What is the cheapest airline that flies from Key West to Wisconsin?

American Airlines, Delta, and Breeze Airways are the most popular carriers operating from Key West to Wisconsin

How many flights depart from Key West to Wisconsin on average per week?

As of May 2026, 29 flights take off from Key West and land in Wisconsin each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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?

There are 2 operators available for flights from Key West Airport to Wisconsin as of May 2026.

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.

$116 Cheap Flights from Key West to Wisconsin in 2026

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Find the cheapest flights from Key West to Wisconsin

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:59 am - 11:55 pm

EYW

ORD

13h 56m

1 stop

2:03 pm - 9:24 am

ORD

EYW

18h 21m

2 stops

$223Multiple Airlines

Thu, Oct 1 - Tue, Oct 6

7:53 pm - 6:47 pm

EYW

ORD

23h 54m

2 stops

4:49 pm - 10:19 am

ORD

EYW

16h 30m

1 stop

$278Multiple Airlines

Thu, Sep 3 - Thu, Sep 10

10:59 am - 11:55 pm

EYW

ORD

13h 56m

1 stop

4:49 pm - 10:19 am

ORD

EYW

16h 30m

1 stop

$295Multiple Airlines

Thu, Oct 1 - Wed, Oct 7

10:59 am - 8:21 am

EYW

ORD

22h 22m

1 stop

2:03 pm - 9:24 am

ORD

EYW

18h 21m

2 stops

$298Multiple Airlines

Sun, Sep 27 - Tue, Oct 6

4:00 pm - 6:55 pm

EYW

ORD

3h 55mnonstop

10:55 am - 3:19 pm

ORD

EYW

3h 24mnonstop

$309United Airlines

Thu, Jul 23 - Sun, Jul 26

7:29 pm - 11:58 pm

EYW

ORD

5h 29m

1 stop

11:00 am - 3:25 pm

ORD

EYW

3h 25mnonstop

$319American Airlines

Thu, Jun 11 - Wed, Jun 17

7:33 pm - 11:42 pm

EYW

MSN

5h 09m

1 stop

6:00 am - 1:45 pm

MSN

EYW

6h 45m

1 stop

$323American Airlines

Wed, Jul 29 - Wed, Aug 5

1:57 pm - 8:53 pm

EYW

MKE

7h 56m

1 stop

5:34 am - 1:00 pm

MKE

EYW

6h 26m

1 stop

$329Delta

Thu, Aug 20 - Sun, Aug 23

6:24 pm - 10:43 pm

EYW

MSN

5h 19m

1 stop

5:52 am - 1:43 pm

MSN

EYW

6h 51m

1 stop

$331Delta

Fri, Jun 26 - Tue, Jun 30

2:20 pm - 11:37 pm

EYW

MKE

10h 17m

1 stop

6:00 am - 1:29 pm

MKE

EYW

6h 29m

1 stop

$949United Airlines

Wed, Aug 26 - Sat, Aug 29

United Airlines flights from Key West to Wisconsin

Our best United Airlines deals on Key West to Wisconsin flight tickets

United Airlines

Jul 29

EYW4:00 pmKey West

6h 41m

1 stop

MSP9:41 pmMinneapolis St Paul

Aug 5

MSP7:34 amMinneapolis St Paul

6h 45m

1 stop

EYW3:19 pmKey West

$449

United Airlines

Jul 30

EYW4:00 pmKey West

8h 10m

1 stop

MSP11:10 pmMinneapolis St Paul

Aug 3

MSP7:34 amMinneapolis St Paul

6h 45m

1 stop

EYW3:19 pmKey West

$484

United Airlines

Jul 1

EYW2:26 pmKey West

9h 46m

2 stops

MSN11:12 pmMadison Truax Field

Jul 4

MSN8:10 amMadison Truax Field

6h 09m

1 stop

EYW3:19 pmKey West

$500

American Airlines flights from Key West to Wisconsin

Our best American Airlines deals on Key West to Wisconsin flight tickets

American Airlines

Jun 11

EYW7:29 pmKey West

5h 29m

1 stop

ORD11:58 pmChicago O'Hare Intl

Jun 17

ORD11:00 amChicago O'Hare Intl

3h 25m

EYW3:25 pmKey West

$319

American Airlines

Jul 29

EYW7:33 pmKey West

5h 09m

1 stop

MSN11:42 pmMadison Truax Field

Aug 5

MSN6:00 amMadison Truax Field

6h 45m

1 stop

EYW1:45 pmKey West

$323

American Airlines

Jul 29

EYW7:33 pmKey West

5h 09m

1 stop

MSN11:42 pmMadison Truax Field

Aug 3

MSN6:00 amMadison Truax Field

6h 40m

1 stop

EYW1:40 pmKey West

$326

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/1

10:59 am-11:55 pm

1 stop13h 56m

Chicago O'Hare Intl

Tue 10/6

2:03 pm-9:24 am

2 stops18h 21m

$223

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

7:53 pm-6:47 pm

2 stops23h 54m

Chicago O'Hare Intl

Thu 9/10

4:49 pm-10:19 am

1 stop16h 30m

$278

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 10/1

10:59 am-11:55 pm

1 stop13h 56m

Chicago O'Hare Intl

Wed 10/7

4:49 pm-10:19 am

1 stop16h 30m

$295

Key WestChicago

EYW - ORD

EYWORD

Key West

Sun 9/27

10:59 am-8:21 am

1 stop22h 22m

Chicago O'Hare Intl

Tue 10/6

2:03 pm-9:24 am

2 stops18h 21m

$298

Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 7/23

4:00 pm-6:55 pm

Nonstop3h 55m

Chicago O'Hare Intl

Sun 7/26

10:55 am-3:19 pm

Nonstop3h 24m

$309

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 6/11

7:29 pm-11:58 pm

1 stop5h 29m

Chicago O'Hare Intl

Wed 6/17

11:00 am-3:25 pm

Nonstop3h 25m

$319

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 7/29

7:33 pm-11:42 pm

1 stop5h 09m

Madison Truax Field

Wed 8/5

6:00 am-1:45 pm

1 stop6h 45m

$323

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

Thu 8/20

1:57 pm-8:53 pm

1 stop7h 56m

Milwaukee-Mitchell

Sun 8/23

5:34 am-1:00 pm

1 stop6h 26m

$329

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 6/26

6:24 pm-10:43 pm

1 stop5h 19m

Madison Truax Field

Tue 6/30

5:52 am-1:43 pm

1 stop6h 51m

$331

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

Wed 8/26

2:20 pm-11:37 pm

1 stop10h 17m

Milwaukee-Mitchell

Sat 8/29

6:00 am-1:29 pm

1 stop6h 29m

$949

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Wisconsin?

If you aren’t able to travel during the month of January, then book flights to Wisconsin from Key West during February instead. Flights to Wisconsin in February, while not as cheap as those in January, still average around $268.

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

You could potentially save up to 20% 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 51m
Direct flights	Mon, Tue, Thu, Fri, Sat and Sun
Airports in Wisconsin	80 airports

The fastest flight from Key West to Wisconsin takes 3h 51m

Direct flights go from Key West to Wisconsin on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

There are 80 airports in Wisconsin. From Key West there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Key West to Wisconsin

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?
There are 2 operators available for flights from Key West Airport to Wisconsin as of May 2026.
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 Airlines	PriceFrom $268	Free Cancellation	Rating 7.1 11,662 reviews		Search American Airlines flights
Delta	PriceFrom $283	Free Cancellation	Rating 7.9 8,455 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.