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Cheap flights from Chicago to Key West from $85

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Key West departing on 1/15. 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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Find the cheapest flights from Chicago to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:32 pm - 7:20 pm
ORD
-
EYW
5h 48m1 stop
American Airlines Logo
6:44 pm - 9:29 pm
EYW
-
ORD
3h 45mnonstop
$286American Airlines
Tue, Feb 24 - Thu, Mar 5
Spirit Airlines Logo
9:34 am - 11:20 am
ORD
-
EYW
24h 46m3 stops
Spirit Airlines Logo
2:25 pm - 9:03 pm
EYW
-
ORD
7h 38m1 stop
$287Spirit Airlines
Mon, Jan 5 - Mon, Jan 12
Spirit Airlines Logo
5:00 am - 1:30 pm
ORD
-
EYW
7h 30m1 stop
Spirit Airlines Logo
2:30 pm - 6:16 pm
EYW
-
ORD
28h 46m3 stops
$288Spirit Airlines
Mon, Jan 5 - Wed, Jan 7
United Airlines Logo
10:45 am - 3:12 pm
ORD
-
EYW
3h 27mnonstop
United Airlines Logo
6:05 pm - 11:39 pm
EYW
-
ORD
6h 34m1 stop
$289United Airlines
Fri, Jan 2 - Fri, Jan 9
Multiple Airlines Logo
1:20 pm - 9:06 am
MDW
-
EYW
18h 46m2 stops
Multiple Airlines Logo
9:46 am - 7:52 pm
EYW
-
MDW
11h 06m1 stop
$289Multiple Airlines
Wed, Feb 4 - Sun, Feb 8
Multiple Airlines Logo
5:00 am - 1:30 pm
ORD
-
EYW
7h 30m1 stop
Multiple Airlines Logo
10:49 am - 4:58 pm
EYW
-
ORD
7h 09m1 stop
$290Multiple Airlines
Mon, Jan 5 - Sat, Jan 10
Multiple Airlines Logo
5:00 am - 1:30 pm
ORD
-
EYW
7h 30m1 stop
Multiple Airlines Logo
12:20 pm - 10:39 pm
EYW
-
ORD
35h 19m2 stops
$291Multiple Airlines
Fri, Jan 2 - Tue, Jan 6
Multiple Airlines Logo
8:27 pm - 9:26 am
ORD
-
EYW
11h 59m1 stop
Multiple Airlines Logo
12:51 pm - 7:38 pm
EYW
-
ORD
7h 47m1 stop
$292Multiple Airlines
Sat, Jan 10 - Sun, Jan 11
Delta Logo
11:01 am - 7:42 pm
MDW
-
EYW
7h 41m1 stop
Delta Logo
6:07 pm - 10:42 pm
EYW
-
MDW
5h 35m1 stop
$294Delta
Sat, Feb 21 - Wed, Feb 25
Delta Logo
11:33 am - 7:41 pm
ORD
-
EYW
7h 08m1 stop
Delta Logo
6:00 pm - 11:55 pm
EYW
-
ORD
6h 55m1 stop
$294Delta
Sat, Apr 11 - Wed, Apr 15

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Feb 24
ORD7:58 amChicago O'Hare Intl
6h 34m
1 stop
EYW3:32 pmKey West
Mar 5
EYW6:44 pmKey West
3h 45m
ORD9:29 pmChicago O'Hare Intl
$286
Find similar
American Airlines
Jan 26
ORD8:14 amChicago O'Hare Intl
3h 31m
EYW12:45 pmKey West
Jan 29
EYW4:01 pmKey West
3h 44m
ORD6:45 pmChicago O'Hare Intl
$297
Find similar
American Airlines
Jan 30
ORD6:05 amChicago O'Hare Intl
5h 37m
1 stop
EYW12:42 pmKey West
Feb 3
EYW1:06 pmKey West
3h 40m
ORD3:46 pmChicago O'Hare Intl
$307
Find similar

Spirit Airlines flights from Chicago to Key West

Our best Spirit Airlines deals on Chicago to Key West flight tickets
Spirit Airlines
Jan 5
ORD9:34 amChicago O'Hare Intl
24h 46m
3 stops
EYW11:20 amKey West
Jan 12
EYW2:25 pmKey West
7h 38m
1 stop
ORD9:03 pmChicago O'Hare Intl
$287
Find similar
Spirit Airlines
Jan 5
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
EYW1:30 pmKey West
Jan 7
EYW2:30 pmKey West
28h 46m
3 stops
ORD6:16 pmChicago O'Hare Intl
$288
Find similar
Spirit Airlines
Mar 30
ORD7:41 pmChicago O'Hare Intl
14h 49m
1 stop
EYW11:30 amKey West
Apr 7
EYW12:25 pmKey West
24h 01m
1 stop
ORD11:26 amChicago O'Hare Intl
$295
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Key West 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/24

12:32 pm-7:20 pm

1 stop5h 48m

Key West

Thu 3/5

6:44 pm-9:29 pm

Nonstop3h 45m

$286

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 1/5

9:34 am-11:20 am

3 stops24h 46m

Key West

Mon 1/12

2:25 pm-9:03 pm

1 stop7h 38m

$287

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 1/5

5:00 am-1:30 pm

1 stop7h 30m

Key West

Wed 1/7

2:30 pm-6:16 pm

3 stops28h 46m

$288

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/2

10:45 am-3:12 pm

Nonstop3h 27m

Key West

Fri 1/9

6:05 pm-11:39 pm

1 stop6h 34m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/4

1:20 pm-9:06 am

2 stops18h 46m

Key West

Sun 2/8

9:46 am-7:52 pm

1 stop11h 06m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 1/5

5:00 am-1:30 pm

1 stop7h 30m

Key West

Sat 1/10

10:49 am-4:58 pm

1 stop7h 09m

$290

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/2

5:00 am-1:30 pm

1 stop7h 30m

Key West

Tue 1/6

12:20 pm-10:39 pm

2 stops35h 19m

$291

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 1/10

8:27 pm-9:26 am

1 stop11h 59m

Key West

Sun 1/11

12:51 pm-7:38 pm

1 stop7h 47m

$292

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 2/21

11:01 am-7:42 pm

1 stop7h 41m

Key West

Wed 2/25

6:07 pm-10:42 pm

1 stop5h 35m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 4/11

11:33 am-7:41 pm

1 stop7h 08m

Key West

Wed 4/15

6:00 pm-11:55 pm

1 stop6h 55m

$294

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 Key West from

How to get the cheapest flight ticket from Chicago to Key West

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 Chicago and Key West?

What is the cheapest month to fly to Key West?

In general, January is the cheapest month to fly from Chicago to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $395. If you are unable to visit Key West during the month of January, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $399.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $383. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Key West for around $541.

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

According to our data, the cheapest time of day to fly to Key West is in the afternoon. momondo users have found flights departing from Chicago to Key West in the afternoon for as low as $454. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Key West flight route?

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

How far in advance should I book a flight to Key West?

You are more likely to see cheaper flights to Key West from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $441 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Chicago for as low as $374 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Key West 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 Chicago to Key West flights?

No. A direct flight is the cheapest option for a flight between Chicago to Key West.

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

As of December 2025, prices for Chicago to Key West flights are approximately 130% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Key West

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

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

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

Best Price Found

$293

Fastest flight time

3h 11m

Direct flights

Every day

Airports in Key West

1 airport
The best one-way flight to Key West from Chicago in the past 72 hours is $293. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $342.
The fastest flight from Chicago to Key West takes 3h 11m
Direct flights go from Chicago to Key West every day.
There is 1 airport in Key West. From Chicago there are direct flights to Key West (EYW).
Search flight deals

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 11m is a normal flight duration for this route.

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

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

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

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

    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 Chicago to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents you'll need for your trip to Key West Airport 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 Key West Airport. 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 Chicago to Key West?

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

Best airlines flying from Chicago to Key West

Compare and see reviews for airlines that fly from Chicago to Key West with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $199Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
DeltaPriceFrom $248Free CancellationRating
7.9
8,005 reviews
Search Delta flights
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
American AirlinesPriceFrom $323Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Key West

    United Airlines flight deals from Chicago to Key West start from $249 round-trip. Over the 3 United Airlines flights for this route in a normal week, average airfare is usually $486 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 11,055 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Key West about 2 times each week, with ticket deals ranging from $323 to $459. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Key West. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Key West from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

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

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

Price alerts on flights to Key West from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Key West 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.
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