Southeast Wisconsin Holidays

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Top Flight + Hotel Deals in Southeast Wisconsin

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

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was €5,121, price is now €4,555 per person
€4,555
per person
1 Oct - 7 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Our stay at the Omni Chicago Hotel was great. Room was clean, the staff was outstanding and bar was great.

Reviewed on 14 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €5,524, price is now €4,697 per person
€4,697
per person
1 Oct - 7 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Room was clean area was fines. Staff was mediocre at best. Last night person seem disinterested and didn’t seem to want to speak. For the price we paid it was honestly not work it too me. Felt that they nickeled and dined you too death. No housekeeping for the entire 5 night. Crazy expensive for parking we had to make other arrangements which was a hassle since i was on crutches but we made it work. Even if we had parties on garage not elevator access. Will not be staying here again. Not worth the money, poor customer service. Had to get towels and empty trash daily. Very disappointing!!

Reviewed on 13 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €6,132, price is now €5,274 per person
€5,274
per person
1 Oct - 7 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
We loved our "upgraded" room with the beautiful view of the river, Lake Michigan and the Saturday night fireworks! This was thanks to Michael, our concierge or check-in man at the front desk. It took us a little while to figure out all the lighting but that was a small thing. The coffee at your restaurant left a little to be desired - it was not hearty enough or warm enough. The cappuccino we replaced it with was very good! All in all, a very happy experience.

Reviewed on 14 Jul 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €5,622, price is now €4,858 per person
€4,858
per person
1 Oct - 7 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Good property but perhaps a bit more modest than reviews

Reviewed on 12 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €5,503, price is now €4,910 per person
€4,910
per person
1 Oct - 7 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super.

Reviewed on 12 Jul 2026

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

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
The price is €198 per night from 20 Jul to 21 Jul
€198
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (1,378 reviews)
"We stayed at Harbor Shores for two nights and it was great! It’s literally across the street from the lake and a minutes walk from anywhere in downtown. The staff provided a list of suggestions on where to go for the best dining and each place we tried was excellent. The room was nice and had everything ..."

Reviewed on 13 Jul 2026

Harbor Shores on Lake Geneva
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is €163 per night from 22 Jul to 23 Jul
€163
22 Jul - 23 Jul
includes taxes & fees
9.2/10 Wonderful! (1,663 reviews)
"Such a fun stay, clean room and late night eats!"

Reviewed on 14 Jul 2026

Potawatomi Hotel & Casino
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 €229 per night from 26 Jul to 27 Jul
€229
26 Jul - 27 Jul
includes taxes & fees
9.6/10 Exceptional! (2,176 reviews)
"Our whole experience was fantastic. Check-in was quick and they offered champagne. The Bellhop that helped us with our luggage and finding our room was an absolute delight and the property was immaculate. Would love to visit again."

Reviewed on 13 Jul 2026

The Pfister Hotel
See all 2,453 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
Open 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

Frequently asked questions

How much does a Southeast Wisconsin holiday package cost?
Much less than you might think — from as low as €4,555, 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.

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