For a cheap lunch in Chicago, try Pierogi Heaven on N. Wells.
It is a hole in the wall place underneath the El but the pierogis are pretty good.
To avoid a drop off charge on the car, bring it back to MKE and turn it in and take one of the 6 Hiawatha trains per day from the airport station to Chicago.

Sorry I forgot a link http://www.roadsideamerica.com/story/2254
Enjoy your trip.

Thanks for the tips, tomfuller. I'm just starting to check rental cars, but it's the same price to rent a one-way with Dollar as it is to pick up and drop off in Milwaukee.

Lee Ann

Downtown Milwaukee along the river has changed quite a bit, you may want to research that area and spend more than a day. Or not, but he may be very interested in seeing the changes.

I stayed at the Palmer House in downtown Chicago for under $150, it was a special (pre-paid I believe) for something like $120 or so. I've also stayed at City Suites for around $110 a night, it is older and the rooms are small. It's north of downtown right on the El so very easy access to downtown.

I can't give specific food recommendations, I pretty much wander around and stop in somewhere that looks good and then I never remember where I was.

Having been to a Red Sox @ White Sox game, it was a unique atmosphere that night at US Cellular Field...Section I was sitting in had a lot of altercations between White Sox fans. Red Sox fans stayed away...

That being said, I enjoyed the stadium and would not hesitate to go back. Its 5 years already since I was in Chicago and Milwaukee. It was a great trip for sure.

Here is the link to my trip report (old but most activities will still be there). Hotels may have changed though...
http://www.fodors.com/community/united-states/chicago-milwaukee-minneapolis-trip-report.cfm

I doubt you'll find the Palmer House or many other places in Chicago for under $150. May 18-21 will see approximately 66,000 people in town for the National Restaurant Association show, one of the largest the city hosts. About 20,000 will stay over May 21-23 for the National Confectioners Association meeting.

If your dates are flexible, look between May 8-18 or May 24-31. The city is only expecting around 12,000 conventioneers those weeks. Another option could be to flip your itinerary to visit Chicago first, then head to Wisconsin.

If you can't change your dates, book something ASAP that you can cancel and keep looking. Most hotels release blocked rooms about 30-days before a meeting, so you may find a deal in mid-April.

Citylghts, my daughter graduates from college May 11th, and Mr. Pickle needs to be home over Memorial Day for inventory at his job, and we don't want to go in June when school gets out, so those are the most likely dates.

Our original thought was to do Chicago first, but we'd like to go to the ball game if we can.

Tchoiniere, thanks for the link to your trip report.

I got some info from AAA today. Once we look over all of that, I'll have more questions!

Lee Ann

Okay, if your dates are fixed, not much you can do. To find a good deal, try the bidding sites like Hotels.com or Priceline. For tips on how to snag the property you want check www.betterbidding.com or www.biddingfortravel.com.

For general tourism info, go to www.choosechicago.com. Transit info for the city is on the CTA site at www.transitchicago.com. It has a trip planner, maps, info on where to buy passes and how to track buses and trains with a smart phone.

To find info on happenings and restaurant listings, check www.chicagoreader.com or www.chicagomag.com. You can search restaurants by cuisine, price or location.

Thanks for all the links, Citylghts. I was just looking at www.choosechicago.com before I came here.

I'll take a look at hotels.com, too. I don't think Priceline will work since there are three of us.

Lee Ann

You can do Hotwire with 3 people. Too bad that is a big convention weekend. I have had a lot of luck with Priceline and Hotwire in Chicago. I would still book something with no cancellation penalty and keep trying Hotwire.

I loved the free Chicago Greeters neighborhood tour I went on last visit. It was just the guide and me. I requested a tour of Old Town. We walked around Old Town and also did the Chicago History Museum--free with the guide and walked over to the Lincoln Park zoo and gardens. You need to reserve ahead of time.

Well, you could always go see the Red Sox play the Twins in Minneapolis over the weekend....that's kind of a terrible idea though lol.

See if you can find something a little further out within your budget in Chicago? I might be weird but I really like riding the El into downtown. And yes, the Palmer is really expensive those dates, like almost $300/night. I got it for less than half that the week after Labor Day.