South Side Mountain Vacations
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Top Mountain vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥133,123, price is now ￥105,900 per person
￥105,900
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The bar was fine we got 2 free drinks.
Reviewed on Apr 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥181,360, price is now ￥120,048 per person
￥120,048
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥207,780, price is now ￥156,566 per person
￥156,566
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥148,203, price is now ￥117,789 per person
￥117,789
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The hotel was better than I expected due to some reviews I had saw online! I really enjoyed my stay here!
Reviewed on Apr 2, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥156,968, price is now ￥126,060 per person
￥126,060
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
Nice staff, clean rooms, however elevator is slow
Reviewed on Apr 2, 2026
5* Mountain vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥207,780, price is now ￥156,566 per person
￥156,566
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥249,671, price is now ￥208,122 per person
￥208,122
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥508,914, price is now ￥463,419 per person
￥463,419
per person
Jun 14 - Jun 17
just found
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
3 Night Mountain vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥438,216, price is now ￥368,292 per person
￥368,292
per person
Jun 14 - Jun 17
just found
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥559,292, price is now ￥469,322 per person
￥469,322
per person
Jun 14 - Jun 17
just found
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥515,752, price is now ￥433,984 per person
￥433,984
per person
Jun 14 - Jun 17
just found
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
