Title: Illinois Ski Vacations 2026 | Expedia.com

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# Illinois Ski Vacations

## Book a Ski Hotel + Flight or Car together to unlock savings

- ##  
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## Top Ski vacation packages in Illinois

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

![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Chicago Lombard

$337

per person

Apr 7 - Apr 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

8.8/10 Excellent! (1,128 reviews)

The hotel is in excellent condition.

Reviewed on Jan 26, 2026

![Lincolnshire Marriott Resort](https://images.trvl-media.com/lodging/1000000/30000/23100/23049/edaa8813_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lincolnshire Marriott Resort

Half Day

$631

per person

Mar 11 - Mar 15

found 1 day ago

Roundtrip flight included

Portland (PDX) to Chicago (ORD)

8.8/10 Excellent! (1,001 reviews)

clean room and the staff was very friendly

Reviewed on Jan 31, 2026

Don't see what you're looking for?

See all available trips from Columbus to Illinois

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Ski vacations in Illinois

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

![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Chicago Lombard

$337

per person

Apr 7 - Apr 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

8.8/10 Excellent! (1,128 reviews)

The hotel is in excellent condition.

Reviewed on Jan 26, 2026

![Lincolnshire Marriott Resort](https://images.trvl-media.com/lodging/1000000/30000/23100/23049/edaa8813_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lincolnshire Marriott Resort

Half Day

$705

per person

Mar 21 - Mar 24

found 1 day ago

Roundtrip flight included

Columbus (CMH) to Chicago (ORD)

8.8/10 Excellent! (1,001 reviews)

clean room and the staff was very friendly

Reviewed on Jan 31, 2026

Don't see what you're looking for?

See all available trips from Columbus to Illinois

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Ski vacations in Illinois

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

![Baymont Inn & Suites by Wyndham Richmond](https://images.trvl-media.com/lodging/1000000/10000/9100/9059/5924ee8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Baymont Inn & Suites by Wyndham Richmond

$353

per person

Apr 20 - Apr 24

found 2 hours ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

7.8/10 Good! (683 reviews)

Room was spotless, spacious, good furniture. Well maintained and clean facilities. Comfortable bed. Laundry room, vending machines for late-night snacks on the same floor. Generous and tasty breakfast, Friendly support staff.

Reviewed on Jan 20, 2026

![The Westin Chicago Lombard](https://images.trvl-media.com/lodging/2000000/1700000/1690600/1690548/ef211bfd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Chicago Lombard

$449

per person

Apr 7 - Apr 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,128 reviews)

The hotel is in excellent condition.

Reviewed on Jan 26, 2026

![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/6279b55c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago/Oak Lawn

$437

per person

Apr 12 - Apr 16

found 5 hours ago

Roundtrip flight included

Seattle (SEA) to Chicago (ORD)

8.2/10 Very Good! (1,126 reviews)

Staff was courteous. Dining server and bartender were super helpful and accommodating. Beds were comfortable,

Reviewed on Feb 4, 2026

Don't see what you're looking for?

See all available trips from Columbus to Illinois

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Planning your Illinois ski vacation

####  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 $337\. 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 $337\. 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](https://images.trvl-media.com/lodging/7000000/6260000/6256300/6256296/d04ca2aa_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chestnut Mountain Resort

8700 W Chestnut Mountain Rd Galena IL

- 2 hours drive from Wrigley Field

$104 nightly

$116 total

Mar 8 - Mar 9

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. ...

8.4/10 Very Good! (1,001 reviews)

.

Reviewed on Feb 1, 2026

[](https://expedia.com/Galena-Hotels-Chestnut-Mountain-Resort.h6256296.Hotel-Information)

![Country Inn & Suites by Radisson, Galena, IL](https://images.trvl-media.com/lodging/1000000/670000/660100/660026/343cab95_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Country Inn & Suites by Radisson, Galena, IL

11334 Oldenburg Ln Galena IL

- 1 hour drive from Wrigley Field

$96 nightly

$107 total

Feb 20 - Feb 21

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. ...

9.2/10 Wonderful! (1,004 reviews)

Very clean room. Quiet and comfortable. Very friendly staff. Good breakfast. Easy to find

Reviewed on Jan 23, 2026

[](https://expedia.com/Galena-Hotels-Country-Inn-Suites-By-Radisson.h660026.Hotel-Information)

![Fabulous Home Away From Home, Fabulous Home Away From Home - 4 Bdr - With Hot Tub!](https://images.trvl-media.com/lodging/19000000/18980000/18973700/18973698/843f20b1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fabulous Home Away From Home, Fabulous Home Away From Home - 4 Bdr - With Hot Tub!

 Guilford Township IL

- 1 hour drive from Wrigley Field

Stay at this vacation home in Galena. Enjoy a fitness center, laundry facilities, and tennis courts. Popular attractions Eagle Ridge Resort Golf and Horseshoe ...

9.6/10 Exceptional! (51 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](https://expedia.com/Galena-Hotels-Fabulous-Home-Away-From-Home.h18973698.Hotel-Information)

[](https://expedia.com/Galena-Hotels-Fabulous-Home-Away-From-Home.h18973698.Hotel-Information)

[See all 10,718 properties in Illinois](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=215)

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.

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