Within driving distance of Chicago
I slide.
Most little hills (in the midwest) are considered day trip skiing or night trip skiing, very few would be more than that, although some are good for a weekend.
You could try Bittersweet in Otsego MI. I think it is under a 3 hour drive east on I94. It isn't spectacular but it does have a high speed lift and "wonder carpets" for the beginners. It is probably the best place in lower MI within 3 hours. I am not saying you won't get bored but at least it is skiing. The hills are at least long enough that you can turn a few times. It is really all relative to what is available. I would rather go there than not at all. Anything better would be another 3-4 hours. It would be worth a try if you are taking beginners or just want to go to get a quick fix.
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$30 for lift ticket, lesson & rental. You'll have to drive a bit though....the closest is probably Bittersweet about 2 hours from Chicago depending on traffic and where in Chicago you start. Bittersweet's not much of a hill, you'll need to go farther for that.
The western UP resorts are worth a trip, but not all that close - about 7 hours. I'd recommend Indianhead or the Porkies. You might like Mt Bohemia (about another 3 hours drive) but don't take your newbie friends there.
On the leeside of lake Michigan, Crystal, the Boynes and Nubs attracts lots of Chicago skiers. Figure 5 hours to Crystal, 6 to the others. Definitely a step up from Bittersweet, but you'll still be disappointed if you have Big Sky dreams.
I'd probably recommend a weekend in Boyne Country. Amenities galore, and lots of easy beginner runs for your friends. If you go to Nubs, you can ski the glades while your friends take the easy groomers and meet up at the same lift.
The other option would be a weekend trip to Caberfae and Crystal near Cadillac. It's a bit closer, and Caberfae has some very cheap lift tickets if you look around.
Regards,
Rusty
Let me know if you have any questions and I'll do my best to answer.
If you want to make a long weekend and don't mind about an eight hour drive Lutsen is an excellent resort with very good lodging deals. You can ski there for a good two days without becoming bored. Plenty of terrain for everyone. Reminds me of some of the NE resorts with about 500-1000ft less vertical. Lutsen does have about a 1000 ft. vertical, three mountains, and even a gondola.
If you and your wife really want to do some challenging skiing in the midwest take a long weekend and hit up Mount Bohemia. You'll be pleasantly surprised at what they offer for a midwest ski hill. Vertical is 900 ft. and all of it is used. No groom runs and acres of acres of glades. You can actually ski powder in the Midwest at Mt. Bohemia. They get dumped on all winter. Not uncommon for them to pick up a few inches every day to every other day and at least once a week get a 8+ inch dumping over a 24 hour period. If you hit up there website they'll send you a DVD for free.
Any day at the hill is better then a day not at the hill. :)
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I've always heard good things about Chestnut, might be a great place to take two probies.
If anyone from the windy city tells you to go to Wilmot, RUN!!!
...i will think twice next time before i post ...this is the last time i will say it GOODBYE
and this time i dont mean it as a joke!!!

Wow, thanks so much for everyone's advise. I lived 6 years in Southern Germany and skied all over the alps, then 3 years in NH and of course our best friends live in Big Sky. It breaks my heart every time I look at the trail maps in the Midwest. Really, black & double black at Wilmont??? By what standard. Guess Chestnut is the best choice within 3 to 5 hours drive.
It is kind of sad and can lead to a rude awakening for beginners moving up to real mountains. The standard for trail ratings in the US is that they are always relative to the mountain, not to other mountains. You asked. On the plus side, an inflated double black trail rating does tend to create a little extra space for people who can actually ski.
Regards,
Rusty
Bohemia and the surrounding bc is the only place I've skied in the midwest for years.You and your wife will not get bored at Bohemia. Maybe you could stay in Houghton, your beginner freinds could ski at Ripley and you and your wife could ski Bohemia? You wouldn't actually be in a group tho. Actually, Ripley would probably be pretty fun for everybody, but it's not worth a 10 hour drive. Bohemia's probably not either unless you hit it just right. Seems to me I remember the second or third year Bohemia was running lifts there was some guy from Chicago who would drive up almost every weekend.
I think you'd be better off all flying out to Big Sky. Maybe if the beginners didn't dig skiing they could go slednecking in W Yellerstone?
closest to chicago is Wilmot, open until 11pm, it's so close that I can do afterwork, I had 50 days skiing easily this way, one hill, 4-5 similar steep runs, they usually set up one mogul run in the later of season.
Cascade Mnt, 3 hr drive, but worth it, I like more than Devil's head. Easy access, right by the highway.
Devil's head, close to Cascade, wider, has more runs than Cascade, but they are pretty much the same, there is an interesting mogul on one side. The parking is quite stupid, it is far away from the main lifts.
Both Cascade & Devil's head has WiFi, no for Wilmot.
For the lower Michigan, 1.5-2hr drive, there are Timber Ridge & Bitter Sweet. I personally prefer Timber Ridge, it's wider, more runs, has WiFi, not sure about Bitter, 'coz I'd been there only twice.
It's a long ways but if you stay a few nites it can be a cheap long ski weekend with some pretty damn good skiing.
It is Nine hours in good weather. More if it snows. Which it does a lot in the Keewenaw.
Maybe you could stay in Houghton, your beginner freinds could ski at Ripley and you and your wife could ski Bohemia?
There's not much for beginners at Ripley. Don't take your beginner friends there. Trust me. My wife and I skied it our second year and it kicked our ass. I've been back since, and I'd say you need to be a solid intermediate to ski it.

If you have to do more than 3 hr drive, I guess you would opt to fly out west,
closest to chicago is Wilmot, open until 11pm, it's so close that I can do afterwork, I had 50 days skiing easily this way, one hill, 4-5 similar steep runs, they usually set up one mogul run in the later of season.
Cascade Mnt, 3 hr drive, but worth it, I like more than Devil's head. Easy access, right by the highway.
Devil's head, close to Cascade, wider, has more runs than Cascade, but they are pretty much the same, there is an interesting mogul on one side. The parking is quite stupid, it is far away from the main lifts.
Both Cascade & Devil's head has WiFi, no for Wilmot.
For the lower Michigan, 1.5-2hr drive, there are Timber Ridge & Bitter Sweet. I personally prefer Timber Ridge, it's wider, more runs, has WiFi, not sure about Bitter, 'coz I'd been there only twice.
Dear Flatlander,
What the hell is WiFi????????????
I'll give you thumbs up on the bar at Wilmot, but don't false advertise the hill, it sucks, point blank...and what's up with the black & red spyder coat-n-pant, is it a Chicago thing?
Sorry, just an observation.
Wilmot:

Lastly, Bohemia is an 8 hour drive from Madison, FIB Town is 2 1/2 hours south, how could it take 7 hours to get there. How can you people tell him these drive times; Lutsen 8 hours??? Ya, if your on the Auto Bond.
...i will think twice next time before i post ...this is the last time i will say it GOODBYE
and this time i dont mean it as a joke!!!
For all of you reading this who are lucky enough to live in the mountains, don't slam us for living in Chicago, work has a habit of sending you places you don't want to be. Besides it is a great city 3 seasons out of the year...
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While Wilmot might be a small little bump, the place has some great history and is older than many out west places, at least respect the history of the place. Also remember that small areas (like Buck Hill) have turned out some US teamers, and Buck is no bigger than Wilmot.
You are 100% correct, I take back my slam on Wilmot, it truly does have allot of great history.
Ever notice when reading pro skier profiles the large amount that grew up in the mid west.
I know statistics don't mean much, specially when measuring quality over quantity, but did you know Michigan with 38 & Wisconsin with 34 are the 2nd & 3rd largest ski area states in the nation [NSAA]. That tells me there are allot of passionate skiers in the mid west.
Seriously, What is this WiFi?
...i will think twice next time before i post ...this is the last time i will say it GOODBYE
and this time i dont mean it as a joke!!!
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The best choices from Chicago are Wilmot, Alpine Valley, and Chestnut. Chestnut is the most interesting, Alpine is like a slightly bigger Wilmot. Devil's Head and Cascade are not worth driving farther than Alpine.
Sunburst in Milwaukee is a great choice for instruction.


