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

## Book a Hotel + Flight or Car together to unlock savings

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.

![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 $838

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

![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 $1,384

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $944

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

Reviewed on Jan 19, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,485

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Staff was wonderful.

Reviewed on Jan 25, 2026

![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 $1,011

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

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/2026-03-05/2026-03-12/?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 $1,384

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,485

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Staff was wonderful.

Reviewed on Jan 25, 2026

![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 $1,627

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

The staff and amenities

Reviewed on Feb 4, 2026

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/2026-03-05/2026-03-12/?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.

![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 $806

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

![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 $902

per person

Mar 12 - Mar 15

found 20 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

![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 $1,282

per person

Mar 12 - Mar 15

found 20 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

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/2026-03-05/2026-03-12/?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.

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $787

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

Reviewed on Jan 19, 2026

![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 $858

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

![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 $1,384

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

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/2026-03-05/2026-03-12/?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! (2,036 reviews)

Staff quick to respond. Amenities were awesome.

Reviewed on Jan 29, 2026

[](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! (3,478 reviews)

Everything was good.

Reviewed on Jan 30, 2026

[](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! (1,152 reviews)

Great place to stay!

Reviewed on Jan 30, 2026

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

[See all 7,403 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)[

Southern Wisconsin Vacations

](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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