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Cheap flights from Key West to Chicago from $134

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
11:19 am - 12:55 amEYW  Key West-ORD Chicago O'Hare Intl
14h 36m1 stop Orlando
Multiple Airlines Logo
6:00 am - 10:19 amORD  Chicago O'Hare Intl-EYW Key West
27h 19m2 stops Atlanta Hartsfield-Jackson Orlando
$242Multiple Airlines
Wed, Feb 3 - Sat, Feb 6
Multiple Airlines Logo
6:25 pm - 11:50 amEYW  Key West-ORD Chicago O'Hare Intl
18h 25m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:16 pm - 10:23 amORD  Chicago O'Hare Intl-EYW Key West
16h 07m1 stop Orlando
$292Multiple Airlines
Thu, Jan 28 - Sat, Jan 30
American Airlines Logo
5:58 pm - 8:59 pmEYW  Key West-ORD Chicago O'Hare Intl
4h 01mnonstop
American Airlines Logo
10:30 am - 5:31 pmORD  Chicago O'Hare Intl-EYW Key West
6h 01m1 stop Miami
$303American Airlines
Thu, Jan 28 - Sat, Jan 30
American Airlines Logo
5:16 pm - 8:09 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 53mnonstop
American Airlines Logo
10:12 am - 5:19 pmORD  Chicago O'Hare Intl-EYW Key West
6h 07m1 stop Miami
$304American Airlines
Thu, Dec 3 - Wed, Dec 9
Multiple Airlines Logo
6:26 pm - 10:14 pmEYW  Key West-ORD Chicago O'Hare Intl
28h 48m1 stop Tampa St. Petersburg
Multiple Airlines Logo
4:00 pm - 2:31 pmORD  Chicago O'Hare Intl-EYW Key West
21h 31m2 stops Atlanta Hartsfield-Jackson Tampa
$306Multiple Airlines
Sat, Dec 5 - Sat, Dec 12
Multiple Airlines Logo
3:31 pm - 9:13 amEYW  Key West-ORD Chicago O'Hare Intl
18h 42m1 stop Tampa St. Petersburg
Multiple Airlines Logo
5:32 pm - 3:17 pmORD  Chicago O'Hare Intl-EYW Key West
20h 45m2 stops Atlanta Hartsfield-Jackson Tampa
$308Multiple Airlines
Mon, Jan 25 - Fri, Jan 29
Multiple Airlines Logo
12:19 pm - 9:13 amEYW  Key West-ORD Chicago O'Hare Intl
21h 54m1 stop Tampa
Multiple Airlines Logo
10:18 am - 11:26 amORD  Chicago O'Hare Intl-EYW Key West
24h 08m1 stop Tampa
$309Multiple Airlines
Wed, Feb 3 - Sat, Feb 6
American Airlines Logo
5:01 pm - 9:41 pmEYW  Key West-ORD Chicago O'Hare Intl
5h 40m1 stop Miami
American Airlines Logo
9:00 am - 5:21 pmORD  Chicago O'Hare Intl-EYW Key West
7h 21m1 stop Charlotte Douglas
$313American Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
1:17 pm - 5:29 pmEYW  Key West-ORD Chicago O'Hare Intl
5h 12m1 stop Charlotte Douglas
American Airlines Logo
10:12 am - 5:19 pmORD  Chicago O'Hare Intl-EYW Key West
6h 07m1 stop Miami
$313American Airlines
Thu, Dec 3 - Wed, Dec 9
American Airlines Logo
11:32 am - 3:43 pmEYW  Key West-ORD Chicago O'Hare Intl
5h 11m1 stop Miami
American Airlines Logo
10:30 am - 5:31 pmORD  Chicago O'Hare Intl-EYW Key West
6h 01m1 stop Miami
$313American Airlines
Thu, Jan 28 - Sat, Jan 30

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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
Dec 3
EYW4:10 pmKey West
3h 50m
ORD7:00 pmChicago O'Hare Intl
Dec 9
ORD7:00 amChicago O'Hare Intl
3h 24m
EYW11:24 amKey West
$403
United Airlines
Jan 28
EYW4:09 pmKey West
3h 51m
ORD7:00 pmChicago O'Hare Intl
Jan 30
ORD7:31 amChicago O'Hare Intl
3h 45m
EYW12:16 pmKey West
$481
United Airlines
Mar 7
EYW4:45 pmKey West
8h 55m
1 stop
ORD12:40 amChicago O'Hare Intl
Mar 11
ORD5:55 pmChicago O'Hare Intl
3h 35m
EYW10:30 pmKey West
$545

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
Nov 7
EYW7:40 amKey West
7h 48m
1 stop
ORD2:28 pmChicago O'Hare Intl
Nov 12
ORD1:30 pmChicago O'Hare Intl
5h 30m
1 stop
EYW8:00 pmKey West
$550
Delta
Nov 7
EYW7:40 amKey West
10h 01m
2 stops
ORD4:41 pmChicago O'Hare Intl
Nov 13
ORD1:30 pmChicago O'Hare Intl
5h 30m
1 stop
EYW8:00 pmKey West
$779
Delta
Nov 8
EYW7:40 amKey West
5h 33m
1 stop
ORD12:13 pmChicago O'Hare Intl
Nov 13
ORD6:49 amChicago O'Hare Intl
5h 10m
1 stop
EYW12:59 pmKey West
$927

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

Wed 2/3

11:19 am-12:55 am

1 stop14h 36m

Chicago O'Hare Intl

Sat 2/6

6:00 am-10:19 am

2 stops27h 19m

$242

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

6:25 pm-11:50 am

2 stops18h 25m

Chicago O'Hare Intl

Sat 1/30

5:16 pm-10:23 am

1 stop16h 07m

$292

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

5:58 pm-8:59 pm

Nonstop4h 01m

Chicago O'Hare Intl

Sat 1/30

10:30 am-5:31 pm

1 stop6h 01m

$303
Quickest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 12/3

5:16 pm-8:09 pm

Nonstop3h 53m

Chicago O'Hare Intl

Wed 12/9

10:12 am-5:19 pm

1 stop6h 07m

$304

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

6:26 pm-10:14 pm

1 stop28h 48m

Chicago O'Hare Intl

Sat 12/12

4:00 pm-2:31 pm

2 stops21h 31m

$306

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Mon 1/25

3:31 pm-9:13 am

1 stop18h 42m

Chicago O'Hare Intl

Fri 1/29

5:32 pm-3:17 pm

2 stops20h 45m

$308

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 2/3

12:19 pm-9:13 am

1 stop21h 54m

Chicago O'Hare Intl

Sat 2/6

10:18 am-11:26 am

1 stop24h 08m

$309

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

5:01 pm-9:41 pm

1 stop5h 40m

Chicago O'Hare Intl

Sat 12/12

9:00 am-5:21 pm

1 stop7h 21m

$313

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 12/3

1:17 pm-5:29 pm

1 stop5h 12m

Chicago O'Hare Intl

Wed 12/9

10:12 am-5:19 pm

1 stop6h 07m

$313

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

11:32 am-3:43 pm

1 stop5h 11m

Chicago O'Hare Intl

Sat 1/30

10:30 am-5:31 pm

1 stop6h 01m

$313

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 March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Key West averaging around $0.

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 $856.

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 $470. 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 49% 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 October 2026, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 122% 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

$134

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 $134. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $242.
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
7.0
12,222 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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

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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