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Cheap flights from Key West to Wisconsin from $53

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 Wisconsin departing on 2/26. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:01 am - 7:37 pm
EYW
-
ORD
9h 36m
1 stop
Multiple Airlines Logo
2:43 pm - 10:21 am
ORD
-
EYW
18h 38m
1 stop
$183Multiple Airlines
Thu, Mar 5 - Wed, Mar 11
Multiple Airlines Logo
4:09 pm - 5:46 pm
EYW
-
ORD
26h 37m
1 stop
Multiple Airlines Logo
2:13 pm - 9:09 am
ORD
-
EYW
17h 56m
1 stop
$211Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
11:01 am - 7:37 pm
EYW
-
ORD
9h 36m
1 stop
Multiple Airlines Logo
7:18 pm - 9:43 pm
ORD
-
EYW
25h 25m
2 stops
$215Multiple Airlines
Thu, Mar 5 - Wed, Mar 11
Multiple Airlines Logo
1:01 pm - 10:51 am
EYW
-
ORD
22h 50m
2 stops
Multiple Airlines Logo
2:43 pm - 11:50 am
ORD
-
EYW
20h 07m
1 stop
$229Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Spirit Airlines Logo
2:25 pm - 11:47 pm
EYW
-
ORD
10h 22m
1 stop
Spirit Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m
1 stop
$237Spirit Airlines
Thu, Feb 19 - Fri, Feb 20
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
1:50 pm - 6:16 pm
ORD
-
EYW
3h 26mnonstop
$249American Airlines
Thu, Apr 9 - Mon, Apr 13
United Airlines Logo
3:56 pm - 6:35 pm
EYW
-
ORD
3h 39mnonstop
United Airlines Logo
8:50 am - 4:07 pm
ORD
-
EYW
6h 17m
1 stop
$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
8:50 am - 4:07 pm
ORD
-
EYW
6h 17m
1 stop
$269United Airlines
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
1:57 pm - 9:25 pm
EYW
-
MSN
8h 28m
1 stop
American Airlines Logo
6:00 am - 12:38 pm
MSN
-
EYW
5h 38m
1 stop
$286American Airlines
Thu, Apr 23 - Tue, Apr 28
Delta Logo
6:00 pm - 11:27 pm
EYW
-
MKE
6h 27m
1 stop
Delta Logo
12:20 pm - 7:44 pm
MKE
-
EYW
6h 24m
1 stop
$569Delta
Mon, Jun 15 - Wed, Jun 17

United Airlines flights from Key West to Wisconsin

Our best United Airlines deals on Key West to Wisconsin flight tickets
United Airlines
Feb 26
EYW3:56 pmKey West
3h 39m
ORD6:35 pmChicago O'Hare Intl
Mar 2
ORD8:50 amChicago O'Hare Intl
6h 17m
1 stop
EYW4:07 pmKey West
$259
United Airlines
Feb 26
EYW6:35 pmKey West
6h 08m
1 stop
ORD11:43 pmChicago O'Hare Intl
Mar 2
ORD8:50 amChicago O'Hare Intl
6h 17m
1 stop
EYW4:07 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

American Airlines flights from Key West to Wisconsin

Our best American Airlines deals on Key West to Wisconsin flight tickets
American Airlines
Apr 9
EYW6:46 pmKey West
3h 49m
ORD9:35 pmChicago O'Hare Intl
Apr 13
ORD1:50 pmChicago O'Hare Intl
3h 26m
EYW6:16 pmKey West
$249
American Airlines
Apr 23
EYW1:57 pmKey West
8h 28m
1 stop
MSN9:25 pmMadison Truax Field
Apr 28
MSN6:00 amMadison Truax Field
5h 38m
1 stop
EYW12:38 pmKey West
$286
American Airlines
Apr 9
EYW6:46 pmKey West
3h 49m
ORD9:35 pmChicago O'Hare Intl
Apr 13
ORD3:26 pmChicago O'Hare Intl
6h 10m
1 stop
EYW10:36 pmKey West
$289

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Wisconsin 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 February 4, 2026.
Use the filters below to find and compare flights from Key West to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 3/5

11:01 am-7:37 pm

1 stop9h 36m

Chicago O'Hare Intl

Wed 3/11

2:43 pm-10:21 am

1 stop18h 38m

$183

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/19

4:09 pm-5:46 pm

1 stop26h 37m

Chicago O'Hare Intl

Sun 2/22

2:13 pm-9:09 am

1 stop17h 56m

$211

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 3/5

11:01 am-7:37 pm

1 stop9h 36m

Chicago O'Hare Intl

Wed 3/11

7:18 pm-9:43 pm

2 stops25h 25m

$215

Key WestChicago

EYW - ORD

EYWORD

Key West

Tue 3/3

1:01 pm-10:51 am

2 stops22h 50m

Chicago O'Hare Intl

Tue 3/10

2:43 pm-11:50 am

1 stop20h 07m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 2/19

2:25 pm-11:47 pm

1 stop10h 22m

Chicago O'Hare Intl

Fri 2/20

5:15 am-1:30 pm

1 stop7h 15m

$237

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:46 pm-9:35 pm

Nonstop3h 49m

Chicago O'Hare Intl

Mon 4/13

1:50 pm-6:16 pm

Nonstop3h 26m

$249

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

8:50 am-4:07 pm

1 stop6h 17m

$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

8:50 am-4:07 pm

1 stop6h 17m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 4/23

1:57 pm-9:25 pm

1 stop8h 28m

Madison Truax Field

Tue 4/28

6:00 am-12:38 pm

1 stop5h 38m

$286

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

Mon 6/15

6:00 pm-11:27 pm

1 stop6h 27m

Milwaukee-Mitchell

Wed 6/17

12:20 pm-7:44 pm

1 stop6h 24m

$569

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 Wisconsin from

How to get the cheapest flight ticket from Key West to Wisconsin

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

Can stopping save me money on Key West to Wisconsin flights?

You could potentially save up to 24% on your flight if you consider stops on a Key West to Wisconsin flight.

Cheap Key West to Wisconsin flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Wisconsin

Fastest flight time

3h 39m

Direct flights

Every day

Airports in Wisconsin

80 airports
The fastest flight from Key West to Wisconsin takes 3h 39m
Direct flights go from Key West to Wisconsin every day.
There are 80 airports in Wisconsin. 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 Wisconsin?

    Prices for flights from Key West Airport to Wisconsin are refreshed on a daily basis.

  • How many operators does momondo search for flights from Key West Airport to Wisconsin?

  • How old do you have to be to fly from Key West Airport to Wisconsin?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Key West Airport to Wisconsin.

  • What documentation or ID do you need to fly to Wisconsin?

    The travel and health documents required for your trip to Wisconsin 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 Wisconsin. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Key West to Wisconsin

Compare and see reviews for airlines that fly from Key West to Wisconsin with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,222 reviews
Search American Airlines flights
DeltaPriceFrom $283Free CancellationRating
7.9
8,146 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Wisconsin?

Finding the right flight to Wisconsin from Key West is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Wisconsin quick and easy, saving you time and money.

Can I find flights from Key West to Wisconsin with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Key West to Wisconsin flights to just show those with flexible booking policies.

How can momondo help me find flights from Key West to Wisconsin?

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 Wisconsin from Key West.

I’m not ready to book a flight from Key West to Wisconsin right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Wisconsin 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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