South Side Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$1,102, price is now S$943 per person
S$943
per person
30 Jan - 1 Feb
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
No complains. Everything was good. Also, the entire team is always very cheerful, friendly and ready to help, making the experience very pleasant.

Reviewed on 30 Dec, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was S$1,539, price is now S$1,215 per person
S$1,215
per person
30 Jan - 1 Feb
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great time and staff

Reviewed on 30 Dec, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was S$1,118, price is now S$987 per person
S$987
per person
30 Jan - 1 Feb
found 20 hours ago
Return flight included
Seattle (SEA) 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 18 Dec, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was S$1,116, price is now S$988 per person
S$988
per person
30 Jan - 1 Feb
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Everything was great!

Reviewed on 29 Dec, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was S$1,584, price is now S$1,424 per person
S$1,424
per person
30 Jan - 1 Feb
found 20 hours ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.

Reviewed on 29 Dec, 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
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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 North Beach and Michigan Maritime Museum.

Find hotels in North Side

Top hotels in South Side

Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 6 Jan to 7 Jan
S$97
6 Jan - 7 Jan, 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 22 Dec, 2025

Baymont by Wyndham South Haven
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

2 out of 5
117 55th St Grand Junction MI
The price is S$158 per night from 5 Jan to 6 Jan
S$158
5 Jan - 6 Jan, 2026
includes taxes & fees
9.6/10 Exceptional! (64 reviews)
Staff what's nice and stayed in contact

Reviewed on 14 Dec, 2025

Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
Captain's Quarters Motel

Captain's Quarters Motel

2 out of 5
3242 Blue Star Highway Saugatuck MI
9.4/10 Exceptional! (847 reviews)
Didn't eat breakfast here, N/A

Reviewed on 15 Nov, 2025

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Captain's Quarters Motel
See all 2,009 properties in South Side
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.

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