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Cheap flights from Chicago to Key West from $53

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 3/2. 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.
Delta Logo
7:14 am - 1:44 pm
ORD
-
EYW
5h 30m
1 stop
Delta Logo
7:33 am - 1:14 pm
EYW
-
ORD
6h 41m
1 stop
$294Delta
Tue, Apr 14 - Sat, Apr 18
Multiple Airlines Logo
4:51 pm - 9:06 am
ORD
-
EYW
15h 15m
2 stops
Multiple Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
$295Multiple Airlines
Wed, Mar 25 - Tue, Apr 7
American Airlines Logo
9:55 am - 4:47 pm
ORD
-
EYW
5h 52m
1 stop
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
$296American Airlines
Sat, Apr 4 - Thu, Apr 9
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m
1 stop
Multiple Airlines Logo
1:01 pm - 9:13 pm
EYW
-
ORD
33h 12m
2 stops
$297Multiple Airlines
Fri, Feb 20 - Tue, Feb 24
Spirit Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m
1 stop
Spirit Airlines Logo
2:25 pm - 6:18 pm
EYW
-
ORD
28h 53m
3 stops
$298Spirit Airlines
Mon, Feb 16 - Thu, Feb 19
Multiple Airlines Logo
4:18 pm - 9:06 am
ORD
-
EYW
15h 48m
1 stop
Multiple Airlines Logo
11:51 am - 11:36 pm
EYW
-
ORD
12h 45m
1 stop
$300Multiple Airlines
Wed, Mar 25 - Wed, Apr 1
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m
1 stop
Multiple Airlines Logo
9:46 am - 10:56 am
EYW
-
ORD
26h 10m
2 stops
$301Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
5:25 am - 3:42 pm
ORD
-
EYW
9h 17m
1 stop
Multiple Airlines Logo
9:49 am - 1:12 am
EYW
-
ORD
16h 23m
1 stop
$302Multiple Airlines
Sun, Apr 5 - Fri, Apr 10
Spirit Airlines Logo
7:00 am - 1:30 pm
ORD
-
EYW
5h 30m
1 stop
Spirit Airlines Logo
2:25 pm - 12:40 am
EYW
-
ORD
35h 15m
3 stops
$303Spirit Airlines
Thu, Feb 26 - Mon, Mar 2
Multiple Airlines Logo
11:25 am - 2:38 pm
ORD
-
EYW
26h 13m
1 stop
Multiple Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
$304Multiple Airlines
Fri, Apr 3 - Tue, Apr 7

Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Apr 14
ORD7:14 amChicago O'Hare Intl
5h 30m
1 stop
EYW1:44 pmKey West
Apr 18
EYW7:33 amKey West
6h 41m
1 stop
ORD1:14 pmChicago O'Hare Intl
$294
Delta
Feb 16
ORD5:25 amChicago O'Hare Intl
7h 23m
1 stop
EYW1:48 pmKey West
Feb 25
EYW5:56 pmKey West
7h 00m
1 stop
ORD11:56 pmChicago O'Hare Intl
$324
Delta
Mar 2
MDW10:49 amChicago Midway
5h 12m
1 stop
EYW5:01 pmKey West
Mar 9
EYW6:25 pmKey West
5h 06m
1 stop
MDW10:31 pmChicago Midway
$334

United Airlines flights from Chicago to Key West

Our best United Airlines deals on Chicago to Key West flight tickets
United Airlines
Feb 19
ORD5:45 pmChicago O'Hare Intl
3h 24m
EYW10:09 pmKey West
Feb 25
EYW3:56 pmKey West
3h 39m
ORD6:35 pmChicago O'Hare Intl
$309
United Airlines
Mar 11
ORD5:55 pmChicago O'Hare Intl
3h 24m
EYW10:19 pmKey West
Mar 16
EYW4:05 pmKey West
3h 39m
ORD6:44 pmChicago O'Hare Intl
$327
United Airlines
Feb 14
ORD5:45 pmChicago O'Hare Intl
3h 24m
EYW10:09 pmKey West
Feb 26
EYW6:35 pmKey West
6h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
$335

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 February 3, 2026.
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 4/14

7:14 am-1:44 pm

1 stop5h 30m

Key West

Sat 4/18

7:33 am-1:14 pm

1 stop6h 41m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 3/25

4:51 pm-9:06 am

2 stops15h 15m

Key West

Tue 4/7

12:25 pm-7:51 pm

1 stop8h 26m

$295

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 4/4

9:55 am-4:47 pm

1 stop5h 52m

Key West

Thu 4/9

6:46 pm-9:35 pm

Nonstop3h 49m

$296

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 2/20

5:15 am-1:30 pm

1 stop7h 15m

Key West

Tue 2/24

1:01 pm-9:13 pm

2 stops33h 12m

$297

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 2/16

5:15 am-1:30 pm

1 stop7h 15m

Key West

Thu 2/19

2:25 pm-6:18 pm

3 stops28h 53m

$298

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 3/25

4:18 pm-9:06 am

1 stop15h 48m

Key West

Wed 4/1

11:51 am-11:36 pm

1 stop12h 45m

$300

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 3/5

5:15 am-1:30 pm

1 stop7h 15m

Key West

Sun 3/8

9:46 am-10:56 am

2 stops26h 10m

$301

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 4/5

5:25 am-3:42 pm

1 stop9h 17m

Key West

Fri 4/10

9:49 am-1:12 am

1 stop16h 23m

$302

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 2/26

7:00 am-1:30 pm

1 stop5h 30m

Key West

Mon 3/2

2:25 pm-12:40 am

3 stops35h 15m

$303

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 4/3

11:25 am-2:38 pm

1 stop26h 13m

Key West

Tue 4/7

12:25 pm-7:51 pm

1 stop8h 26m

$304

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 $380. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Key West for around $523.

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 morning, with an average ticket price of $469. Departure times in the morning 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 $430 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 $366 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?

You could potentially save up to 6% on your flight if you consider stops on a Chicago to Key West flight.

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

As of February 2026, prices for Chicago to Key West flights are approximately 90% 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

$236

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 $236. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $329.
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 $145Free CancellationRating
6.3
8,407 reviews
Search Spirit Airlines flights
DeltaPriceFrom $248Free CancellationRating
7.9
8,138 reviews
Search Delta flights
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
American AirlinesPriceFrom $322Free CancellationRating
7.2
11,216 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 7 United Airlines flights for this route in a normal week, average airfare is usually $443 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 11,216 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Key West about 14 times each week, with ticket deals ranging from $322 to $460. 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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