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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

₩2,348,662

per person

May 14 - May 19

found 16 hours ago

Roundtrip non-stop flight included

Seoul (ICN) to Chicago (ORD)

9/10 Wonderful! (1,204 reviews)

The room was beautiful!! I will definitely be back for another event. The staff was wonderful and the Hotel was very clean.!

Reviewed on Mar 1, 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 ...

7.6/10 Good! (1,113 reviews)

The Room was good but the heat was out On one side , the maintenance guy brought us a portable heater! Nice! The TV went out and the Wifi was improved Overall a good stay.

Reviewed on Mar 2, 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)

Everything was clean. It was a good stay overall. Staff were nice. The only complaint was the kitchen ran out of regular milk. I drink milk daily so it was disappointing. I’m not sure how a hotel runs out of regular milk over a holiday weekend when you have all the cereals displayed.

Reviewed on Feb 21, 2026

See all 5,616 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.