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Cheap flights from Chicago O'Hare Intl Airport to Key West from $113

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 10/4. 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

Logo
5:50 am - 4:04 pmORD-EYW
9h 14m1 stop
Logo
10:02 am - 1:15 pmEYW-ORD
28h 13m1 stop
$210
Find Deal
Sun, Oct 19 - Wed, Oct 22
Logo
7:43 pm - 2:40 pmORD-EYW
17h 57m1 stop
Logo
11:45 am - 10:08 amEYW-ORD
23h 23m1 stop
$217
Find Deal
Sat, Oct 11 - Tue, Oct 14
Logo
8:00 am - 8:15 amORD-EYW
23h 15m1 stop
Logo
8:55 am - 7:34 amEYW-ORD
23h 39m1 stop
$221
Find Deal
Sat, Oct 4 - Thu, Oct 9
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
$245Spirit Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
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
$250Spirit Airlines
Find Deal
Thu, Feb 19 - Tue, Feb 24
Delta Logo
11:19 am - 5:13 pmORD-EYW
4h 54m1 stop
Delta Logo
1:30 pm - 7:25 pmEYW-ORD
6h 55m1 stop
$269Delta
Find Deal
Tue, Feb 24 - Thu, Mar 5
Delta Logo
1:26 pm - 8:06 pmORD-EYW
5h 40m1 stop
Delta Logo
6:17 pm - 11:58 pmEYW-ORD
6h 41m1 stop
$289Delta
Find Deal
Sat, Oct 25 - Tue, Oct 28
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
United Airlines Logo
4:00 pm - 6:46 pmEYW-ORD
3h 46mnonstop
$295United Airlines
Find Deal
Wed, Nov 5 - Sat, Nov 8
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
United Airlines Logo
4:00 pm - 6:46 pmEYW-ORD
3h 46mnonstop
$297United Airlines
Find Deal
Tue, Oct 28 - Fri, Oct 31
American Airlines Logo
10:59 am - 3:29 pmORD-EYW
3h 30mnonstop
American Airlines Logo
4:00 pm - 6:36 pmEYW-ORD
3h 36mnonstop
$303American Airlines
Find Deal
Tue, Feb 24 - Wed, Mar 4

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
Dec 11
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
EYW1:30 pmKey West
Dec 15
EYW2:25 pmKey West
7h 35m
1 stop
ORD9:00 pmChicago O'Hare Intl
$245
Find similar
Spirit Airlines
Feb 19
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
EYW1:30 pmKey West
Feb 24
EYW2:25 pmKey West
10h 17m
1 stop
ORD11:42 pmChicago O'Hare Intl
$250
Find similar
Spirit Airlines
Jan 29
ORD5:05 amChicago O'Hare Intl
7h 25m
1 stop
EYW1:30 pmKey West
Feb 2
EYW2:25 pmKey West
7h 35m
1 stop
ORD9:00 pmChicago O'Hare Intl
$255
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
Nov 5
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
Nov 8
EYW4:00 pmKey West
3h 46m
ORD6:46 pmChicago O'Hare Intl
$295
Find similar
United Airlines
Oct 28
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
Oct 31
EYW4:00 pmKey West
3h 46m
ORD6:46 pmChicago O'Hare Intl
$297
Find similar
United Airlines
Sep 28
ORD6:00 amChicago O'Hare Intl
7h 29m
1 stop
EYW2:29 pmKey West
Oct 2
EYW3:12 pmKey West
7h 14m
1 stop
ORD9:26 pmChicago O'Hare Intl
$677
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 September 15, 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

Sun 10/19

5:50 am-4:04 pm

1 stop9h 14m

Key West

Wed 10/22

10:02 am-1:15 pm

1 stop28h 13m

$210

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/11

7:43 pm-2:40 pm

1 stop17h 57m

Key West

Tue 10/14

11:45 am-10:08 am

1 stop23h 23m

$217

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/4

8:00 am-8:15 am

1 stop23h 15m

Key West

Thu 10/9

8:55 am-7:34 am

1 stop23h 39m

$221

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 12/11

5:05 am-1:30 pm

1 stop7h 25m

Key West

Mon 12/15

2:25 pm-9:00 pm

1 stop7h 35m

$245

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 2/19

5:05 am-1:30 pm

1 stop7h 25m

Key West

Tue 2/24

2:25 pm-11:42 pm

1 stop10h 17m

$250

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/24

11:19 am-5:13 pm

1 stop4h 54m

Key West

Thu 3/5

1:30 pm-7:25 pm

1 stop6h 55m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/25

1:26 pm-8:06 pm

1 stop5h 40m

Key West

Tue 10/28

6:17 pm-11:58 pm

1 stop6h 41m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 11/5

11:00 am-3:19 pm

Nonstop3h 19m

Key West

Sat 11/8

4:00 pm-6:46 pm

Nonstop3h 46m

$295

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 10/28

11:00 am-3:19 pm

Nonstop3h 19m

Key West

Fri 10/31

4:00 pm-6:46 pm

Nonstop3h 46m

$297

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/24

10:59 am-3:29 pm

Nonstop3h 30m

Key West

Wed 3/4

4:00 pm-6:36 pm

Nonstop3h 36m

$303

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 October is also very affordable. Most momondo users find prices during this month for around $387.

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 $360. 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 $536.

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 $467. 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 $438 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 $367 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

$272

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 $272. The best round-trip flight deal from Chicago O'Hare Intl Airport to Key West found on momondo in the last 72 hours is $434.
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 $218Free CancellationRating
7.9
7,954 reviews
Search Delta flights
United AirlinesPriceFrom $260Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
American AirlinesPriceFrom $303Free CancellationRating
7.2
10,000 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

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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