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Cheap flights from Chicago to Key West from $90

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 1/18. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:00 am - 1:30 pmORD-EYW
7h 30m1 stop
Multiple Airlines Logo
2:30 pm - 11:35 amEYW-ORD
22h 05m2 stops
$298Multiple Airlines
Find Deal
Sat, Jan 3 - Mon, Jan 5
Delta Logo
5:30 am - 11:43 amORD-EYW
5h 13m1 stop
Delta Logo
6:10 pm - 10:43 pmEYW-ORD
5h 33m1 stop
$299Delta
Find Deal
Sun, Dec 7 - Sat, Dec 13
Spirit Airlines Logo
5:00 am - 1:30 pmORD-EYW
7h 30m1 stop
Spirit Airlines Logo
12:20 pm - 12:30 amEYW-ORD
13h 10m1 stop
$300Spirit Airlines
Find Deal
Fri, Dec 19 - Tue, Dec 23
Spirit Airlines Logo
4:38 pm - 1:30 pmORD-EYW
19h 52m3 stops
Spirit Airlines Logo
2:30 pm - 8:01 pmEYW-ORD
6h 31m1 stop
$302Spirit Airlines
Find Deal
Fri, Dec 5 - Sat, Dec 13
Spirit Airlines Logo
7:29 am - 1:30 pmORD-EYW
5h 01m1 stop
Spirit Airlines Logo
2:25 pm - 12:42 pmEYW-ORD
23h 17m3 stops
$303Spirit Airlines
Find Deal
Fri, Jan 23 - Mon, Jan 26
Spirit Airlines Logo
3:25 pm - 1:30 pmORD-EYW
21h 05m3 stops
Spirit Airlines Logo
12:15 pm - 2:19 pmEYW-ORD
27h 04m2 stops
$304Spirit Airlines
Find Deal
Sun, Feb 1 - Thu, Feb 5
Multiple Airlines Logo
12:17 pm - 11:05 amORD-EYW
21h 48m2 stops
Multiple Airlines Logo
12:20 pm - 12:09 amEYW-ORD
12h 49m1 stop
$305Multiple Airlines
Find Deal
Mon, Dec 1 - Thu, Dec 4
Spirit Airlines Logo
9:09 pm - 1:30 pmORD-EYW
15h 21m2 stops
Spirit Airlines Logo
12:20 pm - 6:39 pmEYW-ORD
7h 19m1 stop
$306Spirit Airlines
Find Deal
Sun, Dec 21 - Sun, Dec 28
Delta Logo
10:48 am - 5:11 pmMDW-EYW
5h 23m1 stop
Delta Logo
6:06 pm - 10:22 pmEYW-MDW
5h 16m1 stop
$319Delta
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Fri, Jan 23 - Sat, Jan 31
Delta Logo
12:50 pm - 8:06 pmMDW-EYW
6h 16m1 stop
Delta Logo
4:25 pm - 10:22 pmEYW-MDW
6h 57m1 stop
$324Delta
Find Deal
Wed, Dec 17 - Wed, Dec 24

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Feb 24
ORD8:22 amChicago O'Hare Intl
3h 25m
EYW12:47 pmKey West
Mar 4
EYW1:17 pmKey West
3h 38m
ORD3:55 pmChicago O'Hare Intl
$303
Find similar
American Airlines
Mar 25
ORD6:05 amChicago O'Hare Intl
8h 18m
1 stop
EYW3:23 pmKey West
Apr 1
EYW4:00 pmKey West
3h 36m
ORD6:36 pmChicago O'Hare Intl
$313
Find similar
American Airlines
Mar 25
ORD6:30 amChicago O'Hare Intl
6h 20m
1 stop
EYW1:50 pmKey West
Apr 1
EYW6:31 amKey West
5h 26m
1 stop
ORD10:57 amChicago O'Hare Intl
$323
Find similar

United Airlines flights from Chicago to Key West

Our best United Airlines deals on Chicago to Key West flight tickets
United Airlines
Dec 21
ORD7:55 amChicago O'Hare Intl
3h 39m
EYW12:34 pmKey West
Dec 24
EYW4:29 pmKey West
8h 45m
1 stop
ORD12:14 amChicago O'Hare Intl
$307
Find similar
United Airlines
Dec 18
ORD8:51 amChicago O'Hare Intl
6h 38m
1 stop
EYW4:29 pmKey West
Dec 21
EYW12:22 pmKey West
3h 45m
ORD3:07 pmChicago O'Hare Intl
$310
Find similar
United Airlines
Dec 18
ORD7:55 amChicago O'Hare Intl
3h 39m
EYW12:34 pmKey West
Dec 21
EYW4:10 pmKey West
3h 33m
ORD6:43 pmChicago O'Hare Intl
$317
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 November 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

Sat 1/3

5:00 am-1:30 pm

1 stop7h 30m

Key West

Mon 1/5

2:30 pm-11:35 am

2 stops22h 05m

$298

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 12/7

5:30 am-11:43 am

1 stop5h 13m

Key West

Sat 12/13

6:10 pm-10:43 pm

1 stop5h 33m

$299

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 12/19

5:00 am-1:30 pm

1 stop7h 30m

Key West

Tue 12/23

12:20 pm-12:30 am

1 stop13h 10m

$300

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 12/5

4:38 pm-1:30 pm

3 stops19h 52m

Key West

Sat 12/13

2:30 pm-8:01 pm

1 stop6h 31m

$302

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/23

7:29 am-1:30 pm

1 stop5h 01m

Key West

Mon 1/26

2:25 pm-12:42 pm

3 stops23h 17m

$303

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 2/1

3:25 pm-1:30 pm

3 stops21h 05m

Key West

Thu 2/5

12:15 pm-2:19 pm

2 stops27h 04m

$304

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 12/1

12:17 pm-11:05 am

2 stops21h 48m

Key West

Thu 12/4

12:20 pm-12:09 am

1 stop12h 49m

$305

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 12/21

9:09 pm-1:30 pm

2 stops15h 21m

Key West

Sun 12/28

12:20 pm-6:39 pm

1 stop7h 19m

$306

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 1/23

10:48 am-5:11 pm

1 stop5h 23m

Key West

Sat 1/31

6:06 pm-10:22 pm

1 stop5h 16m

$319

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 12/17

12:50 pm-8:06 pm

1 stop6h 16m

Key West

Wed 12/24

4:25 pm-10:22 pm

1 stop6h 57m

$324

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, August 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 $404. If you are unable to visit Key West during the month of August, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $407.

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 $361. 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 $543.

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 morning. momondo users have found flights departing from Chicago to Key West in the morning for as low as $477. 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 $444 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 $401 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 22% 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 November 2025, prices for Chicago to Key West flights are approximately 5% cheaper 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

$253

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 $253. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $357.
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 near Key West: Key West (EYW)
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  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 19m 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
DeltaPriceFrom $218Free CancellationRating
7.9
8,003 reviews
Search Delta flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
9,019 reviews
Search United Airlines flights
American AirlinesPriceFrom $314Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Key West

    United Airlines flight deals from Chicago to Key West start from $255 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $490 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 11,045 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Key West about 1 time each week, with ticket deals ranging from $314 to $452. 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

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