Northwest Chicago Ski Vacations 2026

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Top Ski vacation packages in Northwest Chicago

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

Renaissance Schaumburg Convention Center Hotel

$718

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

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3 Night Ski vacations in Northwest Chicago

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

Renaissance Schaumburg Convention Center Hotel

$602

per person

Nov 26 - Nov 29

found 9 hours ago

Roundtrip flight included

Moline (MLI) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

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See all available trips from Columbus to Northwest Chicago

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4 Night Ski vacations in Northwest Chicago

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

Extended Stay America Suites Chicago Schaumburg Conv Center

$340

per person

Oct 17 - Oct 21

found 16 hours ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

6/10 (1,005 reviews)

I got two rooms reservation, they only see one room! The guy at the front desk do not help!

Reviewed on Sep 15, 2026

Holiday Inn Chicago Northwest-Elgin by IHG

$440

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

Just on

Reviewed on Sep 16, 2026

Candlewood Suites Elgin by IHG

$526

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Pensacola (PNS) to Chicago (ORD)

8.6/10 Excellent! (399 reviews)

Very nice property and room.

Reviewed on Sep 8, 2026

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What are some things I should consider when booking a Northwest Chicago 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 Northwest Chicago ski packages?

Right now, ski trips start at just $340. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Northwest Chicago?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Northwest Chicago. 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 Northwest Chicago cost?

Sensational ski trips to Northwest Chicago start from $340. 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 Northwest Chicago?

The best time to hit the slopes in Northwest Chicago 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 Northwest Chicago 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 Northwest Chicago 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 Northwest Chicago with Expedia?

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

Top Ski Northwest Chicago Hotels

Comfort Suites Elgin Northwest

2480 Bushwood Drive Elgin IL

19 min drive from Woodfield Mall

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

8/10 Very Good! (1,000 reviews)

"The first room that I was given, the bed had black long hair in it when I pulled back the covers. There was also hair in the bathroom and hair on the bench in the room. The Desk person was very kind and apologized and immediately switched me to another room. However, that room was on the second floor ..."

Reviewed on Sep 13, 2026

Country Inn & Suites by Radisson, Elgin, IL

2270 Point Blvd Elgin IL

18 min drive from Woodfield Mall

Book a stay at this business-friendly hotel in Elgin. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...

Best Western Plus Elgin - Chicago

2175 Marriott Dr West Dundee IL

15 min drive from Woodfield Mall

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

See all 3,909 properties in Northwest 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.