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Cheap flights from Key West to Illinois from $112

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 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Key West to Illinois

Cheap round-trip flights

Multiple Airlines Logo
10:47 am - 3:45 pmEYW-ORD
5h 58m1 stop
Multiple Airlines Logo
7:43 pm - 8:15 amORD-EYW
11h 32m1 stop
$219Multiple Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Multiple Airlines Logo
8:55 am - 4:20 pmEYW-MDW
8h 25m1 stop
Multiple Airlines Logo
11:31 am - 8:15 amMDW-EYW
19h 44m1 stop
$223Multiple Airlines
Find Deal
Fri, Oct 24 - Sat, Oct 25
Multiple Airlines Logo
10:59 am - 10:08 amEYW-ORD
24h 09m1 stop
Multiple Airlines Logo
6:54 pm - 8:15 amORD-EYW
12h 21m1 stop
$244Multiple Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Multiple Airlines Logo
10:47 am - 8:48 pmEYW-ORD
11h 01m2 stops
Multiple Airlines Logo
7:43 pm - 8:15 amORD-EYW
11h 32m1 stop
$256Multiple Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
7:40 am - 12:16 pmEYW-ORD
5h 36m1 stop
Delta Logo
5:20 am - 11:27 amORD-EYW
5h 07m1 stop
$269Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
6:17 pm - 10:14 pmEYW-MDW
4h 57m1 stop
Delta Logo
6:00 am - 1:02 pmMDW-EYW
6h 02m1 stop
$269Delta
Find Deal
Tue, Oct 21 - Sun, Oct 26
United Airlines Logo
3:12 pm - 11:30 pmEYW-ORD
9h 18m1 stop
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
$325United Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
United Airlines Logo
3:12 pm - 11:30 pmEYW-ORD
9h 18m1 stop
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
$339United Airlines
Find Deal
Tue, Oct 21 - Sun, Oct 26
American Airlines Logo
11:35 am - 11:54 pmEYW-BMI
13h 19m2 stops
American Airlines Logo
6:10 am - 4:07 pmBMI-EYW
8h 57m1 stop
$422American Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9
American Airlines Logo
12:50 pm - 7:41 pmEYW-BMI
7h 51m2 stops
American Airlines Logo
5:00 am - 5:52 pmBMI-EYW
11h 52m2 stops
$427American Airlines
Find Deal
Sat, Dec 6 - Tue, Dec 9

United Airlines flights from Key West to Illinois

Our best United Airlines deals on Key West to Illinois flight tickets
United Airlines
Oct 24
EYW3:12 pmKey West
9h 18m
1 stop
ORD11:30 pmChicago O'Hare Intl
Oct 27
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
$325
Find similar
United Airlines
Oct 21
EYW3:12 pmKey West
9h 18m
1 stop
ORD11:30 pmChicago O'Hare Intl
Oct 26
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
$339
Find similar
United Airlines
Oct 22
EYW3:12 pmKey West
7h 14m
1 stop
ORD9:26 pmChicago O'Hare Intl
Oct 25
ORD6:08 pmChicago O'Hare Intl
18h 44m
2 stops
EYW1:52 pmKey West
$402
Find similar

Delta flights from Key West to Illinois

Our best Delta deals on Key West to Illinois flight tickets
Delta
Oct 22
EYW7:40 amKey West
5h 36m
1 stop
ORD12:16 pmChicago O'Hare Intl
Oct 27
ORD5:20 amChicago O'Hare Intl
5h 07m
1 stop
EYW11:27 amKey West
$269
Find similar
Delta
Nov 24
EYW6:18 pmKey West
6h 14m
1 stop
MDW11:32 pmChicago Midway
Nov 29
MDW12:47 pmChicago Midway
6h 06m
1 stop
EYW7:53 pmKey West
$289
Find similar
Delta
Oct 1
EYW7:00 amKey West
5h 48m
1 stop
MDW11:48 amChicago Midway
Oct 5
MDW12:43 pmChicago Midway
6h 24m
1 stop
EYW8:07 pmKey West
$309
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 September 18, 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

Sat 10/18

10:47 am-3:45 pm

1 stop5h 58m

Chicago O'Hare Intl

Sat 10/25

7:43 pm-8:15 am

1 stop11h 32m

$219

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 10/24

8:55 am-4:20 pm

1 stop8h 25m

Chicago Midway

Sat 10/25

11:31 am-8:15 am

1 stop19h 44m

$223

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/23

10:59 am-10:08 am

1 stop24h 09m

Chicago O'Hare Intl

Thu 10/30

6:54 pm-8:15 am

1 stop12h 21m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 10/18

10:47 am-8:48 pm

2 stops11h 01m

Chicago O'Hare Intl

Sat 10/25

7:43 pm-8:15 am

1 stop11h 32m

$256

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 10/22

7:40 am-12:16 pm

1 stop5h 36m

Chicago O'Hare Intl

Mon 10/27

5:20 am-11:27 am

1 stop5h 07m

$269

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 10/21

6:17 pm-10:14 pm

1 stop4h 57m

Chicago Midway

Sun 10/26

6:00 am-1:02 pm

1 stop6h 02m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 10/24

3:12 pm-11:30 pm

1 stop9h 18m

Chicago O'Hare Intl

Mon 10/27

11:00 am-3:19 pm

Nonstop3h 19m

$325

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 10/21

3:12 pm-11:30 pm

1 stop9h 18m

Chicago O'Hare Intl

Sun 10/26

11:00 am-3:19 pm

Nonstop3h 19m

$339

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Sat 12/6

11:35 am-11:54 pm

2 stops13h 19m

Bloomington-Normal

Tue 12/9

6:10 am-4:07 pm

1 stop8h 57m

$422

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Sat 12/6

12:50 pm-7:41 pm

2 stops7h 51m

Bloomington-Normal

Tue 12/9

5:00 am-5:52 pm

2 stops11h 52m

$427

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 $343. Flights from Key West to Illinois on a Sunday will generally be more expensive and average around $939. 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 $359. 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

$304

Fastest flight time

3h 25m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Illinois

1 airport
The best one-way flight to Illinois from Key West in the past 72 hours is $304. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $424.
The fastest flight from Key West to Illinois takes 3h 25m
Direct flights go from Key West to Illinois on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Illinois: 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 $224Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $259Free CancellationRating
7.2
10,000 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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