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Cheap flights from Key West to Chicago from $118

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 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:54 am - 9:27 am
EYW
-
ORD
22h 33m
1 stop
Multiple Airlines Logo
1:59 pm - 1:24 pm
ORD
-
EYW
22h 25m
2 stops
$279Multiple Airlines
Sat, May 16 - Wed, May 20
Multiple Airlines Logo
8:48 pm - 9:21 am
EYW
-
ORD
13h 33m
1 stop
Multiple Airlines Logo
7:05 am - 4:10 pm
ORD
-
EYW
32h 05m
2 stops
$282Multiple Airlines
Thu, Jul 2 - Tue, Jul 14
Multiple Airlines Logo
11:46 am - 12:37 pm
EYW
-
ORD
25h 51m
2 stops
Multiple Airlines Logo
5:25 pm - 11:25 am
ORD
-
EYW
17h 00m
1 stop
$297Multiple Airlines
Wed, May 27 - Wed, Jun 10
Multiple Airlines Logo
8:48 pm - 9:21 am
EYW
-
ORD
13h 33m
1 stop
Multiple Airlines Logo
12:58 pm - 4:10 pm
ORD
-
EYW
26h 12m
1 stop
$302Multiple Airlines
Thu, Jul 2 - Tue, Jul 14
Multiple Airlines Logo
11:46 am - 12:23 pm
EYW
-
ORD
25h 37m
1 stop
Multiple Airlines Logo
7:52 am - 9:41 am
ORD
-
EYW
48h 49m
2 stops
$308Multiple Airlines
Wed, May 27 - Wed, Jun 10
Multiple Airlines Logo
1:14 pm - 12:23 pm
EYW
-
ORD
24h 09m
1 stop
Multiple Airlines Logo
5:30 pm - 11:25 am
ORD
-
EYW
16h 55m
1 stop
$309Multiple Airlines
Tue, May 12 - Sat, May 16
American Airlines Logo
5:37 pm - 12:38 am
EYW
-
ORD
8h 01m
1 stop
American Airlines Logo
10:59 am - 3:24 pm
ORD
-
EYW
3h 25mnonstop
$319American Airlines
Wed, May 27 - Wed, Jun 10
Multiple Airlines Logo
11:54 am - 9:27 am
EYW
-
ORD
22h 33m
1 stop
Multiple Airlines Logo
8:30 am - 10:24 am
ORD
-
EYW
24h 54m
1 stop
$320Multiple Airlines
Sat, May 16 - Wed, May 20
Multiple Airlines Logo
1:14 pm - 12:23 pm
EYW
-
ORD
24h 09m
1 stop
Multiple Airlines Logo
1:59 pm - 10:24 am
ORD
-
EYW
19h 25m
2 stops
$321Multiple Airlines
Tue, May 12 - Sat, May 16
Multiple Airlines Logo
9:24 pm - 10:14 pm
EYW
-
ORD
25h 50m
1 stop
Multiple Airlines Logo
8:05 am - 3:46 pm
ORD
-
EYW
30h 41m
2 stops
$323Multiple Airlines
Sun, May 24 - Sun, May 31

United Airlines flights from Key West to Chicago O'Hare Intl Airport

Our best United Airlines deals on Key West to Chicago O'Hare Intl Airport flight tickets
United Airlines
May 12
EYW4:05 pmKey West
3h 55m
ORD7:00 pmChicago O'Hare Intl
May 16
ORD10:43 amChicago O'Hare Intl
3h 24m
EYW3:07 pmKey West
$369
United Airlines
May 12
EYW4:47 pmKey West
7h 28m
1 stop
ORD11:15 pmChicago O'Hare Intl
May 16
ORD10:43 amChicago O'Hare Intl
3h 24m
EYW3:07 pmKey West
$379
United Airlines
May 14
EYW4:05 pmKey West
3h 55m
ORD7:00 pmChicago O'Hare Intl
May 18
ORD10:43 amChicago O'Hare Intl
3h 24m
EYW3:07 pmKey West
$429

American Airlines flights from Key West to Chicago O'Hare Intl Airport

Our best American Airlines deals on Key West to Chicago O'Hare Intl Airport flight tickets
American Airlines
May 27
EYW5:37 pmKey West
8h 01m
1 stop
ORD12:38 amChicago O'Hare Intl
Jun 10
ORD10:59 amChicago O'Hare Intl
3h 25m
EYW3:24 pmKey West
$319
American Airlines
May 29
EYW1:01 pmKey West
7h 47m
1 stop
ORD7:48 pmChicago O'Hare Intl
May 31
ORD5:10 amChicago O'Hare Intl
6h 06m
1 stop
EYW12:16 pmKey West
$329
American Airlines
Sep 5
EYW10:16 amKey West
5h 24m
1 stop
ORD2:40 pmChicago O'Hare Intl
Sep 9
ORD9:20 amChicago O'Hare Intl
8h 07m
2 stops
EYW6:27 pmKey West
$334

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Chicago O'Hare Intl Airport 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 April 30, 2026.
Use the filters below to find and compare flights from Key West to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 5/16

11:54 am-9:27 am

1 stop22h 33m

Chicago O'Hare Intl

Wed 5/20

1:59 pm-1:24 pm

2 stops22h 25m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/2

8:48 pm-9:21 am

1 stop13h 33m

Chicago O'Hare Intl

Tue 7/14

7:05 am-4:10 pm

2 stops32h 05m

$282

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/27

11:46 am-12:37 pm

2 stops25h 51m

Chicago O'Hare Intl

Wed 6/10

5:25 pm-11:25 am

1 stop17h 00m

$297

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/2

8:48 pm-9:21 am

1 stop13h 33m

Chicago O'Hare Intl

Tue 7/14

12:58 pm-4:10 pm

1 stop26h 12m

$302

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/27

11:46 am-12:23 pm

1 stop25h 37m

Chicago O'Hare Intl

Wed 6/10

7:52 am-9:41 am

2 stops48h 49m

$308

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 5/12

1:14 pm-12:23 pm

1 stop24h 09m

Chicago O'Hare Intl

Sat 5/16

5:30 pm-11:25 am

1 stop16h 55m

$309
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 5/27

5:37 pm-12:38 am

1 stop8h 01m

Chicago O'Hare Intl

Wed 6/10

10:59 am-3:24 pm

Nonstop3h 25m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 5/16

11:54 am-9:27 am

1 stop22h 33m

Chicago O'Hare Intl

Wed 5/20

8:30 am-10:24 am

1 stop24h 54m

$320

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 5/12

1:14 pm-12:23 pm

1 stop24h 09m

Chicago O'Hare Intl

Sat 5/16

1:59 pm-10:24 am

2 stops19h 25m

$321

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 5/24

9:24 pm-10:14 pm

1 stop25h 50m

Chicago O'Hare Intl

Sun 5/31

8:05 am-3:46 pm

2 stops30h 41m

$323

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 O'Hare Intl Airport

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 typical price of a round-trip flight between Key West and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Key West averaging around $268.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $332. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Key West because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $773.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Key West in the morning is the least expensive time of day to depart. momondo users have found prices as low as $427 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $432. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Key West to Chicago O'Hare Intl flight route?

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

Can stopping save me money on Key West to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Key West to Chicago O'Hare Intl Airport.

How have Key West to Chicago O'Hare Intl Airport flight prices changed over time?

As of April 2026, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 10% cheaper when compared to flights at the same time last year.

When to book flights from Key West to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Key West to Chicago O'Hare Intl 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 O'Hare Intl Airport (EYW to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Chicago O'Hare Intl Airport

Best Price Found

$333

Fastest flight time

3h 44m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $333. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $354.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 44m
Direct flights go from Key West to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Key West to Chicago O'Hare Intl Airport

  • How far is Key West to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 1252.7 mi away from Key West. Typically, this will take 3h 44m by plane in normal conditions.

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

    Prices for flights from Key West Airport to Chicago O'Hare Intl Airport refresh daily.

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

  • How old do you have to be to fly from Key West Airport to Chicago O'Hare Intl 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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Key West to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Key West to Chicago O'Hare Intl Airport?

Best airlines flying from Key West to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Key West to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,677 reviews
Search United Airlines flights
American AirlinesPriceFrom $344Free CancellationRating
7.1
11,681 reviews
Search American Airlines flights

  • United Airlines Flights From Key West to Chicago O'Hare Intl Airport

    Across 7 United Airlines flights from Key West to Chicago O'Hare Intl Airport this week, the average price was $315, with the best United Airlines deals starting from $249 round-trip. 9,677 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Key West to Chicago O'Hare Intl Airport

    $344 is the best American Airlines flight deal from Key West to Chicago O'Hare Intl Airport found on momondo over the last 72 hours. The average American Airlines ticket price found was closer to $561, however, with flight time and availability significantly affecting the price. American Airlines (7.1/10 from 11,681 user reviews) flies into Chicago O'Hare Intl Airport from Key West 13 times in an average week so prices can vary.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Key West to Chicago for you.

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

Flights from Key West to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Key West.

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 simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Key West and alert you when they change.

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