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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
8:10 am - 12:38 pm
ORD
-
EYW
3h 28mnonstop
$289American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
11:56 am - 4:21 pm
EYW
-
ORD
5h 25m
1 stop
American Airlines Logo
8:10 am - 12:38 pm
ORD
-
EYW
3h 28mnonstop
$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 - 5:58 pm
EYW
-
ORD
7h 02m
1 stop
American Airlines Logo
6:05 am - 1:21 pm
ORD
-
EYW
6h 16m
1 stop
$309American Airlines
Thu, Apr 9 - Mon, Apr 13
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
Multiple Airlines Logo
11:51 am - 4:56 pm
EYW
-
ORD
6h 05m
1 stop
Multiple Airlines Logo
8:58 pm - 3:42 pm
ORD
-
EYW
17h 44m
2 stops
$364Multiple Airlines
Wed, Apr 1 - Wed, Apr 1
Multiple Airlines Logo
11:01 am - 10:52 am
EYW
-
ORD
24h 51m
2 stops
Multiple Airlines Logo
12:00 pm - 1:37 pm
ORD
-
EYW
24h 37m
1 stop
$367Multiple Airlines
Sun, Mar 29 - Thu, Apr 2
Multiple Airlines Logo
7:56 pm - 3:14 pm
EYW
-
ORD
20h 18m
2 stops
Multiple Airlines Logo
8:04 pm - 7:16 pm
ORD
-
EYW
22h 12m
1 stop
$375Multiple Airlines
Thu, Aug 6 - Wed, Aug 12

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

Our best Spirit Airlines deals on Key West to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Mar 26
EYW12:25 pmKey West
5h 50m
1 stop
ORD5:15 pmChicago O'Hare Intl
Mar 30
ORD9:06 amChicago O'Hare Intl
25h 24m
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
Spirit Airlines
Mar 17
EYW12:25 pmKey West
8h 26m
1 stop
ORD7:51 pmChicago O'Hare Intl
Mar 19
ORD5:05 amChicago O'Hare Intl
5h 25m
1 stop
EYW11:30 amKey West
$458

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
Apr 9
EYW6:46 pmKey West
3h 49m
ORD9:35 pmChicago O'Hare Intl
Apr 13
ORD1:50 pmChicago O'Hare Intl
3h 26m
EYW6:16 pmKey West
$289
American Airlines
Apr 9
EYW6:46 pmKey West
3h 49m
ORD9:35 pmChicago O'Hare Intl
Apr 13
ORD9:45 amChicago O'Hare Intl
5h 45m
1 stop
EYW4:30 pmKey West
$299
American Airlines
Apr 9
EYW11:56 amKey West
5h 25m
1 stop
ORD4:21 pmChicago O'Hare Intl
Apr 13
ORD3:26 pmChicago O'Hare Intl
6h 10m
1 stop
EYW10:36 pmKey West
$309

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 March 16, 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
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

8:10 am-12:38 pm

Nonstop3h 28m

$289

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

8:10 am-12:38 pm

Nonstop3h 28m

$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-5:58 pm

1 stop7h 02m

Chicago O'Hare Intl

Mon 4/13

6:05 am-1:21 pm

1 stop6h 16m

$309

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 - ORD

EYWORD

Key West

Wed 4/1

11:51 am-4:56 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 4/1

8:58 pm-3:42 pm

2 stops17h 44m

$364

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 3/29

11:01 am-10:52 am

2 stops24h 51m

Chicago O'Hare Intl

Thu 4/2

12:00 pm-1:37 pm

1 stop24h 37m

$367

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 8/6

7:56 pm-3:14 pm

2 stops20h 18m

Chicago O'Hare Intl

Wed 8/12

8:04 pm-7:16 pm

1 stop22h 12m

$375

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of July is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Key West averaging around $309.

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 $326. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $787.

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 in the afternoon because they tend to be around $434. 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

What cabin class options are available on Key West to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Key West to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

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

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

As of March 2026, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 28% 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

$310

Fastest flight time

3h 39m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $310. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $349.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 39m
Direct flights go from Key West to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 39m 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
9,428 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 O'Hare Intl Airport

    Across 12 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. 9,428 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 $457, however, with flight time and availability significantly affecting the price. American Airlines (7.1/10 from 11,467 user reviews) flies into Chicago O'Hare Intl Airport from Key West 14 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
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

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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