Within driving distance of Chicago

I don't know if this makes much sense.  To get from Chicago to SLC is about a ~3 hour flight.  You have to get to the airport about 1 hour before your flight time.  It'll take you an additional hour to get off the plane, get luggage and rental car.  Then it'll take about 45 minutes to get to a resort.  That's almost 6 hours to get to one fo the SLC area resorts which are probably the most accessible major resorts in the US.  In addition, flying out west incurs significant additional expense ($250+ airfare, rental car, increased cost of housing, increased cost of lift tickets, etc).

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Mt. Bohemia is probably 9.5 hours from Chicago.  To get to Lutsen is around 10 hours.  This is assuming good driving conditions.

You will get bored of Chestnut after 1 ski day.  But, you'll get bored of all the ski areas within 5 hour drive of Chicago after a day except for Granite Peak.  However, most of these areas have another resorts close by which you can ski for a 2nd day.  You can do Chestnut and Sundown Mtn (in Iowa about 45 minutes away) together or Cascade and Devil's Head together.

I agree that going to Wilmot is worth a couple of times a season.  I'd definitely avoid it during the weekends.  Very crowded with lots of out of control skiers and boarders.  If you can go during a weekday it's much more manageable.  If it isn't too cold, getting up to Wilmot for night skiing can be fun.  BTW, you can ski at night a almost all Midwest resorts.

I would recommend that wherever you decide to take your beginner friends that you call and do a little research on the ski school and what kind of facilities they have for beginners - for example "wonder carpets" vs tow ropes.  I have had more friends trying to learn to ski give up because of the dreaded tow rope than just about anything else.  While some of the midwestern hills that are close might be small they can be a surprisingly good place for a person to have a first experience.  Make it as easy for them as possible and stay close. 

One other thing is that Chestnut takes their Ski School very serious. They have at least 3 mid-west division examiners on staff.

Not many have mentioned Alpine Valley, but I grew up in Chicago, (wilmette), and always thought it was way better than Wilmot, but not really any harder, maybe some longer runs.  Easy drive.

I agree.  The terrain at Alpine Valley is a more interesting but that isn't saying much.  It's about 25 minutes further from Chicago than Wilmot and a bit more expensive for lift tickets.  Alpine Valley does have 2 high speed quads to access all 388 ft of vertical and vast 90 acres of terrain.  If you have skiing kids under 6 years old, Alpine Valley charges for them.  Most all other resorts in the US don't.  If you do have kids that ski, Cascade doesn't charge until they're older than 12 with a paying adult.

BTW, there are three resorts in the midwest called Alpine Valley.  One is near Chicago, one is near Detroit, and the other one is in Ohio somewhere.

You guys are talking about the one near Chicago.  Carry on.

I was very close to registering under the username "Stevie Ray Vaughn" just so I could recommend Alpine Valley. Pretty tasteless, huh?

For all you Wifi enthusiasts: DO NOT go to Bohemia. You can't even get a cellphone signal there. Last year I swore I saw a pterodactyl flying around that place.

Well said,

I ski Minnesota quite a bit. I take what I can when I can. Makes you appreciate the mountains. Also I realize that when I ski out west with my friends who live in Colorado that I make quite a few more turns then they do. 

The point I was making about Mt. Boehemia was the midwest has some terrain that will test the skiing ability of most people, not how many minutes/hrs from Chicago.
If a weekend ski trip is desired that can be interesting to advanced and still accommodating to beginners - try Nubs Nob and/or Boyne Highlands - from Chicago, drive up Friday evening ski Sat/Sun and drive back Sun night.
Not sure I get the connection between WiFi and skiing.
West(mountain) bound - I figure 4 days total to get 2 days skiing from Chi/Minn/Detr/Indy or Cinc counting getting to airport wait time at both ends and then the drive to the area and return to home.
I ski both the midwest and the mountains - have for many yrs and still enjoy both (prefer the mountains) but I live in the midwest.

I grew up skiing in Michigan, but now I just ski the midwest once or twice a year with the kids. 

From Chicago there is no reason to blow a travel day going out west. Between ORD and MDW, you can almost  always get somewhere after work.  Aspen has the best flights,  three directs daily under three hours or lots of connection options and the airport is three miles from town.   

Alpine Valley, Wisc., is OK and relatively scenic. While Wilmot is closer and the people are very nice, to me it looks rather industrial in that there are so many lifts and very few trees.

Grand Geneva is another quaint little area.

The most vertical is a long drive from Chicago to Granite Peak in Wausau.

I think we all concur that getting on a plane for a couple of hours yields better skiing then driving 5 hours.  Unfortunately my beginner friends will never agree.  Seems that the winners are Chestnut and Granite for a little more driving.  Beyond that it starts turning into a weekend trip.

By the way, it's great to see so many people from Chicago on this web site. 

 For sure there is better skiing west and east, but we make do with what we have. I have always found that the travel days are waisted anyways unless you are able to hit up Keystone the night you get in.

Chestnut has a good school and i prefer it as folks there are plain friendly, nice town too.   I'd agree that the instructors are quite serious, most do weekend duty from far away lands such as Iowa City, Iowa.   From the Wheaton area it runs just about the same as going to Granite Peak.

Did Granite for the first time last yr, it seems quite a bit larger, though the grade is not as consistent, steeper top, tapered/near flat at bottom.

With Chestnut I know it's well worth hitting it a weekday if at all possible as certain weekends you'll be in very crowded conditions.

With Granite, I've heard unless you have fresh snow, the surface will be hard, not positive on weekend crowds. 

I'm planning both this yr, however in the off season of the 'Dells' one may consider overnight out (or back) at one of the waterparks, then hit Granite, Cascade or one of other near by slopes next morning and return that night.  not much more than a regular hotel room.

draw a circle from your home, Michigan may be a great option.

if it does turn into weekend .....

i've eyed some last minute fares out on American from ORD and Midway has SWA. flights run under $200 rdtp.

lastly, for an escape should you have time to blow, Amtrak Calif Zepher leaves ~ noon and arrives in Winterpark at 10am next day.  yes, long but some folks like to walk about, read, drink, watch DVD's, hone/wax the ski's ... etc.  Really doesn't run any cheaper than flying, but can be an experience worth trying once.  Sleeper for two ups cost quite a bit but could offer some excitement.

 Take a weekend trip to southern Wisconsin and hit Devil's Head and Cascade Mountain in Wisconsin.  At least you get some variety that way.  

Bittersweet, Mi, mentioned previously, is the hill I grew up on.  I love that little mound of dirt but I would not recommend it for anyone from Chicago- your expectations are too high.