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

Allegiant Air, United Airlines, and Delta are the most popular carriers operating 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 September 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.

$114 Cheap Flights from Key West to Illinois in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

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

9h 27m2 stops Tampa Atlanta Hartsfield-Jackson

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

24h 28m1 stop Orlando

$303Multiple Airlines

Sat, Oct 17 - Sat, Oct 31

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

21h 52m1 stop Orlando

8:04 am - 9:24 amORD Chicago O'Hare Intl-EYW Key West

24h 20m2 stops Fort Lauderdale Tampa

$304Multiple Airlines

Fri, Oct 16 - Tue, Oct 20

10:14 am - 3:40 pmEYW Key West-MDW Chicago Midway

6h 26m1 stop Knoxville McGhee Tyson

6:21 am - 9:24 amMDW Chicago Midway-EYW Key West

26h 03m2 stops Atlanta Hartsfield-Jackson Tampa

$337Multiple Airlines

Fri, Oct 16 - Tue, Oct 20

4:49 pm - 7:44 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

$359American Airlines

Sat, Dec 5 - Mon, Dec 7

10:04 am - 9:20 amEYW Key West-ORD Chicago O'Hare Intl

48h 16m2 stops Tampa Atlanta Hartsfield-Jackson

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

17h 29m1 stop Orlando

$361Multiple Airlines

Sat, Oct 3 - Wed, Oct 7

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

7h 12m1 stop Miami

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

3h 22mnonstop

$369American Airlines

Thu, Oct 29 - Sun, Nov 1

4:49 pm - 7:44 pmEYW Key West-ORD Chicago O'Hare Intl

3h 55mnonstop

5:19 am - 1:03 pmORD Chicago O'Hare Intl-EYW Key West

6h 44m1 stop Charlotte Douglas

$369American Airlines

Sat, Dec 5 - Mon, Dec 7

8:34 am - 10:59 pmEYW Key West-ORD Chicago O'Hare Intl

15h 25m1 stop Orlando Sanford Intl

7:11 am - 9:24 amORD Chicago O'Hare Intl-EYW Key West

25h 13m2 stops Fort Lauderdale Tampa

$370Multiple Airlines

Fri, Oct 2 - Tue, Oct 6

10:59 am - 6:23 pmEYW Key West-ORD Chicago O'Hare Intl

32h 24m2 stops Orlando Atlanta Hartsfield-Jackson

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

17h 29m1 stop Orlando

$371Multiple Airlines

Sun, Oct 4 - Wed, Oct 7

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

13h 00m1 stop Orlando

7:11 am - 9:24 amORD Chicago O'Hare Intl-EYW Key West

25h 13m2 stops Fort Lauderdale Tampa

$376Multiple Airlines

Thu, Oct 1 - Tue, Oct 6

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American Airlines flights from Key West to Illinois

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

American Airlines

Dec 5

EYW4:49 pmKey West

3h 55m

ORD7:44 pmChicago O'Hare Intl

Dec 7

ORD12:10 pmChicago O'Hare Intl

3h 22m

EYW4:32 pmKey West

$359

American Airlines

Dec 5

EYW4:49 pmKey West

3h 55m

ORD7:44 pmChicago O'Hare Intl

Dec 7

ORD5:19 amChicago O'Hare Intl

6h 44m

1 stop

EYW1:03 pmKey West

$369

American Airlines

Oct 17

EYW8:03 pmKey West

5h 35m

1 stop

ORD12:38 amChicago O'Hare Intl

Oct 31

ORD10:01 amChicago O'Hare Intl

5h 57m

1 stop

EYW4:58 pmKey West

$445

Delta flights from Key West to Illinois

Our best Delta deals on Key West to Illinois flight tickets

Delta

Dec 5

EYW2:06 pmKey West

5h 59m

1 stop

ORD7:05 pmChicago O'Hare Intl

Dec 7

ORD5:30 amChicago O'Hare Intl

6h 41m

1 stop

EYW1:11 pmKey West

$379

Delta

Dec 5

EYW6:06 pmKey West

5h 49m

1 stop

MDW10:55 pmChicago Midway

Dec 7

MDW11:28 amChicago Midway

4h 43m

1 stop

EYW5:11 pmKey West

$406

Delta

Oct 1

EYW11:42 amKey West

5h 55m

1 stop

ORD4:37 pmChicago O'Hare Intl

Oct 6

ORD1:23 pmChicago O'Hare Intl

5h 38m

1 stop

EYW8:01 pmKey West

$439

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 10/17

10:04 am-6:31 pm

2 stops9h 27m

Chicago O'Hare Intl

Sat 10/31

9:51 am-11:19 am

1 stop24h 28m

$303

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 10/16

10:59 am-7:51 am

1 stop21h 52m

Chicago O'Hare Intl

Tue 10/20

8:04 am-9:24 am

2 stops24h 20m

$304

Key WestChicago

EYW Key West - MDW Chicago Midway

EYWMDW

Key West

Fri 10/16

10:14 am-3:40 pm

1 stop6h 26m

Chicago Midway

Tue 10/20

6:21 am-9:24 am

2 stops26h 03m

$337

Quickest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

4:49 pm-7:44 pm

Nonstop3h 55m

Chicago O'Hare Intl

Mon 12/7

12:10 pm-4:32 pm

Nonstop3h 22m

$359

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 10/3

10:04 am-9:20 am

2 stops48h 16m

Chicago O'Hare Intl

Wed 10/7

3:50 pm-10:19 am

1 stop17h 29m

$361

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 10/29

1:43 pm-7:55 pm

1 stop7h 12m

Chicago O'Hare Intl

Sun 11/1

12:10 pm-4:32 pm

Nonstop3h 22m

$369

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sat 12/5

4:49 pm-7:44 pm

Nonstop3h 55m

Chicago O'Hare Intl

Mon 12/7

5:19 am-1:03 pm

1 stop6h 44m

$369

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Fri 10/2

8:34 am-10:59 pm

1 stop15h 25m

Chicago O'Hare Intl

Tue 10/6

7:11 am-9:24 am

2 stops25h 13m

$370

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Sun 10/4

10:59 am-6:23 pm

2 stops32h 24m

Chicago O'Hare Intl

Wed 10/7

3:50 pm-10:19 am

1 stop17h 29m

$371

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 10/1

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Tue 10/6

7:11 am-9:24 am

2 stops25h 13m

$376

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

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Key West is in March. 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 March, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $268.

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 $484. 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 $443.

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 43% 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	$114
Fastest flight time	3h 39m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Illinois	98 airports

The best one-way flight to Illinois from Key West in the past 72 hours is $114. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $303.

The fastest flight from Key West to Illinois takes 3h 39m

Direct flights go from Key West to Illinois on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is American Airlines.

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 September 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 29.63% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 25.93%, 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 7.1 12,075 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.