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Cheap flights from Key West to Chicago from $111

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 5/12. 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
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
1:50 pm - 6:16 pm
ORD
-
EYW
3h 26mnonstop
$289American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
9:45 am - 4:30 pm
ORD
-
EYW
5h 45m
1 stop
$299American Airlines
Thu, Apr 9 - Mon, Apr 13
Multiple Airlines Logo
9:46 am - 4:56 pm
EYW
-
ORD
8h 10m
1 stop
Multiple Airlines Logo
4:05 pm - 12:21 pm
ORD
-
EYW
19h 16m
1 stop
$306Multiple Airlines
Thu, Mar 26 - Mon, Mar 30
American Airlines Logo
11:56 am - 4:21 pm
EYW
-
ORD
5h 25m
1 stop
American Airlines Logo
3:26 pm - 10:36 pm
ORD
-
EYW
6h 10m
1 stop
$309American Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
6:00 pm - 9:45 pm
EYW
-
MDW
4h 45m
1 stop
Delta Logo
6:00 am - 1:09 pm
MDW
-
EYW
6h 09m
1 stop
$329Delta
Thu, Aug 6 - Wed, Aug 12
Multiple Airlines Logo
1:06 pm - 12:04 am
EYW
-
ORD
11h 58m
2 stops
Multiple Airlines Logo
5:05 am - 1:37 pm
ORD
-
EYW
7h 32m
1 stop
$354Multiple Airlines
Fri, Apr 3 - Fri, Apr 10
Multiple Airlines Logo
11:01 am - 8:42 pm
EYW
-
ORD
10h 41m
1 stop
Multiple Airlines Logo
6:10 pm - 12:21 pm
ORD
-
EYW
17h 11m
2 stops
$356Multiple Airlines
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
4:22 pm - 6:26 pm
EYW
-
ORD
27h 04m
1 stop
Multiple Airlines Logo
12:00 pm - 1:37 pm
ORD
-
EYW
24h 37m
1 stop
$360Multiple Airlines
Sun, Mar 29 - Thu, Apr 2
Delta Logo
11:43 am - 5:22 pm
EYW
-
MDW
6h 39m
1 stop
Delta Logo
12:47 pm - 7:41 pm
MDW
-
EYW
5h 54m
1 stop
$444Delta
Thu, Mar 26 - Mon, Mar 30
Allegiant Air Logo
10:33 pm - 6:28 pm
EYW
-
RFD
20h 55m
1 stop
Allegiant Air Logo
10:37 am - 10:06 am
RFD
-
EYW
22h 29m
2 stops
$499Allegiant Air
Sun, Mar 29 - Thu, Apr 2

United Airlines flights from Key West to Chicago

Our best United Airlines deals on Key West to Chicago flight tickets
United Airlines
Apr 15
EYW3:52 pmKey West
3h 44m
ORD6:36 pmChicago O'Hare Intl
Apr 22
ORD7:30 amChicago O'Hare Intl
7h 27m
1 stop
EYW3:57 pmKey West
$319
United Airlines
Apr 23
EYW4:38 pmKey West
9h 07m
1 stop
ORD12:45 amChicago O'Hare Intl
Apr 26
ORD10:35 amChicago O'Hare Intl
3h 16m
EYW2:51 pmKey West
$379
United Airlines
Apr 23
EYW6:22 pmKey West
6h 21m
1 stop
ORD11:43 pmChicago O'Hare Intl
Apr 26
ORD5:48 amChicago O'Hare Intl
9h 09m
1 stop
EYW3:57 pmKey West
$389

Spirit Airlines flights from Key West to Chicago

Our best Spirit Airlines deals on Key West to Chicago flight tickets
Spirit Airlines
Mar 31
EYW12:25 pmKey West
11h 52m
1 stop
ORD11:17 pmChicago O'Hare Intl
Apr 4
ORD4:51 pmChicago O'Hare Intl
17h 39m
3 stops
EYW11:30 amKey West
$403
Spirit Airlines
Mar 31
EYW12:25 pmKey West
24h 25m
2 stops
ORD11:50 amChicago O'Hare Intl
Apr 4
ORD4:51 pmChicago O'Hare Intl
17h 39m
3 stops
EYW11:30 amKey West
$452
Spirit Airlines
Mar 29
EYW12:25 pmKey West
26h 51m
3 stops
ORD2:16 pmChicago O'Hare Intl
Apr 2
ORD5:05 amChicago O'Hare Intl
5h 25m
1 stop
EYW11:30 amKey West
$454

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 March 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
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:46 pm-9:35 pm

Nonstop3h 49m

Chicago O'Hare Intl

Mon 4/13

1:50 pm-6:16 pm

Nonstop3h 26m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:46 pm-9:35 pm

Nonstop3h 49m

Chicago O'Hare Intl

Mon 4/13

9:45 am-4:30 pm

1 stop5h 45m

$299

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 3/26

9:46 am-4:56 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 3/30

4:05 pm-12:21 pm

1 stop19h 16m

$306

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

11:56 am-4:21 pm

1 stop5h 25m

Chicago O'Hare Intl

Mon 4/13

3:26 pm-10:36 pm

1 stop6h 10m

$309

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 8/6

6:00 pm-9:45 pm

1 stop4h 45m

Chicago Midway

Wed 8/12

6:00 am-1:09 pm

1 stop6h 09m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 4/3

1:06 pm-12:04 am

2 stops11h 58m

Chicago O'Hare Intl

Fri 4/10

5:05 am-1:37 pm

1 stop7h 32m

$354

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 3/26

11:01 am-8:42 pm

1 stop10h 41m

Chicago O'Hare Intl

Mon 3/30

6:10 pm-12:21 pm

2 stops17h 11m

$356

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 3/29

4:22 pm-6:26 pm

1 stop27h 04m

Chicago O'Hare Intl

Thu 4/2

12:00 pm-1:37 pm

1 stop24h 37m

$360

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 3/26

11:43 am-5:22 pm

1 stop6h 39m

Chicago Midway

Mon 3/30

12:47 pm-7:41 pm

1 stop5h 54m

$444

Key WestChicago

EYW - RFD

EYWRFD

Key West

Sun 3/29

10:33 pm-6:28 pm

1 stop20h 55m

Chicago Greater Rockford

Thu 4/2

10:37 am-10:06 am

2 stops22h 29m

$499

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 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 $326. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $787.

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 $427. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $434.

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?

You could potentially save up to 44% on your flight if you consider stops on a Key West to Chicago flight.

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

$310

Fastest flight time

3h 39m

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 $310. The best round-trip flight deal from Key West to Chicago found on momondo in the last 72 hours is $349.
The fastest flight from Key West to Chicago takes 3h 39m
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

  • 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 39m.

  • 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
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,428 reviews
Search United Airlines flights
American AirlinesPriceFrom $344Free CancellationRating
7.1
11,467 reviews
Search American Airlines flights

  • United Airlines Flights From Key West to Chicago

    Across 12 United Airlines flights from Key West to Chicago this week, the average price was $315, with the best United Airlines deals starting from $249 round-trip. 9,428 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Key West to Chicago

    Another popular option for Key West to Chicago flights is American Airlines (7.1/10, 11,467 ratings). American Airlines flies from Key West to Chicago around 14 times per week, with deals starting from $344 round-trip and rising to an average price of around $457.

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
Saint Joseph
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?

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