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Top Ski vacation packages in Chicago

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

The Westin Chicago Lombard

￥346,129

per person

Jun 12 - Jun 15

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (1,235 reviews)

Karmina was so super helpful! She was my first point of contact there and answered all my questions. I will credit her for making our stay extra special! Our room was spacious, extra clean and a great view. We hope to get a view facing East next time. There is also plenty to do in the area, we felt it was centrally located. We are definitely coming back!

Reviewed on Apr 25, 2026

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3 Night Ski vacations in Chicago

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

The Westin Chicago Lombard

￥346,129

per person

Jun 12 - Jun 15

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (1,235 reviews)

Karmina was so super helpful! She was my first point of contact there and answered all my questions. I will credit her for making our stay extra special! Our room was spacious, extra clean and a great view. We hope to get a view facing East next time. There is also plenty to do in the area, we felt it was centrally located. We are definitely coming back!

Reviewed on Apr 25, 2026

Don't see what you're looking for?

See all available trips from Tokyo to Chicago

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4 Night Ski vacations in Chicago

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

Studio 6 Extended Stay Chicago Lisle

￥239,146

per person

Jul 9 - Jul 13

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

7/10 Good! (557 reviews)

We had a surprisingly pleasant experience. Staff was very friendly. The room was good-size and very clean. Temperature control was simple and rapid. Entrance doors were a bit of a challenge (took plenty of effort to swing open), and the posted instructions in the entryway for how to use the phone for assistance (if no one was at the desk) were incorrect. The elevator worked, but made some unusual squeaky and banging noises...took some getting use to. Would stay again with hesitation.

Reviewed on Jan 15, 2026

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Top Ski Chicago Hotels

Victorian Rose Garden

314 Washington Street Algonquin IL

51 min drive from Wrigley Field

Stay at this B&B in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Buffalo Park Forest Preserve and Algonquin Lakes Trailhead ...

9.4/10 Exceptional! (290 reviews)

The space was beautiful and Sherry was the sweetest hostess! We loved every minute of our stay!

Reviewed on Oct 30, 2025

Hyatt Regency Lisle near Naperville

1400 Corporetum Drive Lisle IL

43 min drive from Wrigley Field

Book a stay at this business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

7.8/10 Good! (1,161 reviews)

The room wasn’t clean when I entered it. I had to go get another room. There was no clock or web portal in that room. I had to charge my phone in the business center, which took forever. There was a red stain and a hairball in the bathroom. The rest of the room was clean and breakfast was good. I ...

Reviewed on Apr 25, 2026

Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG

2595 Bunker Hill Dr Algonquin IL

53 min drive from Wrigley Field

Book a stay at this business-friendly hotel in Algonquin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

8.2/10 Very Good! (1,001 reviews)

If you want to hear every footstep on the floor above you. This is the place for you

Reviewed on Apr 10, 2026

See all 5,546 properties in Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.