
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.

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ¥956,866, price is now ¥674,341 per person
¥674,341
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,160 reviews)
Lovely property, great location, helpful staff.
Reviewed on Jul 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥1,111,172, price is now ¥727,868 per person
¥727,868
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Pendry Chicago
Downtown Chicago
Price was ¥1,127,210, price is now ¥762,888 per person
¥762,888
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Wonderful hotel with attentive staff. Should bring back ice machines.
Reviewed on Jul 3, 2026

The Langham, Chicago
Downtown Chicago
Price was ¥1,528,190, price is now ¥1,043,539 per person
¥1,043,539
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026

Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was ¥1,079,842, price is now ¥758,383 per person
¥758,383
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,524 reviews)
Great experiment like always!
Reviewed on Jul 3, 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 ¥716,212, price is now ¥560,173 per person
¥560,173
per person
Sep 20 - Sep 26
found 17 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

The Langham, Chicago
Downtown Chicago
Price was ¥1,528,190, price is now ¥1,043,539 per person
¥1,043,539
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026

Four Seasons Hotel Chicago
Downtown Chicago
Price was ¥1,212,717, price is now ¥909,976 per person
¥909,976
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Excellent hotel. We love staying there whenever we visit Chicago.
Reviewed on Jul 3, 2026
3 Night Adventure vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Eaglewood Resort and Spa
Price was ¥317,782, price is now ¥298,702 per person
¥298,702
per person
Aug 12 - Aug 15
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,168 reviews)
The property was amazing and Brisa at the front desk made our trip even more special. The food was great, the rooms were clean and the staff was very attentive. Thank you Eaglewood Spa & Brisa for making our girls trip a very memorable experience. Keep up the great job!
Reviewed on Jul 3, 2026

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 24 hours 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

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥344,980, price is now ¥315,396 per person
¥315,396
per person
Aug 12 - Aug 15
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,668 reviews)
Staff was amazing and very helpful when checking in. When we got to the room it was on the smaller side which was not a bad thing. Would say it will need more dusting off and a deeper clean on the furniture.
Reviewed on Jul 4, 2026
Things 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.


