South Side Vacations from ￥200,594
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The Latest South Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥256,630, price is now ￥200,594 per person
￥200,594
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Amazing room view great service just no microwave that’s all they need
Reviewed on Dec 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥385,898, price is now ￥274,520 per person
￥274,520
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Absolutely loved the hotel.Grand Dulxe Suite was huge with amazing views.All staff top notch.
Reviewed on Dec 27, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥399,685, price is now ￥297,235 per person
￥297,235
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Beautifully decorated for Christmas. Spotless as always.
Reviewed on Dec 27, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥271,780, price is now ￥207,398 per person
￥207,398
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Early check in available for $25, worth it for getting rest between flights. Very friendly staff
Reviewed on Dec 27, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥285,935, price is now ￥221,613 per person
￥221,613
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
North Side
While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.
South Side Hotel Deals
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven MI
10/10 Exceptional! (189 reviews)
We love South Haven in October and this trip did not disappoint! The location and charm of Crimson Sun was just what we were looking for.
Reviewed on Oct 21, 2025
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is ￥10,645 per night from Jan 4 to Jan 5
￥10,645
￥11,816 total
Jan 4 - Jan 5, 2026
includes taxes & fees
7.6/10 Good! (1,000 reviews)
Staff was wonderful to me and my family, very family friendly, and clean!
Reviewed on Dec 22, 2025
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
117 55th St Grand Junction MI
The price is ￥13,935 per night from Jan 4 to Jan 5
￥13,935
￥21,410 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9.6/10 Exceptional! (64 reviews)
Staff what's nice and stayed in contact
Reviewed on Dec 14, 2025
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.
Discover the most popular places to visit in South Side
Michigan Maritime Museum
You can spend an afternoon browsing the exhibits at Michigan Maritime Museum in South Haven. While you're in the area, stroll along the beautiful beaches.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.