North 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 North Side

Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side
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Downtown

1 out of top 10 points of interest in this area

Downtown might not have many top sights, but Kal Haven Trail and North Beach are two attractions nearby that you can check out.

Find hotels in Downtown

Top hotels in North Side

Yelton Manor Bed & Breakfast

Yelton Manor Bed & Breakfast

3 out of 5
140 North Shore Drive South Haven MI
Fully refundableReserve now, pay when you stay
The price is S$268 per night from 11 Jan to 12 Jan
S$268
11 Jan - 12 Jan, 2026
includes taxes & fees
9.2/10 Wonderful! (121 reviews)
Good time enjoying the weekend here!

Reviewed on 19 Oct, 2025

Yelton Manor Bed & Breakfast
Victoria Resort and Bed & Breakfast

Victoria Resort and Bed & Breakfast

4 out of 5
241 Oak St South Haven MI
9.4/10 Exceptional! (139 reviews)
Super nice cozy place. We LL repeat for sure

Reviewed on 10 Dec, 2025

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Victoria Resort and Bed & Breakfast
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
See all 2,102 properties in North 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.