Name: The Iron Horse Hotel
Price range: $187 total
Rating: 9.2

Your Southeast Wisconsin Vacation

Our Southeast Wisconsin vacation packages provide an affordable, easy and immersive way to enjoy everything this exciting destination has to offer. If it's distilleries and craft breweries and dining you're yearning for, this is the place to come. With so many things to see and do on a trip to Southeast Wisconsin, it can be tricky to know where to begin. Kick off your journey in Milwaukee at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another top city worth adding to your itinerary is Lake Geneva. Be sure not to miss Geneva Lake and Walworth County Fairgrounds. Expedia has everything you need for planning your Southeast Wisconsin vacation. From accommodations and flights, to car rentals and activities, we know how to curate a travel experience like no other.

The Latest Southeast Wisconsin vacation packages

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

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$397

per person

Jul 8 - Jul 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (2,137 reviews)

It's ok, no rats or cockroaches but did I expect better for the price? Yes. And don't be fooled, there are hidden fees, something called a "city resort tax" or something like that (even though it's not a resort--no perks), that you'll be charged additional for at the hotel, no matter what Expedia says about fees and taxes being included in the price.

Reviewed on May 4, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$462

per person

Jul 8 - Jul 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (3,991 reviews)

Wonderful location !

Reviewed on May 5, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$762

per person

Jun 25 - Jun 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (468 reviews)

Love the amenities. Great location too

Reviewed on May 3, 2026

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$571

per person

Jul 8 - Jul 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,124 reviews)

Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$654

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,478 reviews)

Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking

Reviewed on May 3, 2026

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Where to stay in Southeast Wisconsin

Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Wisconsin

Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

Historic Third Ward

1 out of top 10 points of interest in this area

4.5/5(32 area reviews)

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

Discover the most popular places to visit in Southeast Wisconsin

American Family Field

4.5/5(777 reviews)

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

Harley-Davidson Museum

4.5/5(342 reviews)

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Henry W. Maier Festival Park

4.5/5(132 reviews)

Enjoy an outing to Henry W. Maier Festival Park during your stay in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Southeast Wisconsin Hotel Deals

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Fully refundableReserve now, pay when you stay

$121 nightly

$137 total

May 6 - May 7

Total with taxes and fees

9.2/10 Wonderful! (1,333 reviews)

Stood for one night for a birthday celebration and unfortunately, the experience did not meet expectations. We called the front desk to request two comforter because the comforters on both beds were stained. They brought two of them up promptly, which I appreciated, but one of the comforters still ...

Reviewed on May 4, 2026

Potawatomi Hotel & Casino

1611 West Canal Street Milwaukee WI

Fully refundableReserve now, pay when you stay

$158 nightly

$186 total

May 25 - May 26

Total with taxes and fees

9.2/10 Wonderful! (1,452 reviews)

Clean, friendly staff, plenty of dining options

Reviewed on May 4, 2026

The Iron Horse Hotel

500 W Florida Street Milwaukee WI

Fully refundableReserve now, pay when you stay

$159 nightly

$187 total

May 24 - May 25

Total with taxes and fees

9.2/10 Wonderful! (1,096 reviews)

As we pulled up it was confusing as to where to go or park or stop for valet. Once we figured it out I will say our valet nick was fantastic. Unfortunately that was the only thing fantastic. The place was absolutely packed for a derby event. Our fault for not checking that before. Not the hotels ...

Reviewed on May 3, 2026

See all 2,440 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.