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Cheap flights from Key West to Illinois from $165

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 10/30. 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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Find the cheapest flights from Key West to Illinois

Cheap round-trip flights

Delta Logo
6:10 pm - 11:54 pmEYW-ORD
6h 44m1 stop
Delta Logo
9:50 am - 5:15 pmORD-EYW
6h 25m1 stop
$324Delta
Find Deal
Fri, Sep 26 - Sun, Sep 28
Delta Logo
6:20 pm - 10:16 pmEYW-BMI
4h 56m1 stop
Delta Logo
6:00 am - 1:05 pmBMI-EYW
6h 05m1 stop
$348Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
6:20 pm - 10:16 pmEYW-BMI
4h 56m1 stop
Delta Logo
6:00 am - 1:05 pmBMI-EYW
6h 05m1 stop
$362Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
7:00 am - 12:16 pmEYW-ORD
6h 16m1 stop
Delta Logo
9:47 am - 5:25 pmORD-EYW
6h 38m1 stop
$363Delta
Find Deal
Tue, Aug 12 - Tue, Sep 9
American Airlines Logo
6:17 pm - 11:12 pmEYW-ORD
5h 55m1 stop
American Airlines Logo
9:20 am - 5:46 pmORD-EYW
7h 26m1 stop
$364American Airlines
Find Deal
Sat, Sep 20 - Mon, Sep 22
American Airlines Logo
7:31 pm - 11:49 pmEYW-ORD
5h 18m1 stop
American Airlines Logo
9:55 am - 6:59 pmORD-EYW
8h 04m2 stops
$369American Airlines
Find Deal
Sat, Sep 20 - Mon, Sep 22
Logo
10:02 am - 11:59 pmEYW-ORD
14h 57m2 stops
Logo
11:36 am - 9:22 amORD-EYW
20h 46m2 stops
$465
Find Deal
Fri, Aug 15 - Tue, Aug 19
Logo
10:02 am - 10:22 pmEYW-ORD
13h 20m1 stop
Logo
5:16 pm - 4:51 pmORD-EYW
22h 35m2 stops
$486
Find Deal
Sun, Aug 17 - Thu, Aug 21
United Airlines Logo
3:12 pm - 7:48 amEYW-ORD
17h 36m2 stops
United Airlines Logo
10:55 am - 2:29 pmORD-EYW
26h 34m2 stops
$565United Airlines
Find Deal
Fri, Sep 26 - Sun, Sep 28
United Airlines Logo
2:22 pm - 7:37 amEYW-ORD
18h 15m2 stops
United Airlines Logo
10:35 am - 2:55 pmORD-EYW
27h 20m2 stops
$567United Airlines
Find Deal
Tue, Aug 12 - Tue, Sep 9

Delta flights from Key West to Illinois

Our best Delta deals on Key West to Illinois flight tickets
Delta
Sep 26
EYW6:10 pmKey West
6h 44m
1 stop
ORD11:54 pmChicago O'Hare Intl
Sep 28
ORD9:50 amChicago O'Hare Intl
6h 25m
1 stop
EYW5:15 pmKey West
$324
Find similar
Delta
Aug 7
EYW11:48 amKey West
6h 08m
1 stop
ORD4:56 pmChicago O'Hare Intl
Sep 9
ORD11:15 amChicago O'Hare Intl
5h 10m
1 stop
EYW5:25 pmKey West
$334
Find similar
Delta
Sep 3
EYW6:20 pmKey West
4h 56m
1 stop
BMI10:16 pmBloomington-Normal
Sep 6
BMI6:00 amBloomington-Normal
6h 05m
1 stop
EYW1:05 pmKey West
$348
Find similar

United Airlines flights from Key West to Illinois

Our best United Airlines deals on Key West to Illinois flight tickets
United Airlines
Sep 26
EYW3:12 pmKey West
17h 36m
2 stops
ORD7:48 amChicago O'Hare Intl
Sep 28
ORD10:55 amChicago O'Hare Intl
26h 34m
2 stops
EYW2:29 pmKey West
$565
Find similar
United Airlines
Aug 12
EYW2:22 pmKey West
18h 15m
2 stops
ORD7:37 amChicago O'Hare Intl
Sep 9
ORD10:35 amChicago O'Hare Intl
27h 20m
2 stops
EYW2:55 pmKey West
$567
Find similar
United Airlines
Aug 15
EYW2:12 pmKey West
29h 17m
2 stops
ORD6:29 pmChicago O'Hare Intl
Aug 19
ORD1:12 pmChicago O'Hare Intl
24h 13m
2 stops
EYW2:25 pmKey West
$635
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 August 2, 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

Fri 9/26

6:10 pm-11:54 pm

1 stop6h 44m

Chicago O'Hare Intl

Sun 9/28

9:50 am-5:15 pm

1 stop6h 25m

$324

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Wed 9/3

6:20 pm-10:16 pm

1 stop4h 56m

Bloomington-Normal

Sat 9/6

6:00 am-1:05 pm

1 stop6h 05m

$348

Key WestBloomington

EYW - BMI

EYWBMI

Key West

Wed 9/3

6:20 pm-10:16 pm

1 stop4h 56m

Bloomington-Normal

Sat 9/6

6:00 am-1:05 pm

1 stop6h 05m

$362

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 8/12

7:00 am-12:16 pm

1 stop6h 16m

Chicago O'Hare Intl

Tue 9/9

9:47 am-5:25 pm

1 stop6h 38m

$363

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/20

6:17 pm-11:12 pm

1 stop5h 55m

Chicago O'Hare Intl

Mon 9/22

9:20 am-5:46 pm

1 stop7h 26m

$364

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/20

7:31 pm-11:49 pm

1 stop5h 18m

Chicago O'Hare Intl

Mon 9/22

9:55 am-6:59 pm

2 stops8h 04m

$369

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 8/15

10:02 am-11:59 pm

2 stops14h 57m

Chicago O'Hare Intl

Tue 8/19

11:36 am-9:22 am

2 stops20h 46m

$465

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 8/17

10:02 am-10:22 pm

1 stop13h 20m

Chicago O'Hare Intl

Thu 8/21

5:16 pm-4:51 pm

2 stops22h 35m

$486

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 9/26

3:12 pm-7:48 am

2 stops17h 36m

Chicago O'Hare Intl

Sun 9/28

10:55 am-2:29 pm

2 stops26h 34m

$565

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 8/12

2:22 pm-7:37 am

2 stops18h 15m

Chicago O'Hare Intl

Tue 9/9

10:35 am-2:55 pm

2 stops27h 20m

$567

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 45% 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

$165

Fastest flight time

3h 37m

Direct flights

Mon, Tue, Thu and Fri

Airports in Illinois

6 airports
The best one-way flight to Illinois from Key West in the past 72 hours is $165. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $324.
The fastest flight from Key West to Illinois takes 3h 37m
Direct flights go from Key West to Illinois on Monday, Tuesday, Thursday and Friday. Airlines offering direct flights are: United Airlines and American Airlines.
There are 6 airports near Illinois: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD), Greater Peoria (PIA), Moline Quad-City (MLI), Bloomington-Normal (BMI)
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
8,904 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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