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Cheap flights from Key West to Chicago from $144

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 9/9. 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.
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
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
American Airlines Logo
11:28 am - 5:18 pm
EYW
-
ORD
6h 50m
1 stop
American Airlines Logo
11:30 am - 3:51 pm
ORD
-
EYW
3h 21mnonstop
$320American 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
$322American Airlines
Mon, Jul 6 - Tue, Jul 14
Multiple Airlines Logo
1:14 pm - 4:00 pm
EYW
-
ORD
27h 46m
2 stops
Multiple Airlines Logo
5:13 pm - 11:25 am
ORD
-
EYW
17h 12m
1 stop
$327Multiple Airlines
Tue, Aug 4 - Wed, Aug 12
American Airlines Logo
7:33 pm - 12:01 am
EYW
-
ORD
5h 28m
1 stop
American Airlines Logo
6:59 am - 1:14 pm
ORD
-
EYW
5h 15m
1 stop
$329American Airlines
Sat, Jul 11 - Tue, Jul 14
American Airlines Logo
7:33 pm - 12:01 am
EYW
-
ORD
5h 28m
1 stop
American Airlines Logo
9:00 am - 4:11 pm
ORD
-
EYW
6h 11m
1 stop
$331American Airlines
Mon, Jul 6 - Tue, Jul 14
American Airlines Logo
4:11 pm - 6:59 pm
EYW
-
ORD
3h 48mnonstop
American Airlines Logo
11:20 am - 3:41 pm
ORD
-
EYW
3h 21mnonstop
$339American Airlines
Thu, Jul 2 - Wed, Jul 8
American Airlines Logo
4:11 pm - 6:59 pm
EYW
-
ORD
3h 48mnonstop
American Airlines Logo
6:10 am - 1:14 pm
ORD
-
EYW
6h 04m
1 stop
$349American Airlines
Thu, Jul 2 - Wed, Jul 8
American Airlines Logo
7:40 pm - 12:26 am
EYW
-
ORD
5h 46m
1 stop
American Airlines Logo
10:05 am - 7:06 pm
ORD
-
EYW
8h 01m
1 stop
$359American Airlines
Thu, Jul 2 - Wed, Jul 8

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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
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 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
American Airlines
Jul 9
EYW11:28 amKey West
6h 50m
1 stop
ORD5:18 pmChicago O'Hare Intl
Jul 12
ORD11:30 amChicago O'Hare Intl
3h 21m
EYW3:51 pmKey West
$320

Delta flights from Key West to Chicago O'Hare Intl Airport

Our best Delta deals on Key West to Chicago O'Hare Intl Airport flight tickets
Delta
Jun 18
EYW6:24 pmKey West
6h 35m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 20
ORD6:35 amChicago O'Hare Intl
7h 20m
1 stop
EYW2:55 pmKey West
$480
Delta
Jun 19
EYW6:24 pmKey West
6h 35m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 22
ORD5:30 amChicago O'Hare Intl
6h 58m
1 stop
EYW1:28 pmKey West
$499
Delta
Jun 19
EYW11:59 amKey West
7h 43m
1 stop
ORD6:42 pmChicago O'Hare Intl
Jun 22
ORD6:35 amChicago O'Hare Intl
5h 53m
1 stop
EYW1:28 pmKey West
$533

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 June 15, 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 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

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 - ORD

EYWORD

Key West

Thu 7/9

11:28 am-5:18 pm

1 stop6h 50m

Chicago O'Hare Intl

Sun 7/12

11:30 am-3:51 pm

Nonstop3h 21m

$320

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 7/6

7:33 pm-12:01 am

1 stop5h 28m

Chicago O'Hare Intl

Tue 7/14

11:22 am-3:43 pm

Nonstop3h 21m

$322

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 8/4

1:14 pm-4:00 pm

2 stops27h 46m

Chicago O'Hare Intl

Wed 8/12

5:13 pm-11:25 am

1 stop17h 12m

$327

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

6:59 am-1:14 pm

1 stop5h 15m

$329

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 7/6

7:33 pm-12:01 am

1 stop5h 28m

Chicago O'Hare Intl

Tue 7/14

9:00 am-4:11 pm

1 stop6h 11m

$331

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/2

4:11 pm-6:59 pm

Nonstop3h 48m

Chicago O'Hare Intl

Wed 7/8

11:20 am-3:41 pm

Nonstop3h 21m

$339

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/2

4:11 pm-6:59 pm

Nonstop3h 48m

Chicago O'Hare Intl

Wed 7/8

6:10 am-1:14 pm

1 stop6h 04m

$349

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/2

7:40 pm-12:26 am

1 stop5h 46m

Chicago O'Hare Intl

Wed 7/8

10:05 am-7:06 pm

1 stop8h 01m

$359

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $339. 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 $484.

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 $366 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $435. 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 Airport flights?

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

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 June 2026, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 33% more expensive 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

$323

Fastest flight time

3h 48m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $323. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $375.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 48m
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 48m 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
American AirlinesPriceFrom $344Free CancellationRating
7.1
11,660 reviews
Search American Airlines flights

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

    Across 4 American Airlines flights from Key West to Chicago O'Hare Intl Airport this week, the average price was $460, with the best American Airlines deals starting from $344 round-trip. 11,660 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
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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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