North Suburbs Mountain Vacations

Book a Mountain Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Mountain vacation packages in North Suburbs

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

Downtown Chicago
¥303,883
per person
Sep 26 - Sep 29
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,145 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥374,326
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
A+

Reviewed on Aug 20, 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥342,336
per person
Nov 4 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥351,676
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.

Reviewed on Aug 20, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
¥704,936
per person
Nov 4 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to North Suburbs
View all trips

5* Mountain vacations in North Suburbs

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥374,326
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
A+

Reviewed on Aug 20, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
¥704,936
per person
Nov 4 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥542,768
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Sapporo to North Suburbs
View all trips

3 Night Mountain vacations in North Suburbs

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

¥219,056
per person
Oct 14 - Oct 17
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (1,008 reviews)
Eaglewood Resort and Spa

Eaglewood Resort and Spa

¥226,998
per person
Oct 14 - Oct 17
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,249 reviews)
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

¥232,888
per person
Oct 14 - Oct 17
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,004 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to North Suburbs
View all trips

4 Night Mountain vacations in North Suburbs

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥314,960
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥374,326
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip flight included
Sapporo (CTS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
A+

Reviewed on Aug 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥351,676
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.

Reviewed on Aug 20, 2026

Don't see what you're looking for?
See all available trips from Sapporo to North Suburbs
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in North Suburbs
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.