What is the cheapest airline that flies from Key West to Illinois?

American Airlines, Delta, and Allegiant Air are the most popular carriers operating from Key West to Illinois

How many flights depart from Key West to Illinois on average per day?

1 flights are operational daily from Key West to Illinois as of October 2026. The most popular departure time for this route is 4:00PM, with 100% of flights per day taking off in the afternoon.

How many flights depart from Key West to Illinois on average per week?

As of October 2026, 8 flights take off from Key West and land in Illinois each week. The most common flight departure day for this route is Wed, with 25% of weekly flights taking off on this day.

When did momondo last update prices for flights from Key West Airport to Illinois?

Prices for flights from Key West Airport to Illinois are refreshed on a daily basis.

How many operators does momondo search for flights from Key West Airport to Illinois?

There is 1 operator available for flights from Key West Airport to Illinois as of October 2026.

How old do you have to be to fly from Key West Airport to Illinois?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Illinois.

What documentation or ID do you need to fly to Illinois?

The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$118 Cheap Flights from Key West to Illinois in 2026/27

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Find the cheapest flights from Key West to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

14h 36m1 stop Orlando

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

27h 19m2 stops Atlanta Hartsfield-Jackson Orlando

$242Multiple Airlines

Wed, Feb 3 - Sat, Feb 6

11:04 am - 7:47 pmEYW Key West-MDW Chicago Midway

9h 43m1 stop Orlando

8:42 pm - 10:19 amMDW Chicago Midway-EYW Key West

12h 37m1 stop Orlando

$260Multiple Airlines

Tue, Nov 24 - Mon, Nov 30

6:25 pm - 11:50 amEYW Key West-ORD Chicago O'Hare Intl

18h 25m2 stops Orlando Sanford Intl Atlanta Hartsfield-Jackson

5:16 pm - 10:23 amORD Chicago O'Hare Intl-EYW Key West

16h 07m1 stop Orlando

$292Multiple Airlines

Thu, Jan 28 - Sat, Jan 30

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

4h 01mnonstop

10:30 am - 5:31 pmORD Chicago O'Hare Intl-EYW Key West

6h 01m1 stop Miami

$303American Airlines

Thu, Jan 28 - Sat, Jan 30

5:16 pm - 8:09 pmEYW Key West-ORD Chicago O'Hare Intl

3h 53mnonstop

10:12 am - 5:19 pmORD Chicago O'Hare Intl-EYW Key West

6h 07m1 stop Miami

$304American Airlines

Thu, Dec 3 - Wed, Dec 9

6:26 pm - 10:14 pmEYW Key West-ORD Chicago O'Hare Intl

28h 48m1 stop Tampa St. Petersburg

4:00 pm - 2:31 pmORD Chicago O'Hare Intl-EYW Key West

21h 31m2 stops Atlanta Hartsfield-Jackson Tampa

$306Multiple Airlines

Sat, Dec 5 - Sat, Dec 12

3:31 pm - 9:13 amEYW Key West-ORD Chicago O'Hare Intl

18h 42m1 stop Tampa St. Petersburg

5:32 pm - 3:17 pmORD Chicago O'Hare Intl-EYW Key West

20h 45m2 stops Atlanta Hartsfield-Jackson Tampa

$308Multiple Airlines

Mon, Jan 25 - Fri, Jan 29

12:19 pm - 9:13 amEYW Key West-ORD Chicago O'Hare Intl

21h 54m1 stop Tampa

10:18 am - 11:26 amORD Chicago O'Hare Intl-EYW Key West

24h 08m1 stop Tampa

$309Multiple Airlines

Wed, Feb 3 - Sat, Feb 6

5:01 pm - 9:41 pmEYW Key West-ORD Chicago O'Hare Intl

5h 40m1 stop Miami

9:00 am - 5:21 pmORD Chicago O'Hare Intl-EYW Key West

7h 21m1 stop Charlotte Douglas

$313American Airlines

Sat, Dec 5 - Sat, Dec 12

1:17 pm - 5:29 pmEYW Key West-ORD Chicago O'Hare Intl

5h 12m1 stop Charlotte Douglas

10:12 am - 5:19 pmORD Chicago O'Hare Intl-EYW Key West

6h 07m1 stop Miami

$313American Airlines

Thu, Dec 3 - Wed, Dec 9

Cheap direct flights

Enter your travel dates to find the best prices.

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

3h 56mnonstop

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

3h 26mnonstop

$379American Airlines

Wed, Nov 25 - Sun, Nov 29

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

3h 56mnonstop

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

3h 26mnonstop

$380American Airlines

Tue, Nov 24 - Sat, Nov 28

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

3h 56mnonstop

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

3h 26mnonstop

$380American Airlines

Wed, Nov 25 - Sun, Nov 29

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

3h 50mnonstop

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

3h 24mnonstop

$403United Airlines

Thu, Dec 3 - Wed, Dec 9

5:07 pm - 8:02 pmEYW Key West-ORD Chicago O'Hare Intl

3h 55mnonstop

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

3h 22mnonstop

$439American Airlines

Fri, Nov 13 - Wed, Nov 18

5:16 pm - 8:09 pmEYW Key West-ORD Chicago O'Hare Intl

3h 53mnonstop

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

3h 31mnonstop

$445American Airlines

Wed, Dec 23 - Tue, Dec 29

5:07 pm - 8:02 pmEYW Key West-ORD Chicago O'Hare Intl

3h 55mnonstop

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

3h 22mnonstop

$475American Airlines

Fri, Nov 13 - Wed, Nov 18

4:09 pm - 7:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 51mnonstop

7:31 am - 12:16 pmORD Chicago O'Hare Intl-EYW Key West

3h 45mnonstop

$481United Airlines

Thu, Jan 28 - Sat, Jan 30

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

3h 56mnonstop

12:15 pm - 4:35 pmORD Chicago O'Hare Intl-EYW Key West

3h 20mnonstop

$489American Airlines

Tue, Nov 24 - Mon, Nov 30

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

3h 56mnonstop

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

3h 26mnonstop

$489American Airlines

Wed, Nov 25 - Mon, Nov 30

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Delta flights from Key West to Illinois

Our best Delta deals on Key West to Illinois flight tickets

Delta

Nov 26

EYW7:30 amKey West

10h 10m

1 stop

ORD4:40 pmChicago O'Hare Intl

Nov 30

ORD6:49 amChicago O'Hare Intl

5h 10m

1 stop

EYW12:59 pmKey West

$533

Delta

Nov 26

EYW7:30 amKey West

8h 45m

1 stop

MDW3:15 pmChicago Midway

Nov 30

MDW11:27 amChicago Midway

7h 33m

1 stop

EYW8:00 pmKey West

$653

Delta

Nov 26

EYW7:30 amKey West

8h 45m

1 stop

MDW3:15 pmChicago Midway

Nov 28

MDW6:00 amChicago Midway

10h 10m

1 stop

EYW5:10 pmKey West

$658

American Airlines flights from Key West to Illinois

Our best American Airlines deals on Key West to Illinois flight tickets

American Airlines

Jan 28

EYW5:58 pmKey West

4h 01m

ORD8:59 pmChicago O'Hare Intl

Jan 30

ORD10:30 amChicago O'Hare Intl

6h 01m

1 stop

EYW5:31 pmKey West

$303

American Airlines

Dec 3

EYW5:16 pmKey West

3h 53m

ORD8:09 pmChicago O'Hare Intl

Dec 9

ORD10:12 amChicago O'Hare Intl

6h 07m

1 stop

EYW5:19 pmKey West

$304

American Airlines

Dec 3

EYW1:17 pmKey West

5h 12m

1 stop

ORD5:29 pmChicago O'Hare Intl

Dec 9

ORD10:12 amChicago O'Hare Intl

6h 07m

1 stop

EYW5:19 pmKey West

$313

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 2/3

11:19 am-12:55 am

1 stop14h 36m

Chicago O'Hare Intl

Sat 2/6

6:00 am-10:19 am

2 stops27h 19m

$242

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Tue 11/24

11:04 am-7:47 pm

1 stop9h 43m

Chicago Midway

Mon 11/30

8:42 pm-10:19 am

1 stop12h 37m

$260

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

6:25 pm-11:50 am

2 stops18h 25m

Chicago O'Hare Intl

Sat 1/30

5:16 pm-10:23 am

1 stop16h 07m

$292

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 1/28

5:58 pm-8:59 pm

Nonstop4h 01m

Chicago O'Hare Intl

Sat 1/30

10:30 am-5:31 pm

1 stop6h 01m

$303

Quickest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 12/3

5:16 pm-8:09 pm

Nonstop3h 53m

Chicago O'Hare Intl

Wed 12/9

10:12 am-5:19 pm

1 stop6h 07m

$304

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

6:26 pm-10:14 pm

1 stop28h 48m

Chicago O'Hare Intl

Sat 12/12

4:00 pm-2:31 pm

2 stops21h 31m

$306

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Mon 1/25

3:31 pm-9:13 am

1 stop18h 42m

Chicago O'Hare Intl

Fri 1/29

5:32 pm-3:17 pm

2 stops20h 45m

$308

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 2/3

12:19 pm-9:13 am

1 stop21h 54m

Chicago O'Hare Intl

Sat 2/6

10:18 am-11:26 am

1 stop24h 08m

$309

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

5:01 pm-9:41 pm

1 stop5h 40m

Chicago O'Hare Intl

Sat 12/12

9:00 am-5:21 pm

1 stop7h 21m

$313

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 12/3

1:17 pm-5:29 pm

1 stop5h 12m

Chicago O'Hare Intl

Wed 12/9

10:12 am-5:19 pm

1 stop6h 07m

$313

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Key West to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Key West is in September. Flight prices, which tend to average around $0, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $0.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Key West to Illinois is on a Wednesday when prices can be found for as low as $339. Flights from Key West to Illinois on a Monday will generally be more expensive and average around $856. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the morning. Flights from Key West to Illinois during this time can be as low as $366. Flights in the afternoon are often more expensive with an average ticket price of $470.

What is the cheapest Key West to Illinois flight route?

Fly from Key West to Chicago O'Hare Intl for the best Key West - Illinois flight prices

What cabin class options are available on Key West to Illinois flights?

There are 4 cabin classes available to choose from on Key West to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Key West to Illinois flights?

You could potentially save up to 49% on your flight if you consider stops on a Key West to Illinois flight.

Cheap Key West to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Illinois

Best Price Found	$118
Fastest flight time	3h 49m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Key West in the past 72 hours is $118. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $242.

The fastest flight from Key West to Illinois takes 3h 49m

Direct flights go from Key West to Illinois every day.

There are 98 airports in Illinois. From Key West there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Key West to Illinois

When did momondo last update prices for flights from Key West Airport to Illinois?
Prices for flights from Key West Airport to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Key West Airport to Illinois?
There is 1 operator available for flights from Key West Airport to Illinois as of October 2026.
How old do you have to be to fly from Key West Airport to Illinois?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Key West to Illinois?
Based on momondo bookings for flights between Key West and Illinois, the leading plane model is Embraer 170, making up 37.04% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 18.52%, Embraer 175 with 14.81%, and Boeing 737-700 with 7.41%.

Best airlines flying from Key West to Illinois

Compare and see reviews for airlines that fly from Key West to Illinois with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $319	Free Cancellation	Rating 7.0 12,209 reviews		Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Illinois?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Key West to Illinois. momondo saves you time and could save you money on your trip.

Can I find flights from Key West to Illinois with flexible booking policies on momondo?

Flights from Key West to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Key West to Illinois?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Illinois from Key West.

I’m not ready to book a flight from Key West to Illinois right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Illinois from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.