Central Chicago Romantic Vacations
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Top Romantic vacation packages in Central Chicago
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
found 1 hour ago
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 Central Chicago
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View all trips3 Night Romantic vacations in Central Chicago
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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)
The hotel was in a great location in Downtown Chicago. Made it easy to walk to any popular attraction during my stay including great restaurants. The room was clean and got the job done. Staff was very helpful for checking in my luggage the day of and answering any questions I had during my stay.
Reviewed on Aug 16, 2026
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View all tripsThings to do
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.
