BootsnAll Travel Community

Hey. I'm planning a road trip next summer in the Midwest USA. I want to visit philly, pittsburgh, cleveland, detroit, chicago, milwaukee and maybe some cities further south like Nashville or Memphis. I'm really into underground music and culture, vintage shops, coffee shops, etc. I was wondering if anyone knows of any places that might be of interest to me. Also any cheap places to crash so i won't have to sleep in my car haha. Thanks so much!

In Chicago, there are some great places to find vintage stuff at ridiculously low prices along Milwaukee Ave at Damen, which is conveniently close to the Blue Line.

I would suggest The Brown Elephant - 1459 N Milwaukee Ave -- as they always have a great selection of books, clothing, household stuff, records for nearly free. Last time I was in Chicago, I brought home an entire suitcase filled with 30 books that I picked up in that place, only spent about $13.

Across the street is Myopic -- another great bookstore.

Same area - Earwax cafe! Great food, open late -- big portions and amusing people watching. 1561 N. Milwaukee Ave.

A bit up the street is Alliance Bakery - 1736 W. Division St. -- great pastries and close to a laundromat -- put your dirty stuff in to spin while you have a snack.

If you want music, try Phyllis' Musical Inn -- it is very dive bar with a crowd of regular hipsters who try really hard not to look like they are trying so hard and often an open mic, but it also has jazz some nights of the week. 1800 W. Division St.

Same area - Atomix - great little coffee shop! 1957 W. Chicago Ave.

If you are looking for something to wear to a 1950's high school reunion, you'll like Wacky Cats.

One of my favorite places to shop in all of Chicago is Uncle Fun. There are some interesting shops in that area, too.

I don't know if you appreciate flea markets -- but there are some really fantastic ones in and around Chicago -- look here. The Maxwell Street Market in Chicago is fantastic -- though the parking is challenging. It is well worth it to just pay $3-4 for the privilege.

There is always a ton of free things happening in Chicago during the summer -- lots of live music and events. Spending 30 minutes looking at all of the fliers in the Chicago Cultural Center is an excellent use of your time.

Other places that are swell:

Lou Mitchell's Restaurant

Orange on Harrison -- One of the best quirky breakfasts in Chicago, IMO. Bring a bottle of vodka or champagne, and they will bring you freshly squeezed juice for the girly drink of your choice and they will only charge you for the cost of the juice. They have fried oatmeal, a fruishi bar (creatively arranged fruit that looks like sushi) and pancake samplers. My favorite was the donut style pancakes.
75 W. Harrison St.

Evil Clown CD Exchange