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Cheap flights from Key West to Chicago from $91

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 12/27. 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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Multiple Airlines Logo
9:36 pm - 12:26 pmEYW-ORD
15h 50m1 stop
Multiple Airlines Logo
3:26 pm - 11:20 amORD-EYW
18h 54m1 stop
$199Multiple Airlines
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Thu, Nov 13 - Sat, Nov 15
Multiple Airlines Logo
8:55 am - 11:06 pmEYW-ORD
15h 11m1 stop
Multiple Airlines Logo
5:25 am - 8:46 pmORD-EYW
14h 21m1 stop
$206Multiple Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
4:00 pm - 6:46 pmEYW-ORD
3h 46mnonstop
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
$269United Airlines
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Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
3:00 pm - 9:16 pmEYW-ORD
7h 16m1 stop
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
$279United Airlines
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Fri, Nov 14 - Sun, Nov 16
Delta Logo
6:18 pm - 12:02 amEYW-ORD
6h 44m1 stop
Delta Logo
5:23 am - 11:31 amORD-EYW
5h 08m1 stop
$289Delta
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Mon, Nov 24 - Sun, Nov 30
Delta Logo
6:18 pm - 12:02 amEYW-ORD
6h 44m1 stop
Delta Logo
5:23 am - 2:03 pmORD-EYW
7h 40m1 stop
$299Delta
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Mon, Nov 24 - Sun, Nov 30
Spirit Airlines Logo
12:15 pm - 11:06 pmEYW-ORD
11h 51m2 stops
Spirit Airlines Logo
1:55 pm - 11:20 amORD-EYW
20h 25m2 stops
$301Spirit Airlines
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Thu, Nov 13 - Sat, Nov 15
Spirit Airlines Logo
12:15 pm - 12:51 pmEYW-ORD
25h 36m3 stops
Spirit Airlines Logo
1:55 pm - 11:20 amORD-EYW
20h 25m3 stops
$317Spirit Airlines
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Thu, Nov 13 - Sat, Nov 15
American Airlines Logo
4:55 pm - 7:35 pmEYW-ORD
3h 40mnonstop
American Airlines Logo
5:00 am - 12:04 pmORD-EYW
6h 04m1 stop
$358American Airlines
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Mon, Nov 24 - Sat, Nov 29
American Airlines Logo
4:55 pm - 7:35 pmEYW-ORD
3h 40mnonstop
American Airlines Logo
12:02 pm - 4:25 pmORD-EYW
3h 23mnonstop
$377American Airlines
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Mon, Nov 24 - Sat, Nov 29

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
Nov 14
EYW4:00 pmKey West
3h 46m
ORD6:46 pmChicago O'Hare Intl
Nov 16
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
$269
Find similar
United Airlines
Nov 14
EYW3:00 pmKey West
7h 16m
1 stop
ORD9:16 pmChicago O'Hare Intl
Nov 16
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
$279
Find similar
United Airlines
Nov 13
EYW4:00 pmKey West
3h 46m
ORD6:46 pmChicago O'Hare Intl
Nov 15
ORD6:02 amChicago O'Hare Intl
7h 02m
1 stop
EYW2:04 pmKey West
$327
Find similar

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 24
EYW6:18 pmKey West
6h 44m
1 stop
ORD12:02 amChicago O'Hare Intl
Nov 30
ORD5:23 amChicago O'Hare Intl
5h 08m
1 stop
EYW11:31 amKey West
$289
Find similar
Delta
Nov 24
EYW6:18 pmKey West
6h 44m
1 stop
ORD12:02 amChicago O'Hare Intl
Nov 30
ORD5:23 amChicago O'Hare Intl
7h 40m
1 stop
EYW2:03 pmKey West
$299
Find similar
Delta
Oct 28
EYW6:17 pmKey West
6h 41m
1 stop
ORD11:58 pmChicago O'Hare Intl
Nov 9
ORD5:23 amChicago O'Hare Intl
7h 40m
1 stop
EYW2:03 pmKey West
$400
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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 October 27, 2025.
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

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/13

9:36 pm-12:26 pm

1 stop15h 50m

Chicago O'Hare Intl

Sat 11/15

3:26 pm-11:20 am

1 stop18h 54m

$199

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 11/14

8:55 am-11:06 pm

1 stop15h 11m

Chicago O'Hare Intl

Sun 11/16

5:25 am-8:46 pm

1 stop14h 21m

$206

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 11/14

4:00 pm-6:46 pm

Nonstop3h 46m

Chicago O'Hare Intl

Sun 11/16

11:00 am-3:19 pm

Nonstop3h 19m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 11/14

3:00 pm-9:16 pm

1 stop7h 16m

Chicago O'Hare Intl

Sun 11/16

11:00 am-3:19 pm

Nonstop3h 19m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Sun 11/30

5:23 am-11:31 am

1 stop5h 08m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Sun 11/30

5:23 am-2:03 pm

1 stop7h 40m

$299

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/13

12:15 pm-11:06 pm

2 stops11h 51m

Chicago O'Hare Intl

Sat 11/15

1:55 pm-11:20 am

2 stops20h 25m

$301

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/13

12:15 pm-12:51 pm

3 stops25h 36m

Chicago O'Hare Intl

Sat 11/15

1:55 pm-11:20 am

3 stops20h 25m

$317

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

4:55 pm-7:35 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sat 11/29

5:00 am-12:04 pm

1 stop6h 04m

$358

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

4:55 pm-7:35 pm

Nonstop3h 40m

Chicago O'Hare Intl

Sat 11/29

12:02 pm-4:25 pm

Nonstop3h 23m

$377

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 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 Thursday when prices can be found for as low as $343. 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 $939.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $379 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $507. 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 69% 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 2025, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 13% 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

$288

Fastest flight time

3h 25m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $288. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $342.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 25m
Direct flights go from Key West to Chicago O'Hare Intl Airport on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.
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 $224Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
11,033 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 $499, with the best United Airlines deals starting from $224 round-trip. 8,997 users have rated United Airlines on momondo, with an average score of 7.4/10.

Traveling to a place near Chicago?

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

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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