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.

$141 Cheap Flights from Key West to Chicago Midway Airport in 2025/26

1 adult

0 bags

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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.

6:06 pm - 10:22 pm

EYW

MDW

5h 16m1 stop

10:48 am - 5:11 pm

MDW

EYW

5h 23m1 stop

$269Delta

Wed, Jan 21 - Thu, Jan 29

6:06 pm - 10:22 pm

EYW

MDW

5h 16m1 stop

10:48 am - 5:11 pm

MDW

EYW

5h 23m1 stop

$294Delta

Wed, Jan 21 - Thu, Jan 29

6:20 pm - 10:22 pm

EYW

MDW

5h 02m1 stop

11:21 am - 5:11 pm

MDW

EYW

4h 50m1 stop

$299Delta

Mon, Dec 29 - Mon, Jan 12

6:25 pm - 10:29 pm

EYW

MDW

5h 04m1 stop

10:35 am - 5:12 pm

MDW

EYW

5h 37m1 stop

$334Delta

Thu, Apr 9 - Mon, Apr 13

8:55 am - 9:58 pm

EYW

MDW

14h 03m1 stop

8:15 am - 11:20 am

MDW

EYW

26h 05m2 stops

$348Multiple Airlines

Thu, Jan 1 - Mon, Jan 5

7:25 am - 11:58 am

EYW

MDW

5h 33m1 stop

6:45 am - 1:48 pm

MDW

EYW

6h 03m1 stop

$354Delta

Mon, Dec 29 - Mon, Jan 12

6:25 pm - 10:29 pm

EYW

MDW

5h 04m1 stop

1:05 pm - 7:44 pm

MDW

EYW

5h 39m1 stop

$359Delta

Thu, Apr 9 - Mon, Apr 13

7:10 am - 11:59 am

EYW

MDW

5h 49m1 stop

9:33 am - 7:40 pm

MDW

EYW

9h 07m2 stops

$852Delta

Wed, Jan 21 - Thu, Jan 29

7:25 am - 5:26 pm

EYW

MDW

11h 01m2 stops

11:21 am - 5:11 pm

MDW

EYW

4h 50m1 stop

$862Delta

Mon, Dec 29 - Mon, Jan 12

7:10 am - 5:55 pm

EYW

MDW

11h 45m2 stops

10:48 am - 5:11 pm

MDW

EYW

5h 23m1 stop

$895Delta

Wed, Jan 21 - Thu, Jan 29

Delta flights from Key West to Chicago Midway Airport

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

Delta

Jan 21

EYW6:06 pmKey West

5h 16m

1 stop

MDW10:22 pmChicago Midway

Jan 29

MDW10:48 amChicago Midway

5h 23m

1 stop

EYW5:11 pmKey West

$269

Find similar

Delta

Jan 21

EYW6:06 pmKey West

5h 16m

1 stop

MDW10:22 pmChicago Midway

Jan 29

MDW10:48 amChicago Midway

5h 23m

1 stop

EYW5:11 pmKey West

$294

Find similar

Delta

Apr 9

EYW6:25 pmKey West

5h 04m

1 stop

MDW10:29 pmChicago Midway

Apr 13

MDW10:35 amChicago Midway

5h 37m

1 stop

EYW5:12 pmKey West

$334

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

Wed 1/21

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

Thu 1/29

10:48 am-5:11 pm

1 stop5h 23m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/21

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

Thu 1/29

10:48 am-5:11 pm

1 stop5h 23m

$294

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/29

6:20 pm-10:22 pm

1 stop5h 02m

Chicago Midway

Mon 1/12

11:21 am-5:11 pm

1 stop4h 50m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

6:25 pm-10:29 pm

1 stop5h 04m

Chicago Midway

Mon 4/13

10:35 am-5:12 pm

1 stop5h 37m

$334

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 1/1

8:55 am-9:58 pm

1 stop14h 03m

Chicago Midway

Mon 1/5

8:15 am-11:20 am

2 stops26h 05m

$348

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/29

7:25 am-11:58 am

1 stop5h 33m

Chicago Midway

Mon 1/12

6:45 am-1:48 pm

1 stop6h 03m

$354

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

6:25 pm-10:29 pm

1 stop5h 04m

Chicago Midway

Mon 4/13

1:05 pm-7:44 pm

1 stop5h 39m

$359

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/21

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

Thu 1/29

9:33 am-7:40 pm

2 stops9h 07m

$852

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/29

7:25 am-5:26 pm

2 stops11h 01m

Chicago Midway

Mon 1/12

11:21 am-5:11 pm

1 stop4h 50m

$862

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/21

7:10 am-5:55 pm

2 stops11h 45m

Chicago Midway

Thu 1/29

10:48 am-5:11 pm

1 stop5h 23m

$895

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	5h 04m
Direct flights	None

The fastest flight from Key West to Chicago Midway Airport takes 5h 04m

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

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 04m.
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.

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

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Crown Point

Munster

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.