Southeast Wisconsin Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago
€1,282
per person
2 Oct - 8 Oct
found 6 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
8.6/10 Excellent! (1,164 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
€1,347
per person
2 Oct - 8 Oct
found 6 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (556 reviews)
Great! But parking was bad.

Reviewed on 26 Aug 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
€2,091
per person
2 Oct - 8 Oct
found 6 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (1,160 reviews)
A

Reviewed on 27 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
€1,431
per person
3 Oct - 7 Oct
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The staff were helpful, the room was nice and clean, and the buffet breakfast was amazing. We enjoyed our stay.

Reviewed on 28 Aug 2026

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago
€1,555
per person
2 Oct - 8 Oct
found 6 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
8.8/10 Excellent! (2,133 reviews)

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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee
A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

1 out of top 10 points of interest in this area

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

Find hotels in West Allis
A stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

Travellers come to Wauwatosa for its abundant dining options, and you can see top attractions like Mayfair Mall and The Mayfair Collection while you're in town.

Find hotels in Wauwatosa
A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience Milwaukee’s hot spot for art and fashion when you check out the dynamic boutiques, restaurants, theaters and galleries that fill this exciting district.

Find hotels in Historic Third Ward
A pedestrian bridge over a river with a city skyline in the background, including a prominent bank building.

East Town

Lake Michigan and Veteran's Park are top sights in East Town, and you should be sure to explore the fantastic nightlife. Hop aboard the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop to see more sights in the area.

Find hotels in East Town

Top hotels in Southeast Wisconsin

The Pfister Hotel

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
€161
8 Sept - 9 Sept
includes taxes & fees
The Pfister Hotel
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
€150
7 Sept - 8 Sept
includes taxes & fees
Harbor Shores on Lake Geneva
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
€79
30 Aug - 31 Aug
includes taxes & fees
AmericInn by Wyndham Brookfield
See all 2,494 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.

Stay near popular Southeast Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.
Photo by Tim Ard

American Family Field

9.0/10 (2,832 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.
See properties
A cityscape with a variety of buildings, including a prominent white structure with a curved roof, a tall tower, and a mix of older and modern architecture.

Fiserv Forum

9.2/10 (2,312 reviews)
Catch an event at Fiserv Forum during your trip to Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties
The Milwaukee County Zoo entrance with a sign, surrounded by trees and plants.

Milwaukee County Zoo

8.6/10 (799 reviews)
This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.
See properties
A wall of vintage motorcycle advertisements and models.

Harley-Davidson Museum

8.8/10 (1,541 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.
See properties
A brightly lit Ferris wheel with multiple cabins at night.

Wisconsin State Fair Park

9.0/10 (217 reviews)
Enjoy an outing to Wisconsin State Fair Park during your stay in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.
See properties
A calm lake with sailboats docked on the left, surrounded by mountains and a clear sky.

Lake Como

8.8/10 (214 reviews)
Commune with nature and explore the great outdoors at Lake Como during your travels in Lake Geneva. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
See properties

Baird Center

8.2/10 (522 reviews)
Learn about the events happening in Baird Center during your trip to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.
See properties

Frequently asked questions

How much does a Southeast Wisconsin holiday package cost?
Much less than you might think — from as low as €1,282, as a matter of fact! By combining hotels, flights and car rentals into your own custom-made holiday package, your getaway to Southeast Wisconsin is just clicks away.
How do I get a cheap travel package to Southeast Wisconsin?
Bundle your flights and hotels, add on extras such as activities, and save with a Southeast Wisconsin holiday package. You won't just pick up exciting discounts on your adventure — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 airlines and 1,000,000 hotels around the globe. Your next big adventure starts right here, right now!
Where should I stay in Southeast Wisconsin?
You'll fall in love with Milwaukee. Renowned sights, such as Milwaukee Art Museum and American Family Field, will keep you busy in this exciting city.
What are the top hotels in Southeast Wisconsin?
For hotels in Milwaukee with friendly service and comfy beds, you can't beat Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr. If you're visiting Lake Geneva as well, you can look forward to a solid night's sleep at Mt. Olympus Water & Theme Park Resort or Hilton Milwaukee City Centre.
How far in advance should I book my Southeast Wisconsin holiday?
Savvy travellers always book early. Air carriers typically release flight tickets up to 12 months prior to departure, and this is your chance to land some of the lowest prices. Boss just told you to use up your holiday time next month? That's fine too — Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Southeast Wisconsin travel package include?
That's up to you. You can choose from a range of Southeast Wisconsin bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your Southeast Wisconsin trip looks like, get set to save!
What should I know before booking a Southeast Wisconsin travel package?
When you book your hotels, flights and car rentals together, you'll land awesome discounts. Whether you're organising a rural escape in a cottage or want to stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Southeast Wisconsin Expedia holiday package?
Definitely. Expedia has over 550 partner airlines to select from around the world. With so much choice, finding the right carrier to take you to Southeast Wisconsin will be a breeze.
If I'm not able to travel, can I cancel my Southeast Wisconsin holiday package?
It is possible to cancel your Southeast Wisconsin booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.