North Side Vacations from ¥295,606

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The Latest North Side Vacation Packages

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

Hotel Riu Plaza Chicago

Downtown Chicago
¥295,606
per person
Dec 26 - Dec 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
We had a good experience, nothing to complain!

Reviewed on Oct 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥368,160
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥369,477
per person
Nov 18 - Nov 24
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on Oct 4, 2026

Arlo Chicago

Arlo Chicago

Downtown Chicago
¥336,010
per person
Nov 18 - Nov 24
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (2,384 reviews)
Staff were super friendly and helpful. Food at the restaurant was great! No complaints

Reviewed on Oct 4, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥333,768
per person
Nov 18 - Nov 24
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I enjoyed my stay at the LondonHouse. The property and room were very clean. The front desk staff was nice. Housekeeping was consistent. The bar staff were friendly but the staff at the rooftop bar could have been nicer. It was busy so I will give them grace but they were a little rude and I didn’t appreciate that considering I was staying at the property. I did not eat at the hotel to rate the food. The views from the vista room were amazing. I would stay again.

Reviewed on Oct 4, 2026

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
A long bridge at sunset with lights along its length.

Downtown

3 out of top 10 points of interest in this area

If you're spending some time in Downtown, Warner Vineyards and South Haven Center for the Arts are top sights worth seeing.

A pier extending into the water at sunset with a lighthouse in the distance.

South Side

If you're spending some time in South Side, South Beach and Southside Municipal Marina are top sights worth seeing.

A beach at sunset with a wooden fence and a distant lighthouse.

Miami Park

While Miami Park isn't home to many top sights, Kal Haven Trail and North Beach are some notable places to visit nearby.

A red lighthouse on a pier with the ocean in the background.

Mt. Pleasant

When in Mt. Pleasant, you can plan a visit to Kal Haven Trail and North Beach, some noteworthy sights in the nearby area.

A pier with a lighthouse, a kite surfer, and a clear sky.

West Wing Estates

While West Wing Estates isn't home to many top sights, Kal Haven Trail and North Beach are some notable places to visit nearby.

North Side Hotel Deals

Yelton Manor Bed & Breakfast

Yelton Manor Bed & Breakfast

140 North Shore Drive South Haven MI
Fully refundableReserve now, pay when you stay
¥26,835
¥29,786 total
Nov 2 - Nov 3
includes taxes & fees
9.2/10 Wonderful! (167 reviews)
"Loved this B&B & our room. The only negative was the French door to the bathroom -prefer a solid one for privacy. The headboard was not mounted to the wall securely & resulted in any movement to make a noise. Otherwise everything was great. The room was inviting & clean. The staff was accommodating ..."

Reviewed on Sep 20, 2026

Yelton Manor Bed & Breakfast
Waters View Inn

Waters View Inn

86 North Shore Drive South Haven MI
¥40,725
¥45,205 total
Oct 6 - Oct 7
includes taxes & fees
8.8/10 Excellent! (107 reviews)
"We loved our stay. Our room was comfy, breakfast was great, and staff were very kind and helpful. The location can’t be beat—across from the beach and Bunde’s Cafe (yum). We hope to be back soon!"

Reviewed on Aug 29, 2026

Waters View Inn
Beachfront Condo on Lake Michigan with heated pool.

Beachfront Condo on Lake Michigan with heated pool.

South Haven MI
10/10 Exceptional! (83 reviews)
"Super clean condo was perfect for a beach getaway! Well appointed with all of the utensils, dishes, cookware, glassware you need! Fantastic private beach with patio overlooking the lake. Close walk to the pier and riverfront. We’ve already booked for next year."

Reviewed on Sep 16, 2026

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Beachfront Condo on Lake Michigan with heated pool.
See all 2,160 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.

Stay near popular North Side attractions

Michigan Maritime Museum

8.8/10 (66 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.
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Stanley Johnson Park

You can take time to visit Stanley Johnson Park during your travels to South Haven.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.