For your request of "off the wall" destinations, you're getting all of the big tourist spots recommended! :laughing:
Here's a few things that I like to do, which probably aren't big tourist destinations:
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SEE
Alfred Caldwell Lily Pond - super cool and mellow place, near the Lincoln Park Zoo and The Peggy Notebaert Nature Museum. FREE
The boat tours are actually pretty cool, despite being a tourist attraction - the best one, hands-down, is the
Chicago Architectural Foundation's boat tours.
There are tons of plays that are really worth seeing - check out the
Steppenwolf Theatre and the
Lookingglass Theatre (owned by David Schwimmer, who's in a lot of the plays).
Movies in the Park - they show new and old movies, in various parks around the city... the one in Grant Park is huge, so get there early! Maybe stop at a nearby grocer or restaurant and get a snack (or meal!) to bring with you. FREE
Also, no one mentioned
Millennium Park - it's awesome, even if it's a major tourist attraction. There's oftentimes noon concerts in the Frank Gehry designed Pritzker Auditorium (FREE). And the Park Grill ain't a bad place to eat, although it's crazy during lunch.
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SHOP
Michigan Avenue is anything BUT "off the wall" - it's not at all "seedy" as your friend called it - it's sheik Chicago shopping at its best... which is exactly why I stay away from there. If I go shopping (yech), I go to the North/Clybourn intersection, which has Erehwon Outfitters, a new huge REI, a new huge Whole Foods, Patagonia, and a few other decent shops. But if you want local shops, go up to Damen Ave in the Bucktown/Wicker Park neighborhood - there are a lot of cool boutique's which will have stuff that you can't get anywhere else.
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EAT!
As for restaurants, I usually stay away from the bigger places (and downtown for that matter, except for the workweek, since I work downtown), and prefer places in the neighborhoods around town:
There are great Indian restaurants on Devon Ave, and worth the trek up there to see all of the Indian grocers and Bollywood movie stores.
Crust Pizza on Division Street uses all organic and mostly locally-grown ingredients - and is certainly not touristy. And it's just west of Damen Ave., so you could eat and then shop on Damen Ave a few blocks north in Bucktown, stopping through Wicker Park as you walk.
Lula Cafe has an amazing special menu starting at 6pm - and is in my neighborhood of Logan Square. It's hopping in the mornings for breakfast, and at night for dinner.
M.Henry is the best breakfast place in town, hands DOWN! If you're here on a weekend, get there EARLY, and expect to WAIT, but fret not! There's an AWESOME greenhouse called
Gethsemane Gardens a 1/2 block up the street, which has cool plants and AWESOME gifts.
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I'm never ever bored here. I love this city dearly, and am glad to call it home! If you see a dude on a bike with a flashlight clipped in his pocket, that'd be me.
(and look out!)
Good luck and have fun!
:thumbsup: john