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Cheap flights from Key West to Illinois from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Illinois departing on 2/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Key West to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:39 pm - 9:20 pm
EYW
-
ORD
3h 41mnonstop
American Airlines Logo
8:00 am - 12:16 pm
ORD
-
EYW
3h 16mnonstop
$249American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
1:15 pm - 3:50 pm
EYW
-
ORD
3h 35mnonstop
American Airlines Logo
10:59 am - 3:25 pm
ORD
-
EYW
3h 26mnonstop
$279American Airlines
Mon, Dec 29 - Mon, Jan 12
American Airlines Logo
11:13 am - 4:47 pm
EYW
-
ORD
6h 34m1 stop
American Airlines Logo
8:14 am - 12:45 pm
ORD
-
EYW
3h 31mnonstop
$289American Airlines
Mon, Dec 29 - Mon, Jan 12
Delta Logo
4:25 pm - 9:14 pm
EYW
-
ORD
5h 49m1 stop
Delta Logo
9:55 am - 5:11 pm
ORD
-
EYW
6h 16m1 stop
$299Delta
Mon, Dec 29 - Mon, Jan 12
Delta Logo
7:25 am - 11:58 am
EYW
-
MDW
5h 33m1 stop
Delta Logo
6:45 am - 1:48 pm
MDW
-
EYW
6h 03m1 stop
$299Delta
Mon, Dec 29 - Mon, Jan 12
American Airlines Logo
4:01 pm - 6:45 pm
EYW
-
ORD
3h 44mnonstop
American Airlines Logo
3:21 pm - 9:47 pm
ORD
-
EYW
5h 26m1 stop
$307American Airlines
Wed, Jan 21 - Thu, Jan 29
United Airlines Logo
12:22 pm - 3:07 pm
EYW
-
ORD
3h 45mnonstop
United Airlines Logo
7:55 am - 12:34 pm
ORD
-
EYW
3h 39mnonstop
$309United Airlines
Fri, Dec 26 - Tue, Dec 30
United Airlines Logo
4:29 pm - 12:14 am
EYW
-
ORD
8h 45m1 stop
United Airlines Logo
10:45 am - 3:12 pm
ORD
-
EYW
3h 27mnonstop
$319United Airlines
Fri, Dec 26 - Tue, Dec 30
Multiple Airlines Logo
1:10 pm - 9:58 pm
EYW
-
MDW
9h 48m1 stop
Multiple Airlines Logo
2:01 pm - 10:39 am
MDW
-
EYW
19h 38m2 stops
$586Multiple Airlines
Mon, Dec 22 - Tue, Dec 23
Multiple Airlines Logo
1:10 pm - 9:58 pm
EYW
-
MDW
9h 48m1 stop
Multiple Airlines Logo
2:01 pm - 9:39 am
MDW
-
EYW
18h 38m2 stops
$665Multiple Airlines
Fri, Dec 26 - Tue, Dec 30

United Airlines flights from Key West to Illinois

Our best United Airlines deals on Key West to Illinois flight tickets
United Airlines
Dec 26
EYW12:22 pmKey West
3h 45m
ORD3:07 pmChicago O'Hare Intl
Dec 30
ORD7:55 amChicago O'Hare Intl
3h 39m
EYW12:34 pmKey West
$309
Find similar
United Airlines
Dec 26
EYW4:29 pmKey West
8h 45m
1 stop
ORD12:14 amChicago O'Hare Intl
Dec 30
ORD10:45 amChicago O'Hare Intl
3h 27m
EYW3:12 pmKey West
$319
Find similar
United Airlines
Jan 14
EYW4:15 pmKey West
6h 21m
1 stop
MLI9:36 pmMoline Quad-City
Jan 18
MLI6:30 amMoline Quad-City
7h 47m
1 stop
EYW3:17 pmKey West
$327
Find similar

Spirit Airlines flights from Key West to Illinois

Our best Spirit Airlines deals on Key West to Illinois flight tickets
Spirit Airlines
Dec 25
EYW12:20 pmKey West
7h 19m
1 stop
ORD6:39 pmChicago O'Hare Intl
Dec 29
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
EYW1:30 pmKey West
$424
Find similar
Spirit Airlines
Dec 18
EYW12:20 pmKey West
7h 19m
1 stop
ORD6:39 pmChicago O'Hare Intl
Dec 25
ORD5:00 amChicago O'Hare Intl
5h 20m
1 stop
EYW11:20 amKey West
$465
Find similar
Spirit Airlines
Dec 24
EYW2:30 pmKey West
11h 00m
1 stop
ORD12:30 amChicago O'Hare Intl
Dec 28
ORD5:00 amChicago O'Hare Intl
5h 20m
1 stop
EYW11:20 amKey West
$525
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Key West to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:39 pm-9:20 pm

Nonstop3h 41m

Chicago O'Hare Intl

Mon 4/13

8:00 am-12:16 pm

Nonstop3h 16m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 12/29

1:15 pm-3:50 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 1/12

10:59 am-3:25 pm

Nonstop3h 26m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 12/29

11:13 am-4:47 pm

1 stop6h 34m

Chicago O'Hare Intl

Mon 1/12

8:14 am-12:45 pm

Nonstop3h 31m

$289

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 12/29

4:25 pm-9:14 pm

1 stop5h 49m

Chicago O'Hare Intl

Mon 1/12

9:55 am-5:11 pm

1 stop6h 16m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/29

7:25 am-11:58 am

1 stop5h 33m

Chicago Midway

Mon 1/12

6:45 am-1:48 pm

1 stop6h 03m

$299

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 1/21

4:01 pm-6:45 pm

Nonstop3h 44m

Chicago O'Hare Intl

Thu 1/29

3:21 pm-9:47 pm

1 stop5h 26m

$307

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/26

12:22 pm-3:07 pm

Nonstop3h 45m

Chicago O'Hare Intl

Tue 12/30

7:55 am-12:34 pm

Nonstop3h 39m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/26

4:29 pm-12:14 am

1 stop8h 45m

Chicago O'Hare Intl

Tue 12/30

10:45 am-3:12 pm

Nonstop3h 27m

$319

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/22

1:10 pm-9:58 pm

1 stop9h 48m

Chicago Midway

Tue 12/23

2:01 pm-10:39 am

2 stops19h 38m

$586

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 12/26

1:10 pm-9:58 pm

1 stop9h 48m

Chicago Midway

Tue 12/30

2:01 pm-9:39 am

2 stops18h 38m

$665

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

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

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 Thursday when prices can be found for as low as $385. Flights from Key West to Illinois on a Sunday will generally be more expensive and average around $910. 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 at noon. Flights from Key West to Illinois during this time can be as low as $399. Flights in the morning are often more expensive with an average ticket price of $507.

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 67% 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

$270

Fastest flight time

3h 25m

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 $270. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $294.
The fastest flight from Key West to Illinois takes 3h 25m
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

  • 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?

  • 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?

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
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
11,050 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.

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