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Cheap flights from Key West to Chicago from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Chicago departing on 8/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Key West to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
10:55 am - 2:38 pm
EYW
-
MDW
28h 43m
1 stop
Allegiant Air Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
$281Allegiant Air
Thu, Jul 30 - Thu, Aug 6
Multiple Airlines Logo
1:14 pm - 10:03 pm
EYW
-
MDW
9h 49m
2 stops
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
$286Multiple Airlines
Tue, Jul 14 - Thu, Jul 16
Multiple Airlines Logo
1:14 pm - 10:03 pm
EYW
-
MDW
9h 49m
2 stops
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
$293Multiple Airlines
Tue, Jul 14 - Thu, Jul 16
Multiple Airlines Logo
1:14 pm - 10:03 pm
EYW
-
MDW
9h 49m
2 stops
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
$297Multiple Airlines
Tue, Jul 14 - Thu, Jul 16
American Airlines Logo
4:11 pm - 6:59 pm
EYW
-
ORD
3h 48mnonstop
American Airlines Logo
11:30 am - 3:51 pm
ORD
-
EYW
3h 21mnonstop
$309American Airlines
Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
4:11 pm - 6:59 pm
EYW
-
ORD
3h 48mnonstop
American Airlines Logo
11:59 am - 4:18 pm
ORD
-
EYW
3h 19mnonstop
$310American Airlines
Thu, Jul 30 - Thu, Aug 6
Multiple Airlines Logo
11:04 am - 10:03 pm
EYW
-
MDW
11h 59m
2 stops
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
$316Multiple Airlines
Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
7:33 pm - 12:01 am
EYW
-
ORD
5h 28m
1 stop
American Airlines Logo
11:22 am - 3:43 pm
ORD
-
EYW
3h 21mnonstop
$319American Airlines
Sat, Jul 11 - Tue, Jul 14
Delta Logo
11:56 am - 4:15 pm
EYW
-
MDW
5h 19m
1 stop
Delta Logo
12:41 pm - 7:51 pm
MDW
-
EYW
6h 10m
1 stop
$587Delta
Tue, Jul 14 - Thu, Jul 16
Delta Logo
6:24 pm - 10:17 pm
EYW
-
MDW
4h 53m
1 stop
Delta Logo
11:05 am - 7:51 pm
MDW
-
EYW
7h 46m
1 stop
$619Delta
Mon, Jul 6 - Tue, Jul 14

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United Airlines flights from Key West to Chicago

Our best United Airlines deals on Key West to Chicago flight tickets
United Airlines
Jul 15
EYW4:00 pmKey West
3h 55m
ORD6:55 pmChicago O'Hare Intl
Jul 31
ORD10:55 amChicago O'Hare Intl
3h 24m
EYW3:19 pmKey West
$509
United Airlines
Jul 9
EYW4:00 pmKey West
3h 55m
ORD6:55 pmChicago O'Hare Intl
Jul 12
ORD10:55 amChicago O'Hare Intl
3h 24m
EYW3:19 pmKey West
$570
United Airlines
Jun 18
EYW3:55 pmKey West
3h 55m
ORD6:50 pmChicago O'Hare Intl
Jun 20
ORD10:45 amChicago O'Hare Intl
3h 24m
EYW3:09 pmKey West
$584

American Airlines flights from Key West to Chicago

Our best American Airlines deals on Key West to Chicago flight tickets
American Airlines
Jul 9
EYW4:11 pmKey West
3h 48m
ORD6:59 pmChicago O'Hare Intl
Jul 12
ORD11:30 amChicago O'Hare Intl
3h 21m
EYW3:51 pmKey West
$309
American Airlines
Jul 30
EYW4:11 pmKey West
3h 48m
ORD6:59 pmChicago O'Hare Intl
Aug 6
ORD11:59 amChicago O'Hare Intl
3h 19m
EYW4:18 pmKey West
$310
American Airlines
Jul 11
EYW7:33 pmKey West
5h 28m
1 stop
ORD12:01 amChicago O'Hare Intl
Jul 14
ORD11:22 amChicago O'Hare Intl
3h 21m
EYW3:43 pmKey West
$319

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 16, 2026.
Use the filters below to find and compare flights from Key West to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 7/30

10:55 am-2:38 pm

1 stop28h 43m

Chicago Midway

Thu 8/6

2:49 pm-9:41 am

1 stop17h 52m

$281

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 7/14

1:14 pm-10:03 pm

2 stops9h 49m

Chicago Midway

Thu 7/16

2:48 pm-9:41 am

1 stop17h 53m

$286

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 7/14

1:14 pm-10:03 pm

2 stops9h 49m

Chicago Midway

Thu 7/16

2:48 pm-9:41 am

1 stop17h 53m

$293

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 7/14

1:14 pm-10:03 pm

2 stops9h 49m

Chicago Midway

Thu 7/16

2:48 pm-9:41 am

1 stop17h 53m

$297

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/9

4:11 pm-6:59 pm

Nonstop3h 48m

Chicago O'Hare Intl

Sun 7/12

11:30 am-3:51 pm

Nonstop3h 21m

$309
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/30

4:11 pm-6:59 pm

Nonstop3h 48m

Chicago O'Hare Intl

Thu 8/6

11:59 am-4:18 pm

Nonstop3h 19m

$310

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 7/9

11:04 am-10:03 pm

2 stops11h 59m

Chicago Midway

Sun 7/12

2:48 pm-9:41 am

1 stop17h 53m

$316

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 7/11

7:33 pm-12:01 am

1 stop5h 28m

Chicago O'Hare Intl

Tue 7/14

11:22 am-3:43 pm

Nonstop3h 21m

$319

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 7/14

11:56 am-4:15 pm

1 stop5h 19m

Chicago Midway

Thu 7/16

12:41 pm-7:51 pm

1 stop6h 10m

$587

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 7/6

6:24 pm-10:17 pm

1 stop4h 53m

Chicago Midway

Tue 7/14

11:05 am-7:51 pm

1 stop7h 46m

$619

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Key West to Chicago

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 month to fly to Chicago?

The month of March is, on average, the cheapest month to fly to Chicago from Key West, with most prices found around $0. If you’re not able to fly to Chicago in March, then December is your next best option. Flight prices from Key West to Chicago during December average around $249.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $339. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $484.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Key West to Chicago during this time can be as low as $366. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $435.

What is the cheapest Key West to Chicago flight route?

Fly from Key West to Chicago O'Hare Intl for the best Key West - Chicago flight prices

What cabin class options are available on Key West to Chicago flights?

There are 4 cabin classes available to choose from on Key West to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Key West to Chicago flights?

No. A direct flight is the cheapest option for a flight between Key West to Chicago.

How have Key West to Chicago flight prices changed over time?

When to book flights from Key West to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Key West to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Key West to Chicago (EYW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Chicago

Best Price Found

$323

Fastest flight time

3h 48m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Key West in the past 72 hours is $323. The best round-trip flight deal from Key West to Chicago found on momondo in the last 72 hours is $375.
The fastest flight from Key West to Chicago takes 3h 48m
Direct flights go from Key West to Chicago every day.
There are 3 airports in Chicago. From Key West there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Key West to Chicago

  • How far is Key West to Chicago by plane?

    Chicago is 1241.6 mi away from Key West. In terms of flight time, this usually takes a little over 3h 48m.

  • When did momondo last update prices for flights from Key West Airport to Chicago?

    Prices for flights from Key West Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Key West Airport to Chicago?

  • How old do you have to be to fly from Key West Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Key West Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Key West to Chicago?

  • What is the most popular airline from Key West to Chicago?

Best airlines flying from Key West to Chicago

Compare and see reviews for airlines that fly from Key West to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $344Free CancellationRating
7.1
11,668 reviews
Search American Airlines flights

  • American Airlines Flights From Key West to Chicago

    Across 5 American Airlines flights from Key West to Chicago this week, the average price was $460, with the best American Airlines deals starting from $344 round-trip. 11,666 users have rated American Airlines on momondo, with an average score of 7.1/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
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?

It is quick and easy to find Key West to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Key West to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Key West on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Key West to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Key West. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Key West to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport