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13 Great Reasons to Ski Chestnut Mountain

If you’re looking for the premier skiing vacation in the Midwest, try Chestnut Mountain Resort skiing in Galena, Illinois. They hosted me and a friend overnight for a ski trip, but all opinions shared are my own.

Skiing with a friend

I grew up skiing in Minnesota every weekend. I know ski hills in the Midwest.

They’re fun, but Chestnut Mountain Resort does Midwest skiing right. I had no idea after my visit last June that the skiing would beat my expectations by so much.

(You haven’t visited Chestnut Mountain Resort in the summer? Do it. There are so many fun activities to keep you busy that you’ll love.)

It’s beyond just strapping on skis and heading down the slopes. Chestnut Mountain Resort figured out how to elevate the Midwest skiing experience from the moment you arrive.

Fun photo at Chestnut Mountain

13 Reasons Chestnut Mountain Resort skiing is THE place head in the Midwest

They have actual slopes.

One of the complaints about ski slopes in the Midwest is that they tend to be fairly short, flat hills. Chestnut Mountain Resort does not fit that model.

In fact, Chestnut Mountain Resort skiing may not be the best for a new adult skier who’s a little nervous. They have one bunny slope, but it’s on the route to the only green hill, so you have more traffic on it than you may expect.

The slopes are longer than I’m used to in this area, up to 3500 feet with a 475 foot drop. It’s nice to ski a longer slope and really get into the rhythm of the hill before you reach the bottom.

In fact, my friend and I did the only “real” green slope for a few runs then headed for a blue slope. We got to the top of it and looked down and down and down. This is not the type of blue I see in the Midwest, and I loved it.

Note: There are technically three green hills for Chestnut Mountain Resort skiing. One is adjacent to the bunny slope and really just leads to Old Man, the main green hill. There is also Rookie’s Ridge, which is a smaller bowl and a good place for new skiers.

Overall, Chestnut Mountain Resort has 19 slopes, including three black diamonds. When I look at the hills, I see around 10 slopes, however, as many are “partial” hills that connect the top to the bottom and are really one long run in my view.

Chair lift at Chestnut Mountain

Chestnut Mountain has a great terrain park, too.

The Farside, the terrain park at Chestnut Mountain, is the largest in the Midwest. It covers seven acres and includes more than 25 rails and other features.

You can find the terrain park opposite the main slopes, which I love. The more adventuresome snowboarders have their own area, which makes me feel safer on the slopes.

The terrain park includes a chair lift and a surface lift to make it easy to get the top again.

Chestnut Mountain is incredibly affordable.

Have you gone skiing in Colorado lately? A single day’s lift ticket costs in the neighborhood of $200. An that’s just the lift ticket, with no rental included.

Thankfully, I can have great skiing at Chesnut Mountain Resort at a fraction of the cost. Discounts on everything from weekday tickets to children to seniors to military to night tickets make it even more affordable.

A straight one day lift ticket costs $60 on weekends and $45 during the week, with a two day ticket at $100 and $80 respectively. I don’t know about you, but his becomes a getaway I can afford.

You can also check their website for specials, as they change regularly. Right now, you can get a lift ticket and equipment rental (skis, boots, and poles, or boards and boots) for $60 Monday through Thursday and just $50 on Fridays after 4pm.

Don’t have your own equipment? No problem.

While my friend who traveled with me had her own equipment, I haven’t owned my own skis since high school. Thankfully, Chestnut Mountain Resort has a great rental program.

For just $35 per day ($60 for two days), you can rent quality ski or snow equipment. With the ski package, you get boots, skis, and poles, while the boarding package gets you boots and a board.

Once you pay for your rental, you fill out the questionnaire so the employees know what equipment to get you. Depending on your height and weight and your ski experience, you want different equipment, and the employees make sure you’re set up correctly.

My Elan skis were the perfect fit for me, even though I didn’t remember how many centimeters I am used to. Once you pick up your equipment and try it on to make sure it fits properly, you’re good to go. If you later decide you want to change out your equipment, note that there is a $5 charge to do so.

You also have the option to rent a helmet for $8 per day ($14 for two days). It isn’t required, but for safety, more and more people wear helmets on the slopes.

The only thing you can’t rent is goggles, so make sure you bring your own. Sunglasses just don’t work on the slopes, so buy or borrow a pair before you come.

The bunny slope offers a magic carpet.

When I learned to ski as a kid, my least favorite part was that tow rope on the bunny slope. It inevitably cramped my hands, and someone always let get and crashed into people behind them.

When I saw the magic carpet offered by Chestnut Mountain, I wished I could go back in time. This is far easier than the J-bars or T-bars that were the improvement on the tow rope. 

You simply ski to the bottom and step on a moving carpet. The carpet moves slowly enough that you won’t fall, and there’s no hand strength required. This is far safer and easier than any method I ever used.

This helps the very, very new skiers get confident enough to get up and down the slopes.

Other skiers have plenty of chair lifts

The remaining hills provide plenty of chair lifts across the resort. Many are triples or quads, which means you can get more people up the hill faster.

I appreciate that when I get to the bottom of a hill, I don’t have to ski across the bottom of the mountain to get to a chair lift. Instead, I can easily ski from my slope to a chair lift and get up.

I love the way the chair lift lines are set up, too. There are different queues for single skiers, doubles, etc. Though the hills weren’t busy on the mid-week visit we took, this line setup ensures efficient loading of the chair lifts so you can spend more time skiing and less time waiting.

Chestnut Mountain chair lift

Chestnut Mountain Resort offers great lessons, too.

Whether you prefer to ski or board, we can all use a brush up on our skills. Whether you want to build confidence or learn new techniques, it’s worth that refresher.

You can take group, private, or semi-private lessons, and that cost remains affordable, too. It’s just $50/hour for a private lesson and $20/hour for a group lesson.

The lessons encompass both snowboarding and skiing with expert instructors who can help with everything from your first snowplow down the bunny slope to working on race techniques.

My friend and I took a group lesson while we enjoyed Chestnut Mountain Resort skiing. Though my friend was initially resistant to taking a lesson “because I’ve been skiing forever and all my bad habits are engrained,” she ended up loving the lesson.

She described herself as a vroom and screech skiier – but she got the tips she needed to start to take a far smoother path down the mountain with a rhythm instead. Whether it was the tip to keep the weight on the balls of her feet or the reminder to use her edges to turn instead of lifting her uphill ski, she gained tremendous confidence and increased her competence.

For me, I got the reminders to subtly crouch and straighten as I shift my weight through my turns, which led me to remembering how to pole my turns. I had been “lazy skiing” prior to the lesson, but afterwards, I actually skiied rather than just heading down the mountain.

The wide slopes give you time to gather your confidence, as needed, to know that your attempt to turn or learn a new skill will work because you have so much room. This definitely helped my friend practice and master her new skills.

Our instructor showed up on time and tailored his instruction to our exact levels after watching us ski to determine what we do and don’t know. The hour flew by, and I could have easily stayed with him for the rest of the day.

Kids have their own ski school lessons, too.

If you have kids who are learning the ropes while you want to hit the slopes, check out the Powder Pup Kids Lessons. They offer both half day and full day ski school.

One word of advice: If you plan to take advantage of this, book early. The weekend after we visited was totally sold out already on a Tuesday, as they max out at 40 kids per session.

These lessons are designed for kids ages 4 to 12 and focus on encouragement and games, especially at the younger ages. You do need to remain on-site during the ski lessons, so this is not a drop your kids and go shop in Galena experience.

Half day lessons run from 9am to noon and then 1pm to 4pm on weekends only. Full day encompasses both time periods with a break (with parents) for lunch.

The half day lessons cost $65 and full day is $115. If you need to rent equipment, kid rentals are $35 per day or $60 for two days.

Chestnut Mountain Resort has a mountain paging system to notify parents if any concerns arise during the lessons. Otherwise, parents can ski on their own, as kids perform best when parents aren’t constantly watching them.

Or choose to learn to snowboard instead….

If you or your kids are more interested in snowboarding than skiing – and I get that! – Chestnut Mountain Resort also offers boarding lessons for those 7 and older through the Burton Learn to Ride program. 

The lessons include the lift ticket, snowboard rental, and a two hour lesson. For Saturdays, Sundays, and holidays, the cost is $100, while non-holiday Monday to Friday LTR program rates are just $50.

The program is designed to get boarders comfortable with a new sport quickly. By the end of the first day, the goal is for new boaders to feel confident enough to link their turns.

Even the younger kids have an alternative while parents ski.

If you have kids too young to ski – but who are potty trained – sign them up for the Powder Playcare instead during weekends. If you wish to use this service, you must preregister.

Let me repeat that one – this is not a drop in service!

Once you’re preregistered, bring your toddlers to the Children’s Center and get them registered. For $12 per child per hour, your child can enjoy the romper room and play activities.

Make sure you bring their snowsuits and gloves and boots and all the gear so they can head outside to play, as well. Label all your items just like you do any time you drop your child off and you aren’t present.

As with the kids’ ski lessons, you must stay on-site while your kids have fun. The Powder Playcare is open only on weekends during ski hours, as it’s designed for care while you ski.

If you need a babysitter instead, you can preregister for a private babysitter for $15 per hour.

To preregister, call 815-777-4650.

You’ve got plenty of options for dining, too.

For a quick stop while skiing, head to the Mountain Top Cafe, just off the bunny slope. I don’t know about you, but I always get so hungry whenever I ski!

The cafe offers the quick bites that are perfect for a lunch break while you ski and offer the usual choices. Enjoy pizza or nachos, soup or burgers and more. The prices are fairly reasonable with a bacon cheddar burger for $6.75 or cheese fries for $2.75.

Bowl of soup

If you want something more healthy, go for the chef salad ($6.25) or a deli multigrain tuna salad sandwich ($6.25). It’s a great stop to get a quick meal then get back to the best skiing in the Midwest.

Inside the lodge, you can find two full service restaurants that serve breakfast, lunch, and dinner, as well. The Summit Sports Bar offers a sports bar type menu with plenty of TVs to catch up on the outside world.

I cannot recommend the cheese curds ($9.99) enough, and the Bavarian pretzel ($13.49) is another favorite. You can enjoy everything from a pulled pork sandwich ($11.99) to pizza, including a gluten free cauliflower crust pizza ($17.99).

Alternatively, you can head to the Sunset Grille, which offers a more fine dining experience. If you visit Chestnut Mountain Resort during a time the Sunset Grille isn’t open, you can almost always order dinner from this menu while at the Summit Sports Bar.

Enjoy tomato bruschetta ($9) or walleye strips with cucumber wasabi sauce ($13) to start off your meal right. I appreciate the variety of options in the menu that allow me to indulge in whatever my mood.

Here you can enjoy that high end dinner with anything from a filet mignon ($32) with local Iowa beef to the baby back ribs ($29) I chose to chicken piccata ($24) and more. You can also choose a salad for a lighter option, with the choice to add grilled or blackened chicken ($4) or shrimp ($5) to make it a more complete meal.

And the best part of the meal is watching the sun set over the Mississippi River. In the winter with the snow covered slope and the frozen river, you have to stop to enjoy the view and take in the beauty of your dining experience.

Chestnut Mountain sunset

Maximize your time at Chestnut Mountain Resort skiing by staying onsite.

You have far more than just skiing when it comes to enjoying a ski weekend or day trip. Chestnut Mountain Resort offers an onsite hotel so you can ski from the time slopes open until they close.

The hotel is clean, but it is not modern in terms of decor. Don’t let that deter you; enjoy the kitsch instead.

Most rooms offer two queen beds that are perfect for families staying – or friends enjoying a night away. In the rooms, you have a coffee maker (with additional coffee in the lobby in the mornings) and refrigerator to store leftovers or food you bring.

Check the hotel’s current specials, as many include ski and stay packages that make your getaway even more affordable. 

For example, the Ski, Stay, and Dine package offers a weekend stay for two with 2 $15 meal vouchers, a one day lift ticket per paying guest in the room for each night of the stay plus a free group ski lesson. For just $379 per night (including taxes!) with a two night minimum, this is your weekend retreat.

Alternatively, take advantage of the Weekend Winter Hot Dates where you can enjoy a two night stay for 20% off a two night stay of the ski packages. If your schedule is flexible, this is the perfect way to find an even more affordable ski getaway.

Did I mention that Chestnut Mountain Resort is about three hours from Chicago? Yes, you need to visit.

They’ve got your runny nose covered.

Whenever I’m outside for an extended period, especially when I’m doing something active, my nose runs. It isn’t a cold or allergies, but it happens every time.

Tell me I’m not alone.

Actually, I know I’m not alone. At the entrance to each chair lift, Chestnut Mountain Resort has a large, weather safe tissue dispenser. I don’t have to carry tissues in my ski jacket because I can grab them as needed.

Ready to ski

And yes, they’re thick and big and just what I need. This is a silly reason to love Chestnut Mountain Resort skiing, but it’s the little touches like this that matter to me.

Have you ever tried Chestnut Mountain Resort skiing?

Best skiing in the Midwest

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