South Side Vacations
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Price found within the past 48 hours. Click for updated prices.
- Level Chicago Fulton Market
Aug 2 - Aug 6Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (480 reviews)"Yes"Reviewed May 12, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥499,829￥395,707found 2 hours agoper traveler - Kimpton Gray Hotel by IHG
Aug 4 - Aug 9Kimpton Gray Hotel by IHG + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (1,004 reviews)"Rooms are very clean and spacious"Reviewed May 18, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥550,415￥455,778found 1 day agoper traveler - ENVITAE Hotel 4 Bedroom Luxury Apartments
Aug 4 - Aug 9ENVITAE Hotel 4 Bedroom Luxury Apartments + Flight
Near North Side5 nights9.6/10 - Exceptional (17 reviews)Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥688,552￥580,174found 1 day agoper traveler - Viceroy Chicago
Aug 4 - Aug 9Viceroy Chicago + Flight
Downtown Chicago5 nights9.4/10 - Exceptional (1,231 reviews)"Nice hotel in a great location. "Reviewed May 15, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥537,203￥452,915found 1 day agoper traveler - The Emily Hotel
Aug 4 - Aug 9The Emily Hotel + Flight
Downtown Chicago5 nights9.2/10 - Wonderful (1,323 reviews)"We had a fantastic experience at this hotel. The room and the entire property were spotless and well-maintained. The staff was incredibly friendly and helpful throughout our stay. We’ll definitely be staying here again, and next time, we’ll try to catch a movie on the rooftop."Reviewed May 18, 2026Roundtrip • Tokyo (NRT) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥524,161￥443,448found 1 day agoper traveler
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
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.
South Side Hotel Deals
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven MI
10/10 Exceptional! (191 reviews)
"A cozy place for a getaway. The host was very responsive and we had a nice stay"
Reviewed on May 17, 2026
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is ￥15,872 per night from May 27 to May 28
￥15,872
￥17,618 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Convenient location with very reasonable pricing."
Reviewed on May 8, 2026
Starlite Resort
3353 Blue Star Highway Saugatuck MI
The price is ￥18,083 per night from May 21 to May 22
￥18,083
￥20,072 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (850 reviews)
"Vey clean room, close to the town, nice hot tub, very helpful staff"
Reviewed on May 17, 2026
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
4/5(5 reviews)
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.