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.

![Radisson Blu Aqua Hotel Chicago](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Radisson Blu Aqua Hotel Chicago

Downtown Chicago

CA $725

per person

Jan 31 - Feb 6

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (1,761 reviews)

Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks!

Reviewed on Dec 14, 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 $988

per person

Feb 23 - Feb 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 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 $1,296

per person

Feb 23 - Feb 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!!

Reviewed on Dec 15, 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 $1,631

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $848

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Good location a modern hotel. Would be nice if a pool or sauna.

Reviewed on Dec 14, 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/2026-01-16/2026-01-23/?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 $988

per person

Feb 23 - Feb 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 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 $1,296

per person

Feb 23 - Feb 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!!

Reviewed on Dec 15, 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 $1,631

per person

Mar 5 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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

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/2026-01-16/2026-01-23/?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.

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago O'Hare Airport

O'Hare

CA $839

per person

Mar 7 - Mar 10

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

8.2/10 Very Good! (2,158 reviews)

It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.

Reviewed on Dec 6, 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 $1,035

per person

Mar 3 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 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 $1,149

per person

Mar 2 - Mar 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!!

Reviewed on Dec 15, 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/2026-01-16/2026-01-23/?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 $548

per person

Feb 23 - Feb 27

found 8 hours 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 $988

per person

Feb 23 - Feb 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 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 $628

per person

Feb 23 - Feb 27

found 8 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Great location, clean room and friendly staff!

Reviewed on Dec 14, 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/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Cheap Hotels in Southern Wisconsin

![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! (1,134 reviews)

Loved everything except the heat was not good. We froze

Reviewed on Dec 10, 2025

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

![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! (2,002 reviews)

Friendly staff, variety of breakfast food options.

Reviewed on Dec 14, 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! (3,375 reviews)

Room was very comfortable and well laid out. Perfect location.

Reviewed on Dec 15, 2025

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

[See all 7,453 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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