Southern Wisconsin Holidays

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Top Flight + Hotel Deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,397, price is now €836 per person
€836
per person
6 Sept - 11 Sept
found 21 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on 14 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,541, price is now €882 per person
€882
per person
25 Sept - 30 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) 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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was €1,510, price is now €897 per person
€897
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that looked a little tired and could use updating but overall we had a good sleep and were refreshed for the next day.

Reviewed on 13 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €1,402, price is now €871 per person
€871
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
The staff were very inattentive . 4 calls over 2 days for housekeeping issues . Meal was corrected 2 times still brought the wrong order after she apologized for the first one . If I managed the place I would not be employed

Reviewed on 14 Jul 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €1,392, price is now €930 per person
€930
per person
25 Sept - 30 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
Great location. Beautiful views from the room. Friendly staff.

Reviewed on 14 Jul 2026

Where to stay in Southern Wisconsin

Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern 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 Southern Wisconsin

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road Wisconsin Dells WI
Fully refundableReserve now, pay when you stay
The price is €108 per night from 3 Aug to 4 Aug
€108
3 Aug - 4 Aug
includes taxes & fees
7/10 Good! (2,869 reviews)
"Clean room, easy check in, no complaints"

Reviewed on 13 Jul 2026

Mt. Olympus Water & Theme Park Resort
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is €147 per night from 2 Aug to 3 Aug
€147
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (4,005 reviews)
"Lots of great things at this place. The only reason we docked a point is because we felt the staff in the bar were bit condescending after they realized that i was not drinking. Obviously, their choice to run their joint as they wish, but it didn’t sit well with us."

Reviewed on 14 Jul 2026

The Madison Concourse Hotel and Governor's Club
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
See all 7,709 properties in Southern 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 Southern 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.
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Frequently asked questions

How much does a Southern Wisconsin holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Southern Wisconsin from just €836. And the more you bundle, the more you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Southern Wisconsin?
Our Southern Wisconsin holiday packages promise plenty of savings for the savvy traveller. For the best deal, simply bundle your flights, hotels and activities into one neat package. But great bargains are only the start of your next awesome adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels throughout the world to choose from. Whatever your style, there's a holiday package with your name on it.
Where should I stay in Southern Wisconsin?
To see popular sights like Milwaukee Art Museum and American Family Field, Milwaukee is the place to be. Lots of travellers also love visiting Appleton, home to Gardens of the Fox Cities and Hearthstone Historic House Museum. If time is on your side, why not visit both cities?
What are the top hotels in Southern Wisconsin?
When it comes to hotels in Milwaukee, Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr are among the favourites. If you're also staying in Wisconsin Dells, Inn of the Pines and Silver Spruce Resort are waiting to welcome you.
How far in advance should I book my Southern Wisconsin holiday?
Savvy travellers often book early. You can usually start comparing international fares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Cheap prices sometimes occur just weeks before departure.
What does an Expedia Southern Wisconsin travel package include?
From hotels and flights to car rentals, Expedia can help you put together a Southern Wisconsin package that works for you. Heading away for a few weeks? Check out a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, a flight and hotel deal could be more your style. Tours and activities can be added once you've made your booking. Our packages make it simple to save and plan.
What should I know before booking a Southern Wisconsin travel package?
So many places to travel to, so many things to do. With a travel package, you can cross more of them off your list. Combine your flights, rental cars and hotels and see how much you save.
If I'm not able to travel, can I cancel my Southern Wisconsin holiday package?
Yes, you can cancel your Southern Wisconsin booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out 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.