Southeast Wisconsin Holidays

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Top Southeast Wisconsin Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
12 Jun - 14 Jun
found 23 hours ago
Return direct flight included
Providence (PVD) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Overall great experience. No complaints!!!

Reviewed on 22 Apr 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
12 Jun - 14 Jun
found 23 hours ago
Return direct flight included
Providence (PVD) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Front desk was very friendly and helpful. We had a corner unit and the view was great. The unit was very comfortable and clean.

Reviewed on 22 Apr 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
11 Jun - 15 Jun
found 1 day ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Great breakfast every morning, the staff does a great job of making sure you enjoy the start of each day. Very walkable, its close proximity to Michigan Ave makes a trip to Chicago without a vehicle totally doable. We will be back - thank you for the great place to stay and enjoy a vacation in Chicago!

Reviewed on 24 Apr 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
11 Jun - 15 Jun
found 1 day ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
The highlight of this hotel is definitely the staff — everyone was kind, professional, and very helpful throughout our stay. Unfortunately, we did experience an issue with housekeeping, as our room wasn’t cleaned for two days. However, when I brought it to the attention of the front desk, they promptly addressed the situation and kindly removed our bar charges, which was very much appreciated. The hotel bar is one of the main attractions and definitely worth checking out!

Reviewed on 22 Apr 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

Drury Plaza Hotel Milwaukee Downtown
Drury Plaza Hotel Milwaukee Downtown
3 out of 5
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is HK$857 per night from 19 May to 20 May
HK$857
HK$1,011 total
includes taxes & fees
19 May - 20 May
9.6/10 Exceptional! (1,712 reviews)
"Excelente ubicación, hotel muy lindo y bien mantenido"

Reviewed on 22 Apr 2025

Drury Plaza Hotel Milwaukee Downtown
Crowne Plaza Milwaukee South by IHG
Crowne Plaza Milwaukee South by IHG
3.5 out of 5
6401 S 13th Street, Milwaukee, WI
Fully refundable
The price is HK$613 per night from 11 May to 12 May
HK$613
HK$723 total
includes taxes & fees
11 May - 12 May
8/10 Very Good! (1,001 reviews)
"."

Reviewed on 16 Apr 2025

Crowne Plaza Milwaukee South by IHG
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 HK$775 per night from 26 May to 27 May
HK$775
HK$1,159 total
includes taxes & fees
26 May - 27 May
8.6/10 Excellent! (2,788 reviews)
"Awesome trip. Downtown lake geneva is close and there are other activities to do outside Timberridgr waterpark. But the waterpark itself has a lot of things to do already especially for those who have kids. I liked how our hotel room is like a mini house, its got kitchen with aplliances (plates, ..."

Reviewed on 21 Apr 2025

Timber Ridge Lodge and Waterpark
See all 2,479 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.

Frequently asked questions

How much does a Southeast Wisconsin vacation package cost?
Much less than you might think — from as low as HK$4,591, as a matter of fact! By combining hotels, flights and car rentals into your own custom-made vacation 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 vacation?
Savvy travelers 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 vacation 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.

Popular places to visit

Lake Geneva Cruise Line

Lake Geneva Cruise Line

5/5(1 review)

Explore the waterfront of Lake Geneva Cruise Line and enjoy other activities such as boating in Lake Geneva. Stroll along the lakeside in this relaxing area or seek out the golf courses.

Lake Geneva Cruise Line
Milwaukee Art Museum showing modern architecture and night scenes

Milwaukee Art Museum

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Milwaukee Art Museum

Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your visit to Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.

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