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Cheap flights from Key West to Wisconsin 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 Wisconsin departing on 2/28. 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 Wisconsin

Cheap round-trip flights

Multiple Airlines Logo
3:30 pm - 7:34 amEYW-ORD
17h 04m1 stop
Multiple Airlines Logo
7:43 pm - 2:40 pmORD-EYW
17h 57m1 stop
$187Multiple Airlines
Find Deal
Thu, Oct 16 - Sat, Oct 18
Multiple Airlines Logo
10:02 am - 1:15 pmEYW-ORD
28h 13m1 stop
Multiple Airlines Logo
6:58 pm - 2:40 pmORD-EYW
18h 42m1 stop
$211Multiple Airlines
Find Deal
Wed, Oct 15 - Sat, Oct 18
Multiple Airlines Logo
3:30 pm - 7:34 amEYW-ORD
17h 04m1 stop
Multiple Airlines Logo
5:50 am - 4:04 pmORD-EYW
9h 14m1 stop
$214Multiple Airlines
Find Deal
Thu, Oct 16 - Sun, Oct 19
Spirit Airlines Logo
2:25 pm - 11:42 pmEYW-ORD
10h 17m1 stop
Spirit Airlines Logo
5:05 am - 1:30 pmORD-EYW
7h 25m1 stop
$220Spirit Airlines
Find Deal
Wed, Feb 25 - Thu, Feb 26
Multiple Airlines Logo
10:02 am - 1:15 pmEYW-ORD
28h 13m1 stop
Multiple Airlines Logo
5:50 am - 4:04 pmORD-EYW
9h 14m1 stop
$227Multiple Airlines
Find Deal
Wed, Oct 15 - Sun, Oct 19
Delta Logo
1:30 pm - 8:56 pmEYW-MKE
8h 26m1 stop
Delta Logo
12:20 pm - 7:44 pmMKE-EYW
6h 24m1 stop
$269Delta
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Wed, Feb 25 - Sun, Mar 1
American Airlines Logo
4:57 pm - 11:51 pmEYW-MSN
7h 54m1 stop
American Airlines Logo
6:00 am - 12:58 pmMSN-EYW
5h 58m1 stop
$269American Airlines
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Fri, Oct 17 - Tue, Oct 21
American Airlines Logo
4:57 pm - 11:51 pmEYW-MSN
7h 54m1 stop
American Airlines Logo
6:00 am - 5:16 pmMSN-EYW
10h 16m2 stops
$274American Airlines
Find Deal
Fri, Oct 17 - Tue, Oct 21
Delta Logo
6:18 pm - 12:02 amEYW-ORD
6h 44m1 stop
Delta Logo
5:23 am - 11:31 amORD-EYW
5h 08m1 stop
$289Delta
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Mon, Nov 24 - Sat, Nov 29
Breeze Airways Logo
1:06 pm - 5:36 pmEYW-MSN
29h 30m1 stop
Breeze Airways Logo
9:48 am - 10:21 amMSN-EYW
23h 33m1 stop
$314Breeze Airways
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Fri, Jan 30 - Wed, Feb 4

Delta flights from Key West to Wisconsin

Our best Delta deals on Key West to Wisconsin flight tickets
Delta
Feb 25
EYW1:30 pmKey West
8h 26m
1 stop
MKE8:56 pmMilwaukee-Mitchell
Mar 1
MKE12:20 pmMilwaukee-Mitchell
6h 24m
1 stop
EYW7:44 pmKey West
$269
Find similar
Delta
Nov 24
EYW6:18 pmKey West
6h 44m
1 stop
ORD12:02 amChicago O'Hare Intl
Nov 29
ORD5:23 amChicago O'Hare Intl
5h 08m
1 stop
EYW11:31 amKey West
$289
Find similar
Delta
Feb 26
EYW7:00 amKey West
5h 18m
1 stop
MKE11:18 amMilwaukee-Mitchell
Mar 2
MKE12:20 pmMilwaukee-Mitchell
6h 24m
1 stop
EYW7:44 pmKey West
$334
Find similar

United Airlines flights from Key West to Wisconsin

Our best United Airlines deals on Key West to Wisconsin flight tickets
United Airlines
Feb 20
EYW3:56 pmKey West
6h 07m
1 stop
MSN9:03 pmMadison Truax Field
Feb 24
MSN6:30 amMadison Truax Field
7h 30m
1 stop
EYW3:00 pmKey West
$411
Find similar
United Airlines
Jan 30
EYW6:05 pmKey West
18h 58m
2 stops
MSN12:03 pmMadison Truax Field
Feb 3
MSN6:30 amMadison Truax Field
8h 52m
2 stops
EYW4:22 pmKey West
$463
Find similar
United Airlines
Jan 30
EYW4:15 pmKey West
5h 50m
1 stop
MSN9:05 pmMadison Truax Field
Feb 5
MSN6:30 amMadison Truax Field
8h 52m
2 stops
EYW4:22 pmKey West
$501
Find similar

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 September 26, 2025.
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 10/16

3:30 pm-7:34 am

1 stop17h 04m

Chicago O'Hare Intl

Sat 10/18

7:43 pm-2:40 pm

1 stop17h 57m

$187

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 10/15

10:02 am-1:15 pm

1 stop28h 13m

Chicago O'Hare Intl

Sat 10/18

6:58 pm-2:40 pm

1 stop18h 42m

$211

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/16

3:30 pm-7:34 am

1 stop17h 04m

Chicago O'Hare Intl

Sun 10/19

5:50 am-4:04 pm

1 stop9h 14m

$214

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 2/25

2:25 pm-11:42 pm

1 stop10h 17m

Chicago O'Hare Intl

Thu 2/26

5:05 am-1:30 pm

1 stop7h 25m

$220

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 10/15

10:02 am-1:15 pm

1 stop28h 13m

Chicago O'Hare Intl

Sun 10/19

5:50 am-4:04 pm

1 stop9h 14m

$227

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

Wed 2/25

1:30 pm-8:56 pm

1 stop8h 26m

Milwaukee-Mitchell

Sun 3/1

12:20 pm-7:44 pm

1 stop6h 24m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 10/17

4:57 pm-11:51 pm

1 stop7h 54m

Madison Truax Field

Tue 10/21

6:00 am-12:58 pm

1 stop5h 58m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 10/17

4:57 pm-11:51 pm

1 stop7h 54m

Madison Truax Field

Tue 10/21

6:00 am-5:16 pm

2 stops10h 16m

$274

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 11/24

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

Sat 11/29

5:23 am-11:31 am

1 stop5h 08m

$289

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 1/30

1:06 pm-5:36 pm

1 stop29h 30m

Madison Truax Field

Wed 2/4

9:48 am-10:21 am

1 stop23h 33m

$314

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

What is the cheapest day to depart on your flight to Wisconsin?

The cheapest day to depart from Key West to Wisconsin is on a Wednesday. Travelers who choose to depart for Wisconsin on a Wednesday will often find tickets for as low as $343. The most expensive day to fly to Wisconsin is Tuesday, with ticket prices averaging around $411.

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

You could potentially save up to 23% 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 25m

Direct flights

Every day

Airports in Wisconsin

1 airport
The fastest flight from Key West to Wisconsin takes 3h 25m
Direct flights go from Key West to Wisconsin every day.
There is 1 airport near Wisconsin: 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.

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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