West Side Adventure Vacations
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Top Adventure vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥302,273, price is now ￥256,960 per person
￥256,960
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
A quiet and comfortable place
Reviewed on Apr 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥350,136, price is now ￥267,302 per person
￥267,302
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Best free Hotel breakfast you will ever have
Reviewed on Apr 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥411,738, price is now ￥327,540 per person
￥327,540
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast.
Reviewed on Apr 4, 2026
Kinzie Hotel
Downtown Chicago
Price was ￥322,890, price is now ￥276,938 per person
￥276,938
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
Very helpful desk staff!! Somewhat limited items at front desk for purchase (ex: we forgot our toothpaste and they didn’t have any)
Reviewed on Apr 3, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥332,782, price is now ￥285,781 per person
￥285,781
per person
Jun 11 - Jun 14
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Was a little noisy but I think that was just my unit. Facilities were top notch!
Reviewed on Apr 4, 2026
5* Adventure vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥411,738, price is now ￥327,540 per person
￥327,540
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast.
Reviewed on Apr 4, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥449,692, price is now ￥396,876 per person
￥396,876
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥376,122, price is now ￥336,173 per person
￥336,173
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
3 Night Adventure vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥302,273, price is now ￥256,960 per person
￥256,960
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
A quiet and comfortable place
Reviewed on Apr 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥350,136, price is now ￥267,302 per person
￥267,302
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Best free Hotel breakfast you will ever have
Reviewed on Apr 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥411,738, price is now ￥327,540 per person
￥327,540
per person
Jun 11 - Jun 14
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast.
Reviewed on Apr 4, 2026
4 Night Adventure vacations in West 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 ￥1,111,450, price is now ￥970,464 per person
￥970,464
per person
May 29 - Jun 2
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant.
Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant.
Reviewed on Apr 4, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥1,072,628, price is now ￥966,250 per person
￥966,250
per person
May 29 - Jun 2
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
