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Cheap flights from Chicago to Key West from $123

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 10/14. 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 to Key West

Cheap round-trip flights

Logo
5:45 pm - 4:00 pmORD-EYW
21h 15m1 stop
Logo
3:26 pm - 10:17 amEYW-ORD
19h 51m1 stop
$215
Find Deal
sáb., sep. 13 - vie., sep. 19
Logo
5:17 pm - 2:40 pmORD-EYW
20h 23m1 stop
Logo
3:08 pm - 3:45 pmEYW-ORD
25h 37m1 stop
$223
Find Deal
sáb., oct. 4 - vie., oct. 17
Logo
7:00 am - 7:46 pmORD-EYW
11h 46m1 stop
Logo
9:36 pm - 12:26 pmEYW-ORD
15h 50m1 stop
$231
Find Deal
jue., nov. 6 - jue., nov. 13
Logo
5:46 pm - 9:02 amORD-EYW
14h 16m1 stop
Logo
10:02 am - 7:10 amEYW-ORD
22h 08m1 stop
$236
Find Deal
vie., sep. 26 - mié., oct. 1
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
Delta Logo
6:00 pm - 9:44 pmEYW-MDW
4h 44m1 stop
$269Delta
Find Deal
mar., dic. 2 - sáb., dic. 6
Delta Logo
5:30 am - 10:55 amORD-EYW
4h 25m1 stop
Delta Logo
6:00 pm - 10:14 pmEYW-ORD
5h 14m1 stop
$269Delta
Find Deal
lun., sep. 22 - mié., oct. 1
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
$293Spirit Airlines
Find Deal
jue., nov. 6 - lun., nov. 10
American Airlines Logo
12:52 pm - 9:56 pmORD-EYW
8h 04m1 stop
American Airlines Logo
1:52 pm - 4:32 pmEYW-ORD
3h 40mnonstop
$313American Airlines
Find Deal
sáb., nov. 1 - mié., nov. 5
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
$317Spirit Airlines
Find Deal
vie., ene. 30 - mar., feb. 3
American Airlines Logo
12:52 pm - 9:56 pmORD-EYW
8h 04m1 stop
American Airlines Logo
1:45 pm - 6:05 pmEYW-ORD
5h 20m1 stop
$323American Airlines
Find Deal
sáb., nov. 1 - mié., nov. 5

Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Dec 2
MDW1:05 pmChicago Midway
5h 39m
1 stop
EYW7:44 pmKey West
Dec 6
EYW6:00 pmKey West
4h 44m
1 stop
MDW9:44 pmChicago Midway
$269
Find similar
Delta
Dec 2
ORD11:19 amChicago O'Hare Intl
7h 25m
1 stop
EYW7:44 pmKey West
Dec 6
EYW6:00 pmKey West
6h 53m
1 stop
ORD11:53 pmChicago O'Hare Intl
$289
Find similar
Delta
Sep 23
ORD7:10 amChicago O'Hare Intl
11h 57m
2 stops
EYW8:07 pmKey West
Oct 1
EYW2:00 pmKey West
6h 00m
1 stop
ORD7:00 pmChicago O'Hare Intl
$311
Find similar

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Nov 1
ORD12:52 pmChicago O'Hare Intl
8h 04m
1 stop
EYW9:56 pmKey West
Nov 5
EYW1:52 pmKey West
3h 40m
ORD4:32 pmChicago O'Hare Intl
$313
Find similar
American Airlines
Nov 1
ORD12:52 pmChicago O'Hare Intl
8h 04m
1 stop
EYW9:56 pmKey West
Nov 5
EYW1:45 pmKey West
5h 20m
1 stop
ORD6:05 pmChicago O'Hare Intl
$323
Find similar
American Airlines
Dec 24
ORD1:24 pmChicago O'Hare Intl
3h 11m
EYW5:35 pmKey West
Dec 30
EYW6:05 pmKey West
3h 34m
ORD8:39 pmChicago O'Hare Intl
$327
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 agosto 18, 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

sáb. 9/13

5:45 pm-4:00 pm

1 stop21h 15m

Key West

vie. 9/19

3:26 pm-10:17 am

1 stop19h 51m

$215

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sáb. 10/4

5:17 pm-2:40 pm

1 stop20h 23m

Key West

vie. 10/17

3:08 pm-3:45 pm

1 stop25h 37m

$223

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jue. 11/6

7:00 am-7:46 pm

1 stop11h 46m

Key West

jue. 11/13

9:36 pm-12:26 pm

1 stop15h 50m

$231

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 9/26

5:46 pm-9:02 am

1 stop14h 16m

Key West

mié. 10/1

10:02 am-7:10 am

1 stop22h 08m

$236

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

mar. 12/2

1:05 pm-7:44 pm

1 stop5h 39m

Key West

sáb. 12/6

6:00 pm-9:44 pm

1 stop4h 44m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

lun. 9/22

5:30 am-10:55 am

1 stop4h 25m

Key West

mié. 10/1

6:00 pm-10:14 pm

1 stop5h 14m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jue. 11/6

5:05 am-1:30 pm

1 stop7h 25m

Key West

lun. 11/10

2:25 pm-9:00 pm

1 stop7h 35m

$293

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sáb. 11/1

12:52 pm-9:56 pm

1 stop8h 04m

Key West

mié. 11/5

1:52 pm-4:32 pm

Nonstop3h 40m

$313

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 1/30

5:05 am-1:30 pm

1 stop7h 25m

Key West

mar. 2/3

2:25 pm-9:00 pm

1 stop7h 35m

$317

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sáb. 11/1

12:52 pm-9:56 pm

1 stop8h 04m

Key West

mié. 11/5

1:45 pm-6:05 pm

1 stop5h 20m

$323

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 typical price of a round-trip flight between Chicago and Key West?

What is the cheapest month to fly to Key West?

In general, October 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 $401. If you are unable to visit Key West during the month of October, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $404.

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 $352. 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 $541.

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 $465. 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 $445 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 $365 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?

You could potentially save up to 6% on your flight if you consider stops on a Chicago to Key West flight.

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

As of August 2025, prices for Chicago to Key West flights are approximately 0% cheaper 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

$123

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 $123. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $215.
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. 3h 11m 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 $216Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $261Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
American AirlinesPriceFrom $295Free 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

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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