
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
Save 100% on your flight
Price was ¥113,740, price is now ¥78,019 per person
¥78,019
per person
Jul 9 - Jul 11
found 1 hour ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (4,258 reviews)
Everything was great for my stay. Only flaws was that the shower pressures were a bit low and water temperatures were not warm enough to my liking. And maybe fresh squeezed juices instead of the machine ones. Other wise it was good breakfast selection.
Reviewed on Jun 1, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥104,562, price is now ¥76,318 per person
¥76,318
per person
Jul 9 - Jul 11
found 1 hour ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.2/10 Very Good! (2,732 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room
Other than that the front desk and cleaning ladies was very nice.
Reviewed on May 29, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥103,897, price is now ¥79,793 per person
¥79,793
per person
Jul 9 - Jul 11
found 1 hour ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (2,156 reviews)
Beautiful hotel. Was surprised they didn’t have any usb ports. I forgot a square
Reviewed on May 31, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥91,274, price is now ¥71,727 per person
¥71,727
per person
Jul 9 - Jul 11
found 1 hour ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,579 reviews)
Overall, our stay at Eurostars Hotel was pleasant, and the staff was courteous and accommodating. However, we experienced an issue with the room doors. Our initial room had a door that did not appear to close properly, leaving a noticeable gap that allowed conversations and other sounds from inside the room to be heard from the hallway. This became apparent when someone outside the room was able to hear activity inside and came to our door.
The staff promptly moved us to another room, but we encountered the same issue, with an even larger gap around the door. We were informed that all rooms on that side of the hotel have similar door gaps and that no other rooms were available for relocation. While we appreciated the staff’s efforts to address our concerns, the lack of privacy caused by the door condition negatively impacted our stay.
Reviewed on May 31, 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 ¥592,273, price is now ¥516,091 per person
¥516,091
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥718,442, price is now ¥581,478 per person
¥581,478
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everyone was so helpful and friendly
Great environment.
Cleaning, room service ,breakfast A+
Reviewed on May 29, 2026

Four Seasons Hotel Chicago
Downtown Chicago
Price was ¥570,020, price is now ¥538,544 per person
¥538,544
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
We had a lovely 2 night stay in Chicago and the room with lake view was superb with lovely touches by the cleaning staff who made the stay very special
Reviewed on Jun 1, 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 Riu Plaza Chicago
Downtown Chicago
Price was ¥558,521, price is now ¥478,312 per person
¥478,312
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,258 reviews)
Everything was great for my stay. Only flaws was that the shower pressures were a bit low and water temperatures were not warm enough to my liking. And maybe fresh squeezed juices instead of the machine ones. Other wise it was good breakfast selection.
Reviewed on Jun 1, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥592,273, price is now ¥516,091 per person
¥516,091
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥567,092, price is now ¥494,990 per person
¥494,990
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,156 reviews)
Beautiful hotel. Was surprised they didn’t have any usb ports. I forgot a square
Reviewed on May 31, 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.
