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Cheap flights from Key West to Chicago from $84

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 2/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
6:51 pm - 9:06 am
ORD
-
EYW
37h 15m
2 stops
$214Multiple Airlines
mar., feb. 24 - mar., mar. 3
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
10:19 am - 11:50 am
ORD
-
EYW
24h 31m
1 stop
$229Multiple Airlines
mar., feb. 24 - mar., mar. 3
American Airlines Logo
6:45 pm - 9:37 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
1:51 pm - 6:15 pm
ORD
-
EYW
3h 24mnonstop
$249American Airlines
jue., abr. 9 - lun., abr. 13
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$259United Airlines
jue., feb. 26 - lun., mar. 2
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
7:10 am - 5:44 pm
ORD
-
EYW
9h 34m
1 stop
$269United Airlines
jue., feb. 26 - lun., mar. 2
Multiple Airlines Logo
2:51 pm - 7:59 am
EYW
-
ORD
18h 08m
1 stop
Multiple Airlines Logo
10:17 am - 3:22 pm
ORD
-
EYW
28h 05m
1 stop
$271Multiple Airlines
vie., may. 29 - mié., jun. 3
United Airlines Logo
3:56 pm - 6:35 pm
EYW
-
ORD
3h 39mnonstop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$279United Airlines
jue., feb. 26 - lun., mar. 2
Multiple Airlines Logo
4:10 pm - 5:10 pm
EYW
-
ORD
26h 00m
1 stop
Multiple Airlines Logo
3:49 pm - 11:25 am
ORD
-
EYW
18h 36m
1 stop
$282Multiple Airlines
dom., may. 31 - mié., jun. 3
American Airlines Logo
6:34 pm - 12:06 am
EYW
-
ORD
6h 32m
1 stop
American Airlines Logo
1:59 pm - 6:24 pm
ORD
-
EYW
3h 25mnonstop
$289American Airlines
mar., feb. 24 - mar., mar. 3
Multiple Airlines Logo
12:10 pm - 7:59 am
EYW
-
ORD
20h 49m
1 stop
Multiple Airlines Logo
10:17 am - 10:24 am
ORD
-
EYW
23h 07m
1 stop
$299Multiple Airlines
lun., jun. 1 - mié., jun. 3

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
EYW6:45 pmKey West
3h 52m
ORD9:37 pmChicago O'Hare Intl
Apr 13
ORD1:51 pmChicago O'Hare Intl
3h 24m
EYW6:15 pmKey West
$249
American Airlines
Feb 24
EYW6:34 pmKey West
6h 32m
1 stop
ORD12:06 amChicago O'Hare Intl
Mar 3
ORD1:59 pmChicago O'Hare Intl
3h 25m
EYW6:24 pmKey West
$289
American Airlines
Feb 11
EYW4:01 pmKey West
3h 44m
ORD6:45 pmChicago O'Hare Intl
Feb 15
ORD9:55 amChicago O'Hare Intl
5h 54m
1 stop
EYW4:49 pmKey West
$319

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
Feb 26
EYW6:35 pmKey West
6h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
Mar 2
ORD10:44 amChicago O'Hare Intl
3h 16m
EYW3:00 pmKey West
$259
United Airlines
Feb 26
EYW6:35 pmKey West
6h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
Mar 2
ORD7:10 amChicago O'Hare Intl
9h 34m
1 stop
EYW5:44 pmKey West
$269
United Airlines
Feb 26
EYW3:56 pmKey West
3h 39m
ORD6:35 pmChicago O'Hare Intl
Mar 2
ORD10:44 amChicago O'Hare Intl
3h 16m
EYW3:00 pmKey West
$279

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 enero 29, 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

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 2/24

1:01 pm-5:03 pm

1 stop29h 02m

Chicago O'Hare Intl

mar. 3/3

6:51 pm-9:06 am

2 stops37h 15m

$214

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 2/24

1:01 pm-5:03 pm

1 stop29h 02m

Chicago O'Hare Intl

mar. 3/3

10:19 am-11:50 am

1 stop24h 31m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 4/9

6:45 pm-9:37 pm

Nonstop3h 52m

Chicago O'Hare Intl

lun. 4/13

1:51 pm-6:15 pm

Nonstop3h 24m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 2/26

6:35 pm-11:43 pm

1 stop6h 08m

Chicago O'Hare Intl

lun. 3/2

10:44 am-3:00 pm

Nonstop3h 16m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 2/26

6:35 pm-11:43 pm

1 stop6h 08m

Chicago O'Hare Intl

lun. 3/2

7:10 am-5:44 pm

1 stop9h 34m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 5/29

2:51 pm-7:59 am

1 stop18h 08m

Chicago O'Hare Intl

mié. 6/3

10:17 am-3:22 pm

1 stop28h 05m

$271

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 2/26

3:56 pm-6:35 pm

Nonstop3h 39m

Chicago O'Hare Intl

lun. 3/2

10:44 am-3:00 pm

Nonstop3h 16m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

dom. 5/31

4:10 pm-5:10 pm

1 stop26h 00m

Chicago O'Hare Intl

mié. 6/3

3:49 pm-11:25 am

1 stop18h 36m

$282

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 2/24

6:34 pm-12:06 am

1 stop6h 32m

Chicago O'Hare Intl

mar. 3/3

1:59 pm-6:24 pm

Nonstop3h 25m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

lun. 6/1

12:10 pm-7:59 am

1 stop20h 49m

Chicago O'Hare Intl

mié. 6/3

10:17 am-10:24 am

1 stop23h 07m

$299

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 $348. 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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $429 when looking at flights departing in the afternoon. 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 46% 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 January 2026, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 113% 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

$346

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 $346. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $413.
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
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
11,205 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 $367, with the best United Airlines deals starting from $249 round-trip. 9,215 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

    $289 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 $427, however, with flight time and availability significantly affecting the price. American Airlines (7.2/10 from 11,205 user reviews) flies into Chicago O'Hare Intl Airport from Key West 9 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
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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