Western Suburbs Ski Vacations

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Top Ski vacation packages in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$595
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$647
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$610
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$719
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.

Reviewed on Aug 14, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
Save 100% on your flight
$609
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
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5* Ski vacations in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$1,060
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
$1,076
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,355
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
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3 Night Ski vacations in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$595
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$647
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$610
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Western Suburbs
View all trips

4 Night Ski vacations in Western Suburbs

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$737
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$805
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$742
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Clean room

Reviewed on Aug 15, 2026

Don't see what you're looking for?
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Planning your Western Suburbs ski vacation

What are some things I should consider when booking a Western Suburbs 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 Western Suburbs ski packages?

Right now, ski trips start at just $595. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Western Suburbs?

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

Sensational ski trips to Western Suburbs start from $595. 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 Western Suburbs?

The best time to hit the slopes in Western Suburbs 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 Western Suburbs 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 Western Suburbs 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 Western Suburbs with Expedia?

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

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.