
West Side Adventure Vacations
Book a Adventure Hotel + Flight or Car together to unlock savings
Photo by throwingsofas
- Plan, book, travel with confidence
- Better togetherSave up to ¥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Adventure vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.


Level Chicago Fulton Market
Downtown Chicago
Price was ¥508,926, price is now ¥399,982 per person
¥399,982
per person
Aug 12 - Aug 18
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥456,972, price is now ¥372,300 per person
¥372,300
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Very nice property in the middle of everything.
Reviewed on Jun 9, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥132,392, price is now ¥109,316 per person
¥109,316
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,176 reviews)
Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay.
Reviewed on Jun 9, 2026

Omni Chicago Hotel
Downtown Chicago
Price was ¥403,598, price is now ¥347,228 per person
¥347,228
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
Best hotel in Chicago for the price. Perfect location. The staff was very friendly. The rooms are stylish and spacious. One minor inconvenience is that they do not offer room service but I was able to put an order in at the restaurant and pick up was fast and easy.
Reviewed on Jun 9, 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 ¥499,640, price is now ¥435,238 per person
¥435,238
per person
Aug 6 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on Jun 6, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥608,964, price is now ¥536,505 per person
¥536,505
per person
Aug 12 - Aug 18
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (860 reviews)
Beautiful room. Well appointed. love the ambiance. Ashley Cartagena was very helpful with reservations!! Great location. Do not eat here, food is not good especially for the price. Rooftop bar view is cute but cocktails not great, I would skip them. There are dozens of cute coffee shops, bakeries, restaurants, bars & shops all steps away. would definitely stay here again.
Reviewed on May 28, 2026

The St. Regis Chicago
Downtown Chicago
Price was ¥824,310, price is now ¥778,639 per person
¥778,639
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (117 reviews)
Absolute perfection - I wish there were a St. Regis hotel every where I travel! My kids loved it, the staff was friendly and helpful. I could live in the room (and the soaking tub!). The restaurant was lovely for breakfast. 10/10
Reviewed on Jun 3, 2026
3 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 ¥415,969, price is now ¥364,222 per person
¥364,222
per person
Aug 6 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Very nice property in the middle of everything.
Reviewed on Jun 9, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥499,640, price is now ¥435,238 per person
¥435,238
per person
Aug 6 - Aug 9
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on Jun 6, 2026

4 Night Adventure vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was ¥403,598, price is now ¥347,228 per person
¥347,228
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,791 reviews)
Best hotel in Chicago for the price. Perfect location. The staff was very friendly. The rooms are stylish and spacious. One minor inconvenience is that they do not offer room service but I was able to put an order in at the restaurant and pick up was fast and easy.
Reviewed on Jun 9, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥456,972, price is now ¥372,300 per person
¥372,300
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Very nice property in the middle of everything.
Reviewed on Jun 9, 2026

The Emily Hotel
Downtown Chicago
Price was ¥422,448, price is now ¥352,542 per person
¥352,542
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on.
The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful.
Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.
Reviewed on Jun 8, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
