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Cheap flights from Chicago O'Hare Intl Airport to Key West from $129

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 8/31. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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.
Multiple Airlines Logo
5:13 pm - 11:27 am
ORD
-
EYW
17h 14m
1 stop
Multiple Airlines Logo
11:04 am - 7:59 pm
EYW
-
ORD
9h 55m
2 stops
$236Multiple Airlines
Thu, Aug 13 - Thu, Aug 20
Multiple Airlines Logo
5:13 pm - 11:27 am
ORD
-
EYW
17h 14m
1 stop
Multiple Airlines Logo
11:04 am - 7:59 pm
EYW
-
ORD
9h 55m
2 stops
$239Multiple Airlines
Thu, Aug 13 - Thu, Aug 20
Multiple Airlines Logo
2:03 pm - 9:24 am
ORD
-
EYW
42h 21m
2 stops
Multiple Airlines Logo
10:59 am - 11:55 pm
EYW
-
ORD
13h 56m
1 stop
$243Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
8:00 am - 12:19 pm
ORD
-
EYW
27h 19m
1 stop
Multiple Airlines Logo
12:59 pm - 7:44 pm
EYW
-
ORD
31h 45m
2 stops
$246Multiple Airlines
Thu, Oct 29 - Fri, Nov 6
Multiple Airlines Logo
7:44 pm - 11:25 am
ORD
-
EYW
14h 41m
1 stop
Multiple Airlines Logo
10:04 am - 12:02 pm
EYW
-
ORD
26h 58m
2 stops
$254Multiple Airlines
Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
4:44 pm - 1:38 pm
ORD
-
EYW
19h 54m
1 stop
Multiple Airlines Logo
12:59 pm - 7:44 pm
EYW
-
ORD
31h 45m
2 stops
$256Multiple Airlines
Sat, Oct 31 - Fri, Nov 6
Multiple Airlines Logo
4:49 pm - 10:19 am
ORD
-
EYW
16h 30m
1 stop
Multiple Airlines Logo
10:59 am - 11:55 pm
EYW
-
ORD
13h 56m
1 stop
$257Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Multiple Airlines Logo
8:00 am - 12:19 pm
ORD
-
EYW
27h 19m
1 stop
Multiple Airlines Logo
10:04 am - 7:44 pm
EYW
-
ORD
10h 40m
2 stops
$262Multiple Airlines
Thu, Oct 29 - Wed, Nov 4
Multiple Airlines Logo
4:44 pm - 1:38 pm
ORD
-
EYW
19h 54m
1 stop
Multiple Airlines Logo
12:54 pm - 3:26 pm
EYW
-
ORD
27h 32m
1 stop
$266Multiple Airlines
Sat, Oct 31 - Wed, Nov 4
Multiple Airlines Logo
5:13 pm - 11:27 am
ORD
-
EYW
17h 14m
1 stop
Multiple Airlines Logo
11:04 am - 7:59 pm
EYW
-
ORD
9h 55m
2 stops
$268Multiple Airlines
Thu, Aug 13 - Thu, Aug 20

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Delta flights from Chicago O'Hare Intl Airport to Key West

Our best Delta deals on Chicago O'Hare Intl Airport to Key West flight tickets
Delta
Aug 27
ORD9:54 amChicago O'Hare Intl
6h 26m
1 stop
EYW5:20 pmKey West
Sep 1
EYW7:40 amKey West
5h 36m
1 stop
ORD12:16 pmChicago O'Hare Intl
$322
Delta
Jul 30
ORD6:35 amChicago O'Hare Intl
5h 48m
1 stop
EYW1:23 pmKey West
Aug 3
EYW6:15 pmKey West
6h 42m
1 stop
ORD11:57 pmChicago O'Hare Intl
$359
Delta
Jul 21
ORD5:30 amChicago O'Hare Intl
6h 53m
1 stop
EYW1:23 pmKey West
Aug 6
EYW6:15 pmKey West
6h 42m
1 stop
ORD11:57 pmChicago O'Hare Intl
$395

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
Aug 29
ORD12:00 pmChicago O'Hare Intl
3h 19m
EYW4:19 pmKey West
Sep 5
EYW4:56 pmKey West
3h 52m
ORD7:48 pmChicago O'Hare Intl
$297
American Airlines
Aug 15
ORD12:00 pmChicago O'Hare Intl
3h 19m
EYW4:19 pmKey West
Aug 22
EYW7:10 pmKey West
5h 20m
1 stop
ORD11:30 pmChicago O'Hare Intl
$306
American Airlines
Aug 29
ORD5:05 amChicago O'Hare Intl
6h 50m
1 stop
EYW12:55 pmKey West
Sep 5
EYW4:56 pmKey West
3h 52m
ORD7:48 pmChicago O'Hare Intl
$307

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 July 17, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/13

5:13 pm-11:27 am

1 stop17h 14m

Key West

Thu 8/20

11:04 am-7:59 pm

2 stops9h 55m

$236

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/13

5:13 pm-11:27 am

1 stop17h 14m

Key West

Thu 8/20

11:04 am-7:59 pm

2 stops9h 55m

$239

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 9/10

2:03 pm-9:24 am

2 stops42h 21m

Key West

Thu 9/17

10:59 am-11:55 pm

1 stop13h 56m

$243

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 10/29

8:00 am-12:19 pm

1 stop27h 19m

Key West

Fri 11/6

12:59 pm-7:44 pm

2 stops31h 45m

$246

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/5

7:44 pm-11:25 am

1 stop14h 41m

Key West

Sat 9/12

10:04 am-12:02 pm

2 stops26h 58m

$254

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/31

4:44 pm-1:38 pm

1 stop19h 54m

Key West

Fri 11/6

12:59 pm-7:44 pm

2 stops31h 45m

$256

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 9/10

4:49 pm-10:19 am

1 stop16h 30m

Key West

Thu 9/17

10:59 am-11:55 pm

1 stop13h 56m

$257

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 10/29

8:00 am-12:19 pm

1 stop27h 19m

Key West

Wed 11/4

10:04 am-7:44 pm

2 stops10h 40m

$262

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/31

4:44 pm-1:38 pm

1 stop19h 54m

Key West

Wed 11/4

12:54 pm-3:26 pm

1 stop27h 32m

$266

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/13

5:13 pm-11:27 am

1 stop17h 14m

Key West

Thu 8/20

11:04 am-7:59 pm

2 stops9h 55m

$268

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, May 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 $369. If you are unable to visit Key West during the month of May, then departing from Chicago O'Hare Intl Airport during the month August is also very affordable. Most momondo users find prices during this month for around $370.

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 $357. 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 O'Hare Intl Airport to Key West for around $500.

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 $449. 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 $458. 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 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 from Chicago O'Hare Intl Airport 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 $432 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 $398 on momondo.

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport 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?

You could potentially save up to 21% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Key West flight.

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

$283

Fastest flight time

2h 08m

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 $283. The best round-trip flight deal from Chicago O'Hare Intl Airport to Key West found on momondo in the last 72 hours is $387.
The fastest flight from Chicago O'Hare Intl Airport to Key West takes 2h 08m
Direct flights go from Chicago O'Hare Intl Airport to Key West every day.
There is 1 airport in Key West. From Chicago O'Hare Intl Airport there are direct flights to Key West (EYW).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Key West

  • 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 2h 08m.

  • 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 $206Free CancellationRating
7.8
8,474 reviews
Search Delta flights
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,997 reviews
Search United Airlines flights
American AirlinesPriceFrom $308Free CancellationRating
7.1
11,818 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 $412, but momondo users have found United Airlines deals from Chicago O'Hare Intl Airport to Key West from as low as $249 round-trip. United Airlines has been scored 7.4/10 in 9,997 reviews.

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

    Across 11,818 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Chicago O'Hare Intl Airport to Key West about 2 times each week, with ticket deals ranging from $308 to $478. 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

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