Sassier, I can only answer questions about Chicago, but, will you already have a car in Chicago? Parking in the city will be very, very expensive and if you are smart, you won't be picking up the car until you are leaving. Secondly, what are your plans for sightseeing in Chicago? The hotel on Ontario St. is one block east of Michigan Ave., which is the big shopping street in Chicago. Is this a shopping trip? Then you will be ideally situated. I suggest you share your plans and then we can comment on recommendations near them.

Thanks for your input. This is not a shopping trip, but we will probably look in some stores. We will go the the art museum. I was hoping that there would be a play in town, but I don't see anything the end of April. Any suggestions for what we MUST see in Chicago would be appreciated. We will fly in on April 25th and will not pick up a rental car until th 27th when we drive to Milwaukee.

How do you plan to get from Door County to Tranverse City and Macincac? Is there a ferry across Lake Michagan? that would be fun! In door county, we like Ege Harbor and I think it was Fishcreek, cute towns and central to everything. In traverse City, be sure and drive Old Mission Peninsula, a lovely drive and full of wineries! On Macinac, if the budget allows there is no place like The Grand Hotel. If you don't stay there, have a meal there so that you get the flavor of that grand hotel..making sure to sit on the porch and rock awhile.

Please forgive my spelling in the above post! I'm on my iPad and it is harder to type than my desktop.

You don't say what you want to see in Chicago. If you wanted to,you can get from Chicago to the Milwaukee airport on Amtrak for $22/pp
6 Hiawatha trains per day. It might be cheaper to rent a car in Milwaukee.
Mapquest says 7.5 hours from Sturgeon Bay WI to Mackinaw City MI. Looks like there are 2 Door County museums in Sturgeon Bay.

The third ward is a nice area for restaurants, a few boutique shops and theaters, but is not "downtown" per se. It is the old warehouse district, renovated over the last few decades. What are you looking to do while in Milwaukee? For nice smaller hotels, look at the Hotel Metro and the Iron Horse.

In Door County, Fish Creek or Sister Bay are the towns central to the area. Each town is quaint in it's own way, no matter where you stay on the peninsula. The west coast is far busier than the east.

On Mackinac Island, we loved the Mission Point resort. It is a bit out of town, but close enough to bike in. It has beautiful gardens and grounds. Most people find the Grand Hotel over-priced, and the rooms tiny. It is a beautiful old building though.

I'd have to say the drive from Door County to Mackinac is at least six hours. The road out of DC is very slow during high summer traffic. You'll need to leave your rental car at the ferry dock at Mackinac. You can book your ferry tickets with your hotel package.

Tomfuller's idea about getting out of Chicago is a good one. You can take the train to Wisconsin and pick up a rental car there. If you have a large group, the train will not be economical though.