Cleveland/Detroit/Chicago/Milwaukee Road Trip - Recommendations

I have a road trip planned in a couple weeks that will take me to games in Cleveland, Detroit, Chicago, and Milwaukee (coming from New Jersey). I was wondering if anyone could recommend some absolutely can't miss restaurants/attractions in these cities? My plan doesn't leave much extra time in each city, but I want to make sure that I leave feeling like I experienced something unique to the area that I can't do anywhere else. This site is a great resource for planning, but it's easy for me to get overwhelmed with ideas and was hoping for some help narrowing down to the must-do's. Thanks in advance for any suggestions!

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Chicago must do is Chicago style pizza. Some swear by Uno's, others by Gino's, others by Lou Mannetti's. If time is a factor, try what is closets to your hotel. If you have time, other classic Chicago activities: The Bean (official name is Cloudgate) at Millenium Park, architecture tour by bus or boat. Which museums depends on your areas of interest. Michigan Avenue is a great walk for people watching and some neat stores. Guide books call Garrett's popcorn a must-do but Nuts on Wacker is so much better. Classic Chicago popcorn is carmel and cheese mix. Oh, and at Macy's, get small box of Frango mints. Original to Chicago when Macy's was the wonderful, iconic Marshall Fields. We always take the train from downtown to ballparks. Cleveland has Rock and Roll Hall of Fame. I think we stayed at the Hilton Garden Inn per BC.com and it was GREAT!! Literally on the corner of the ballpark and about a mile from Rock and Roll Hall of Fame.

Thanks Jennifer! I appreciate all the input. I'll have a couple days in Chicago so that's probably where I'll be able to experience more of the city and the place I'm most excited for.

My pleasure. Chicago is one of my favorite cities, Wrigley is one of the two best ballparks (Fenway being the other), although I haven't been to the new Wrigley. Obviously you'll hang out in Wrigleyville before the game and we always try to do a ballpark tour before our games.

If it works for your budget, stay downtown or near Michigan Avenue and enjoy Chicago before and after your games. The train is super easy and safe. 99% sure red line goes to Wrigley, not sure about Cellular right now. By the round trip ticket on your way to the game, you do not want to deal with the machines in the crowds afterwards.

Famous sports bars/restaurants-- you'll find on trip advisor or a simple Google search. Harry Carrey's has excellent food, the one in water tower has a cute little museum attached.

The Chicago Art Institute is continually rated one of the top 20 in the world. You can walk the beach (Oak Street) and if it rains, the planetarium and aquarium are together on what's called Museum campus. The Museum of Science and Industry is a great indoor-day for kids and sometimes have unique special exhibits; Field Museum of Natural History is equally attractive to those into Natural History. Shopping is Michigan Avenue and Water Tower Place. We really enjoyed the tour of Soldier Field a few years ago.

You may be coming to the wrong place for this. When I did my trip to those four cities Chicago was the only city I was in long enough to try restaurants. I did go to the Rock and Roll Hall of Fame and wish I'd gone to the Football Hall of Fame instead.

If you want to get recommendations on hotels, public transportation, game tickets, and the stadium you're in the right place. If you want to do other things you may want to ask other people.

Thanks David! I have a feeling my trip will be the same and I'll end up with not much time for anything other than getting food and going to the games. I've been searching other places for things to do too but figured it might be helpful to see what other people who mainly care about visiting the stadiums thought was worthwhile and close by. Thanks!

The Football Hall of Fame is in Canton, OH, about an hour from Cleveland. If you're not into all kinds of music, then yes, David Lasdon is probably right. I'd check the websites for each, see if there are any special exhibits at either that interest you. Trip Advisor is great for in-city things like restaurants, sites, etc.

Milwaukee has a great art museum if that's your type of thing, and Hofbrauhaus is a neat place for a cold beverage there.

The Henry Ford Museum in Detroit has the actual car JFK was riding in when he was shot.

When going between Cleveland and Detroit, stop and spend a day at Cedar Point. If you enjoy roller coasters, the Point is the best place in the country for theme and an absolute can't miss.

As you head west, the Indiana Dunes on the SE corner if Lake Michichan are an under appreciated and inexpensive place to spend an afternoon.

Cleveland native here,

Depending on your preference, either the Rock Hall or the Pro Football Hall of Fame are great choices. They have recently renovated the Pro Football Hall of Fame so I assume it is even better than it already was. A fun little side trip for baseball fans that would appreciate some history is a trip to League Park on Cleveland's near East side. It just re-opened last summer after a $5 million renovation. The upgrades included a new baseball diamond and a restored ticket house from the original.

For those who don't know, League Park was the original home of the Indians, saw the Tribe win the 1920 World Series and was like Cleveland's Wrigley Field before they moved downtown. Among the things that happened on that field were: Babe Ruth's 500th home run, the only unassisted triple play in a World Series, the first World Series grand slam and first World Series home run by a pitcher. The new site also includes the Baseball Heritage Museum, a museum dedicated to baseball's role in society. But you have to go on a Saturday for it to be open unfortunately.

Cleveland has all the other big city stuff, a world famous art museum, fun downtown with lots of good bars and great people. Hope you enjoy your trip!

Milwaukee's Harley Davidson museum is interesting, Also during the summer on the weekends there are a number of summer festivals on the Summerfest Grounds, which runs along Lake Michigan, My favorite is German Fest.

As others have noted, I take the train (Red Line) out to Wrigley for Cubs games. There is very little parking around Wrigley Field. (and if there is, it's around $40 a spot)

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