Southeast Wisconsin Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Southeast Wisconsin

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
5 Nov - 9 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
5 Nov - 9 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on 16 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Great view of the lake and city

Reviewed on 18 Aug 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (260 reviews)
Fantastic experience. Staff was friendly and accommodating. Highly recommend

Reviewed on 15 Aug 2025

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
Milwaukee

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

Top hotels in Southeast Wisconsin

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,213 reviews)
"Location is perfect. Lake Geneva is not a place to be using the car, everything is walking distance, so this hotel by the lake and main walking area was perfect for us. It was surprisingly quiet for the location, we have a 3 year old so that worked out pretty well. Highly recommended."

Reviewed on 15 Aug 2025

Get rates
Harbor Shores on Lake Geneva
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is €186 per night from 7 Sept to 8 Sept
€186
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,699 reviews)
"Beautiful building and great service"

Reviewed on 16 Aug 2025

The Pfister Hotel
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is €178 per night from 16 Sept to 17 Sept
€178
16 Sept - 17 Sept
includes taxes & fees
8.6/10 Excellent! (2,938 reviews)
"We can never have a bad stay at Timber Ridge, amazing family friendly waterpark, great restaurants on both properties, and amazing amenities."

Reviewed on 12 Aug 2025

Timber Ridge Lodge and Waterpark
See all 2,491 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.

Popular places to visit

Harley-Davidson Museum which includes interior views

Harley-Davidson Museum

4.5/5(3 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.

Harley-Davidson Museum
Milwaukee County Zoo which includes interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo

Fiserv Forum

Catch an event at Fiserv Forum during your trip to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Fiserv Forum

Frequently asked questions

How much does a Southeast Wisconsin holiday package cost?
Much less than you might think — from as low as €780, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.