Cheap flights from Chicago to Key West from $90

Round-trip
2 travelers
Economy
0 bags
From?
To?
Tue 8/16
Tue 8/23

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Flight information for Chicago to Key West
(CHI to EYW)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Key West

Best Price Found

$90

Fastest flight time

3h 00m

Direct flights

None

Airports in Key West

1 airport
The best one-way flight to Key West from Chicago in the past 72 hours is $90. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $226.
The fastest flight from Chicago to Key West takes 3h 00m
There are no direct flights from Chicago to Key West. Popular non-direct routes for this connection are Chicago Midway Airport - Key West Airport and Chicago O'Hare Intl Airport - Key West Airport.
There is 1 airport near Key West: Key West (EYW)

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?

September

The cheapest time of year to fly to Key West from Chicago is September. 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?

in the evening

Chicago to Key West flights are approximately 93% more expensive in the morning than in the evening

What is the cheapest airline that flies to Key West from Chicago?

Juneyao Airlines

American Airlines, Delta, and Juneyao Airlines are the most popular carriers operating from Chicago to Key West

What is the cheapest Chicago to Key West flight route?

Chicago Midway - Key West

Fly from Chicago Midway to Key West for the best Chicago - Key West flight prices

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

60 days before

The cheapest time to buy a flight from Chicago to Key West is approximately 60 days to departure

When traveling from Chicago to Key West, the most popular airport to fly into is Key West Airport. The majority of travelers flying into Key West Airport from Chicago are departing from Chicago O'Hare Intl Airport. You may be looking for an airport near Chicago O'Hare Intl Airport to depart from when traveling to Key West and Chicago Midway Airport, located in Chicago is a great option. The least expensive flight option from Chicago to Key West will typically be ORD — EYW during the month of August with an average price of $226 RT.

Chicago O'Hare Intl Airport (ORD) to Key West Airport (EYW)$226
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Chicago Midway Airport (MDW) to Key West Airport (EYW)$237
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Easily compare round-trip flights from Chicago to Key West

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Key West by changing tabs
Multiple Airlines
Aug 26
ORD4:59 pmChicago O'Hare Intl
12h 09m
1 stop
EYW5:08 amKey West
Aug 29
EYW5:15 amKey West
12h 43m
1 stop
ORD5:58 pmChicago O'Hare Intl
American Airlines
Jan 10
ORD3:20 amChicago O'Hare Intl
3h 00m
EYW6:20 amKey West
Jan 14
EYW8:30 amKey West
3h 30m
ORD12:00 pmChicago O'Hare Intl
Delta
Sep 17
MDW2:00 amChicago Midway
6h 08m
1 stop
EYW8:08 amKey West
Sep 20
EYW2:15 pmKey West
5h 35m
1 stop
MDW7:50 pmChicago Midway
American Airlines
Dec 12
ORD3:20 amChicago O'Hare Intl
3h 00m
EYW6:20 amKey West
Dec 20
EYW3:05 amKey West
5h 08m
1 stop
ORD8:13 amChicago O'Hare Intl
Multiple Airlines
Oct 21
ORD4:45 pmChicago O'Hare Intl
11h 50m
1 stop
EYW4:35 amKey West
Oct 26
EYW1:06 pmKey West
16h 05m
1 stop
ORD5:11 amChicago O'Hare Intl
American Airlines
Dec 5
ORD3:20 amChicago O'Hare Intl
3h 00m
EYW6:20 amKey West
Dec 10
EYW9:03 amKey West
7h 17m
1 stop
ORD4:20 pmChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Key West

If you're looking for one-way flights from Chicago to Key West, view some of our deals below provided by Allegiant Air, American Airlines and Delta
Multiple Airlines
Aug 30
ORD8:25 amChicago O'Hare Intl
20h 28m
2 stops
EYW4:53 amKey West
Multiple Airlines
Aug 30
ORD7:38 amChicago O'Hare Intl
21h 15m
1 stop
EYW4:53 amKey West
Allegiant Air
Oct 17
MDW5:06 pmChicago Midway
35h 00m
2 stops
EYW4:06 amKey West

Search last-minute flights to Key West from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Key West
American Airlines
Aug 17
ORD5:00 amChicago O'Hare Intl
5h 37m
1 stop
EYW10:37 amKey West
Aug 22
EYW4:00 amKey West
7h 15m
1 stop
ORD11:15 amChicago O'Hare Intl
Multiple Airlines
Aug 19
ORD4:59 pmChicago O'Hare Intl
12h 09m
1 stop
EYW5:08 amKey West
Aug 21
EYW1:18 pmKey West
17h 38m
2 stops
ORD6:56 amChicago O'Hare Intl
Delta
Aug 17
MDW2:00 amChicago Midway
4h 45m
1 stop
EYW6:45 amKey West
Aug 23
EYW1:00 pmKey West
6h 48m
1 stop
MDW7:48 pmChicago Midway
United Airlines
Aug 17
ORD10:30 amChicago O'Hare Intl
28h 15m
1 stop
EYW2:45 pmKey West
Aug 22
EYW3:05 pmKey West
15h 37m
1 stop
ORD6:42 amChicago O'Hare Intl
American Airlines
Aug 17
ORD3:26 amChicago O'Hare Intl
8h 04m
2 stops
EYW11:30 amKey West
Aug 22
EYW4:00 amKey West
7h 15m
1 stop
ORD11:15 amChicago O'Hare Intl
Multiple Airlines
Aug 20
MDW4:00 pmChicago Midway
12h 15m
1 stop
EYW4:15 amKey West
Aug 22
EYW1:54 pmKey West
22h 38m
2 stops
MDW12:32 pmChicago Midway

Best airlines flying from Chicago to Key West

Compare and see reviews for airlines that fly from Chicago to Key West with momondo
AirlineRatingFree CancellationPrice
Juneyao AirlinesPriceFrom $10Free CancellationRating
0.0
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United AirlinesPriceFrom $220Free CancellationRating
7.1
7.5

Boarding

7.0

Comfort

8.0

Crew

6.9

Entertainment

6.4

Food

Reviews

Nothing in specific right now

1 / 10
Search United Airlines flights
DeltaPriceFrom $245Free CancellationRating
7.8
7.9

Boarding

8.0

Comfort

8.3

Crew

7.7

Entertainment

7.3

Food

Reviews

This is another disease as if you have the Internet, you are ordinary deceivers!

1 / 10
Search Delta flights
American AirlinesPriceFrom $262Free CancellationRating
6.9
7.3

Boarding

7.1

Comfort

7.9

Crew

6.8

Entertainment

6.4

Food

Reviews

Left Early Arrived Early Great Staff. No complaints.

1 / 10
Search American Airlines flights
  • American Airlines Flights From Chicago to Key West

    American Airlines flight deals from Chicago to Key West start from $262 round-trip. Over the 2 American Airlines flights for this route in a normal week, average airfare is usually $457 round-trip - but some users have found much cheaper deals with momondo.


Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Sep 17
MDW2:00 amChicago Midway
6h 08m
1 stop
EYW8:08 amKey West
Sep 20
EYW2:15 pmKey West
5h 35m
1 stop
MDW7:50 pmChicago Midway
Delta
Oct 18
ORD1:40 amChicago O'Hare Intl
4h 50m
1 stop
EYW6:30 amKey West
Oct 25
EYW2:14 pmKey West
6h 41m
1 stop
ORD8:55 pmChicago O'Hare Intl
Delta
Sep 17
MDW2:00 amChicago Midway
6h 08m
1 stop
EYW8:08 amKey West
Sep 24
EYW2:15 pmKey West
5h 35m
1 stop
MDW7:50 pmChicago Midway

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Jan 10
ORD3:20 amChicago O'Hare Intl
3h 00m
EYW6:20 amKey West
Jan 14
EYW8:30 amKey West
3h 30m
ORD12:00 pmChicago O'Hare Intl
American Airlines
Dec 12
ORD3:20 amChicago O'Hare Intl
3h 00m
EYW6:20 amKey West
Dec 20
EYW3:05 amKey West
5h 08m
1 stop
ORD8:13 amChicago O'Hare Intl
American Airlines
Dec 5
ORD3:20 amChicago O'Hare Intl
3h 00m
EYW6:20 amKey West
Dec 10
EYW9:03 amKey West
7h 17m
1 stop
ORD4:20 pmChicago O'Hare Intl

  • Are airlines flying from Chicago to Key West offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from Chicago to Key West, such as American Airlines, United Airlines, and Delta may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 00m is a normal flight duration for this route.



Alternative routes for Chicago to Key West

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Fort Lauderdale Flights
Fastest flight time2h 53m
Cheapest price$85
Chicago to Orlando Flights
Fastest flight time2h 35m
Cheapest price$108
Chicago to Miami Flights
Fastest flight time3h 00m
Cheapest price$80
Chicago to Tampa Flights
Fastest flight time2h 25m
Cheapest price$67
Chicago to Fort Myers Flights
Fastest flight time2h 47m
Cheapest price$125
St. Louis to Orlando Flights
Fastest flight time2h 17m
Cheapest price$69
Chicago to West Palm Beach Flights
Fastest flight time2h 55m
Cheapest price$213
Chicago to Jacksonville Flights
Fastest flight time2h 10m
Cheapest price$221
Chicago to Pensacola Flights
Fastest flight time2h 18m
Cheapest price$240
St. Louis to Miami Flights
Fastest flight time2h 42m
Cheapest price$157
St. Louis to Fort Lauderdale Flights
Fastest flight time2h 35m
Cheapest price$123
Chicago to Daytona Beach Flights
Fastest flight time3h 55m
Cheapest price$311

Similar Chicago to Key West flights

Flexible with your destination? Broaden your search and find flights similar to your Chicago to Key West route

Why use momondo?

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.

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.

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.

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.