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.

$114 CHEAP FLIGHTS from Illinois to Key West

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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

Fri, Oct 30 - Fri, Nov 6

6:16 am - 9:24 amMDW Chicago Midway-EYW Key West

26h 08m2 stops Atlanta Hartsfield-Jackson Tampa

10:14 am - 7:19 pmEYW Key West-MDW Chicago Midway

10h 05m1 stop Knoxville McGhee Tyson

$245Multiple Airlines

Mon, Nov 9 - Fri, Nov 13

6:08 am - 12:36 pmMDW Chicago Midway-EYW Key West

29h 28m2 stops Atlanta Hartsfield-Jackson Tampa

10:14 am - 2:26 pmEYW Key West-MDW Chicago Midway

5h 12m1 stop Knoxville McGhee Tyson

$275Multiple Airlines

Sun, Nov 15 - Thu, Nov 19

7:05 pm - 8:30 amBMI Bloomington-Normal-EYW Key West

12h 25m1 stop Orlando Sanford Intl

3:06 pm - 7:30 amEYW Key West-BMI Bloomington-Normal

17h 24m1 stop Tampa St. Petersburg

$285Allegiant Air

Mon, Nov 2 - Wed, Nov 11

12:10 pm - 4:32 pmORD Chicago O'Hare Intl-EYW Key West

3h 22mnonstop

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

3h 55mnonstop

$292American Airlines

Mon, Nov 2 - Wed, Nov 11

12:10 pm - 4:32 pmORD Chicago O'Hare Intl-EYW Key West

3h 22mnonstop

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

3h 55mnonstop

$293American 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

Sat, Nov 14 - Wed, Nov 18

11:27 am - 5:10 pmMDW Chicago Midway-EYW Key West

4h 43m1 stop Atlanta Hartsfield-Jackson

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

5h 46m1 stop Atlanta Hartsfield-Jackson

$313Delta

Sat, Dec 5 - Thu, Dec 10

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

$313Delta

Sat, Oct 24 - Tue, Oct 27

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

3h 24mnonstop

4:10 pm - 6:59 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$359United Airlines

Sat, Oct 24 - Thu, Oct 29

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

3h 24mnonstop

4:10 pm - 6:59 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$359United Airlines

Recent last minute flight deals from Illinois to Key West

Wed, Oct 7 - Sat, Oct 10

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

17h 29m1 stop Orlando

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

9h 27m2 stops Tampa Atlanta Hartsfield-Jackson

$384Multiple Airlines

Wed, Oct 7 - Fri, Oct 9

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

17h 29m1 stop Orlando

10:59 am - 7:51 amEYW Key West-ORD Chicago O'Hare Intl

21h 52m1 stop Orlando

$404Multiple Airlines

Tue, Oct 6 - Thu, Oct 8

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

25h 54m2 stops Denver Intl Tampa

10:59 am - 5:53 pmEYW Key West-ORD Chicago O'Hare Intl

7h 54m1 stop Orlando

$432Multiple Airlines

Thu, Oct 8 - Thu, Oct 15

6:14 am - 1:03 pmORD Chicago O'Hare Intl-EYW Key West

5h 49m1 stop Miami

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

7h 12m1 stop Miami

$494American Airlines

Wed, Oct 7 - Sat, Oct 10

5:05 am - 1:03 pmORD Chicago O'Hare Intl-EYW Key West

6h 58m1 stop Miami

10:24 am - 3:31 pmEYW Key West-ORD Chicago O'Hare Intl

6h 07m1 stop Miami

$511American Airlines

Wed, Oct 7 - Sat, Oct 10

10:59 am - 5:15 pmMDW Chicago Midway-EYW Key West

5h 16m1 stop Atlanta Hartsfield-Jackson

6:11 pm - 10:33 pmEYW Key West-MDW Chicago Midway

5h 22m1 stop Atlanta Hartsfield-Jackson

$511Delta

Tue, Oct 6 - Sat, Oct 10

8:43 am - 4:58 pmORD Chicago O'Hare Intl-EYW Key West

7h 15m1 stop Miami

8:03 pm - 12:38 amEYW Key West-ORD Chicago O'Hare Intl

5h 35m1 stop Miami

$511American Airlines

Thu, Oct 8 - Sun, Oct 11

11:21 am - 8:01 pmORD Chicago O'Hare Intl-EYW Key West

7h 40m1 stop Atlanta Hartsfield-Jackson

6:10 pm - 11:57 pmEYW Key West-ORD Chicago O'Hare Intl

6h 47m1 stop Atlanta Hartsfield-Jackson

$549Delta

Wed, Oct 7 - Sat, Oct 10

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

$611United Airlines

Tue, Oct 6 - Sat, Oct 10

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

$611United Airlines

Useful Info

Low season	September
High season	February
Cheapest flight	$114

Best time to beat the crowds but there is an average 5% 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.