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Cheap flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Key West departing on 2/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
10:59 am - 3:25 pmORD-EYW
3h 26mnonstop
American Airlines Logo
6:43 pm - 11:27 pmEYW-ORD
5h 44m1 stop
$289American Airlines
Find Deal
Tue, Jan 20 - Sun, Jan 25
Multiple Airlines Logo
11:23 am - 8:15 amORD-EYW
19h 52m1 stop
Multiple Airlines Logo
8:55 am - 10:24 pmEYW-ORD
14h 29m2 stops
$291Multiple Airlines
Find Deal
Wed, Dec 24 - Sun, Dec 28
Spirit Airlines Logo
9:34 am - 11:20 amORD-EYW
24h 46m3 stops
Spirit Airlines Logo
12:15 pm - 6:39 pmEYW-ORD
31h 24m3 stops
$292Spirit Airlines
Find Deal
Wed, Jan 7 - Sun, Jan 11
Spirit Airlines Logo
7:29 am - 1:30 pmORD-EYW
5h 01m1 stop
Spirit Airlines Logo
12:15 pm - 5:52 pmEYW-ORD
30h 37m3 stops
$293Spirit Airlines
Find Deal
Fri, Jan 9 - Thu, Jan 15
Delta Logo
5:30 am - 11:25 amORD-EYW
4h 55m1 stop
Delta Logo
6:06 pm - 11:56 pmEYW-ORD
6h 50m1 stop
$294Delta
Find Deal
Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
4:44 pm - 1:30 pmORD-EYW
19h 46m1 stop
Multiple Airlines Logo
2:30 pm - 12:30 amEYW-ORD
11h 00m1 stop
$297Multiple Airlines
Find Deal
Sun, Dec 21 - Fri, Dec 26
Multiple Airlines Logo
6:00 am - 1:30 pmORD-EYW
30h 30m2 stops
Multiple Airlines Logo
2:30 pm - 12:30 amEYW-ORD
11h 00m1 stop
$298Multiple Airlines
Find Deal
Tue, Dec 23 - Sat, Dec 27
Delta Logo
9:49 am - 5:15 pmORD-EYW
6h 26m1 stop
Delta Logo
7:40 am - 12:10 pmEYW-ORD
5h 30m1 stop
$299Delta
Find Deal
Sat, Dec 13 - Thu, Dec 18
Multiple Airlines Logo
3:26 pm - 10:29 amORD-EYW
18h 03m2 stops
Multiple Airlines Logo
2:30 pm - 6:36 pmEYW-ORD
29h 06m3 stops
$301Multiple Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
Multiple Airlines Logo
3:24 pm - 12:26 pmORD-EYW
20h 02m2 stops
Multiple Airlines Logo
1:06 pm - 9:02 amEYW-ORD
20h 56m1 stop
$302Multiple Airlines
Find Deal
Thu, Mar 5 - Mon, Mar 9

United Airlines flights from Chicago O'Hare Intl Airport to Key West

Our best United Airlines deals on Chicago O'Hare Intl Airport to Key West flight tickets
United Airlines
Dec 18
ORD7:55 amChicago O'Hare Intl
3h 39m
EYW12:34 pmKey West
Dec 24
EYW4:08 pmKey West
3h 33m
ORD6:41 pmChicago O'Hare Intl
$331
Find similar
United Airlines
Feb 24
ORD7:10 amChicago O'Hare Intl
9h 44m
1 stop
EYW5:54 pmKey West
Mar 5
EYW3:51 pmKey West
3h 39m
ORD6:30 pmChicago O'Hare Intl
$339
Find similar
United Airlines
Dec 18
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
$340
Find similar

American Airlines flights from Chicago O'Hare Intl Airport to Key West

Our best American Airlines deals on Chicago O'Hare Intl Airport to Key West flight tickets
American Airlines
Jan 20
ORD10:59 amChicago O'Hare Intl
3h 26m
EYW3:25 pmKey West
Jan 25
EYW6:43 pmKey West
5h 44m
1 stop
ORD11:27 pmChicago O'Hare Intl
$289
Find similar
American Airlines
Feb 24
ORD8:19 amChicago O'Hare Intl
3h 27m
EYW12:46 pmKey West
Mar 4
EYW1:19 pmKey West
3h 39m
ORD3:58 pmChicago O'Hare Intl
$303
Find similar
American Airlines
Dec 18
ORD6:40 amChicago O'Hare Intl
6h 07m
1 stop
EYW1:47 pmKey West
Dec 18
EYW6:32 pmKey West
3h 33m
ORD9:05 pmChicago O'Hare Intl
$307
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 26, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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 1/20

10:59 am-3:25 pm

Nonstop3h 26m

Key West

Sun 1/25

6:43 pm-11:27 pm

1 stop5h 44m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 12/24

11:23 am-8:15 am

1 stop19h 52m

Key West

Sun 12/28

8:55 am-10:24 pm

2 stops14h 29m

$291

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 1/7

9:34 am-11:20 am

3 stops24h 46m

Key West

Sun 1/11

12:15 pm-6:39 pm

3 stops31h 24m

$292

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/9

7:29 am-1:30 pm

1 stop5h 01m

Key West

Thu 1/15

12:15 pm-5:52 pm

3 stops30h 37m

$293

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/23

5:30 am-11:25 am

1 stop4h 55m

Key West

Mon 1/26

6:06 pm-11:56 pm

1 stop6h 50m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 12/21

4:44 pm-1:30 pm

1 stop19h 46m

Key West

Fri 12/26

2:30 pm-12:30 am

1 stop11h 00m

$297

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 12/23

6:00 am-1:30 pm

2 stops30h 30m

Key West

Sat 12/27

2:30 pm-12:30 am

1 stop11h 00m

$298

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 12/13

9:49 am-5:15 pm

1 stop6h 26m

Key West

Thu 12/18

7:40 am-12:10 pm

1 stop5h 30m

$299

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 12/11

3:26 pm-10:29 am

2 stops18h 03m

Key West

Sat 12/13

2:30 pm-6:36 pm

3 stops29h 06m

$301

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 3/5

3:24 pm-12:26 pm

2 stops20h 02m

Key West

Mon 3/9

1:06 pm-9:02 am

1 stop20h 56m

$302

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 O'Hare Intl Airport 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 cheapest month to fly to Key West?

In general, June is the cheapest month to fly from Chicago O'Hare Intl Airport to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $387. If you are unable to visit Key West during the month of June, then departing from Chicago O'Hare Intl Airport during the month July is also very affordable. Most momondo users find prices during this month for around $402.

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 O'Hare Intl Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $369. 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 O'Hare Intl Airport 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 afternoon. momondo users have found flights departing from Chicago O'Hare Intl Airport 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 O'Hare Intl to Key West flight route?

Fly from Chicago O'Hare Intl to Key West for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $443 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 O'Hare Intl Airport for as low as $401 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Key West flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Key West flights?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Key West.

How have Chicago O'Hare Intl Airport to Key West flight prices changed over time?

When to book flights from Chicago O'Hare Intl Airport to Key West

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

Cheap Chicago O'Hare Intl Airport to Key West (ORD to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Key West

Best Price Found

$345

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 O'Hare Intl Airport in the past 72 hours is $345. The best round-trip flight deal from Chicago O'Hare Intl Airport to Key West found on momondo in the last 72 hours is $371.
The fastest flight from Chicago O'Hare Intl Airport to Key West takes 3h 11m
Direct flights go from Chicago O'Hare Intl Airport to Key West every day.
There is 1 airport near Key West: Key West (EYW)
Search flight deals

  • How far is Chicago O'Hare Intl to Key West by plane?

    Key West is 1252.7 mi away from Chicago O'Hare Intl. A reasonable flight in good conditions will take 3h 19m.

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

    Prices for flights from Chicago O'Hare Intl Airport to Key West Airport are refreshed on a daily basis.

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

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Key West Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Key West Airport.

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

    The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Key West?

  • What is the most popular airline from Chicago O'Hare Intl Airport to Key West?

Best airlines flying from Chicago O'Hare Intl Airport to Key West

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $248Free CancellationRating
7.9
7,998 reviews
Search Delta flights
United AirlinesPriceFrom $252Free CancellationRating
7.4
9,046 reviews
Search United Airlines flights
American AirlinesPriceFrom $319Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago O'Hare Intl Airport to Key West

    United Airlines operates around 7 flights from Chicago O'Hare Intl Airport to Key West every week. The average price of these flights found in the last 72 hours has been $491, but momondo users have found United Airlines deals from Chicago O'Hare Intl Airport to Key West from as low as $252 round-trip. United Airlines has been scored 7.4/10 in 9,046 reviews.

  • American Airlines Flights From Chicago O'Hare Intl Airport to Key West

    Across 11,038 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago O'Hare Intl Airport to Key West about 5 times each week, with ticket deals ranging from $319 to $455. 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 compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Key West. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Key West on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Key West.

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

If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Chicago and alert you when they change.

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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