Southern Wisconsin Mountain Vacations
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Flight and Mountain hotel deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,939, price is now CA $1,428 per person
CA $1,428
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026
Hotel Arista
Price was CA $1,425, price is now CA $1,058 per person
CA $1,058
per person
Jun 3 - Jun 9
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!!
The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista.
Reviewed on Mar 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $2,387, price is now CA $1,773 per person
CA $1,773
per person
May 18 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
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See all available trips from Columbus to Southern Wisconsin
View all trips5* Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was CA $2,387, price is now CA $1,773 per person
CA $1,773
per person
May 18 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,456, price is now CA $1,939 per person
CA $1,939
per person
May 8 - May 12
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips3 Night Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,735, price is now CA $1,277 per person
CA $1,277
per person
Jun 4 - Jun 7
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,939, price is now CA $1,428 per person
CA $1,428
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips4 Night Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,455, price is now CA $1,058 per person
CA $1,058
per person
May 23 - May 27
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all tripsMore vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
