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Cheap flights from Key West to Chicago from $104

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.
Multiple Airlines Logo
10:45 am - 9:48 amEYW  Key West-ORD Chicago O'Hare Intl
24h 03m1 stop Tampa
Multiple Airlines Logo
8:19 pm - 12:36 pmORD  Chicago O'Hare Intl-EYW Key West
15h 17m1 stop Tampa
$266Multiple Airlines
Sat, Dec 5 - Mon, Dec 7
Multiple Airlines Logo
10:59 am - 1:09 amEYW  Key West-ORD Chicago O'Hare Intl
15h 10m1 stop Orlando
Multiple Airlines Logo
2:31 pm - 10:19 amORD  Chicago O'Hare Intl-EYW Key West
18h 48m1 stop Orlando
$277Multiple Airlines
Fri, Dec 4 - Mon, Dec 7
Multiple Airlines Logo
10:45 am - 9:48 amEYW  Key West-ORD Chicago O'Hare Intl
24h 03m1 stop Tampa
Multiple Airlines Logo
8:19 pm - 12:36 pmORD  Chicago O'Hare Intl-EYW Key West
15h 17m1 stop Tampa
$298Multiple Airlines
Wed, Dec 2 - Mon, Dec 7
Multiple Airlines Logo
10:45 am - 7:05 amEYW  Key West-ORD Chicago O'Hare Intl
21h 20m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:19 pm - 12:19 pmORD  Chicago O'Hare Intl-EYW Key West
15h 00m1 stop Tampa
$331Multiple Airlines
Wed, Dec 2 - Sun, Dec 6
Multiple Airlines Logo
10:45 am - 7:05 amEYW  Key West-ORD Chicago O'Hare Intl
21h 20m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:19 pm - 12:36 pmORD  Chicago O'Hare Intl-EYW Key West
15h 17m1 stop Tampa
$332Multiple Airlines
Wed, Dec 2 - Mon, Dec 7
Multiple Airlines Logo
10:04 am - 6:23 pmEYW  Key West-ORD Chicago O'Hare Intl
9h 19m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
3:50 pm - 2:13 pmORD  Chicago O'Hare Intl-EYW Key West
21h 23m1 stop Orlando
$338Multiple Airlines
Wed, Sep 30 - Sat, Oct 3
American Airlines Logo
4:49 pm - 7:44 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
American Airlines Logo
12:10 pm - 4:32 pmORD  Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
$339American Airlines
Sat, Dec 5 - Mon, Dec 7
American Airlines Logo
6:25 pm - 9:20 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
American Airlines Logo
12:10 pm - 4:32 pmORD  Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
$339American Airlines
Wed, Dec 2 - Sun, Dec 6
Multiple Airlines Logo
10:45 am - 9:48 amEYW  Key West-ORD Chicago O'Hare Intl
24h 03m1 stop Tampa
Multiple Airlines Logo
8:19 pm - 12:19 pmORD  Chicago O'Hare Intl-EYW Key West
15h 00m1 stop Tampa
$339Multiple Airlines
Wed, Dec 2 - Sun, Dec 6
American Airlines Logo
5:05 pm - 8:00 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 55mnonstop
American Airlines Logo
12:10 pm - 4:32 pmORD  Chicago O'Hare Intl-EYW Key West
3h 22mnonstop
$339American Airlines
Fri, Dec 4 - Mon, Dec 7

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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
Dec 2
EYW6:25 pmKey West
3h 55m
ORD9:20 pmChicago O'Hare Intl
Dec 6
ORD12:10 pmChicago O'Hare Intl
3h 22m
EYW4:32 pmKey West
$339
American Airlines
Dec 2
EYW1:52 pmKey West
6h 44m
1 stop
ORD7:36 pmChicago O'Hare Intl
Dec 7
ORD7:30 amChicago O'Hare Intl
3h 24m
EYW11:54 amKey West
$349
American Airlines
Dec 5
EYW4:11 pmKey West
7h 19m
1 stop
ORD10:30 pmChicago O'Hare Intl
Dec 7
ORD11:47 amChicago O'Hare Intl
5h 09m
1 stop
EYW5:56 pmKey West
$359

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
Sep 26
EYW4:20 pmKey West
3h 39m
ORD6:59 pmChicago O'Hare Intl
Sep 29
ORD5:00 amChicago O'Hare Intl
7h 29m
1 stop
EYW1:29 pmKey West
$429
United Airlines
Sep 26
EYW4:20 pmKey West
3h 39m
ORD6:59 pmChicago O'Hare Intl
Sep 29
ORD6:00 amChicago O'Hare Intl
6h 29m
1 stop
EYW1:29 pmKey West
$470
United Airlines
Sep 25
EYW2:15 pmKey West
9h 13m
1 stop
ORD10:28 pmChicago O'Hare Intl
Sep 28
ORD6:00 amChicago O'Hare Intl
6h 29m
1 stop
EYW1:29 pmKey West
$618

momondo Fare Finder

 
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 Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

10:45 am-9:48 am

1 stop24h 03m

Chicago O'Hare Intl

Mon 12/7

8:19 pm-12:36 pm

1 stop15h 17m

$266

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 12/4

10:59 am-1:09 am

1 stop15h 10m

Chicago O'Hare Intl

Mon 12/7

2:31 pm-10:19 am

1 stop18h 48m

$277

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 12/2

10:45 am-9:48 am

1 stop24h 03m

Chicago O'Hare Intl

Mon 12/7

8:19 pm-12:36 pm

1 stop15h 17m

$298

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 12/2

10:45 am-7:05 am

2 stops21h 20m

Chicago O'Hare Intl

Sun 12/6

8:19 pm-12:19 pm

1 stop15h 00m

$331

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 12/2

10:45 am-7:05 am

2 stops21h 20m

Chicago O'Hare Intl

Mon 12/7

8:19 pm-12:36 pm

1 stop15h 17m

$332

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 9/30

10:04 am-6:23 pm

2 stops9h 19m

Chicago O'Hare Intl

Sat 10/3

3:50 pm-2:13 pm

1 stop21h 23m

$338
Quickest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

4:49 pm-7:44 pm

Nonstop3h 55m

Chicago O'Hare Intl

Mon 12/7

12:10 pm-4:32 pm

Nonstop3h 22m

$339

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 12/2

6:25 pm-9:20 pm

Nonstop3h 55m

Chicago O'Hare Intl

Sun 12/6

12:10 pm-4:32 pm

Nonstop3h 22m

$339

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 12/2

10:45 am-9:48 am

1 stop24h 03m

Chicago O'Hare Intl

Sun 12/6

8:19 pm-12:19 pm

1 stop15h 00m

$339

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 12/4

5:05 pm-8:00 pm

Nonstop3h 55m

Chicago O'Hare Intl

Mon 12/7

12:10 pm-4:32 pm

Nonstop3h 22m

$339

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 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 $443. 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?

You could potentially save up to 43% 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 September 2026, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 12% 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

$104

Fastest flight time

3h 49m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $104. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $266.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 49m
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 49m 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 $319Free CancellationRating
7.1
12,055 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Janesville
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Skokie

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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