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.

$113 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

Mon, Nov 23 - Thu, Dec 10

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

25h 54m1 stop Tampa

12:01 pm - 10:14 pmEYW Key West-ORD Chicago O'Hare Intl

11h 13m1 stop Tampa

$215Multiple Airlines

Sat, Oct 24 - Wed, Oct 28

4:30 pm - 12:38 pmSTL Lambert-St Louis-EYW Key West

19h 08m1 stop Orlando

10:04 am - 5:40 pmEYW Key West-STL Lambert-St Louis

8h 36m2 stops Tampa Atlanta Hartsfield-Jackson

$228Multiple Airlines

Wed, Oct 28 - Tue, Nov 3

9:51 am - 12:38 pmORD Chicago O'Hare Intl-EYW Key West

25h 47m1 stop Orlando

1:16 pm - 12:51 pmEYW Key West-ORD Chicago O'Hare Intl

24h 35m2 stops Tampa Atlanta Hartsfield-Jackson

$248Multiple Airlines

Sat, Oct 24 - Wed, Oct 28

8:48 am - 4:54 pmSTL Lambert-St Louis-EYW Key West

7h 06m1 stop Dallas/Fort Worth

2:34 pm - 10:00 pmEYW Key West-STL Lambert-St Louis

8h 26m1 stop Dallas/Fort Worth

$309American Airlines

Tue, Jan 19 - Tue, Jan 26

7:25 am - 5:19 pmSTL Lambert-St Louis-EYW Key West

8h 54m1 stop Chicago O'Hare Intl

1:52 pm - 5:49 pmEYW Key West-STL Lambert-St Louis

4h 57m1 stop Charlotte Douglas

$323American Airlines

Tue, Jan 5 - Wed, May 19

7:30 am - 3:12 pmSTL Lambert-St Louis-EYW Key West

6h 42m1 stop Chicago O'Hare Intl

4:05 pm - 10:54 pmEYW Key West-STL Lambert-St Louis

7h 49m1 stop Chicago O'Hare Intl

$323United Airlines

Tue, Dec 1 - Sat, Dec 5

7:26 am - 4:35 pmSTL Lambert-St Louis-EYW Key West

8h 09m1 stop Chicago O'Hare Intl

4:49 pm - 11:59 pmEYW Key West-STL Lambert-St Louis

8h 10m1 stop Chicago O'Hare Intl

$323American Airlines

Tue, Oct 6 - Wed, Oct 14

12:13 pm - 8:01 pmBMI Bloomington-Normal-EYW Key West

6h 48m1 stop Atlanta Hartsfield-Jackson

7:40 am - 11:26 amEYW Key West-BMI Bloomington-Normal

4h 46m1 stop Atlanta Hartsfield-Jackson

$349Delta

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

6:05 pm - 11:08 pmEYW Key West-MLI Moline Quad-City

6h 03m1 stop Atlanta Hartsfield-Jackson

$359Delta

Recent last minute flight deals from Illinois to Key West

Tue, Sep 22 - Sat, Sep 26

12:00 pm - 8:00 pmSTL Lambert-St Louis-EYW Key West

7h 00m1 stop Atlanta Hartsfield-Jackson

7:40 am - 12:32 pmEYW Key West-STL Lambert-St Louis

5h 52m1 stop Atlanta Hartsfield-Jackson

$423Delta

Sat, Sep 19 - Sat, Sep 26

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

17h 29m1 stop Orlando

10:04 am - 6:23 pmEYW Key West-ORD Chicago O'Hare Intl

9h 19m2 stops Tampa Atlanta Hartsfield-Jackson

$449Multiple Airlines

Tue, Sep 22 - Mon, Sep 28

5:00 am - 10:57 amORD Chicago O'Hare Intl-EYW Key West

4h 57m1 stop Miami

6:27 pm - 11:59 pmEYW Key West-ORD Chicago O'Hare Intl

6h 32m1 stop Charlotte Douglas

$475American Airlines

Tue, Sep 22 - Mon, Sep 28

6:45 am - 1:11 pmORD Chicago O'Hare Intl-EYW Key West

5h 26m1 stop Charlotte Douglas

7:47 pm - 12:33 amEYW Key West-ORD Chicago O'Hare Intl

5h 46m1 stop Miami

$475American Airlines

Tue, Sep 22 - Mon, Sep 28

5:30 am - 12:53 pmORD Chicago O'Hare Intl-EYW Key West

6h 23m1 stop Atlanta Hartsfield-Jackson

6:19 pm - 11:59 pmEYW Key West-ORD Chicago O'Hare Intl

6h 40m1 stop Atlanta Hartsfield-Jackson

$475Delta

Wed, Sep 23 - Thu, Oct 1

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

$475Delta

Sun, Sep 20 - Thu, Sep 24

11:15 am - 10:19 amORD Chicago O'Hare Intl-EYW Key West

22h 04m1 stop Orlando

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

13h 00m1 stop Orlando

$510Multiple Airlines

Sun, Sep 20 - Thu, Sep 24

7:25 am - 12:19 pmORD Chicago O'Hare Intl-EYW Key West

27h 54m2 stops Philadelphia Tampa

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

13h 00m1 stop Orlando

$510Multiple Airlines

Sun, Sep 20 - Sat, Sep 26

6:00 am - 1:29 pmORD Chicago O'Hare Intl-EYW Key West

6h 29m1 stop Newark

4:20 pm - 6:59 pmEYW Key West-ORD Chicago O'Hare Intl

3h 39mnonstop

$520United Airlines

Sat, Sep 19 - Sat, Sep 26

6:00 am - 1:28 pmORD Chicago O'Hare Intl-EYW Key West

6h 28m1 stop Newark

4:20 pm - 6:59 pmEYW Key West-ORD Chicago O'Hare Intl

3h 39mnonstop

$525United Airlines

Useful Info

Low season	September
High season	February
Cheapest flight	$113

Best time to beat the crowds but there is an average 6% 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.