
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.


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥1,111,172, price is now ¥727,868 per person
¥727,868
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
stay away, no one told us it had been damage and under repair, staff could not even help get me bording pass, room service sub par. We got a notice from Expedia after we checked in saying we could cancil, a bit to late.
Reviewed on Jul 3, 2026


Pendry Chicago
Downtown Chicago
Price was ¥1,127,210, price is now ¥762,888 per person
¥762,888
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Wonderful hotel with attentive staff. Should bring back ice machines.
Reviewed on Jul 3, 2026

The Langham, Chicago
Downtown Chicago
Price was ¥1,528,190, price is now ¥1,043,539 per person
¥1,043,539
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
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View all trips5* Romantic vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.


The Langham, Chicago
Downtown Chicago
Price was ¥1,528,190, price is now ¥1,043,539 per person
¥1,043,539
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026

Four Seasons Hotel Chicago
Downtown Chicago
Price was ¥1,212,717, price is now ¥909,976 per person
¥909,976
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Excellent hotel. We love staying there whenever we visit Chicago.
Reviewed on Jul 3, 2026
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View all trips3 Night Romantic vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Eaglewood Resort and Spa
Price was ¥339,482, price is now ¥323,212 per person
¥323,212
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,168 reviews)
The property was amazing and Brisa at the front desk made our trip even more special. The food was great, the rooms were clean and the staff was very attentive. Thank you Eaglewood Spa & Brisa for making our girls trip a very memorable experience. Keep up the great job!
Reviewed on Jul 3, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥466,594, price is now ¥426,552 per person
¥426,552
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.
Reviewed on Jul 2, 2026

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥362,966, price is now ¥337,755 per person
¥337,755
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,332 reviews)
Only thing I dont like is after a long haul flight I had to pull my luggage through their unbearable deep shaggy carpets. I was pulling 2 large bags through the lobby and to the room because they do not have porters to help you. That was brutal
Reviewed on Jul 3, 2026
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View all tripsThings to do

Chicago: Navy Pier Centennial Wheel Ticket
¥3,853
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.


