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Cheap flights from Chicago to Key West from $112

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 to Key West departing on 10/19. 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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Cheap round-trip flights

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
$215Spirit Airlines
Find Deal
Wed, Feb 25 - Tue, Mar 3
Multiple Airlines Logo
7:43 pm - 2:40 pmORD-EYW
17h 57m1 stop
Multiple Airlines Logo
11:45 am - 10:08 amEYW-ORD
23h 23m1 stop
$217Multiple Airlines
Find Deal
Sat, Oct 11 - Tue, Oct 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
$223Spirit Airlines
Find Deal
Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
6:18 pm - 9:12 amORD-EYW
13h 54m1 stop
Multiple Airlines Logo
11:45 am - 12:53 pmEYW-ORD
26h 08m1 stop
$225Multiple Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 28
Multiple Airlines Logo
7:43 pm - 2:40 pmORD-EYW
17h 57m1 stop
Multiple Airlines Logo
11:45 am - 12:53 pmEYW-ORD
26h 08m1 stop
$227Multiple Airlines
Find Deal
Sat, Oct 25 - Tue, Oct 28
Multiple Airlines Logo
6:00 pm - 10:19 amORD-EYW
15h 19m1 stop
Multiple Airlines Logo
11:45 am - 10:08 amEYW-ORD
23h 23m1 stop
$229Multiple Airlines
Find Deal
Sat, Oct 11 - Tue, Oct 14
Delta Logo
6:00 am - 1:12 pmMDW-EYW
6h 12m1 stop
Delta Logo
6:00 pm - 9:46 pmEYW-MDW
4h 46m1 stop
$269Delta
Find Deal
Tue, Feb 24 - Thu, Mar 5
Delta Logo
11:19 am - 5:12 pmORD-EYW
4h 53m1 stop
Delta Logo
1:30 pm - 9:46 pmEYW-ORD
9h 16m1 stop
$269Delta
Find Deal
Tue, Feb 24 - Tue, Mar 3
Delta Logo
12:48 pm - 8:06 pmMDW-EYW
6h 18m1 stop
Delta Logo
12:22 pm - 4:09 pmEYW-MDW
4h 47m1 stop
$289Delta
Find Deal
Wed, Oct 15 - Wed, Oct 22
Delta Logo
11:19 am - 7:44 pmORD-EYW
7h 25m1 stop
Delta Logo
6:00 pm - 11:54 pmEYW-ORD
6h 54m1 stop
$289Delta
Find Deal
Wed, Feb 18 - Wed, Feb 25

Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Feb 24
ORD11:19 amChicago O'Hare Intl
4h 53m
1 stop
EYW5:12 pmKey West
Mar 3
EYW1:30 pmKey West
9h 16m
1 stop
ORD9:46 pmChicago O'Hare Intl
$269
Find similar
Delta
Oct 15
MDW12:48 pmChicago Midway
6h 18m
1 stop
EYW8:06 pmKey West
Oct 22
EYW12:22 pmKey West
4h 47m
1 stop
MDW4:09 pmChicago Midway
$289
Find similar
Delta
Feb 4
MDW1:05 pmChicago Midway
5h 39m
1 stop
EYW7:44 pmKey West
Feb 13
EYW1:30 pmKey West
24h 05m
2 stops
MDW12:35 pmChicago Midway
$307
Find similar

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Oct 1
ORD5:00 amChicago O'Hare Intl
5h 13m
1 stop
EYW11:13 amKey West
Oct 4
EYW12:24 pmKey West
5h 59m
1 stop
ORD5:23 pmChicago O'Hare Intl
$391
Find similar
American Airlines
Sep 18
ORD7:00 amChicago O'Hare Intl
8h 17m
2 stops
EYW4:17 pmKey West
Sep 23
EYW12:24 pmKey West
5h 59m
1 stop
ORD5:23 pmChicago O'Hare Intl
$419
Find similar
American Airlines
Oct 1
ORD8:10 amChicago O'Hare Intl
8h 36m
2 stops
EYW5:46 pmKey West
Oct 4
EYW12:24 pmKey West
5h 59m
1 stop
ORD5:23 pmChicago O'Hare Intl
$442
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 17, 2025.
Use the filters below to find and compare flights from Chicago 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 2/25

5:05 am-1:30 pm

1 stop7h 25m

Key West

Tue 3/3

2:25 pm-9:00 pm

1 stop7h 35m

$215

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

Fri 12/12

5:05 am-1:30 pm

1 stop7h 25m

Key West

Mon 12/15

2:25 pm-11:42 pm

1 stop10h 17m

$223

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 10/14

6:18 pm-9:12 am

1 stop13h 54m

Key West

Tue 10/28

11:45 am-12:53 pm

1 stop26h 08m

$225

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/25

7:43 pm-2:40 pm

1 stop17h 57m

Key West

Tue 10/28

11:45 am-12:53 pm

1 stop26h 08m

$227

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/11

6:00 pm-10:19 am

1 stop15h 19m

Key West

Tue 10/14

11:45 am-10:08 am

1 stop23h 23m

$229

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/24

6:00 am-1:12 pm

1 stop6h 12m

Key West

Thu 3/5

6:00 pm-9:46 pm

1 stop4h 46m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/24

11:19 am-5:12 pm

1 stop4h 53m

Key West

Tue 3/3

1:30 pm-9:46 pm

1 stop9h 16m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 10/15

12:48 pm-8:06 pm

1 stop6h 18m

Key West

Wed 10/22

12:22 pm-4:09 pm

1 stop4h 47m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 2/18

11:19 am-7:44 pm

1 stop7h 25m

Key West

Wed 2/25

6:00 pm-11:54 pm

1 stop6h 54m

$289

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 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, August is the cheapest month to fly from Chicago to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $404. If you are unable to visit Key West during the month of August, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $409.

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 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 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 to Key West in the morning for as low as $469. 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 to Key West flight route?

Fly from Chicago O'Hare Intl to Key West for the best Chicago - 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 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 for as low as $367 on momondo.

What cabin class options are available on Chicago to Key West flights?

There are 3 cabin classes available to choose from on Chicago 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 to Key West flights?

No. A direct flight is the cheapest option for a flight between Chicago to Key West.

How have Chicago to Key West flight prices changed over time?

As of September 2025, prices for Chicago to Key West flights are approximately 41% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Key West

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

Cheap Chicago to Key West (CHI to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago 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 in the past 72 hours is $253. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $411.
The fastest flight from Chicago to Key West takes 3h 11m
Direct flights go from Chicago to Key West every day.
There is 1 airport near Key West: Key West (EYW)
Search flight deals

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 4h 40m is a normal flight duration for this route.

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

    Prices for flights from Chicago to Key West Airport refresh daily.

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

  • How old do you have to be to fly from Chicago to Key West Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Key West Airport.

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

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Key West?

  • What is the most popular airline from Chicago to Key West?

Best airlines flying from Chicago to Key West

Compare and see reviews for airlines that fly from Chicago to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $218Free CancellationRating
7.9
7,961 reviews
Search Delta flights
United AirlinesPriceFrom $258Free CancellationRating
7.4
8,926 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 collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Key West. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Key West from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Key West from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Key West from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Key West trip

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