Title: Cheap Vacations in Southern Wisconsin 2026 | Expedia.ca

![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Southern Wisconsin Cheap Vacations

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Photo by Evae

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## Flight and Cheap hotel deals in Southern Wisconsin

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

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $425

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $773

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $521

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $487

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 2025

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $552

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap holidays in Southern Wisconsin

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

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $773

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,307

per person

Jan 23 - Jan 26

found 9 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,183

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Excellent service throughout the hotel

Reviewed on Nov 29, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap holidays in Southern Wisconsin

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

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $425

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $773

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Amazing hotel, location, staff, and food!!

Reviewed on Dec 8, 2025

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $521

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap holidays in Southern Wisconsin

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

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $652

per person

Feb 12 - Feb 16

just found

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $883

per person

Feb 12 - Feb 16

just found

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

9.2/10 Wonderful! (317 reviews)

The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Swissotel - Chicago

Downtown Chicago

CA $714

per person

Feb 12 - Feb 16

just found

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (2,947 reviews)

The room is very clean, staff was great, the lobby bar and restaurant was very nice.

Reviewed on Dec 9, 2025

Don't see what you're looking for?

See all available trips from Columbus to Southern Wisconsin

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Cheap Hotels in Southern Wisconsin

![Drury Plaza Hotel Milwaukee Downtown](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/ac1d9528_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

- 3 hours drive from University of Wisconsin-Madison

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...

9.6/10 Exceptional! (2,005 reviews)

Everything was great! Love the staff!

Reviewed on Dec 8, 2025

[](https://expedia.ca/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.Hotel-Information)

![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI

- 5 min drive from University of Wisconsin-Madison

Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...

9.4/10 Exceptional! (3,372 reviews)

Everything was great!

Reviewed on Dec 9, 2025

[](https://expedia.ca/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information)

![Natura Treescape Resort](https://images.trvl-media.com/lodging/18000000/17680000/17679300/17679264/162a5fb3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Natura Treescape Resort

400 County Road A Wisconsin Dells WI

- 2 hours drive from University of Wisconsin-Madison

Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, 2 indoor pools, and a private beach. Our guests praise the pool and the helpful staff in ...

8/10 Very Good! (1,128 reviews)

The hot tub was not hot. It was a nice place, nothing special.

Reviewed on Dec 4, 2025

[](https://expedia.ca/Wisconsin-Dells-Hotels-Natura-Treescape-Resort.h17679264.Hotel-Information)

[See all 7,427 properties in Southern Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635975749457)

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.

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## More Vacations Ideas

[Flights to Southern Wisconsin

](https://expedia.ca/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[

Southern Wisconsin Hotels

](https://expedia.ca/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[

Southern Wisconsin Vacation Rentals

](https://expedia.ca/Southern-Wisconsin-Vacation-Rentals.d553248635975749457.Travel-Guide-VacationRentals)[

Southern Wisconsin Car Rentals

](https://expedia.ca/Car-Rentals-In-Southern-Wisconsin.d553248635975749457.Car-Rental-Guide)[

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](https://expedia.ca/Southern-Wisconsin.d553248635975749457.Destination-Travel-Guides)

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

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