
Northwest Chicago Mountain Vacations
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Top Mountain vacation packages in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.

Hilton Chicago
Downtown Chicago
Price was ¥191,656, price is now ¥159,849 per person
¥159,849
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Overall it was a great pick. However housekeeping missed us the first day and then the next day they didn’t leave enough towels so we found ourselves always having to call for something though I would say the response was quite fast and efficient. Great food options and the hotel room was spacious.
Reviewed on Dec 8, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥469,150, price is now ¥362,502 per person
¥362,502
per person
Mar 1 - Mar 6
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025

Pendry Chicago
Downtown Chicago
Price was ¥366,125, price is now ¥306,544 per person
¥306,544
per person
Mar 1 - Mar 6
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on Dec 4, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥357,830, price is now ¥301,772 per person
¥301,772
per person
Mar 1 - Mar 6
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥348,000, price is now ¥293,570 per person
¥293,570
per person
Mar 1 - Mar 6
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast was great and they made sure you got a table based on your party size. Staff were also pleasant and the location was great. Would definitely stay there again.
Reviewed on Dec 8, 2025
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View all trips5* Mountain vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥469,150, price is now ¥362,502 per person
¥362,502
per person
Mar 1 - Mar 6
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025


Nobu Hotel Chicago
Downtown Chicago
Price was ¥433,592, price is now ¥395,478 per person
¥395,478
per person
Mar 1 - Mar 6
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
The sink clogged at some point the staff was not that attentive
Reviewed on Nov 29, 2025
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View all trips4 Night Mountain vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥193,216, price is now ¥153,960 per person
¥153,960
per person
Feb 19 - Feb 23
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast was great and they made sure you got a table based on your party size. Staff were also pleasant and the location was great. Would definitely stay there again.
Reviewed on Dec 8, 2025

Chicago luxury home suites
Downtown Chicago
Save 100% on your flight
Price was ¥474,046, price is now ¥349,150 per person
¥349,150
per person
Feb 19 - Feb 23
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥199,060, price is now ¥158,508 per person
¥158,508
per person
Feb 19 - Feb 23
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025
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See all available trips from Tokyo to Northwest Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
