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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥542,266, price is now ￥421,644 per person
￥421,644
per person
Sep 20 - Sep 26
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
This is a spectacular property. Location is amazing. Rooms and beds are comfortable. Breakfast is top notch. And the rooftop is next to none. This is our second time staying here.
Reviewed on Jul 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥716,212, price is now ￥560,173 per person
￥560,173
per person
Sep 20 - Sep 26
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥606,160, price is now ￥477,030 per person
￥477,030
per person
Sep 20 - Sep 26
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) 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
Omni Chicago Hotel
Downtown Chicago
Price was ￥560,823, price is now ￥445,210 per person
￥445,210
per person
Sep 20 - Sep 26
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The room was very clean and spacious. Very helpful staff. We were able to get into our room early and get a later checkout due to our flights. The Doorman were also very courteous and helpful. Great location!
Reviewed on Jul 3, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips5* Romantic vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥716,212, price is now ￥560,173 per person
￥560,173
per person
Sep 20 - Sep 26
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was ￥740,956, price is now ￥625,204 per person
￥625,204
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Nagoya (NGO) 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
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips3 Night Romantic vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
Price was ￥462,314, price is now ￥404,850 per person
￥404,850
per person
Aug 12 - Aug 15
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
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥580,704, price is now ￥522,144 per person
￥522,144
per person
Aug 8 - Aug 11
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips4 Night Romantic vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ￥393,212, price is now ￥333,220 per person
￥333,220
per person
Aug 19 - Aug 23
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The room was very clean and spacious. Very helpful staff. We were able to get into our room early and get a later checkout due to our flights. The Doorman were also very courteous and helpful. Great location!
Reviewed on Jul 3, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥513,962, price is now ￥426,949 per person
￥426,949
per person
Aug 19 - Aug 23
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
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.
