
North Side Vacations from ¥296,774
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The Latest North Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Swissotel - Chicago
Downtown Chicago
Price was ¥366,209, price is now ¥330,599 per person
¥330,599
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
It was quiet and near everything and I love the bathtub right by the window.
Reviewed on Oct 15, 2025

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥351,899, price is now ¥318,035 per person
¥318,035
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Front desk very helpful with a check-in update. Good access to loop transportation.
Reviewed on Oct 14, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥351,929, price is now ¥326,088 per person
¥326,088
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Beautiful hotel! Would stay again
Reviewed on Oct 14, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was ¥332,237, price is now ¥308,102 per person
¥308,102
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.4/10 Very Good! (3,910 reviews)
Friendly helpful staff for late check out due to work event timing.
Reviewed on Oct 15, 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

Downtown
2 out of top 10 points of interest in this area
Downtown might not have many top sights, but Michigan Maritime Museum and Kal Haven Trail are two attractions nearby that you can check out.
North Side Hotel Deals

Waters View Inn
86 North Shore Drive, South Haven, MI
The price is ¥29,375 per night from Oct 19 to Oct 20
¥29,375
¥32,607 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (102 reviews)
Really cute bed and breakfast.
"Loved the setting, room was cozy. Nice little sitting area on the second floor with a bathroom,"
Reviewed on Oct 6, 2025

Yelton Manor Bed & Breakfast
140 North Shore Drive, South Haven, MI
Fully refundableReserve now, pay when you stay
The price is ¥25,655 per night from Nov 16 to Nov 17
¥25,655
¥28,477 total
Nov 16 - Nov 17
includes taxes & fees
9.2/10 Wonderful! (116 reviews)
"Breakfast was great! Simple menu makes it easy to choose from!! Coffee was terrific and Victoria was so polite, friendly and helpful!"
Reviewed on Oct 7, 2025

Victoria Resort and Bed & Breakfast
241 Oak St, South Haven, MI
9.4/10 Exceptional! (131 reviews)
"Clean and accommodating."
Reviewed on Oct 1, 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 North 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.