Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
9:01 am - 2:37 pmEYW-MDW
6h 36m1 stop
Multiple Airlines Logo
6:06 pm - 9:17 amMDW-EYW
14h 11m1 stop
$193Multiple Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
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
Find Deal
Thu, Nov 13 - Sat, Nov 15
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
Find Deal
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
Find Deal
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
Find Deal
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
Find Deal
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
Find Deal
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
Find Deal
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
Find Deal
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
Find Deal
Mon, Nov 24 - Sat, Nov 29

United Airlines flights from Key West to Chicago

Our best United Airlines deals on Key West to Chicago 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

Our best Delta deals on Key West to Chicago 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
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Chicago 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 that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 11/14

9:01 am-2:37 pm

1 stop6h 36m

Chicago Midway

Sun 11/16

6:06 pm-9:17 am

1 stop14h 11m

$193

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

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
1
2

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $939.

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 at noon. Flights from Key West to Chicago during this time can be as low as $379. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $507.

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 69% on your flight if you consider stops on a Key West to Chicago flight.

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

$288

Fastest flight time

3h 25m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Key West in the past 72 hours is $288. The best round-trip flight deal from Key West to Chicago found on momondo in the last 72 hours is $354.
The fastest flight from Key West to Chicago takes 3h 25m
Direct flights go from Key West to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • 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 3h 39m.

  • 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
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

    Across 7 United Airlines flights from Key West to Chicago 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 11/26
Wed 12/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport