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

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥366,161, price is now ¥272,356 per person
¥272,356
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
I had a wonderful stay at Riu Plaza Chicago. Even though I live in Chicago, I wanted a nice staycation and this hotel did not disappoint. The rooms were very clean, comfortable, and the staff was welcoming and professional. The breakfast was also great with a good variety of options to choose from. Overall, I had a great time and really enjoyed my stay. I would definitely recommend this hotel and would stay again!
Reviewed on Mar 16, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥616,773, price is now ¥446,362 per person
¥446,362
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥636,178, price is now ¥461,446 per person
¥461,446
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms clean friendly staff best location
Reviewed on Mar 16, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥571,375, price is now ¥419,385 per person
¥419,385
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.
Reviewed on Mar 14, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥629,788, price is now ¥466,404 per person
¥466,404
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Great location and staff
Reviewed on Mar 15, 2026
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View all trips5* Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥658,961, price is now ¥491,472 per person
¥491,472
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
Room was perfect/staff was great
Reviewed on Mar 12, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥622,958, price is now ¥572,730 per person
¥572,730
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (798 reviews)
I really enjoyed my stay at Nobu. The food was very nice and the atmosphere was what I really wanted (the main reason I chose to stay there). I also really liked the location of the hotel. Everything was very walkable and I enjoyed exploring when I had free time. My only thoughts as negatives are the view from the rooms are not super impressive, I had opted in for the upgraded room at a discounted price which I did get (but wasn’t informed that when I checked in which was stated when I opted in), and I had quite a few issues with the Wi-Fi and working the tv so I just gave up on that. If you’re looking for a reliable, clean place that offers a lot for food and beverages then I’d definitely recommend staying!
Reviewed on Mar 15, 2026

The Ritz-Carlton, Chicago
Downtown Chicago
Price was ¥646,773, price is now ¥619,749 per person
¥619,749
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Excellent service, room was very clean. The food at the on site restaurant was great as well.
Reviewed on Mar 14, 2026
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View all trips3 Night Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥346,907, price is now ¥298,999 per person
¥298,999
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥415,852, price is now ¥321,026 per person
¥321,026
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
I had a wonderful stay at Riu Plaza Chicago. Even though I live in Chicago, I wanted a nice staycation and this hotel did not disappoint. The rooms were very clean, comfortable, and the staff was welcoming and professional. The breakfast was also great with a good variety of options to choose from. Overall, I had a great time and really enjoyed my stay. I would definitely recommend this hotel and would stay again!
Reviewed on Mar 16, 2026

Level Chicago - River North
Downtown Chicago
Price was ¥391,172, price is now ¥335,005 per person
¥335,005
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (876 reviews)
Clean room, Great amenities and super helpful and accommodating staff
Reviewed on Mar 15, 2026
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See all available trips from Tokyo to Northwest Side
View all trips4 Night Adventure vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥298,458, price is now ¥251,150 per person
¥251,150
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥366,161, price is now ¥272,356 per person
¥272,356
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
I had a wonderful stay at Riu Plaza Chicago. Even though I live in Chicago, I wanted a nice staycation and this hotel did not disappoint. The rooms were very clean, comfortable, and the staff was welcoming and professional. The breakfast was also great with a good variety of options to choose from. Overall, I had a great time and really enjoyed my stay. I would definitely recommend this hotel and would stay again!
Reviewed on Mar 16, 2026

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ¥330,334, price is now ¥278,310 per person
¥278,310
per person
May 12 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
