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Cheap flights from Chicago O'Hare Intl Airport to Key West from $85

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 11/27. 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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0 bags

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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.
United Airlines Logo
10:44 am - 3:00 pmORD-EYW
3h 16mnonstop
United Airlines Logo
4:34 pm - 12:26 amEYW-ORD
8h 52m1 stop
$292United Airlines
Find Deal
dom., feb. 22 - sáb., feb. 28
Delta Logo
11:15 am - 5:15 pmORD-EYW
5h 00m1 stop
Delta Logo
6:10 pm - 10:43 pmEYW-ORD
5h 33m1 stop
$294Delta
Find Deal
mar., dic. 2 - mar., dic. 9
Multiple Airlines Logo
4:20 pm - 10:07 amORD-EYW
16h 47m2 stops
Multiple Airlines Logo
12:20 pm - 11:02 pmEYW-ORD
11h 42m1 stop
$295Multiple Airlines
Find Deal
vie., dic. 5 - dom., dic. 14
Multiple Airlines Logo
6:23 pm - 8:15 amORD-EYW
12h 52m1 stop
Multiple Airlines Logo
9:57 am - 3:12 pmEYW-ORD
30h 15m2 stops
$296Multiple Airlines
Find Deal
jue., nov. 27 - lun., dic. 1
Spirit Airlines Logo
12:09 pm - 1:30 pmORD-EYW
24h 21m3 stops
Spirit Airlines Logo
12:15 pm - 6:47 pmEYW-ORD
7h 32m1 stop
$301Spirit Airlines
Find Deal
mar., ene. 6 - dom., ene. 11
American Airlines Logo
8:22 am - 12:47 pmORD-EYW
3h 25mnonstop
American Airlines Logo
1:17 pm - 3:55 pmEYW-ORD
3h 38mnonstop
$303American Airlines
Find Deal
mar., feb. 24 - mié., mar. 4
United Airlines Logo
10:50 am - 3:17 pmORD-EYW
3h 27mnonstop
United Airlines Logo
4:15 pm - 6:48 pmEYW-ORD
3h 33mnonstop
$304United Airlines
Find Deal
mar., ene. 6 - dom., ene. 11
Spirit Airlines Logo
10:05 pm - 1:30 pmORD-EYW
14h 25m2 stops
Spirit Airlines Logo
12:15 pm - 9:44 amEYW-ORD
22h 29m2 stops
$308Spirit Airlines
Find Deal
jue., ene. 8 - dom., ene. 11
American Airlines Logo
8:50 am - 1:20 pmORD-EYW
3h 30mnonstop
American Airlines Logo
8:05 pm - 12:37 amEYW-ORD
5h 32m1 stop
$313American Airlines
Find Deal
mar., dic. 9 - sáb., dic. 13
Delta Logo
6:45 am - 8:06 pmORD-EYW
12h 21m2 stops
Delta Logo
6:10 pm - 10:43 pmEYW-ORD
5h 33m1 stop
$317Delta
Find Deal
mar., dic. 9 - mar., dic. 16

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 6
ORD12:09 pmChicago O'Hare Intl
24h 21m
3 stops
EYW1:30 pmKey West
Jan 11
EYW12:15 pmKey West
7h 32m
1 stop
ORD6:47 pmChicago O'Hare Intl
$301
Find similar
Spirit Airlines
Jan 8
ORD10:05 pmChicago O'Hare Intl
14h 25m
2 stops
EYW1:30 pmKey West
Jan 11
EYW12:15 pmKey West
22h 29m
2 stops
ORD9:44 amChicago O'Hare Intl
$308
Find similar
Spirit Airlines
Dec 22
ORD7:30 amChicago O'Hare Intl
5h 00m
1 stop
EYW1:30 pmKey West
Dec 30
EYW12:20 pmKey West
13h 10m
1 stop
ORD12:30 amChicago O'Hare Intl
$318
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
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
Dec 9
ORD8:50 amChicago O'Hare Intl
3h 30m
EYW1:20 pmKey West
Dec 13
EYW8:05 pmKey West
5h 32m
1 stop
ORD12:37 amChicago O'Hare Intl
$313
Find similar
American Airlines
Mar 25
ORD8:11 amChicago O'Hare Intl
6h 12m
1 stop
EYW3:23 pmKey West
Mar 31
EYW5:24 pmKey West
7h 49m
1 stop
ORD12:13 amChicago O'Hare Intl
$323
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 noviembre 6, 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

dom. 2/22

10:44 am-3:00 pm

Nonstop3h 16m

Key West

sáb. 2/28

4:34 pm-12:26 am

1 stop8h 52m

$292

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 12/2

11:15 am-5:15 pm

1 stop5h 00m

Key West

mar. 12/9

6:10 pm-10:43 pm

1 stop5h 33m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 12/5

4:20 pm-10:07 am

2 stops16h 47m

Key West

dom. 12/14

12:20 pm-11:02 pm

1 stop11h 42m

$295

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jue. 11/27

6:23 pm-8:15 am

1 stop12h 52m

Key West

lun. 12/1

9:57 am-3:12 pm

2 stops30h 15m

$296

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 1/6

12:09 pm-1:30 pm

3 stops24h 21m

Key West

dom. 1/11

12:15 pm-6:47 pm

1 stop7h 32m

$301

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 2/24

8:22 am-12:47 pm

Nonstop3h 25m

Key West

mié. 3/4

1:17 pm-3:55 pm

Nonstop3h 38m

$303

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 1/6

10:50 am-3:17 pm

Nonstop3h 27m

Key West

dom. 1/11

4:15 pm-6:48 pm

Nonstop3h 33m

$304

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jue. 1/8

10:05 pm-1:30 pm

2 stops14h 25m

Key West

dom. 1/11

12:15 pm-9:44 am

2 stops22h 29m

$308

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 12/9

8:50 am-1:20 pm

Nonstop3h 30m

Key West

sáb. 12/13

8:05 pm-12:37 am

1 stop5h 32m

$313

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 12/9

6:45 am-8:06 pm

2 stops12h 21m

Key West

mar. 12/16

6:10 pm-10:43 pm

1 stop5h 33m

$317

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 $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 $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 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 morning. momondo users have found flights departing from Chicago O'Hare Intl Airport 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 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 $442 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 $370 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 $357.
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 16m.

  • 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
8,001 reviews
Search Delta flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
9,007 reviews
Search United Airlines flights
American AirlinesPriceFrom $314Free CancellationRating
7.2
11,040 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 $490, but momondo users have found United Airlines deals from Chicago O'Hare Intl Airport to Key West from as low as $255 round-trip. United Airlines has been scored 7.4/10 in 9,007 reviews.

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

    Across 11,040 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 $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 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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