South Side Ski Vacations 2026

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 Ski vacation packages in South Side

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

Hotel 55 Chicago Downtown

Downtown Chicago

￥936,657

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

8.8/10 Excellent! (1,567 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

￥946,412

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (5,340 reviews)

Amables y todo cerca

Reviewed on Sep 30, 2026

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

￥971,866

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (3,867 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

￥950,842

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (2,681 reviews)

Fairmont Chicago at Millennium Park

Downtown Chicago

￥956,199

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

8.8/10 Excellent! (2,314 reviews)

Don't see what you're looking for?

See all available trips from Tokyo to South Side

View all trips

5* Ski vacations in South Side

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

Four Seasons Hotel Chicago

Downtown Chicago

￥1,131,304

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.4/10 Exceptional! (1,001 reviews)

The Langham, Chicago

Downtown Chicago

￥1,155,664

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

The Peninsula Chicago

Downtown Chicago

￥1,217,536

per person

Nov 9 - Nov 13

found 3 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Chicago (ORD)

9.8/10 Exceptional! (1,010 reviews)

It is the greatest will be there again

Reviewed on Sep 29, 2026

Don't see what you're looking for?

See all available trips from Tokyo to South Side

View all trips

3 Night Ski vacations in South Side

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

The Talbott, Autograph Collection

Downtown Chicago

￥322,696

per person

Nov 21 - Nov 24

just found

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (178 reviews)