Southern Wisconsin Mountain Vacations
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Top Mountain vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥284,348
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!
Reviewed on Oct 5, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
￥306,844
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I enjoyed my stay at the LondonHouse. The property and room were very clean. The front desk staff was nice. Housekeeping was consistent. The bar staff were friendly but the staff at the rooftop bar could have been nicer. It was busy so I will give them grace but they were a little rude and I didn’t appreciate that considering I was staying at the property. I did not eat at the hotel to rate the food. The views from the vista room were amazing. I would stay again.
Reviewed on Oct 4, 2026
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View all trips5* Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
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View all trips3 Night Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥506,220
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!
Reviewed on Oct 5, 2026
Le Méridien Essex Chicago
Downtown Chicago
￥512,146
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
The rooms are very small ,the pictures and videos is what sells the hotel for sure. Disappointed with the stay and the amount I was charged
Reviewed on Oct 4, 2026
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View all trips4 Night Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥284,348
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!
Reviewed on Oct 5, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
￥306,844
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I enjoyed my stay at the LondonHouse. The property and room were very clean. The front desk staff was nice. Housekeeping was consistent. The bar staff were friendly but the staff at the rooftop bar could have been nicer. It was busy so I will give them grace but they were a little rude and I didn’t appreciate that considering I was staying at the property. I did not eat at the hotel to rate the food. The views from the vista room were amazing. I would stay again.
Reviewed on Oct 4, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
