How does KAYAK find such low prices on flights from Illinois to Key West?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Key West.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Key West?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Illinois to Key West?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Illinois with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Key West?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$127 CHEAP FLIGHTS from Illinois to Key West

Save 26% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

Cheap Flights from Illinois to Key West

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Illinois to Key West

Sun, Jan 31 - Tue, Feb 9

5:32 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

15h 47m2 stops Atlanta Hartsfield-Jackson Orlando

1:16 pm - 9:13 amEYW Key West-ORD Chicago O'Hare Intl

20h 57m1 stop Tampa

$359Multiple Airlines

Wed, Dec 16 - Fri, Dec 18

4:00 pm - 11:21 amORD Chicago O'Hare Intl-EYW Key West

18h 21m2 stops Atlanta Hartsfield-Jackson Tampa

12:59 pm - 11:31 pmEYW Key West-ORD Chicago O'Hare Intl

11h 32m1 stop Tampa

$359Multiple Airlines

Mon, Feb 1 - Mon, Feb 8

5:32 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

15h 47m2 stops Atlanta Hartsfield-Jackson Orlando

12:59 pm - 9:13 amEYW Key West-ORD Chicago O'Hare Intl

21h 14m1 stop Tampa

$359Multiple Airlines

Sat, Jan 16 - Sat, Jan 23

9:00 am - 5:54 pmORD Chicago O'Hare Intl-EYW Key West

7h 54m1 stop Charlotte Douglas

6:01 pm - 1:05 amEYW Key West-ORD Chicago O'Hare Intl

8h 04m1 stop Miami

$366American Airlines

Fri, Feb 26 - Fri, Mar 5

12:01 pm - 6:40 pmORD Chicago O'Hare Intl-EYW Key West

5h 39m1 stop Charlotte Douglas

4:08 pm - 9:25 pmEYW Key West-ORD Chicago O'Hare Intl

6h 17m1 stop Miami

$366American Airlines

Sat, Dec 12 - Thu, Dec 17

11:28 am - 8:01 pmMDW Chicago Midway-EYW Key West

7h 33m1 stop Atlanta Hartsfield-Jackson

6:06 pm - 10:54 pmEYW Key West-MDW Chicago Midway

5h 48m1 stop Atlanta Hartsfield-Jackson

$366Delta

Thu, Jan 21 - Sun, Jan 24

10:30 am - 7:20 pmORD Chicago O'Hare Intl-EYW Key West

7h 50m1 stop Miami

7:50 pm - 1:05 amEYW Key West-ORD Chicago O'Hare Intl

6h 15m1 stop Miami

$366American Airlines

Mon, Dec 21 - Sat, Dec 26

6:10 am - 3:23 pmMLI Moline Quad-City-EYW Key West

8h 13m1 stop Chicago O'Hare Intl

5:52 pm - 10:40 pmEYW Key West-MLI Moline Quad-City

5h 48m1 stop Chicago O'Hare Intl

$369United Airlines

Tue, Dec 15 - Mon, Dec 21

10:55 am - 3:26 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:22 pm - 3:11 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$382United Airlines

Wed, Dec 2 - Wed, Dec 9

1:02 pm - 8:01 pmMDW Chicago Midway-EYW Key West

5h 59m1 stop Atlanta Hartsfield-Jackson

6:06 pm - 10:54 pmEYW Key West-MDW Chicago Midway

5h 48m1 stop Atlanta Hartsfield-Jackson

$391Delta

Recent last minute flight deals from Illinois to Key West

Sat, Nov 14 - Wed, Nov 18

9:00 am - 5:56 pmORD Chicago O'Hare Intl-EYW Key West

7h 56m1 stop Charlotte Douglas

6:25 pm - 9:20 pmEYW Key West-ORD Chicago O'Hare Intl

3h 55mnonstop

$384American Airlines

Sat, Nov 14 - Tue, Nov 17

8:15 am - 4:27 pmORD Chicago O'Hare Intl-EYW Key West

7h 12m1 stop Miami

6:35 pm - 9:30 pmEYW Key West-ORD Chicago O'Hare Intl

3h 55mnonstop

$384American Airlines

Sat, Nov 14 - Tue, Nov 17

8:15 am - 4:27 pmORD Chicago O'Hare Intl-EYW Key West

7h 12m1 stop Miami

6:35 pm - 9:30 pmEYW Key West-ORD Chicago O'Hare Intl

3h 55mnonstop

$384American Airlines

Sun, Nov 15 - Mon, Nov 23

9:51 am - 10:19 amORD Chicago O'Hare Intl-EYW Key West

23h 28m1 stop Orlando

12:59 pm - 11:34 pmEYW Key West-ORD Chicago O'Hare Intl

35h 35m2 stops Tampa Fort Lauderdale

$385Multiple Airlines

Sun, Nov 15 - Sun, Nov 22

9:51 am - 10:19 amORD Chicago O'Hare Intl-EYW Key West

23h 28m1 stop Orlando

12:01 pm - 11:34 pmEYW Key West-ORD Chicago O'Hare Intl

36h 33m2 stops Tampa Fort Lauderdale

$386Multiple Airlines

Sat, Nov 14 - Wed, Nov 18

11:27 am - 8:00 pmMDW Chicago Midway-EYW Key West

7h 33m1 stop Atlanta Hartsfield-Jackson

6:08 pm - 10:54 pmEYW Key West-MDW Chicago Midway

5h 46m1 stop Atlanta Hartsfield-Jackson

$394Delta

Sat, Nov 14 - Tue, Nov 17

1:30 pm - 8:00 pmORD Chicago O'Hare Intl-EYW Key West

5h 30m1 stop Atlanta Hartsfield-Jackson

7:30 am - 12:20 pmEYW Key West-ORD Chicago O'Hare Intl

5h 50m1 stop Atlanta Hartsfield-Jackson

$394Delta

Sun, Nov 15 - Wed, Nov 18

9:41 am - 2:01 pmPIA Greater Peoria-EYW Key West

27h 20m1 stop Tampa St. Petersburg

4:51 pm - 7:54 amEYW Key West-PIA Greater Peoria

16h 03m1 stop Tampa St. Petersburg

$499Allegiant Air

Mon, Nov 16 - Fri, Nov 20

11:00 am - 3:29 pmORD Chicago O'Hare Intl-EYW Key West

3h 29mnonstop

2:51 pm - 10:18 pmEYW Key West-ORD Chicago O'Hare Intl

8h 27m1 stop Newark

$612United Airlines

Mon, Nov 16 - Fri, Nov 20

6:00 am - 1:52 pmORD Chicago O'Hare Intl-EYW Key West

6h 52m1 stop Newark

2:51 pm - 9:30 pmEYW Key West-ORD Chicago O'Hare Intl

7h 39m1 stop Newark

$622United Airlines

Recent direct flight deals from Illinois to Key West

Fri, Jan 1 - Fri, Jan 8

12:15 pm - 4:46 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:12 pm - 3:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

$380American Airlines

Tue, Dec 15 - Mon, Dec 21

12:15 pm - 4:46 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:51 pm - 3:40 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$382American Airlines

Tue, Dec 15 - Mon, Dec 21

10:55 am - 3:26 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:22 pm - 3:11 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$382United Airlines

Wed, Dec 23 - Mon, Dec 28

12:25 pm - 5:11 pmORD Chicago O'Hare Intl-EYW Key West

3h 46mnonstop

5:52 pm - 8:40 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

$389United Airlines

Fri, Jan 1 - Fri, Jan 8

12:15 pm - 4:46 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:12 pm - 3:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

$389American Airlines

Wed, Dec 23 - Mon, Dec 28

7:20 am - 11:51 amORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:51 pm - 3:40 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$389American Airlines

Fri, Jan 1 - Fri, Jan 8

12:15 pm - 4:46 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

12:12 pm - 3:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

$389American Airlines

Wed, Jan 6 - Thu, Jan 14

7:10 am - 11:42 amORD Chicago O'Hare Intl-EYW Key West

3h 32mnonstop

12:12 pm - 3:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

$389American Airlines

Mon, Mar 1 - Wed, Mar 31

7:05 am - 11:27 amORD Chicago O'Hare Intl-EYW Key West

3h 22mnonstop

11:57 am - 2:43 pmEYW Key West-ORD Chicago O'Hare Intl

3h 46mnonstop

$389American Airlines

Sat, May 8 - Thu, May 13

10:55 am - 3:06 pmORD Chicago O'Hare Intl-EYW Key West

3h 11mnonstop

4:05 pm - 6:30 pmEYW Key West-ORD Chicago O'Hare Intl

3h 25mnonstop

$389United Airlines

Useful Info

Low season	September
High season	March
Cheapest flight	$127

Best time to beat the crowds but there is an average 4% increase in price.

Most popular time to fly with an average 9% increase in price.

Flight from Chicago O'Hare Airport to Key West

How does KAYAK find such low prices on flights from Illinois to Key West?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Key West.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Key West?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Illinois is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Illinois to Key West?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Illinois with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Key West?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.