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.

$134 Cheap Flights from Key West to Chicago Midway Airport in 2026/27

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.

6:06 pm - 10:54 pmEYW Key West-MDW Chicago Midway

5h 48m1 stop Atlanta Hartsfield-Jackson

1:02 pm - 8:01 pmMDW Chicago Midway-EYW Key West

5h 59m1 stop Atlanta Hartsfield-Jackson

$346Delta

Sat, Dec 5 - Tue, Dec 8

10:59 am - 8:14 amEYW Key West-MDW Chicago Midway

46h 15m2 stops Orlando Atlanta Hartsfield-Jackson

8:42 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 37m1 stop Orlando

$410Multiple Airlines

Sun, Nov 22 - Sat, Nov 28

10:59 am - 7:47 pmEYW Key West-MDW Chicago Midway

9h 48m1 stop Orlando

8:42 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 37m1 stop Orlando

$433Multiple Airlines

Sun, Nov 22 - Sat, Nov 28

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

5h 22m1 stop Atlanta Hartsfield-Jackson

12:49 pm - 8:01 pmMDW Chicago Midway-EYW Key West

6h 12m1 stop Atlanta Hartsfield-Jackson

$439Delta

Sat, Oct 24 - Wed, Oct 28

10:59 am - 8:14 amEYW Key West-MDW Chicago Midway

46h 15m2 stops Orlando Atlanta Hartsfield-Jackson

8:42 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 37m1 stop Orlando

$441Multiple Airlines

Sun, Nov 22 - Mon, Nov 30

10:59 am - 7:47 pmEYW Key West-MDW Chicago Midway

9h 48m1 stop Orlando

8:42 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 37m1 stop Orlando

$461Multiple Airlines

Sun, Nov 22 - Mon, Nov 30

6:06 pm - 10:54 pmEYW Key West-MDW Chicago Midway

5h 48m1 stop Atlanta Hartsfield-Jackson

1:02 pm - 8:01 pmMDW Chicago Midway-EYW Key West

5h 59m1 stop Atlanta Hartsfield-Jackson

$467Delta

Sat, Dec 5 - Mon, Dec 7

6:00 pm - 10:10 pmEYW Key West-MDW Chicago Midway

5h 10m1 stop Atlanta Hartsfield-Jackson

6:00 am - 1:08 pmMDW Chicago Midway-EYW Key West

6h 08m1 stop Atlanta Hartsfield-Jackson

$477Delta

Fri, Mar 5 - Mon, Mar 8

12:59 pm - 11:46 pmEYW Key West-MDW Chicago Midway

11h 47m2 stops Tampa Atlanta Hartsfield-Jackson

8:47 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 32m1 stop Orlando

$535Multiple Airlines

Fri, Mar 5 - Mon, Mar 8

10:59 am - 7:42 pmEYW Key West-MDW Chicago Midway

9h 43m1 stop Orlando

8:47 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 32m1 stop Orlando

$536Multiple Airlines

Fri, Mar 5 - Sun, Mar 7

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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

Dec 5

EYW6:06 pmKey West

5h 48m

1 stop

MDW10:54 pmChicago Midway

Dec 8

MDW1:02 pmChicago Midway

5h 59m

1 stop

EYW8:01 pmKey West

$346

Delta

Dec 5

EYW6:06 pmKey West

5h 48m

1 stop

MDW10:54 pmChicago Midway

Dec 7

MDW1:02 pmChicago Midway

5h 59m

1 stop

EYW8:01 pmKey West

$467

Delta

Mar 5

EYW6:00 pmKey West

5h 10m

1 stop

MDW10:10 pmChicago Midway

Mar 8

MDW6:00 amChicago Midway

6h 08m

1 stop

EYW1:08 pmKey West

$477

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

Sat 12/5

6:06 pm-10:54 pm

1 stop5h 48m

Chicago Midway

Tue 12/8

1:02 pm-8:01 pm

1 stop5h 59m

$346

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sun 11/22

10:59 am-8:14 am

2 stops46h 15m

Chicago Midway

Sat 11/28

8:42 pm-10:19 am

1 stop12h 37m

$410

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sun 11/22

10:59 am-7:47 pm

1 stop9h 48m

Chicago Midway

Sat 11/28

8:42 pm-10:19 am

1 stop12h 37m

$433

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sat 10/24

6:11 pm-10:33 pm

1 stop5h 22m

Chicago Midway

Wed 10/28

12:49 pm-8:01 pm

1 stop6h 12m

$439

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sun 11/22

10:59 am-8:14 am

2 stops46h 15m

Chicago Midway

Mon 11/30

8:42 pm-10:19 am

1 stop12h 37m

$441

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sun 11/22

10:59 am-7:47 pm

1 stop9h 48m

Chicago Midway

Mon 11/30

8:42 pm-10:19 am

1 stop12h 37m

$461

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Sat 12/5

6:06 pm-10:54 pm

1 stop5h 48m

Chicago Midway

Mon 12/7

1:02 pm-8:01 pm

1 stop5h 59m

$467

Quickest round-trip

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 3/5

6:00 pm-10:10 pm

1 stop5h 10m

Chicago Midway

Mon 3/8

6:00 am-1:08 pm

1 stop6h 08m

$477

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 3/5

12:59 pm-11:46 pm

2 stops11h 47m

Chicago Midway

Mon 3/8

8:47 pm-10:19 am

1 stop12h 32m

$535

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 3/5

10:59 am-7:42 pm

1 stop9h 43m

Chicago Midway

Sun 3/7

8:47 pm-10:19 am

1 stop12h 32m

$536

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

Best Price Found	$134
Fastest flight time	5h 23m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Key West in the past 72 hours is $134. The best round-trip flight deal from Key West to Chicago Midway Airport found on momondo in the last 72 hours is $346.

The fastest flight from Key West to Chicago Midway Airport takes 5h 23m

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 23m.
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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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.