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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,428, price is now CA $1,624 per person
CA $1,624
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $2,244, price is now CA $1,564 per person
CA $1,564
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,126, price is now CA $1,503 per person
CA $1,503
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
London House Hilton Chicago was fabulous. Great location. Wonderful view nice rooms rooftop bar is amazing, make reservations. For a quieter atmosphere the lounge on the second floor is a great place to hang out.. We’ll definitely stay there again.
Reviewed on May 11, 2026
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View all trips5* Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,401, price is now CA $2,710 per person
CA $2,710
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,825, price is now CA $2,267 per person
CA $2,267
per person
Jul 23 - Jul 26
found 7 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile.
When I return to Chicago I will definitely stay at the Park Hyatt.
Reviewed on Apr 4, 2026
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View all trips3 Night Mountain holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,228, price is now CA $864 per person
CA $864
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,574 reviews)
Great hotel in the perfect location. The staff was super friendly. We would definitely stay here again.
Reviewed on May 12, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $2,244, price is now CA $1,564 per person
CA $1,564
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,297, price is now CA $1,507 per person
CA $1,507
per person
Jun 19 - Jun 23
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
