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.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥311,696
per person
Nov 9 - Nov 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,352 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥375,400
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥374,042
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥398,572
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Clean. On site laundry was awesome.

Reviewed on Oct 6, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥530,538
per person
Nov 9 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
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5* Mountain vacations in Northwest Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥183,367
per person
Nov 26 - Nov 29
found 15 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥530,538
per person
Nov 9 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
¥1,004,705
per person
Dec 25 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Don't see what you're looking for?
See all available trips from San Francisco to Northwest Chicago
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3 Night Mountain vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥110,138
per person
Nov 26 - Nov 29
found 15 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
Ok

Reviewed on Oct 6, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥183,367
per person
Nov 26 - Nov 29
found 15 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥133,903
per person
Nov 26 - Nov 29
found 15 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.2/10 Wonderful! (2,414 reviews)
My stay was great...I was treated very well, especially by Beverly (I hope I got your name right, gurl!!)! I'm kinda used to breakfast being provided (kind of a perk for me when staying at a hotel). The hotel is nice, clean, and comfortable! The BEST thing about the Silversmith is the LOCATION! Close to everything, especially transportation! I would stay there again!! Oh, and I left my prescription eyeglasses behind. They were mailed to me, for a nominal fee for shipping (Thank you Victor!), and I received them about 7 days after I'd checked out. So, all in all, it was a GREAT trip, I had a GREAT time in a wonderful and comfortable hotel!!

Reviewed on Oct 8, 2026

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See all available trips from San Francisco to Northwest Chicago
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4 Night Mountain vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥300,418
per person
Nov 9 - Nov 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥375,291
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥311,696
per person
Nov 9 - Nov 13
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,352 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Chicago
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Northwest Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.