If you’re trying to find the best ski trips snow and terrain out of Chicago, look no further. This guide is written for the serious powder seekers looking to make the most out of their time on the slopes. Chicago has many great things but proximity to advanced and expert ski terrain isn’t one of them.
Not to bash Boyne Mountain or Granite Peak but you’re going to have to get on a plane. Luckily Chicago O’Hare (ORD) has nonstop flights to some pretty awesome places. All the resorts below get loads of snow, have expert terrain, tend to be uncrowded and are pretty simple to get to from Chicago.
When you’re ready to book a trip check out Skizi’s online tools and Contact Us to quickly and easily get the best trip booked for you!
Table of Contents
Crested Butte, Colorado
Known for the “most lift-served double black diamond terrain in North America”, generous snowfall, and a laid-back atmosphere Crested Butte is the place. Called “The Last Great Colorado Ski Town,” this is a bucket-list destination for powder hunters. A bit off the beaten path in the Elk Mountains this place will scratch your itch for some steep lines without the crowds at many other resorts.
Quick Facts
- Over 2,700 vertical feet
- 12,162 ft Summit elevation
- 561 Acres of Expert Terrain
- Steepest lift served Glades
- World-class backcountry access
- Over 230 inches of snow annually
- EPIC Pass
The town of Crested Butte is originally a mining town. Some of the trails, such as Upper, Middle & Lower Gallowich are named after the one of the original mining families who helped start the ski resort in the 1960s. The town has come a long way since then but walking around you will still find no traffic lights, chain stores or high rise buildings. The vibe is relaxed and everyone is friendly and welcoming.
This place is known for expert acreage. Some awesome runs are Headwall, Big Chute, Teocalli Bowls if you’re ready for a 15 minute hike, or pretty much anything off the High Lift. Even signature runs like Rambo (the steepest cut run in North America) require you navigate almost 1000 vertical feet of double black diamond glades, bowls and gullies to get to.
Seriously, check out the trail map and chart some runs and realize just how much there is to conquer at this place.
Getting here is fairly convenient. A direct flight from Chicago O’Hare (ORD) to Gunnison-Crested Butte Regional Airport (GUC) takes a little over 3 hours, followed by a scenic 40-minute drive or shuttle ride to the town of Crested Butte and the resort.
For more details, check out Skizi’s Complete Guide to Crested Butte.
Jackson Hole, Wyoming
Combine over 450 inches of snow, over 4100 feet of vertical, National Park scenery, and some of most impressive ski infrastructure in the world and you’ll get Jackson Hole. This place is an expert’s playground and bucket list ski destination with the highest vertical drop of any ski resort in the United States. You’ll be inside of Grand Teton National Park with top tier facilities and your choice of luxury to budget accommodations.
Quick Facts
- Over 4,139 vertical feet
- 10,450 ft Summit elevation
- 2500 acres of skiable terrain
- Over 50% Advanced to Expert Terrain
- Open bowls, glades, and expert runs
- World-class backcountry access
- Over 458 inches of snow annually
- IKON and Mountain Collective
The Aerial Tram or “Big Red” runs from the base to the top of Rendezvous Mountain. The tram climbs a whopping 4,139 feet in 9 minutes. Coming down from the peak you’ll find chutes, bowls, and the famous Corbet’s Couloir where they host the Kings and Queens of Corbet’s ski competition every year.
Jackson Hole knows its steep and even offers the Steep & Deep Ski Camp for those who want to master riding on expert terrain. Beyond Corbet’s Couloir, highlights include Alta Chutes, Tower Three, and Expert Chutes. Steep, technical descents and tight lines offer an adrenaline rush unmatched by most ski resorts.
A direct flight from Chicago O’Hare (ORD) to Jackson Hole Airport (JAC) is about 3.5 hours with an easy 35 minutes drive or shuttle ride to Teton Village, where Jackson Hole Resort is located.
For more details checkout Skizi’s Complete Guide to Jackson Hole.
Big Sky, Montana
Big Sky is BIG. Over 5800 acres big. This is one of the largest ski areas in North America with a range of trails catering to every skill level, from beginner-friendly green runs to expert chutes. Over 50% of the terrain is advanced to expert but with 5800 acres there’s plenty of room for everyone to play.
If you want to expert terrain like the steep runs off Lone Peak, or to ride through one of the 4+ mile long wide, groomed beginner runs like Mr. K and Morningstar, or to pair a world class ski trip with a winter visit to Yellowstone National Park then a trip Big Sky Resort is for you.
Quick Facts
- Over 4,350 vertical feet
- 11,166 ft Summit elevation
- 5,850 acres of skiable terrain
- Over 2900 Acres of Advanced to Expert Terrain
- Chutes, bowls gullies.
- 5 Terrain Parks
- World-class backcountry
- Over 400 inches of snow annually
- Headlamp night skiing
- IKON and Mountain Collective
Big Sky’s Lone Peak is infamous. The Lone Peak Tram carries up to 75 skiers to the summit of Lone Mountain. At the top you’ll find views 360 degree views of Montana, Wyoming, and Idaho as well as Yellowstone National Park. You’ll find the gnarliest “triple black diamond” terrain coming down Big Couloir. Big Sky defines triple black diamond as “exposure to uncontrollable falls along a steep, continuous pitch, route complexity, and high consequence terrain.” Which pretty much means don’t fall on these runs, be careful, and have a lot of fun.
You’ll also find expert gullies down through the bowl if you want to loop the Lone Peak Tram or go off the backside of the mountain to take black and double black runs and glades to loop the Dakota or Sledhorn lifts. Make sure your lift ticket has tram access, IKON, Mountain Collective, and other ski passes may not allow access.
If you’ve never been to Montana now is the time to go. Getting to Big Sky is straightforward.
There’s direct flights available from Chicago O’Hare (ORD) to Bozeman Yellowstone International Airport (BZN) which take about 3 hours, followed by a scenic 65-minute drive or shuttle ride to the resort.
For more details, check out Skizi’s Complete Guide to Big Sky Resort.
Steamboat, Colorado
This is “Ski Town USA.” Steamboat Ski Resort’s snow is so unique, it’s trademarked as Champagne Powder® and with over 3700 acres of skiable terrain you will not be disappointed. If you’re looking for tree runs, the best snow in the Rockies, a laid back atmosphere, or top tier family amenities then Steamboat is the place to visit.
Quick Facts
- Over 3,668 vertical feet
- 10,568 ft Summit elevation
- 3,741 acres of skiable terrain
- The best tree skiing
- Over 300 inches of Champagne Powder® annually
- Night Skiing
- IKON Pass
What is Champagne Powder®? The snow that is so light and dry you can’t make a snowball out of it. Steamboat after a good snow day really has the best conditions you could ask for. This distinctive snow is the result of Steamboat’s location in the Rocky Mountains, where cold temperatures and low humidity create the perfect conditions for snowflakes to stay soft and powdery. With an average of over 300 inches of snowfall annually, Steamboat offers some of the most consistent powder skiing in the world. Combine Champagne Powder® with classic Steamboat glades and some boards strapped to your feet and you’ll have the best time of your life.
Steamboat’s Crown Jewel are the glades (tree skiing), and these are some of the best in the world. For skiers who love weaving through perfectly spaced trees, the options are nearly endless. Explore the expert renowned terrain in the Christmas Tree Bowl, chutes,the advanced glades of Mahogany Ridge, or the famous Closets and Shadows tree skiing areas. Check out the trail map, plan your route, and book your trip. You will not be disappointed.
Getting to Steamboat is convenient. A direct flight from Chicago O’Hare (ORD) to Yampa Valley Regional Airport (HDN) takes just under 3 hours, followed by a short 30-minute drive or shuttle ride to the resort.
For more details, check out Skizi’s Complete Guide to Steamboat Resort.
Photo courtesy of Steamboat Resort
Snowbird, Utah
Of course we needed some Utah representation on this list. Snowbird is the spot outside of Salt Lake City for advanced terrain and the classic light, fluffy Utah pow we all hold near and dear to our hearts.
Quick Facts
- Over 3,240 vertical feet
- 11,000 ft Summit elevation
- 2500 acres of skiable terrain
- Peruvian Gulch Tunnel – ski tunnel/carpet lift through the mountain
- Over 500 inches of snow annually
- IKON Pass and Mountain Collective
Snowbird, Utah should be your first pick if you are a Powder Hound planning a Utah ski trip. This is where you will find the largest vertical drop in the Salt Lake City area at 3,240 feet and over 35% of terrain being advanced to expert. Due to geographic positioning in Little Cottonwood Canyon Snowbird Ski area gets more snow than other Utah resorts, averaging 500 inches annually. This area is part of the Wasatch Mountains, which capture cold, dry air from the Great Salt Lake, creating a weather pattern that dumps more snow at Snowbird.
Start planning your adventure! Just 45 minutes from Salt Lake City International Airport, Snowbird offers the region’s best snow and 2,500 acres of iconic terrain ready for you to explore.
Getting to Snowbird is simple. Numerous nonstop flights from Chicago O’Hare (ORD) and Chicago Midway International Airport (MDW) to Salt Lake City International Airport (SLC) takes around 3.5 hours, followed by a 45-minute drive or shuttle ride to the resort.
For more details, check out Skizi’s Complete Guide to Snowbird Resort.
Ready to Chase the Powder? Let’s Make It Happen
Whether it’s tackling the steep lines at Jackson Hole, navigating the legendary tree runs of Steamboat, or summiting the iconic Lone Peak at Big Sky, your next adventure is calling—and the powder is waiting.
Let us create the ultimate trip for you! From lodging and flights to lift tickets, transportation, and activities, we handle all the details—at no extra cost to you.
Send in a Trip Intake Form or Book online to start planning your perfect getaway today!
After submitting the contact form I will reach out to you via email with either some itineraries or to set up a quick call to discuss your specific needs. Before your trip you will receive confirmations and a detailed itinerary, so you can focus on enjoying your adventure.
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