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Cheap flights from Key West to Chicago from $129

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
8:34 am - 10:59 pmEYW  Key West-ORD Chicago O'Hare Intl
15h 25m1 stop Orlando Sanford Intl
Multiple Airlines Logo
7:11 am - 9:24 amORD  Chicago O'Hare Intl-EYW Key West
25h 13m2 stops Fort Lauderdale Tampa
$279Multiple Airlines
Fri, Oct 2 - Tue, Oct 6
Multiple Airlines Logo
8:34 am - 7:31 amEYW  Key West-ORD Chicago O'Hare Intl
23h 57m1 stop Orlando Sanford Intl
Multiple Airlines Logo
6:00 am - 12:02 pmORD  Chicago O'Hare Intl-EYW Key West
29h 02m2 stops Atlanta Hartsfield-Jackson Tampa
$286Multiple Airlines
Fri, Oct 16 - Tue, Oct 20
Multiple Airlines Logo
10:59 am - 10:59 pmEYW  Key West-ORD Chicago O'Hare Intl
13h 00m1 stop Orlando
Multiple Airlines Logo
7:28 pm - 9:24 amORD  Chicago O'Hare Intl-EYW Key West
36h 56m2 stops Atlanta Hartsfield-Jackson Tampa
$294Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
10:59 am - 10:59 pmEYW  Key West-ORD Chicago O'Hare Intl
13h 00m1 stop Orlando
Multiple Airlines Logo
7:11 am - 9:24 amORD  Chicago O'Hare Intl-EYW Key West
25h 13m2 stops Fort Lauderdale Tampa
$311Multiple Airlines
Fri, Sep 18 - Fri, Sep 25
American Airlines Logo
4:00 pm - 6:44 pmEYW  Key West-ORD Chicago O'Hare Intl
3h 44mnonstop
American Airlines Logo
10:01 am - 4:49 pmORD  Chicago O'Hare Intl-EYW Key West
5h 48m1 stop Miami
$329American Airlines
Thu, Jan 28 - Sat, Jan 30
American Airlines Logo
1:47 pm - 6:07 pmEYW  Key West-ORD Chicago O'Hare Intl
5h 20m1 stop Miami
American Airlines Logo
8:05 am - 4:11 pmORD  Chicago O'Hare Intl-EYW Key West
7h 06m1 stop Charlotte Douglas
$331American Airlines
Fri, Oct 2 - Tue, Oct 6
American Airlines Logo
12:29 pm - 5:51 pmEYW  Key West-ORD Chicago O'Hare Intl
6h 22m1 stop Charlotte Douglas
American Airlines Logo
10:01 am - 4:58 pmORD  Chicago O'Hare Intl-EYW Key West
5h 57m1 stop Miami
$339American Airlines
Sat, Oct 17 - Sat, Oct 24
American Airlines Logo
4:04 pm - 11:00 pmEYW  Key West-ORD Chicago O'Hare Intl
7h 56m1 stop Charlotte Douglas
American Airlines Logo
10:01 am - 7:10 pmORD  Chicago O'Hare Intl-EYW Key West
8h 09m1 stop Miami
$339American Airlines
Thu, Jan 28 - Sat, Jan 30
American Airlines Logo
1:43 pm - 7:55 pmEYW  Key West-ORD Chicago O'Hare Intl
7h 12m1 stop Miami
American Airlines Logo
8:05 am - 2:36 pmORD  Chicago O'Hare Intl-EYW Key West
5h 31m1 stop Charlotte Douglas
$339American Airlines
Fri, Oct 16 - Tue, Oct 20
Multiple Airlines Logo
10:59 am - 10:59 pmEYW  Key West-ORD Chicago O'Hare Intl
13h 00m1 stop Orlando
Multiple Airlines Logo
7:11 am - 9:24 amORD  Chicago O'Hare Intl-EYW Key West
49h 13m2 stops Fort Lauderdale Tampa
$340Multiple Airlines
Thu, Sep 10 - Mon, Sep 14

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American Airlines flights from Key West to Chicago

Our best American Airlines deals on Key West to Chicago flight tickets
American Airlines
Jan 28
EYW4:00 pmKey West
3h 44m
ORD6:44 pmChicago O'Hare Intl
Jan 30
ORD10:01 amChicago O'Hare Intl
5h 48m
1 stop
EYW4:49 pmKey West
$329
American Airlines
Oct 2
EYW1:47 pmKey West
5h 20m
1 stop
ORD6:07 pmChicago O'Hare Intl
Oct 6
ORD8:05 amChicago O'Hare Intl
7h 06m
1 stop
EYW4:11 pmKey West
$331
American Airlines
Oct 16
EYW1:43 pmKey West
7h 12m
1 stop
ORD7:55 pmChicago O'Hare Intl
Oct 20
ORD8:05 amChicago O'Hare Intl
5h 31m
1 stop
EYW2:36 pmKey West
$339

Delta flights from Key West to Chicago

Our best Delta deals on Key West to Chicago flight tickets
Delta
Sep 24
EYW7:40 amKey West
5h 14m
1 stop
MDW11:54 amChicago Midway
Sep 28
MDW10:48 amChicago Midway
5h 35m
1 stop
EYW5:23 pmKey West
$359
Delta
Sep 5
EYW1:31 pmKey West
6h 28m
1 stop
ORD6:59 pmChicago O'Hare Intl
Sep 8
ORD6:40 amChicago O'Hare Intl
5h 13m
1 stop
EYW12:53 pmKey West
$396
Delta
Sep 10
EYW6:19 pmKey West
5h 25m
1 stop
MDW10:44 pmChicago Midway
Sep 14
MDW1:00 pmChicago Midway
6h 00m
1 stop
EYW8:00 pmKey West
$416

momondo Fare Finder

 
Use the filters below to find and compare flights from Key West to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 10/2

8:34 am-10:59 pm

1 stop15h 25m

Chicago O'Hare Intl

Tue 10/6

7:11 am-9:24 am

2 stops25h 13m

$279

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 10/16

8:34 am-7:31 am

1 stop23h 57m

Chicago O'Hare Intl

Tue 10/20

6:00 am-12:02 pm

2 stops29h 02m

$286

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/24

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Mon 9/28

7:28 pm-9:24 am

2 stops36h 56m

$294

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 9/18

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Fri 9/25

7:11 am-9:24 am

2 stops25h 13m

$311
Quickest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

4:00 pm-6:44 pm

Nonstop3h 44m

Chicago O'Hare Intl

Sat 1/30

10:01 am-4:49 pm

1 stop5h 48m

$329

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 10/2

1:47 pm-6:07 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 10/6

8:05 am-4:11 pm

1 stop7h 06m

$331

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 10/17

12:29 pm-5:51 pm

1 stop6h 22m

Chicago O'Hare Intl

Sat 10/24

10:01 am-4:58 pm

1 stop5h 57m

$339

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

4:04 pm-11:00 pm

1 stop7h 56m

Chicago O'Hare Intl

Sat 1/30

10:01 am-7:10 pm

1 stop8h 09m

$339

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 10/16

1:43 pm-7:55 pm

1 stop7h 12m

Chicago O'Hare Intl

Tue 10/20

8:05 am-2:36 pm

1 stop5h 31m

$339

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/10

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Mon 9/14

7:11 am-9:24 am

2 stops49h 13m

$340

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

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?

The month of March is, on average, the cheapest month to fly to Chicago from Key West, with most prices found around $0. If you’re not able to fly to Chicago in March, then December is your next best option. Flight prices from Key West to Chicago during December average around $268.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $484.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Key West to Chicago during this time can be as low as $366. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $442.

What is the cheapest Key West to Chicago flight route?

Fly from Key West to Chicago O'Hare Intl for the best Key West - Chicago flight prices

What cabin class options are available on Key West to Chicago flights?

There are 4 cabin classes available to choose from on Key West to Chicago 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 flights?

You could potentially save up to 43% on your flight if you consider stops on a Key West to Chicago flight.

How have Key West to Chicago flight prices changed over time?

When to book flights from Key West to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Key West to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Key West to Chicago (EYW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Chicago

Best Price Found

$129

Fastest flight time

2h 27m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Key West in the past 72 hours is $129. The best round-trip flight deal from Key West to Chicago found on momondo in the last 72 hours is $279.
The fastest flight from Key West to Chicago takes 2h 27m
Direct flights go from Key West to Chicago every day.
There are 3 airports in Chicago. From Key West there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Key West to Chicago

  • How far is Key West to Chicago by plane?

    Chicago is 1241.6 mi away from Key West. In terms of flight time, this usually takes a little over 2h 27m.

  • When did momondo last update prices for flights from Key West Airport to Chicago?

    Prices for flights from Key West Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Key West Airport to Chicago?

  • How old do you have to be to fly from Key West Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Key West Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Key West to Chicago?

  • What is the most popular airline from Key West to Chicago?

Best airlines flying from Key West to Chicago

Compare and see reviews for airlines that fly from Key West to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $319Free CancellationRating
7.1
11,995 reviews
Search American Airlines flights

  • American Airlines Flights From Key West to Chicago

    Across 3 American Airlines flights from Key West to Chicago this week, the average price was $409, with the best American Airlines deals starting from $319 round-trip. 11,993 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
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Chicago?

It is quick and easy to find Key West to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Key West to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Key West on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Key West to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Key West. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Key West to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport