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.

$123 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

Thu, Jan 7 - Mon, Jan 11

7:52 pm - 3:12 pmORD Chicago O'Hare Intl-EYW Key West

18h 20m1 stop Tampa

4:02 pm - 9:13 amEYW Key West-ORD Chicago O'Hare Intl

18h 11m1 stop Tampa St. Petersburg

$229Multiple Airlines

Tue, Jan 5 - Tue, Jan 12

9:40 am - 10:39 amORD Chicago O'Hare Intl-EYW Key West

23h 59m2 stops Atlanta Hartsfield-Jackson Orlando

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

20h 57m1 stop Tampa

$237Multiple Airlines

Tue, Jan 5 - Tue, Jan 12

7:52 pm - 11:39 amORD Chicago O'Hare Intl-EYW Key West

14h 47m1 stop Tampa

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

20h 57m1 stop Tampa

$239Multiple Airlines

Tue, Jan 5 - Fri, Jan 15

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

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

Mon, Dec 7 - Sat, Dec 12

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

3h 31mnonstop

7:57 pm - 12:53 amEYW Key West-ORD Chicago O'Hare Intl

5h 56m1 stop Miami

$303American Airlines

Tue, Mar 2 - Mon, Mar 8

12:50 pm - 5:34 pmORD Chicago O'Hare Intl-EYW Key West

3h 44mnonstop

4:45 pm - 12:40 amEYW Key West-ORD Chicago O'Hare Intl

8h 55m1 stop Houston George Bush Intcntl

$346United Airlines

Tue, Jan 5 - Wed, Jan 13

6:00 am - 1:08 pmMDW Chicago Midway-EYW Key West

6h 08m1 stop Atlanta Hartsfield-Jackson

6:00 pm - 10:10 pmEYW Key West-MDW Chicago Midway

5h 10m1 stop Atlanta Hartsfield-Jackson

$346Delta

Fri, Jan 8 - Thu, Jan 14

6:00 am - 1:08 pmMDW Chicago Midway-EYW Key West

6h 08m1 stop Atlanta Hartsfield-Jackson

6:00 pm - 10:10 pmEYW Key West-MDW Chicago Midway

5h 10m1 stop Atlanta Hartsfield-Jackson

$346Delta

Thu, Dec 17 - Mon, Dec 21

10:35 am - 3:23 pmORD Chicago O'Hare Intl-EYW Key West

3h 48mnonstop

4:04 pm - 6:53 pmEYW Key West-ORD Chicago O'Hare Intl

3h 49mnonstop

$379United Airlines

Recent last minute flight deals from Illinois to Key West

Thu, Oct 29 - Mon, Nov 2

8:20 pm - 7:39 amBMI Bloomington-Normal-EYW Key West

10h 19m1 stop Orlando Sanford Intl

9:34 am - 10:27 amEYW Key West-BMI Bloomington-Normal

25h 53m1 stop Orlando Sanford Intl

$274Allegiant Air

Thu, Oct 29 - Mon, Nov 2

8:20 pm - 7:39 amBMI Bloomington-Normal-EYW Key West

10h 19m1 stop Orlando Sanford Intl

11:09 am - 10:27 amEYW Key West-BMI Bloomington-Normal

24h 18m2 stops Knoxville McGhee Tyson Orlando Sanford Intl

$370Allegiant Air

Sat, Oct 31 - Sat, Nov 7

9:51 am - 11:19 amORD Chicago O'Hare Intl-EYW Key West

24h 28m1 stop Orlando

10:04 am - 6:30 pmEYW Key West-ORD Chicago O'Hare Intl

9h 26m2 stops Tampa Atlanta Hartsfield-Jackson

$395Multiple Airlines

Fri, Oct 30 - Fri, Nov 6

6:14 am - 4:11 pmPIA Greater Peoria-EYW Key West

8h 57m2 stops Chicago O'Hare Intl Charlotte Douglas

7:18 pm - 11:56 pmEYW Key West-PIA Greater Peoria

5h 38m1 stop Charlotte Douglas

$469American Airlines

Sat, Oct 31 - Thu, Nov 5

10:01 am - 4:58 pmORD Chicago O'Hare Intl-EYW Key West

5h 57m1 stop Miami

1:14 pm - 4:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 46mnonstop

$485American Airlines

Sat, Oct 31 - Thu, Nov 5

10:01 am - 4:58 pmORD Chicago O'Hare Intl-EYW Key West

5h 57m1 stop Miami

7:18 pm - 12:01 amEYW Key West-ORD Chicago O'Hare Intl

5h 43m1 stop Charlotte Douglas

$495American Airlines

Wed, Oct 28 - Sat, Oct 31

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

3h 29mnonstop

2:50 pm - 10:23 pmEYW Key West-ORD Chicago O'Hare Intl

8h 33m1 stop Newark

$521United Airlines

Tue, Oct 27 - Sat, Oct 31

12:49 pm - 8:01 pmMDW Chicago Midway-EYW Key West

6h 12m1 stop Atlanta Hartsfield-Jackson

4:00 pm - 10:33 pmEYW Key West-MDW Chicago Midway

7h 33m1 stop Atlanta Hartsfield-Jackson

$531Delta

Mon, Oct 26 - Sat, Oct 31

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

6h 48m1 stop Atlanta Hartsfield-Jackson

4:00 pm - 10:36 pmEYW Key West-BMI Bloomington-Normal

7h 36m1 stop Atlanta Hartsfield-Jackson

$532Delta

Sat, Oct 31 - Thu, Nov 5

10:58 am - 3:29 pmORD Chicago O'Hare Intl-EYW Key West

3h 31mnonstop

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

3h 50mnonstop

$585United Airlines

Useful Info

Low season	September
High season	February
Cheapest flight	$123

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

Most popular time to fly and prices are also 1% lower on average.

Flight from Chicago Midway 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.