Southeast Wisconsin Holidays

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Southeast Wisconsin Flight & Hotel Packages

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

The Ingleside Hotel

S$550
per person
23 Oct - 26 Oct
found 5 hours ago
Return flight included
Chicago (CHI) to Milwaukee (MKE)
8.6/10 Excellent! (927 reviews)
The staff was really polite, the room was clean but it smelled of weed so badly. Everytime you stepped outside of your room it was an instant headache. Everything else was good.

Reviewed on 14 Sept, 2026

The Iron Horse Hotel

The Iron Horse Hotel

Fifth Ward
S$815
per person
23 Oct - 26 Oct
found 5 hours ago
Return flight included
Chicago (CHI) to Milwaukee (MKE)
9.2/10 Wonderful! (1,310 reviews)
Dubbel Dutch

Dubbel Dutch

Downtown Milwaukee
S$675
per person
23 Oct - 26 Oct
found 5 hours ago
Return flight included
Chicago (CHI) to Milwaukee (MKE)
9.2/10 Wonderful! (185 reviews)
This is a nice boutique hotel. It’s a low key setup with no front desk. However, staff is very responsive. They are available by text/call. We loved the experience at the Agency cocktail lounge.

Reviewed on 10 Sept, 2026

Home2 Suites by Hilton Milwaukee Downtown

Home2 Suites by Hilton Milwaukee Downtown

Downtown Milwaukee
S$691
per person
23 Oct - 26 Oct
found 5 hours ago
Return flight included
Chicago (CHI) to Milwaukee (MKE)
8.8/10 Excellent! (1,003 reviews)
The staff was helpful, breakfast was fresh daily, the facility was well located and clean.

Reviewed on 17 Sept, 2026

Ramada by Wyndham Milwaukee

Ramada by Wyndham Milwaukee

Marquette
S$780
per person
23 Oct - 26 Oct
found 5 hours ago
Return flight included
Chicago (CHI) to Milwaukee (MKE)
8/10 Very good! (527 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 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 buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

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.

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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
S$293
27 Sept - 28 Sept
includes taxes & fees
The Pfister Hotel
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
S$115
21 Sept - 22 Sept
includes taxes & fees
8/10 Very good! (1,597 reviews)
"I stay at this hotel a couple of times a month and the rooms need an upgrade - - mainly the bathroom. There have been a few hairs on the walls of the tub/shower."

Reviewed on 16 Sept, 2026

AmericInn by Wyndham Brookfield
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
S$140
29 Sept - 30 Sept
includes taxes & fees
Hyatt Regency Milwaukee
See all 2,477 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 sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.
Photo by trenton.badillo

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
A church with two tall spires and a clock tower.
Photo by ‎‎Debra Fischer

Marquette University

8.8/10 (968 reviews)
Explore the campus of Marquette University during your visit to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.
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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 relaxing area's lakeside and enjoy its top-notch restaurants.
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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.
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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.
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The Rave-Eagles Club

8.0/10 (699 reviews)
You can enjoy a show at The Rave-Eagles Club 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 S$550, 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.