Southern Wisconsin Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Southern Wisconsin Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Good location and clean room

Reviewed on 17 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul, 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
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
It’s super convenient bc it’s on the pier but beware it’s connected so it’s not its own building. Still we felt safe and it was very clean

Reviewed on 16 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 1 day ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Family of 6 got two rooms near one another on the same floor. A wonderful property in a great location. We loved it

Reviewed on 16 Jul, 2025

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
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 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 S$130 per night from 10 Aug to 11 Aug
S$130
10 Aug - 11 Aug
includes taxes & fees
6.6/10 (2,215 reviews)
"We stayed at hotel Rome and it was good."

Reviewed on 16 Jul, 2025

Mt. Olympus Water & Theme Park Resort
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 S$271 per night from 3 Aug to 4 Aug
S$271
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (1,183 reviews)
"Beautiful place and wish I could have stayed longer. Lovely and clean"

Reviewed on 16 Jul, 2025

Harbor Shores on Lake Geneva
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
9.4/10 Exceptional! (2,849 reviews)
"Parking ramp is terrifying for anything that is not a sedan. I know it’s not something that can be changed, but oof."

Reviewed on 15 Jul, 2025

Get rates
The Madison Concourse Hotel and Governor's Club
See all 7,713 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.

Popular places to visit

Harley-Davidson Museum showing 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

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 S$437. 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.

* 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.