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Cheap flights from Key West to Chicago from $126

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 9/1. 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.
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
8:05 am - 12:34 pm
ORD
-
EYW
27h 29m
2 stops
$262Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
8:05 am - 12:34 pm
ORD
-
EYW
27h 29m
2 stops
$263Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
10:59 am - 10:20 am
EYW
-
ORD
24h 21m
1 stop
Multiple Airlines Logo
10:26 am - 12:19 pm
ORD
-
EYW
24h 53m
2 stops
$274Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
12:07 pm - 11:08 pm
EYW
-
ORD
12h 01m
1 stop
Multiple Airlines Logo
7:05 am - 12:34 pm
ORD
-
EYW
52h 29m
2 stops
$285Multiple Airlines
Mon, Aug 24 - Sun, Aug 30
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
8:05 am - 12:34 pm
ORD
-
EYW
27h 29m
2 stops
$305Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
Multiple Airlines Logo
8:05 am - 12:34 pm
ORD
-
EYW
27h 29m
2 stops
$316Multiple Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
11:59 am - 4:18 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Wed, Aug 26 - Mon, Aug 31
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
11:59 am - 4:18 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Fri, Sep 4 - Sun, Sep 6
American Airlines Logo
4:56 pm - 7:48 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
12:08 pm - 4:27 pm
ORD
-
EYW
3h 19mnonstop
$319American Airlines
Mon, Aug 24 - Sun, Aug 30

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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
Oct 7
EYW6:10 pmKey West
6h 42m
1 stop
ORD11:52 pmChicago O'Hare Intl
Oct 9
ORD11:21 amChicago O'Hare Intl
7h 40m
1 stop
EYW8:01 pmKey West
$460
Delta
Oct 1
EYW11:42 amKey West
9h 48m
2 stops
ORD8:30 pmChicago O'Hare Intl
Oct 3
ORD1:51 pmChicago O'Hare Intl
5h 09m
1 stop
EYW8:00 pmKey West
$695
Delta
Aug 26
EYW11:48 amKey West
6h 03m
1 stop
ORD4:51 pmChicago O'Hare Intl
Aug 31
ORD8:28 amChicago O'Hare Intl
10h 29m
2 stops
EYW7:57 pmKey West
$723

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
Sep 3
EYW4:56 pmKey West
3h 52m
ORD7:48 pmChicago O'Hare Intl
Sep 7
ORD11:59 amChicago O'Hare Intl
3h 19m
EYW4:18 pmKey West
$319
American Airlines
Sep 3
EYW4:56 pmKey West
3h 52m
ORD7:48 pmChicago O'Hare Intl
Sep 7
ORD5:00 amChicago O'Hare Intl
4h 56m
1 stop
EYW10:56 amKey West
$329
American Airlines
Oct 1
EYW1:47 pmKey West
6h 51m
1 stop
ORD7:38 pmChicago O'Hare Intl
Oct 3
ORD11:50 amChicago O'Hare Intl
5h 05m
1 stop
EYW5:55 pmKey West
$331

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 August 1, 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

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$262

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$263

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/10

10:59 am-10:20 am

1 stop24h 21m

Chicago O'Hare Intl

Sun 9/13

10:26 am-12:19 pm

2 stops24h 53m

$274

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 8/24

12:07 pm-11:08 pm

1 stop12h 01m

Chicago O'Hare Intl

Sun 8/30

7:05 am-12:34 pm

2 stops52h 29m

$285

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$305

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$316
Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 8/26

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 8/31

11:59 am-4:18 pm

Nonstop3h 19m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 9/7

11:59 am-4:18 pm

Nonstop3h 19m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 9/4

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Sun 9/6

12:08 pm-4:27 pm

Nonstop3h 19m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 8/24

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Sun 8/30

12:08 pm-4:27 pm

Nonstop3h 19m

$319

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?

Prices are currently low for flights on this route.

Typical prices usually range from $353 to $409.
The lowest price recently found on this route was $262.

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 $438. 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?

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

$328

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 $328. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $343.
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 $329Free CancellationRating
7.1
11,845 reviews
Search American Airlines flights

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

    Across 1 American Airlines flight from Key West to Chicago O'Hare Intl Airport this week, the average price was $460, with the best American Airlines deals starting from $329 round-trip. 11,845 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
Lake Geneva
Schaumburg
South Haven
Merrillville
Rockford
Gurnee
Rosemont
Orland Park
Oak Brook
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
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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