6:24 pm - 10:17 pm

EYW

MDW

4h 53m

1 stop

6:05 am - 1:28 pm

MDW

EYW

6h 23m

1 stop

$629Delta

Fri, Jun 26 - Mon, Jul 6

7:30 am - 11:56 am

EYW

MDW

5h 26m

1 stop

6:23 am - 12:27 pm

MDW

EYW

5h 04m

1 stop

$868Delta

Sun, May 17 - Wed, May 20

Delta flights from Key West to Chicago Midway Airport

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

Delta

May 1

EYW6:23 pmKey West

5h 05m

1 stop

MDW10:28 pmChicago Midway

May 8

MDW10:59 amChicago Midway

7h 50m

1 stop

EYW7:49 pmKey West

$329

Delta

Jul 15

EYW11:56 amKey West

5h 19m

1 stop

MDW4:15 pmChicago Midway

Aug 5

MDW11:05 amChicago Midway

7h 46m

1 stop

EYW7:51 pmKey West

$384

Delta

Apr 9

EYW6:25 pmKey West

5h 06m

1 stop

MDW10:31 pmChicago Midway

Apr 13

MDW6:00 amChicago Midway

6h 44m

1 stop

EYW1:44 pmKey West

$444

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 - MDW

EYWMDW

Key West

Fri 5/1

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Fri 5/8

10:59 am-7:49 pm

1 stop7h 50m

$329

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/1

11:46 am-10:11 pm

2 stops11h 25m

Chicago Midway

Sun 7/5

2:48 pm-9:41 am

1 stop17h 53m

$353

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/15

11:56 am-4:15 pm

1 stop5h 19m

Chicago Midway

Wed 8/5

11:05 am-7:51 pm

1 stop7h 46m

$384

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 4/15

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Sun 4/19

6:00 am-1:44 pm

1 stop6h 44m

$444

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 4/14

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Sat 4/18

6:00 am-1:44 pm

1 stop6h 44m

$504

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/29

6:18 pm-10:15 pm

1 stop4h 57m

Chicago Midway

Mon 8/3

11:05 am-5:23 pm

1 stop5h 18m

$509

Quickest round-trip

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/1

6:24 pm-10:17 pm

1 stop4h 53m

Chicago Midway

Sun 7/5

6:05 am-12:23 pm

1 stop5h 18m

$544

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 4/28

6:23 pm-10:28 pm

1 stop5h 05m

Chicago Midway

Wed 4/29

12:52 pm-7:40 pm

1 stop5h 48m

$587

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 6/26

6:24 pm-10:17 pm

1 stop4h 53m

Chicago Midway

Mon 7/6

6:05 am-1:28 pm

1 stop6h 23m

$629

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 5/17

7:30 am-11:56 am

1 stop5h 26m

Chicago Midway

Wed 5/20

6:23 am-12:27 pm

1 stop5h 04m

$868

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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	4h 53m
Direct flights	None

The fastest flight from Key West to Chicago Midway Airport takes 4h 53m

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 4h 53m.
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.

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

How do I get Price Alerts for flights from Key West to Chicago Midway Airport?
You can take advantage of momondo’s Price Alerts by first searching for your flights to Key West from Chicago Midway Airport. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.
How can I save money on flights from Key West to Chicago Midway Airport with momondo?
By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.
How does momondo find its flight prices?
We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

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.