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.

$126 CHEAP FLIGHTS from Illinois to Key West

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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

Tue, Nov 17 - Tue, Nov 24

7:15 am - 9:24 amORD Chicago O'Hare Intl-EYW Key West

25h 09m2 stops Atlanta Hartsfield-Jackson Tampa

10:04 am - 12:43 amEYW Key West-ORD Chicago O'Hare Intl

15h 39m1 stop Tampa

$288Multiple Airlines

Sat, Dec 5 - Sat, Dec 12

2:29 pm - 11:20 amPIA Greater Peoria-EYW Key West

19h 51m1 stop Orlando Sanford Intl

6:26 pm - 8:03 amEYW Key West-PIA Greater Peoria

14h 37m1 stop Tampa St. Petersburg

$293Allegiant Air

Tue, Dec 1 - Fri, Dec 4

7:32 pm - 3:50 pmORD Chicago O'Hare Intl-EYW Key West

19h 18m2 stops Atlanta Hartsfield-Jackson Tampa

12:59 pm - 10:11 pmEYW Key West-ORD Chicago O'Hare Intl

10h 12m1 stop Tampa

$310Multiple Airlines

Tue, Mar 23 - Tue, Mar 30

8:20 am - 12:57 pmORD Chicago O'Hare Intl-EYW Key West

3h 37mnonstop

1:27 pm - 4:07 pmEYW Key West-ORD Chicago O'Hare Intl

3h 40mnonstop

$359American Airlines

Tue, Nov 10 - Thu, Nov 19

7:29 am - 11:53 amORD Chicago O'Hare Intl-EYW Key West

3h 24mnonstop

5:05 pm - 8:01 pmEYW Key West-ORD Chicago O'Hare Intl

3h 56mnonstop

$359American Airlines

Sat, Jan 9 - Sat, Jan 16

12:25 pm - 5:10 pmORD Chicago O'Hare Intl-EYW Key West

3h 45mnonstop

5:51 pm - 8:40 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$359United Airlines

Mon, Oct 26 - Wed, Nov 4

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

3h 29mnonstop

4:10 pm - 7:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 50mnonstop

$359United Airlines

Mon, Nov 2 - Thu, Nov 12

11:08 am - 5:15 pmMLI Moline Quad-City-EYW Key West

5h 07m1 stop Atlanta Hartsfield-Jackson

6:08 pm - 11:08 pmEYW Key West-MLI Moline Quad-City

6h 00m1 stop Atlanta Hartsfield-Jackson

$359Delta

Thu, Jan 7 - Thu, Jan 14

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

3h 32mnonstop

5:58 pm - 9:01 pmEYW Key West-ORD Chicago O'Hare Intl

4h 03mnonstop

$359American 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

$379Delta

Recent last minute flight deals from Illinois to Key West

Fri, Oct 2 - Sun, Oct 4

6:30 am - 9:24 amORD Chicago O'Hare Intl-EYW Key West

25h 54m2 stops Denver Intl Tampa

10:59 am - 10:59 pmEYW Key West-ORD Chicago O'Hare Intl

13h 00m1 stop Orlando

$460Multiple Airlines

Wed, Sep 30 - Mon, Oct 5

3:50 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

17h 29m1 stop Orlando

12:59 pm - 11:51 amEYW Key West-ORD Chicago O'Hare Intl

23h 52m2 stops Tampa Atlanta Hartsfield-Jackson

$470Multiple Airlines

Wed, Sep 30 - Mon, Oct 5

3:50 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

17h 29m1 stop Orlando

10:59 am - 10:59 pmEYW Key West-ORD Chicago O'Hare Intl

13h 00m1 stop Orlando

$471Multiple Airlines

Sat, Oct 3 - Wed, Oct 7

10:05 am - 7:17 pmORD Chicago O'Hare Intl-EYW Key West

8h 12m1 stop Miami

12:48 pm - 5:51 pmEYW Key West-ORD Chicago O'Hare Intl

6h 03m1 stop Charlotte Douglas

$475American Airlines

Fri, Oct 2 - Fri, Oct 9

5:20 am - 1:11 pmORD Chicago O'Hare Intl-EYW Key West

6h 51m1 stop Charlotte Douglas

1:43 pm - 7:55 pmEYW Key West-ORD Chicago O'Hare Intl

7h 12m1 stop Miami

$494American Airlines

Wed, Sep 30 - Tue, Oct 6

1:00 pm - 8:00 pmMDW Chicago Midway-EYW Key West

6h 00m1 stop Atlanta Hartsfield-Jackson

6:10 pm - 10:33 pmEYW Key West-MDW Chicago Midway

5h 23m1 stop Atlanta Hartsfield-Jackson

$511Delta

Sat, Oct 3 - Wed, Oct 7

5:00 am - 11:00 amORD Chicago O'Hare Intl-EYW Key West

5h 00m1 stop Miami

5:28 pm - 12:38 amEYW Key West-ORD Chicago O'Hare Intl

8h 10m1 stop Miami

$511American Airlines

Wed, Sep 30 - Mon, Oct 5

6:05 am - 12:53 pmMDW Chicago Midway-EYW Key West

5h 48m1 stop Atlanta Hartsfield-Jackson

6:19 pm - 10:44 pmEYW Key West-MDW Chicago Midway

5h 25m1 stop Atlanta Hartsfield-Jackson

$530Delta

Sat, Oct 3 - Wed, Oct 7

11:00 am - 3:24 pmORD Chicago O'Hare Intl-EYW Key West

3h 24mnonstop

2:15 pm - 10:28 pmEYW Key West-ORD Chicago O'Hare Intl

9h 13m1 stop Newark

$575United Airlines

Sat, Oct 3 - Wed, Oct 7

11:00 am - 3:24 pmORD Chicago O'Hare Intl-EYW Key West

3h 24mnonstop

2:15 pm - 10:28 pmEYW Key West-ORD Chicago O'Hare Intl

9h 13m1 stop Newark

$611United Airlines

Useful Info

Low season	September
High season	February
Cheapest flight	$126

Best time to beat the crowds but there is an average 7% 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.