short "vacation" in the Chicago area
 

after attending a conference in the Chicago area in July, several couples want a few days (4 or 5) of "R&R" with beautiful scenery, water, good food, relaxation. Considered traveling to Mackinac Island but getting there seems problematic and we gather it's crowded with families that time of year. Any suggestions?

Many people say that Traverse City, MI is a beautiful place to travel with great weekend activities, wineries, etc. It is a bit of a drive from Chicago though.

On the Wisconsin side, you could do Door County, WI. Again, they have nice parks, trails, restaurants, wineries, etc. From Chicago, it's more like 3.5 - 4 hours drive.

Another option: the beautiful beaches and small towns in southwest Michigan like New Buffalo or South Haven (or Grand Haven). Nice beaches, quaint small downtowns, wineries, etc. New Buffalo also has a casino, if that's your style. It is about 1 - 1.5 hours from Chicago.

Hope this helps. Enjoy.

Are you and the others returning to Chicago after the R&R or heading for home(s)?
My thought would be to take a train to Milwaukee or Wisconsin Dells and rent a vehicle there that could be returned where you rented. For water, head for Door County.

I've never even heard of Door County so obviously I need to do some research! That is very helpful in that we would all love to go someplace we haven't been before. How would the logistics for that work if we're flying in and out of Chicago? Or is there a closer airport to Door County and we could fly back from a different airport. We all live on the East Coast. Thanks for the great suggestions!

We have been every place suggested and all are good ideas, you will have fun no matter what you choose. But, if you have never been to Mackinac Island that's the one I vote for. The ferry ride over on a sunny July day, walking the main street and stopping for fudge, renting bikes and riding around the island, taking a carriage ride, and enjoying the most beautiful view as you have lunch at the Grand Hotel, afterwards rocking a few minutes on the huge porch.
On your way to MI you could take a few hours and drive Old Mission Peninsula in Traverse City and view all the vineyards, stopping at a few for tastings.

Milwaukee airport would be closer to Door County. We used to visit Door County when we lived in Chicago. It reminded us of Maine. Nice small towns. You also could go to the American Club in Wisconsin, closer than Door County. Also look at Lake Geneva.
Or the other side of the lake, Saugatuck,MI or several of the waterfeont communities south of it, easy drive from Chicago.

The Amtrak Hiawatha trains stop at the Milwaukee airport before they stop in Milwaukee. Rent your vehicle there and then you don't have to return to Chicago to fly back home.

All of the suggestions are great. Wisconsin Dells may be a bit crowded that time of the year. It is the water park capital of the world.

Depending on where your conference is, you may want to fly in and out of Milwaukee. If memory serves me correctly, it is about an hour north of Chicago and very easy to get around. Rental cars are available on site.

Where in the Chicago area is the conference? From the Milwaukee airport, it will take (if there's no traffic) about 1 3/4 hours to get to DT Chicago.

Cross Mackinac Island off the list if it's anywhere around the CYC Mac sailboat race ( begins July 19). Room prices will double.
http://www.cycracetomackinac.com/

If 'crowded with families' doesn't sound too good to you, I don't think you want to keep The Dells on your recommended list. Door County is the peninsula just northeast of Green Bay. (Hold up your left hand; Chicago is the base of your wrist the rest of your hand is Wisconsin; Door County is the thumb.) While a family-friendly location, it draws visitors of all stripes and ages, with more than 200 miles of Lake Michigan and Green Bay shoreline, tons of beaches, three state parks, a variety of restaurants; great hiking/biking trails, good kayaking, fun shopping AND fabulous sunsets.