Top Adventure vacation packages in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.

Lodge Geneva National

$220

per person

Dec 12 - Dec 14

found 4 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

9/10 Wonderful! (1,308 reviews)

Exorbitant resort fees!!! Very limited breakfast options, no orange juice. Golf shop very small with limited merchandise options.

Reviewed on Oct 8, 2025

Saint Kate - The Arts Hotel

Downtown Milwaukee

Save 100% on your flight

$438

per person

Dec 9 - Dec 13

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Milwaukee (MKE)

9.8/10 Exceptional! (2,405 reviews)

Rooms very clean. Staff friendly. Walkable with lots of things near by.

Reviewed on Oct 3, 2025

The Iron Horse Hotel

Fifth Ward

Save 100% on your flight

$451

per person

Dec 9 - Dec 13

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Milwaukee (MKE)

9.2/10 Wonderful! (1,014 reviews)

The room was extremely nice and quiet. The bed was ultra comfortable. The area was walking distance to the downtown restaurant area. One thing: we could not increase the tv volume. We are older and hard of hearing. We assume it was set up to avoid loudness for the other guests but the volume was too low.

Reviewed on Oct 8, 2025

Kimpton Journeyman Hotel by IHG

Downtown Milwaukee

$423

per person

Dec 9 - Dec 13

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Milwaukee (MKE)

9.4/10 Exceptional! (902 reviews)

Loved this hotel in the Third Ward of Milwaukee. The staff was so helpful and friendly. We enjoyed complimentary happy hour before walking around the area. Finished the evening at the rooftop bar.

Reviewed on Sep 29, 2025

Grand Geneva Resort & Spa

$369

per person

Dec 12 - Dec 14

found 4 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

8.6/10 Excellent! (1,008 reviews)

excellent place to get away, very clean retaurants top notch. just wish the outdoor pool was bigger

Reviewed on Oct 1, 2025

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3 Night Adventure vacations in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.

DoubleTree by Hilton Milwaukee - Brookfield

$356

per person

Dec 13 - Dec 16

found 20 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Milwaukee (MKE)

8.4/10 Very Good! (1,000 reviews)

Ice machine wasn’t working on our floor

Reviewed on Oct 3, 2025

Saint Kate - The Arts Hotel

Downtown Milwaukee

$416

per person

Dec 13 - Dec 16

found 20 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Milwaukee (MKE)

9.8/10 Exceptional! (2,405 reviews)

Rooms very clean. Staff friendly. Walkable with lots of things near by.

Reviewed on Oct 3, 2025

The Iron Horse Hotel

Fifth Ward

$848

per person

Nov 7 - Nov 10

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

9.2/10 Wonderful! (1,014 reviews)

The room was extremely nice and quiet. The bed was ultra comfortable. The area was walking distance to the downtown restaurant area. One thing: we could not increase the tv volume. We are older and hard of hearing. We assume it was set up to avoid loudness for the other guests but the volume was too low.

Reviewed on Oct 8, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southeast Wisconsin

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4 Night Adventure vacations in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.

Kimpton Journeyman Hotel by IHG

Downtown Milwaukee

$423

per person

Dec 9 - Dec 13

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Milwaukee (MKE)

9.4/10 Exceptional! (902 reviews)

Loved this hotel in the Third Ward of Milwaukee. The staff was so helpful and friendly. We enjoyed complimentary happy hour before walking around the area. Finished the evening at the rooftop bar.

Reviewed on Sep 29, 2025

Saint Kate - The Arts Hotel

Downtown Milwaukee

Save 100% on your flight

$438

per person

Dec 9 - Dec 13

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Milwaukee (MKE)

9.8/10 Exceptional! (2,405 reviews)

Rooms very clean. Staff friendly. Walkable with lots of things near by.

Reviewed on Oct 3, 2025

The Iron Horse Hotel

Fifth Ward

Save 100% on your flight

$451

per person

Dec 9 - Dec 13

found 19 hours ago

Roundtrip flight included

Chicago (ORD) to Milwaukee (MKE)

9.2/10 Wonderful! (1,014 reviews)

The room was extremely nice and quiet. The bed was ultra comfortable. The area was walking distance to the downtown restaurant area. One thing: we could not increase the tv volume. We are older and hard of hearing. We assume it was set up to avoid loudness for the other guests but the volume was too low.

Reviewed on Oct 8, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southeast Wisconsin

View all trips

How can I book the best Southeast Wisconsin adventure trips?

Choose your own adventure in Southeast Wisconsin, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Southeast Wisconsin family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Southeast Wisconsin. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Southeast Wisconsin adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Southeast Wisconsin adventure vacation for couples?

Book a Southeast Wisconsin couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Southeast Wisconsin?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Southeast Wisconsin with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Southeast Wisconsin adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

Top Adventure Southeast Wisconsin Hotels

Abbey Resort and Avani Spa

269 Fontana Boulevard, Fontana, WI

1 hour drive from American Family Field

Stay at this 3.5-star beach resort in Fontana. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff ...

8.4/10 Very Good! (1,570 reviews)

"Pool was nice"

Reviewed on Oct 1, 2025

Hyatt Regency Milwaukee

333 W Kilbourn Ave, Milwaukee, WI

6 min drive from American Family Field

Stay at this 4-star business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...

8.4/10 Very Good! (1,169 reviews)

"Best last minute decision I ever made"

Reviewed on Oct 7, 2025

Grand Geneva Resort & Spa

7036 Grand Geneva Wy, Lake Geneva, WI

1 hour drive from American Family Field

Stay at this 4-star spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

8.4/10 Very Good! (1,002 reviews)

"Wonderful place"

Reviewed on Oct 7, 2025

See all 2,427 properties in Southeast Wisconsin

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.