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Cheap flights from Chicago O'Hare Intl Airport to Key West from $102

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 11/16. 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.
Spirit Airlines Logo
5:00 am - 1:30 pmORD-EYW
7h 30m1 stop
Spirit Airlines Logo
2:25 pm - 9:00 pmEYW-ORD
7h 35m1 stop
$191Spirit Airlines
Find Deal
Wed, Jan 7 - Wed, Jan 14
Multiple Airlines Logo
11:32 am - 9:37 pmORD-EYW
9h 05m1 stop
Multiple Airlines Logo
3:46 pm - 5:04 pmEYW-ORD
26h 18m1 stop
$193Multiple Airlines
Find Deal
Sun, Jan 18 - Thu, Jan 22
Spirit Airlines Logo
5:10 am - 11:20 amORD-EYW
5h 10m1 stop
Spirit Airlines Logo
12:15 pm - 8:27 pmEYW-ORD
9h 12m1 stop
$196Spirit Airlines
Find Deal
Sun, Nov 16 - Thu, Nov 20
Multiple Airlines Logo
8:15 am - 9:06 amORD-EYW
23h 51m1 stop
Multiple Airlines Logo
4:06 pm - 7:00 pmEYW-ORD
27h 54m1 stop
$206Multiple Airlines
Find Deal
Wed, Jan 7 - Wed, Jan 14
Spirit Airlines Logo
5:05 am - 1:30 pmORD-EYW
7h 25m1 stop
Spirit Airlines Logo
2:25 pm - 11:42 pmEYW-ORD
10h 17m1 stop
$207Spirit Airlines
Find Deal
Tue, Jan 27 - Sat, Jan 31
Spirit Airlines Logo
5:00 am - 1:30 pmORD-EYW
7h 30m1 stop
Spirit Airlines Logo
2:25 pm - 11:42 pmEYW-ORD
10h 17m1 stop
$212Spirit Airlines
Find Deal
Wed, Jan 7 - Sun, Jan 11
Spirit Airlines Logo
5:05 am - 1:30 pmORD-EYW
7h 25m1 stop
Spirit Airlines Logo
2:25 pm - 9:00 pmEYW-ORD
7h 35m1 stop
$213Spirit Airlines
Find Deal
Fri, Feb 6 - Tue, Feb 10
United Airlines Logo
10:50 am - 3:17 pmORD-EYW
3h 27mnonstop
United Airlines Logo
12:22 pm - 2:55 pmEYW-ORD
3h 33mnonstop
$249United Airlines
Find Deal
Tue, Jan 27 - Sat, Jan 31
United Airlines Logo
8:52 am - 4:22 pmORD-EYW
6h 30m1 stop
United Airlines Logo
12:22 pm - 2:55 pmEYW-ORD
3h 33mnonstop
$259United Airlines
Find Deal
Tue, Jan 27 - Sat, Jan 31
Delta Logo
7:10 am - 1:12 pmORD-EYW
5h 02m1 stop
Delta Logo
7:00 am - 1:23 pmEYW-ORD
7h 23m1 stop
$269Delta
Find Deal
Fri, Jan 30 - Tue, Feb 3

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

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Key West flight tickets
Spirit Airlines
Jan 7
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
EYW1:30 pmKey West
Jan 14
EYW2:25 pmKey West
7h 35m
1 stop
ORD9:00 pmChicago O'Hare Intl
$191
Find similar
Spirit Airlines
Nov 16
ORD5:10 amChicago O'Hare Intl
5h 10m
1 stop
EYW11:20 amKey West
Nov 20
EYW12:15 pmKey West
9h 12m
1 stop
ORD8:27 pmChicago O'Hare Intl
$196
Find similar
Spirit Airlines
Jan 27
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
EYW1:30 pmKey West
Jan 31
EYW2:25 pmKey West
10h 17m
1 stop
ORD11:42 pmChicago O'Hare Intl
$207
Find similar

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
Jan 27
ORD10:50 amChicago O'Hare Intl
3h 27m
EYW3:17 pmKey West
Jan 31
EYW12:22 pmKey West
3h 33m
ORD2:55 pmChicago O'Hare Intl
$249
Find similar
United Airlines
Jan 27
ORD8:52 amChicago O'Hare Intl
6h 30m
1 stop
EYW4:22 pmKey West
Jan 31
EYW12:22 pmKey West
3h 33m
ORD2:55 pmChicago O'Hare Intl
$259
Find similar
United Airlines
Jan 7
ORD10:50 amChicago O'Hare Intl
3h 27m
EYW3:17 pmKey West
Jan 14
EYW2:25 pmKey West
6h 48m
1 stop
ORD8:13 pmChicago O'Hare Intl
$270
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 October 20, 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

Wed 1/7

5:00 am-1:30 pm

1 stop7h 30m

Key West

Wed 1/14

2:25 pm-9:00 pm

1 stop7h 35m

$191

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 1/18

11:32 am-9:37 pm

1 stop9h 05m

Key West

Thu 1/22

3:46 pm-5:04 pm

1 stop26h 18m

$193

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sun 11/16

5:10 am-11:20 am

1 stop5h 10m

Key West

Thu 11/20

12:15 pm-8:27 pm

1 stop9h 12m

$196

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 1/7

8:15 am-9:06 am

1 stop23h 51m

Key West

Wed 1/14

4:06 pm-7:00 pm

1 stop27h 54m

$206

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 1/27

5:05 am-1:30 pm

1 stop7h 25m

Key West

Sat 1/31

2:25 pm-11:42 pm

1 stop10h 17m

$207

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 1/7

5:00 am-1:30 pm

1 stop7h 30m

Key West

Sun 1/11

2:25 pm-11:42 pm

1 stop10h 17m

$212

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 2/6

5:05 am-1:30 pm

1 stop7h 25m

Key West

Tue 2/10

2:25 pm-9:00 pm

1 stop7h 35m

$213

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 1/27

10:50 am-3:17 pm

Nonstop3h 27m

Key West

Sat 1/31

12:22 pm-2:55 pm

Nonstop3h 33m

$249

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 1/27

8:52 am-4:22 pm

1 stop6h 30m

Key West

Sat 1/31

12:22 pm-2:55 pm

Nonstop3h 33m

$259

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Fri 1/30

7:10 am-1:12 pm

1 stop5h 02m

Key West

Tue 2/3

7:00 am-1:23 pm

1 stop7h 23m

$269

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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Key West?

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 $388. 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 $403.

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 $364. 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 $545.

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 O'Hare Intl Airport to Key West in the morning for as low as $475. 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 $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 O'Hare Intl Airport for as low as $359 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?

You could potentially save up to 2% 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

$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 O'Hare Intl Airport in the past 72 hours is $253. The best round-trip flight deal from Chicago O'Hare Intl Airport to Key West found on momondo in the last 72 hours is $377.
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 27m.

  • 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 $218Free CancellationRating
7.9
7,978 reviews
Search Delta flights
United AirlinesPriceFrom $254Free CancellationRating
7.4
8,991 reviews
Search United Airlines flights
American AirlinesPriceFrom $308Free CancellationRating
7.2
11,024 reviews
Search American Airlines flights

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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