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Cheap flights from Key West to Illinois from $84

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 2/27. 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.
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
6:51 pm - 9:06 am
ORD
-
EYW
37h 15m
2 stops
$214Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
10:19 am - 11:50 am
ORD
-
EYW
24h 31m
1 stop
$229Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
6:45 pm - 9:37 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
1:51 pm - 6:15 pm
ORD
-
EYW
3h 24mnonstop
$249American Airlines
Thu, Apr 9 - Mon, Apr 13
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$259United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
7:10 am - 5:44 pm
ORD
-
EYW
9h 34m
1 stop
$269United Airlines
Thu, Feb 26 - Mon, Mar 2
Multiple Airlines Logo
2:51 pm - 7:59 am
EYW
-
ORD
18h 08m
1 stop
Multiple Airlines Logo
10:17 am - 3:22 pm
ORD
-
EYW
28h 05m
1 stop
$271Multiple Airlines
Fri, May 29 - Wed, Jun 3
United Airlines Logo
3:56 pm - 6:35 pm
EYW
-
ORD
3h 39mnonstop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$279United Airlines
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
6:34 pm - 12:06 am
EYW
-
ORD
6h 32m
1 stop
American Airlines Logo
1:59 pm - 6:24 pm
ORD
-
EYW
3h 25mnonstop
$289American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
7:10 am - 11:59 am
EYW
-
MDW
5h 49m
1 stop
Delta Logo
10:49 am - 5:01 pm
MDW
-
EYW
5h 12m
1 stop
$404Delta
Tue, Feb 24 - Tue, Mar 3
Delta Logo
7:10 am - 11:59 am
EYW
-
MDW
5h 49m
1 stop
Delta Logo
12:45 pm - 7:42 pm
MDW
-
EYW
5h 57m
1 stop
$414Delta
Tue, Feb 24 - Tue, Mar 3

American Airlines flights from Key West to Illinois

Our best American Airlines deals on Key West to Illinois flight tickets
American Airlines
Apr 9
EYW6:45 pmKey West
3h 52m
ORD9:37 pmChicago O'Hare Intl
Apr 13
ORD1:51 pmChicago O'Hare Intl
3h 24m
EYW6:15 pmKey West
$249
American Airlines
Feb 24
EYW6:34 pmKey West
6h 32m
1 stop
ORD12:06 amChicago O'Hare Intl
Mar 3
ORD1:59 pmChicago O'Hare Intl
3h 25m
EYW6:24 pmKey West
$289
American Airlines
Feb 11
EYW4:01 pmKey West
3h 44m
ORD6:45 pmChicago O'Hare Intl
Feb 15
ORD9:55 amChicago O'Hare Intl
5h 54m
1 stop
EYW4:49 pmKey West
$319

United Airlines flights from Key West to Illinois

Our best United Airlines deals on Key West to Illinois flight tickets
United Airlines
Feb 26
EYW6:35 pmKey West
6h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
Mar 2
ORD10:44 amChicago O'Hare Intl
3h 16m
EYW3:00 pmKey West
$259
United Airlines
Feb 26
EYW6:35 pmKey West
6h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
Mar 2
ORD7:10 amChicago O'Hare Intl
9h 34m
1 stop
EYW5:44 pmKey West
$269
United Airlines
Feb 26
EYW3:56 pmKey West
3h 39m
ORD6:35 pmChicago O'Hare Intl
Mar 2
ORD10:44 amChicago O'Hare Intl
3h 16m
EYW3:00 pmKey West
$279

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 January 29, 2026.
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

Tue 2/24

1:01 pm-5:03 pm

1 stop29h 02m

Chicago O'Hare Intl

Tue 3/3

6:51 pm-9:06 am

2 stops37h 15m

$214

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 2/24

1:01 pm-5:03 pm

1 stop29h 02m

Chicago O'Hare Intl

Tue 3/3

10:19 am-11:50 am

1 stop24h 31m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:45 pm-9:37 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 4/13

1:51 pm-6:15 pm

Nonstop3h 24m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

6:35 pm-11:43 pm

1 stop6h 08m

Chicago O'Hare Intl

Mon 3/2

10:44 am-3:00 pm

Nonstop3h 16m

$259

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

6:35 pm-11:43 pm

1 stop6h 08m

Chicago O'Hare Intl

Mon 3/2

7:10 am-5:44 pm

1 stop9h 34m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 5/29

2:51 pm-7:59 am

1 stop18h 08m

Chicago O'Hare Intl

Wed 6/3

10:17 am-3:22 pm

1 stop28h 05m

$271

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/26

3:56 pm-6:35 pm

Nonstop3h 39m

Chicago O'Hare Intl

Mon 3/2

10:44 am-3:00 pm

Nonstop3h 16m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 2/24

6:34 pm-12:06 am

1 stop6h 32m

Chicago O'Hare Intl

Tue 3/3

1:59 pm-6:24 pm

Nonstop3h 25m

$289

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 2/24

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

Tue 3/3

10:49 am-5:01 pm

1 stop5h 12m

$404

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 2/24

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

Tue 3/3

12:45 pm-7:42 pm

1 stop5h 57m

$414

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 $348. Flights from Key West to Illinois on a Sunday will generally be more expensive and average around $787. 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 afternoon. Flights from Key West to Illinois during this time can be as low as $429. 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 46% 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

$346

Fastest flight time

3h 33m

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 $346. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $413.
The fastest flight from Key West to Illinois takes 3h 33m
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
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
11,205 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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