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.

$116 CHEAP FLIGHTS from Illinois to Key West

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Cheap Flights from Illinois to Key West

Cheap flights from Illinois to Key West with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Mon, Dec 7 - Tue, Dec 15

5:24 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

15h 55m1 stop Orlando

10:59 am - 1:01 amEYW Key West-ORD Chicago O'Hare Intl

15h 02m1 stop Orlando

$173Multiple Airlines

Mon, Dec 7 - Tue, Dec 15

8:15 am - 10:19 amORD Chicago O'Hare Intl-EYW Key West

25h 04m2 stops Atlanta Hartsfield-Jackson Orlando

10:59 am - 9:48 amEYW Key West-ORD Chicago O'Hare Intl

23h 49m1 stop Orlando

$241Multiple Airlines

Sat, Jan 9 - Wed, Jan 13

6:00 am - 10:19 amORD Chicago O'Hare Intl-EYW Key West

27h 19m2 stops Atlanta Hartsfield-Jackson Orlando

11:19 am - 12:55 amEYW Key West-ORD Chicago O'Hare Intl

14h 36m1 stop Orlando

$242Multiple Airlines

Tue, Jan 5 - Thu, Jan 14

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

3h 31mnonstop

5:58 pm - 8:59 pmEYW Key West-ORD Chicago O'Hare Intl

4h 01mnonstop

$293American Airlines

Tue, Dec 1 - Fri, Dec 11

7:20 am - 11:46 amORD Chicago O'Hare Intl-EYW Key West

3h 26mnonstop

1:01 pm - 3:50 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$293American Airlines

Fri, Jan 22 - Thu, Jan 28

10:35 am - 3:22 pmORD Chicago O'Hare Intl-EYW Key West

3h 47mnonstop

5:54 pm - 8:40 pmEYW Key West-ORD Chicago O'Hare Intl

3h 46mnonstop

$293United Airlines

Tue, Jan 5 - Thu, Jan 14

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

$293American Airlines

Fri, Jan 8 - Wed, Jan 13

9:30 am - 5:11 pmORD Chicago O'Hare Intl-EYW Key West

6h 41m1 stop Atlanta Hartsfield-Jackson

11:45 am - 4:37 pmEYW Key West-ORD Chicago O'Hare Intl

5h 52m1 stop Atlanta Hartsfield-Jackson

$313Delta

Tue, Feb 9 - Thu, Feb 25

11:10 am - 7:43 pmORD Chicago O'Hare Intl-EYW Key West

7h 33m1 stop Atlanta Hartsfield-Jackson

2:35 pm - 9:10 pmEYW Key West-ORD Chicago O'Hare Intl

7h 35m1 stop Atlanta Hartsfield-Jackson

$313Delta

Sat, Dec 5 - Mon, Dec 21

7:00 am - 11:24 amORD Chicago O'Hare Intl-EYW Key West

3h 24mnonstop

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

3h 48mnonstop

$326United Airlines

Thu, Oct 15 - Mon, Oct 19

6:58 pm - 7:44 amORD Chicago O'Hare Intl-EYW Key West

11h 46m1 stop Orlando

2:54 pm - 7:51 amEYW Key West-ORD Chicago O'Hare Intl

17h 57m1 stop Orlando Sanford Intl

$278Multiple Airlines

Wed, Oct 14 - Sat, Oct 24

8:46 am - 10:19 amORD Chicago O'Hare Intl-EYW Key West

24h 33m1 stop Orlando

10:04 am - 6:31 pmEYW Key West-ORD Chicago O'Hare Intl

9h 27m2 stops Tampa Atlanta Hartsfield-Jackson

$377Multiple Airlines

Thu, Oct 15 - Sat, Oct 24

6:58 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

14h 21m1 stop Orlando

10:04 am - 6:31 pmEYW Key West-ORD Chicago O'Hare Intl

9h 27m2 stops Tampa Atlanta Hartsfield-Jackson

$378Multiple Airlines

Wed, Oct 14 - Wed, Oct 21

6:14 am - 4:58 pmPIA Greater Peoria-EYW Key West

9h 44m2 stops Chicago O'Hare Intl Miami

4:45 pm - 11:56 pmEYW Key West-PIA Greater Peoria

8h 11m1 stop Charlotte Douglas

$469American Airlines

Wed, Oct 14 - Wed, Oct 21

6:14 am - 4:58 pmPIA Greater Peoria-EYW Key West

9h 44m2 stops Chicago O'Hare Intl Miami

12:48 pm - 12:10 amEYW Key West-PIA Greater Peoria

12h 22m2 stops Charlotte Douglas Chicago O'Hare Intl

$474American Airlines

Tue, Oct 13 - Fri, Oct 23

6:30 am - 12:53 pmORD Chicago O'Hare Intl-EYW Key West

5h 23m1 stop Atlanta Hartsfield-Jackson

2:00 pm - 8:38 pmEYW Key West-ORD Chicago O'Hare Intl

7h 38m1 stop Atlanta Hartsfield-Jackson

$475Delta

Tue, Oct 13 - Sat, Oct 24

6:30 am - 12:53 pmORD Chicago O'Hare Intl-EYW Key West

5h 23m1 stop Atlanta Hartsfield-Jackson

11:42 am - 4:58 pmEYW Key West-ORD Chicago O'Hare Intl

6h 16m1 stop Atlanta Hartsfield-Jackson

$475Delta

Tue, Oct 13 - Tue, Oct 20

8:05 am - 4:11 pmORD Chicago O'Hare Intl-EYW Key West

7h 06m1 stop Charlotte Douglas

2:15 pm - 7:51 pmEYW Key West-ORD Chicago O'Hare Intl

6h 36m1 stop Charlotte Douglas

$475American Airlines

Wed, Oct 14 - Sat, Oct 24

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

$575United Airlines

Tue, Oct 13 - Sat, Oct 24

5:00 am - 1:29 pmORD Chicago O'Hare Intl-EYW Key West

7h 29m1 stop Newark

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

3h 39mnonstop

$575United Airlines

Low season	September
High season	February
Cheapest flight	$116

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.