
Northwest Side Romantic Vacations
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Top Romantic vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
¥379,826
per person
Oct 1 - Oct 8
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026



Kimpton Gray Hotel by IHG
Downtown Chicago
¥500,735
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
2nd stay at the Kimpton Gray in Chicago and loved it! Service was exceptional! Felt like a guest at a family member’s home! Shout out to Savannah and Noah and the entire housekeeping team!
Reviewed on Aug 15, 2026

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
¥413,212
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
Staff was great, and the location was very nice. But the room didn’t have many amenities and the outlets weren’t working well by the bed which made it hard to charge my phone. No mini-fridge and no iron made it less convenient.
Reviewed on Aug 16, 2026
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View all trips5* Romantic vacations in Northwest Side
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Hotel 55 Chicago Downtown
Downtown Chicago
¥269,151
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,577 reviews)
We really liked the decor of the room, it was very chic and stylish. Robes were so comfortable, water pressure was great, and we loved the amenities - all the soaps and shampoos smelled amazing. Nespresso machine in the room was great, but it was not reset back to the factory setting, so espresso button was running longer than it should. Staff were very accommodating, they let us check in early, and helped with storing luggage as well. The restaurant attached to the hotel was excellent - their food was great, and cocktail menu was really good too. The location was really convenient, and we really enjoyed staying here - definitely coming back again!
Reviewed on Aug 16, 2026
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Chicago: Navy Pier Centennial Wheel Ticket
¥3,920
per adult
90% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket
¥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

