Illinois Ski Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 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 Illinois

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

The Westin Chicago Lombard

$439

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,365 reviews)

Lincolnshire Marriott Resort

Half Day

$542

per person

Sep 17 - Sep 20

found 16 hours ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

8.8/10 Excellent! (1,008 reviews)

Property needs some major renovations dirty carpet bedding gross and old furniture

Reviewed on Aug 10, 2026

Don't see what you're looking for?

See all available trips from Columbus to Illinois

View all trips

3 Night Ski vacations in Illinois

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

The Westin Chicago Lombard

$439

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,365 reviews)

Lincolnshire Marriott Resort

Half Day

$542

per person

Sep 17 - Sep 20

found 16 hours ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

8.8/10 Excellent! (1,008 reviews)

Property needs some major renovations dirty carpet bedding gross and old furniture

Reviewed on Aug 10, 2026

Don't see what you're looking for?

See all available trips from Columbus to Illinois

View all trips

4 Night Ski vacations in Illinois

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

Comfort Suites Elgin Northwest

$307

per person

Oct 2 - Oct 6

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8/10 Very Good! (1,006 reviews)

The Westin Chicago Lombard

$754

per person

Sep 17 - Sep 21

found 21 hours ago

Roundtrip non-stop flight included

Charleston (CHS) to Chicago (ORD)

9/10 Wonderful! (1,365 reviews)

Super 8 by Wyndham Crystal Lake

$316

per person

Oct 2 - Oct 6

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

6.6/10 (574 reviews)

The cleanest

Reviewed on Jul 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to Illinois

View all trips

What are some things I should consider when booking a Illinois ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Illinois ski packages?

Right now, ski trips start at just $307. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Illinois?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Illinois. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Illinois cost?

Sensational ski trips to Illinois start from $307. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Illinois?

The best time to hit the slopes in Illinois depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Illinois ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Illinois ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Illinois with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Illinois ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

Top Ski Illinois Hotels

Chestnut Mountain Resort

8700 W Chestnut Mountain Rd Galena IL

2 hours drive from Wrigley Field

$115 nightly

$128 total

Aug 24 - Aug 25

Total with taxes and fees

Book a stay at this ski resort in Galena. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...

8.6/10 Excellent! (1,003 reviews)

"Great view from the hotel room. Pool was pleasant and open until midnight, which was a plus. We hope to come back next year!"

Reviewed on Aug 17, 2026

Country Inn & Suites by Radisson, Galena, IL

11334 Oldenburg Ln Galena IL

1 hour drive from Wrigley Field

$98 nightly

$109 total

Aug 24 - Aug 25

Total with taxes and fees

Book a stay at this family-friendly hotel in Galena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...

Fabulous Home Away From Home

Guilford Township IL

1 hour drive from Wrigley Field

Stay at this vacation home in Galena. Enjoy laundry facilities, a pool table, and an in-room coffeemaker. Popular attractions Eagle Ridge Resort Golf and Horseshoe ...

9.6/10 Exceptional! (55 reviews)

"This was an exceptional home away from home. We thouroughly enjoyed the screened in porch for meals as well as visiting and playing cards in the evening. It was in a beautiful location and the siblings and spouses had a great time reconnecting. The host/manager was very accommodating and answered ..."

Reviewed on Sep 27, 2025

Get rates

See all 10,311 properties in Illinois

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.