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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥458,800, price is now ￥362,534 per person
￥362,534
per person
Jun 4 - Jun 8
found 19 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality
Reviewed on Mar 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥546,288, price is now ￥399,292 per person
￥399,292
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was great except the tv. It was hard to understand and use
Reviewed on Mar 29, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥432,268, price is now ￥366,664 per person
￥366,664
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!
Reviewed on Mar 29, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥446,148, price is now ￥381,583 per person
￥381,583
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
This was perfect for a night in the city! Great all around and will stay again. Great staff at check-in!
Reviewed on Mar 27, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥443,372, price is now ￥382,310 per person
￥382,310
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Great location. The staff was nice. It was everything we needed.
Reviewed on Mar 29, 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 ￥458,800, price is now ￥362,534 per person
￥362,534
per person
Jun 4 - Jun 8
found 19 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality
Reviewed on Mar 29, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥748,800, price is now ￥672,508 per person
￥672,508
per person
Apr 29 - May 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
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 ￥309,641, price is now ￥271,776 per person
￥271,776
per person
May 2 - May 5
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!
Reviewed on Mar 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥408,254, price is now ￥327,376 per person
￥327,376
per person
Jun 12 - Jun 15
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was great except the tv. It was hard to understand and use
Reviewed on Mar 29, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥468,653, price is now ￥389,648 per person
￥389,648
per person
Jun 12 - Jun 15
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality
Reviewed on Mar 29, 2026
4 Night Adventure vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥453,854, price is now ￥352,169 per person
￥352,169
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was great except the tv. It was hard to understand and use
Reviewed on Mar 29, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥458,800, price is now ￥362,534 per person
￥362,534
per person
Jun 4 - Jun 8
found 19 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality
Reviewed on Mar 29, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥456,004, price is now ￥390,838 per person
￥390,838
per person
Apr 29 - May 3
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon
Reviewed on Mar 29, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.