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Cheap flights from Chicago to Key West from $100

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 12/10. 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 to Key West

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Key West that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Key West.

Cheap last minute flights

Planning a quick getaway from Chicago to Key West? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Key West, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Key West

Find recent round-trip train or bus tickets from Chicago to Key West.

All round-trip flight deals to Key West

The cheapest plane tickets to Key West found on KAYAK recently.
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
12:26 pm - 2:55 pmEYW-ORD
3h 29mnonstop
$199United Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
1:00 pm - 6:49 pmEYW-ORD
6h 49m1 stop
$209United Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
12:44 pm - 8:11 pmMDW-EYW
6h 27m1 stop
7:00 am - 11:59 amEYW-MDW
5h 59m1 stop
$218Delta
Find Deal
Tue, Jan 28 - Tue, Feb 4
11:05 am - 5:12 pmORD-EYW
5h 07m1 stop
3:03 pm - 8:48 pmEYW-ORD
6h 45m1 stop
$218Delta
Find Deal
Wed, Jan 22 - Wed, Jan 29
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$224American Airlines
Find Deal
Tue, Dec 17 - Sun, Dec 22
9:30 am - 5:24 pmORD-EYW
6h 54m1 stop
7:25 am - 12:32 pmEYW-ORD
6h 07m1 stop
$227Delta
Find Deal
Wed, Dec 18 - Wed, Dec 25
8:14 pm - 9:51 amORD-EYW
12h 37m1 stop
5:33 pm - 7:47 amEYW-ORD
15h 14m1 stop
Wed, Dec 18 - Wed, Dec 25
12:44 pm - 8:34 pmMDW-EYW
6h 50m1 stop
3:50 pm - 10:06 pmEYW-MDW
7h 16m1 stop
$243Delta
Find Deal
Wed, Dec 18 - Wed, Dec 25
6:31 am - 1:55 pmORD-EYW
6h 24m1 stop
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$254American Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
12:09 pm - 10:03 amORD-EYW
20h 54m2 stops
10:52 am - 8:49 pmEYW-ORD
10h 57m1 stop
Mon, Jan 6 - Wed, Jan 8
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$100American Airlines
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Tue, Dec 10
1:59 pm - 8:34 pmORD-EYW
5h 35m1 stop
$109Delta
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Tue, Dec 17
7:20 am - 4:22 pmORD-EYW
8h 02m1 stop
Sat, Feb 8
12:43 pm - 8:30 pmMDW-EYW
6h 47m1 stop
$118Delta
Find Deal
Tue, Nov 26
6:00 am - 11:38 amORD-EYW
4h 38m1 stop
$118Delta
Find Deal
Tue, Nov 26
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$140United Airlines
Find Deal
Tue, Dec 17
7:35 am - 4:01 pmORD-EYW
7h 26m1 stop
$149United Airlines
Find Deal
Sat, Jan 18
8:15 am - 12:52 pmORD-EYW
3h 37mnonstop
$169American Airlines
Find Deal
Mon, Jan 6
5:15 pm - 9:03 amORD-EYW
14h 48m1 stop
Tue, Dec 3
10:57 am - 5:25 pmMDW-EYW
5h 28m1 stop
$178Delta
Find Deal
Mon, Jan 6
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
$349American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
10:29 am - 6:48 pmORD-EYW
7h 19m1 stop
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
$359American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
10:41 am - 5:18 pmMDW-EYW
5h 37m1 stop
7:25 am - 11:58 amEYW-MDW
5h 33m1 stop
$377Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
9:25 am - 5:18 pmORD-EYW
6h 53m1 stop
7:25 am - 12:21 pmEYW-ORD
5h 56m1 stop
$377Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
$439American Airlines
Find Deal
Fri, Nov 22 - Wed, Nov 27
5:15 pm - 8:11 amORD-EYW
13h 56m1 stop
5:11 pm - 2:31 pmEYW-ORD
22h 20m2 stops
Sat, Nov 23 - Mon, Nov 25
9:09 pm - 3:07 pmMDW-EYW
16h 58m2 stops
5:15 pm - 11:55 amEYW-MDW
19h 40m2 stops
$524Allegiant Air
Find Deal
Fri, Nov 22 - Tue, Nov 26
10:25 am - 8:11 amORD-EYW
20h 46m2 stops
5:11 pm - 2:31 pmEYW-ORD
22h 20m2 stops
Sat, Nov 23 - Mon, Nov 25
6:00 am - 5:15 pmORD-EYW
10h 15m2 stops
7:40 pm - 9:33 amEYW-ORD
14h 53m1 stop
$607United Airlines
Find Deal
Mon, Nov 25 - Wed, Nov 27
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
$614United Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
12:26 pm - 2:55 pmEYW-ORD
3h 29mnonstop
$199United Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$224American Airlines
Find Deal
Tue, Dec 17 - Sun, Dec 22
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$244United Airlines
Find Deal
Wed, Feb 5 - Wed, Feb 12
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
4:19 pm - 6:50 pmEYW-ORD
3h 31mnonstop
$249United Airlines
Find Deal
Mon, Dec 16 - Sat, Dec 21
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
4:19 pm - 6:50 pmEYW-ORD
3h 31mnonstop
$262United Airlines
Find Deal
Sat, Dec 14 - Sat, Dec 21
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$268American Airlines
Find Deal
Tue, Dec 17 - Thu, Dec 19
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$279United Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
$283United Airlines
Find Deal
Wed, Dec 4 - Tue, Dec 10
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
1:06 pm - 3:37 pmEYW-ORD
3h 31mnonstop
$289American Airlines
Find Deal
Sat, Jan 11 - Wed, Jan 15
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
4:12 pm - 6:41 pmEYW-ORD
3h 29mnonstop
$304United Airlines
Find Deal
Wed, Dec 18 - Sun, Dec 22

United Airlines flights from Chicago to Key West

Our best United Airlines deals on Chicago to Key West flight tickets
United Airlines
Dec 18
ORD10:55 amChicago O'Hare Intl
3h 06m
EYW3:01 pmKey West
Dec 25
EYW12:26 pmKey West
3h 29m
ORD2:55 pmChicago O'Hare Intl
United Airlines
Dec 18
ORD10:55 amChicago O'Hare Intl
3h 06m
EYW3:01 pmKey West
Dec 25
EYW1:00 pmKey West
6h 49m
1 stop
ORD6:49 pmChicago O'Hare Intl
United Airlines
Feb 5
ORD10:35 amChicago O'Hare Intl
3h 14m
EYW2:49 pmKey West
Feb 12
EYW3:50 pmKey West
3h 31m
ORD6:21 pmChicago O'Hare Intl

Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Jan 28
MDW12:44 pmChicago Midway
6h 27m
1 stop
EYW8:11 pmKey West
Feb 4
EYW7:00 amKey West
5h 59m
1 stop
MDW11:59 amChicago Midway
Delta
Dec 18
ORD9:30 amChicago O'Hare Intl
6h 54m
1 stop
EYW5:24 pmKey West
Dec 25
EYW7:25 amKey West
6h 07m
1 stop
ORD12:32 pmChicago O'Hare Intl
Delta
Dec 18
MDW12:44 pmChicago Midway
6h 50m
1 stop
EYW8:34 pmKey West
Dec 25
EYW3:50 pmKey West
7h 16m
1 stop
MDW10:06 pmChicago Midway

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 from Chicago to Key West?

August. The cheapest time of year to fly to Key West from Chicago is August. Most expensive is March

What is the cheapest day to depart Chicago for Key West?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Thursday

When is the cheapest time to fly from Chicago to Key West?

At noon. Chicago to Key West flights are approximately 40% more expensive in the evening than at noon

What is the cheapest Chicago to Key West flight route?

Chicago O'Hare Intl - Key West. Fly from Chicago O'Hare Intl to Key West for the best Chicago - Key West flight prices

How far in advance should you book Chicago to Key West flights?

20 days before. The cheapest time to buy a flight from Chicago to Key West is approximately 20 days to departure

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

There are 2 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 November 2024, prices for Chicago to Key West flights are approximately 69% more expensive when compared to flights at the same time last year.

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


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

$100

Fastest flight time

3h 06m

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 $100. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $199.
The fastest flight from Chicago to Key West takes 3h 06m
Direct flights go from Chicago to Key West every day.
There is 1 airport near Key West: Key West (EYW)

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 06m 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
8,756 reviews
Search Delta flights
American AirlinesPriceFrom $246Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $263Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Key West

    United Airlines flight deals from Chicago to Key West start from $263 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $481 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 10,000 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Key West about 6 times each week, with ticket deals ranging from $246 to $476. Price data is based on momondo searches in the last 72 hours.


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.


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