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

Delta, American Airlines, and United Airlines 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 August 2026, 16 flights take off from Key West and land in Wisconsin each week. The most common flight departure day for this route is Mon, with 19% 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 August 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.

$127 Cheap Flights from Key West to Wisconsin in 2026

Discover deals from 900+ travel sites with momondo.

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.

12:01 pm - 9:20 amEYW Key West-ORD Chicago O'Hare Intl

22h 19m2 stops Tampa Atlanta Hartsfield-Jackson

3:50 pm - 11:35 amORD Chicago O'Hare Intl-EYW Key West

18h 45m1 stop Orlando

$268Multiple Airlines

Thu, Sep 24 - Sat, Sep 26

12:01 pm - 9:20 amEYW Key West-ORD Chicago O'Hare Intl

22h 19m2 stops Tampa Atlanta Hartsfield-Jackson

3:50 pm - 11:35 amORD Chicago O'Hare Intl-EYW Key West

18h 45m1 stop Orlando

$269Multiple Airlines

Thu, Sep 24 - Sat, Sep 26

10:59 am - 10:59 pmEYW Key West-ORD Chicago O'Hare Intl

13h 00m1 stop Orlando

3:50 pm - 11:35 amORD Chicago O'Hare Intl-EYW Key West

18h 45m1 stop Orlando

$273Multiple Airlines

Thu, Sep 24 - Sat, Sep 26

12:05 pm - 11:08 pmEYW Key West-ORD Chicago O'Hare Intl

12h 03m1 stop Orlando

7:05 am - 9:24 amORD Chicago O'Hare Intl-EYW Key West

25h 19m2 stops Atlanta Hartsfield-Jackson Tampa

$276Multiple Airlines

Thu, Sep 3 - Tue, Sep 8

10:59 am - 1:09 amEYW Key West-ORD Chicago O'Hare Intl

15h 10m1 stop Orlando

2:31 pm - 10:19 amORD Chicago O'Hare Intl-EYW Key West

18h 48m1 stop Orlando

$277Multiple Airlines

Thu, Dec 3 - Mon, Dec 7

10:59 am - 10:59 pmEYW Key West-ORD Chicago O'Hare Intl

13h 00m1 stop Orlando

4:44 pm - 1:38 pmORD Chicago O'Hare Intl-EYW Key West

19h 54m1 stop Orlando

$284Multiple Airlines

Thu, Oct 1 - Sat, Oct 31

12:07 pm - 6:25 pmEYW Key West-MSP Minneapolis St Paul

7h 18m1 stop Orlando

9:30 am - 11:21 amMSP Minneapolis St Paul-EYW Key West

24h 51m2 stops Atlanta Hartsfield-Jackson Tampa

$293Multiple Airlines

Fri, Sep 4 - Sat, Sep 19

10:59 am - 10:59 pmEYW Key West-ORD Chicago O'Hare Intl

13h 00m1 stop Orlando

6:30 am - 9:22 amORD Chicago O'Hare Intl-EYW Key West

25h 52m2 stops Atlanta Hartsfield-Jackson Tampa

$303Multiple Airlines

Thu, Oct 1 - Sat, Oct 31

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$311American Airlines

Thu, Sep 3 - Tue, Sep 8

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$319American Airlines

Wed, Aug 26 - Mon, Aug 31

Cheap last minute flights

Enter your travel dates to find the best prices.

12:05 pm - 11:10 pmEYW Key West-ORD Chicago O'Hare Intl

12h 05m1 stop Orlando

5:13 pm - 1:42 pmORD Chicago O'Hare Intl-EYW Key West

19h 29m1 stop Orlando

$379Multiple Airlines

Thu, Aug 6 - Wed, Aug 12

12:07 pm - 11:10 pmEYW Key West-ORD Chicago O'Hare Intl

12h 03m1 stop Orlando

12:44 am - 12:34 pmORD Chicago O'Hare Intl-EYW Key West

34h 50m2 stops San Juan Luis Munoz Marin Intl Tampa

$389Multiple Airlines

Mon, Aug 10 - Sun, Aug 23

8:09 pm - 12:35 amEYW Key West-ORD Chicago O'Hare Intl

5h 26m1 stop Miami

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$414American Airlines

Mon, Aug 10 - Mon, Aug 24

1:59 pm - 8:55 pmEYW Key West-ORD Chicago O'Hare Intl

7h 56m1 stop Atlanta Hartsfield-Jackson

5:30 am - 1:00 pmORD Chicago O'Hare Intl-EYW Key West

6h 30m1 stop Atlanta Hartsfield-Jackson

$424Delta

Mon, Aug 10 - Mon, Aug 24

12:05 pm - 11:10 pmEYW Key West-ORD Chicago O'Hare Intl

12h 05m1 stop Orlando

7:05 am - 1:42 pmORD Chicago O'Hare Intl-EYW Key West

29h 37m2 stops Atlanta Hartsfield-Jackson Orlando

$451Multiple Airlines

Thu, Aug 6 - Wed, Aug 12

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$462American Airlines

Thu, Aug 6 - Wed, Aug 12

10:15 am - 3:05 pmEYW Key West-ORD Chicago O'Hare Intl

5h 50m1 stop Miami

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$472American Airlines

Thu, Aug 6 - Wed, Aug 12

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$487American Airlines

Mon, Aug 10 - Mon, Aug 24

11:48 am - 9:47 pmEYW Key West-ORD Chicago O'Hare Intl

10h 59m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul

6:59 am - 5:20 pmORD Chicago O'Hare Intl-EYW Key West

9h 21m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$1,183Delta

Mon, Aug 10 - Mon, Aug 24

1:59 pm - 8:30 pmEYW Key West-ORD Chicago O'Hare Intl

7h 31m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County

6:59 am - 7:57 pmORD Chicago O'Hare Intl-EYW Key West

11h 58m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$1,273Delta

Thu, Aug 6 - Wed, Aug 12

Cheap direct flights

Enter your travel dates to find the best prices.

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$311American Airlines

Thu, Sep 3 - Tue, Sep 8

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$319American Airlines

Wed, Aug 26 - Mon, Aug 31

12:41 pm - 3:31 pmEYW Key West-ORD Chicago O'Hare Intl

3h 50mnonstop

9:00 am - 1:11 pmORD Chicago O'Hare Intl-EYW Key West

3h 11mnonstop

$319United Airlines

Thu, Dec 3 - Sun, Dec 6

4:05 pm - 6:30 pmEYW Key West-ORD Chicago O'Hare Intl

3h 25mnonstop

7:00 am - 11:11 amORD Chicago O'Hare Intl-EYW Key West

3h 11mnonstop

$319United Airlines

Thu, Dec 3 - Mon, Dec 7

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$349American Airlines

Thu, Aug 20 - Tue, Aug 25

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$373American Airlines

Thu, Aug 20 - Tue, Aug 25

4:56 pm - 7:48 pmEYW Key West-ORD Chicago O'Hare Intl

3h 52mnonstop

11:59 am - 4:18 pmORD Chicago O'Hare Intl-EYW Key West

3h 19mnonstop

$481American Airlines

Sat, Aug 15 - Thu, Aug 20

5:01 pm - 8:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 59mnonstop

12:10 pm - 4:31 pmORD Chicago O'Hare Intl-EYW Key West

3h 21mnonstop

$667American Airlines

Mon, Nov 9 - Wed, Nov 11

1:12 pm - 4:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

12:09 pm - 4:30 pmORD Chicago O'Hare Intl-EYW Key West

3h 21mnonstop

$667American Airlines

Mon, Nov 16 - Tue, Nov 17

1:12 pm - 4:00 pmEYW Key West-ORD Chicago O'Hare Intl

3h 48mnonstop

12:10 pm - 4:31 pmORD Chicago O'Hare Intl-EYW Key West

3h 21mnonstop

$667American Airlines

Mon, Nov 16 - Wed, Nov 18

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Delta flights from Key West to Wisconsin

Our best Delta deals on Key West to Wisconsin flight tickets

Delta

Sep 6

EYW7:40 amKey West

6h 00m

1 stop

ORD12:40 pmChicago O'Hare Intl

Sep 8

ORD6:40 amChicago O'Hare Intl

5h 13m

1 stop

EYW12:53 pmKey West

$339

Delta

Sep 2

EYW1:59 pmKey West

7h 13m

1 stop

MSP8:12 pmMinneapolis St Paul

Sep 8

MSP5:30 amMinneapolis St Paul

6h 23m

1 stop

EYW12:53 pmKey West

$359

Delta

Oct 3

EYW6:19 pmKey West

6h 40m

1 stop

ORD11:59 pmChicago O'Hare Intl

Oct 5

ORD6:40 amChicago O'Hare Intl

5h 13m

1 stop

EYW12:53 pmKey West

$366

United Airlines flights from Key West to Wisconsin

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

United Airlines

Dec 3

EYW4:05 pmKey West

3h 25m

ORD6:30 pmChicago O'Hare Intl

Dec 7

ORD7:00 amChicago O'Hare Intl

3h 11m

EYW11:11 amKey West

$319

United Airlines

Oct 3

EYW4:00 pmKey West

2h 27m

ORD5:27 pmChicago O'Hare Intl

Oct 5

ORD5:00 amChicago O'Hare Intl

7h 29m

1 stop

EYW1:29 pmKey West

$440

United Airlines

Dec 8

EYW4:05 pmKey West

7h 34m

1 stop

MKE10:39 pmMilwaukee-Mitchell

Dec 12

MKE5:00 amMilwaukee-Mitchell

5h 11m

1 stop

EYW11:11 amKey West

$477

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/24

12:01 pm-9:20 am

2 stops22h 19m

Chicago O'Hare Intl

Sat 9/26

3:50 pm-11:35 am

1 stop18h 45m

$268

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/24

12:01 pm-9:20 am

2 stops22h 19m

Chicago O'Hare Intl

Sat 9/26

3:50 pm-11:35 am

1 stop18h 45m

$269

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/24

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Sat 9/26

3:50 pm-11:35 am

1 stop18h 45m

$273

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Tue 9/8

7:05 am-9:24 am

2 stops25h 19m

$276

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 12/3

10:59 am-1:09 am

1 stop15h 10m

Chicago O'Hare Intl

Mon 12/7

2:31 pm-10:19 am

1 stop18h 48m

$277

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 10/1

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Sat 10/31

4:44 pm-1:38 pm

1 stop19h 54m

$284

Key WestMinneapolis

EYW Key West - MSP Minneapolis St Paul

EYWMSP

Key West

Fri 9/4

12:07 pm-6:25 pm

1 stop7h 18m

Minneapolis St Paul

Sat 9/19

9:30 am-11:21 am

2 stops24h 51m

$293

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 10/1

10:59 am-10:59 pm

1 stop13h 00m

Chicago O'Hare Intl

Sat 10/31

6:30 am-9:22 am

2 stops25h 52m

$303

Quickest round-trip

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Thu 9/3

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Tue 9/8

11:59 am-4:18 pm

Nonstop3h 19m

$311

Key WestChicago

EYW Key West - ORD Chicago O'Hare Intl

EYWORD

Key West

Wed 8/26

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 8/31

11:59 am-4:18 pm

Nonstop3h 19m

$319

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 July, then book flights to Wisconsin from Key West during January instead. Flights to Wisconsin in January, while not as cheap as those in July, still average around $0.

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

You could potentially save up to 1% 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	Mon, Tue, Wed, Thu, Fri and Sun
Airports in Wisconsin	80 airports

The fastest flight from Key West to Wisconsin takes 3h 25m

Direct flights go from Key West to Wisconsin on Monday, Tuesday, Wednesday, Thursday, Friday 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 August 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
Delta	PriceFrom $283	Free Cancellation	Rating 7.8 8,490 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.