Magical, Offbeat Chicago
August 17, 2017 8:13 AM   Subscribe

I will be visiting Chicago in the fall. Please tell me what gives Chicago its own unique sense of place. Bonus points for places you would take a special person, places with a strong sense of place, things that are highly typical of or unique to Chicago, restaurants with wonderful food, striking or unusual architecture, neighborhoods to explore

Examples: a subway station with a wooden escalator, a store that sells nothing but maps, a beautiful park, a restaurant or corner store that has not changed since the 60s
posted by sleepy psychonaut to Travel & Transportation around Chicago, IL (17 answers total) 27 users marked this as a favorite
driving on Lake Street under the El for miles and miles
the Winter Garden at the HWLC (Loop location public library)
posted by phunniemee at 8:41 AM on August 17, 2017 [1 favorite]

You should definitely go to the DuSable Museum of African American History and visit the nearby Fountain of Time in Washington Park. You can take the red line from downtown. (You should absolutely take the El.)

Also, you could go to the Haymarket Monument and then to the Frank Lloyd Wright studio in Oak Park. The River Forrest graveyard where the monument is located has a lot of other significant graves, including Elizabeth Gurley Flynn's, and it's a sprawling and peaceful place which is oddly nice for an autumnal walk. (I'm not really one for cemeteries - you don't need to be a haunter of graveyards to find this one interesting.) You can easily take the blue line out of the city and then walk to the Frank Lloyd Wright studio.
posted by Frowner at 8:55 AM on August 17, 2017 [2 favorites]

Here's a list of great neighborhood restaurants. If you're looking for an "unchanged since the 60s" vibe, I might also recommend Margie's Candies (old school ice cream parlor where the Beatles went) and Lou Mitchell's (hearty diner breakfasts with free doughnut holes while you wait).

I always recommend American Science & Surplus to people seeking a quirky Chicago experience.

It is fun to take an unsuspecting person for a walk past Shit Fountain.

It's the Year of Public Art in Chicago, and there's a ton of worthwhile stuff to check out, including a Floating Museum and the famous Bean (formally known as Cloud Gate) in Millennium Park.

If your visit happens to coincide with Open House Chicago, there's no better way to see unique and striking architecture. Walking around the Prairie Avenue historic district is also pretty neat.

posted by torridly at 9:08 AM on August 17, 2017 [2 favorites]

Take the red line to Argyle or Berwyn and walk through Andersonville to Simon's Tavern on Clark, enjoy the bar's vintage mural, and drink aquavit, or glogg if it's winter. (The variety of international food in the neighborhood--Mexican bakery to Lebanese grocery and beyond--is unique too!)
posted by esoterrica at 9:10 AM on August 17, 2017

Come during the week of the first Wednesday of the month and we will welcome you into the cabal* at the Billy Goat Tavern, which is itself a quirky chicago cubs place of legend and lore.

*there is no cabal
posted by tivalasvegas at 9:21 AM on August 17, 2017 [2 favorites]

driving on Lake Street under the El for miles and miles

warning, don't do this if you don't like the concept of huge trains overhead, or if the idea of metal beams sticking out of the road makes you nervous.
posted by tivalasvegas at 9:23 AM on August 17, 2017

Go to Happy Village,
get a shot of Malort, and drink $2 Old Styles until the Tamale Guy shows up. Get some tamales and wash them down with more Old Style.
posted by Fig at 9:28 AM on August 17, 2017 [1 favorite]

Millennium Park is a must-see. Volare is some of the best Italian cuisine ever.
posted by DrAstroZoom at 9:54 AM on August 17, 2017

Chicago looks great from the river. For a shorter trip you can take the Water Taxi; for a longer narrated one the Chicago Architecture Foundation does boat tours.

See a movie at the Music Box! For extra atmosphere, see if your visit coincides with their monthly silent film screening complete with live organist.

Unabridged Bookstore is a lovely place, and a few blocks north of it you'll find The Coffee & Tea Exchange, a neighborhood institution worth visiting just for the fragrance.
posted by Fish, fish, are you doing your duty? at 11:02 AM on August 17, 2017 [2 favorites]

There was a fantastic local TV show called "Wild Chicago" that is no longer airing... But lots available online. Might be just what you are looking for. Here's a snippet...
posted by jimmereeno at 12:00 PM on August 17, 2017

Ah... Also, local access show, Chic-a-Go-Go
posted by jimmereeno at 12:08 PM on August 17, 2017 [1 favorite]

The National Museum of Mexican Art is one of my favorite places ever. It's where I take everyone who comes to visit. If you'll be here between Sept 22 - Dec 10 the annual Dia de los Muertos exhibit is gorgeous and powerful. But even if you can't make it for that it is worthwhile for the permanent collection, special exhibits and the gift shop.
posted by Serene Empress Dork at 12:09 PM on August 17, 2017 [1 favorite]

Promontory Point is one of my favorite places in the world!

And a bit farther out but more isolated and very beautiful: the South Shore Nature Sanctuary.

In between those two (take the #6 bus): stop off at 57th St for Powell's Books, Salonica, and/or the Med.

The whole Museum Campus area is great -- it's a mainstream tourist thing to go to the museums but also the whole area is good for wandering around and finding tiny underlooked stuff. Also, amazing views of the lake and city.

The whole lakefront is parkland and walking any stretch of that trail is great -- lots of public art along the way, too.

On the north side, Quimby's is a unique zine store.
posted by anotherthink at 1:22 PM on August 17, 2017 [1 favorite]

In between those two (take the #6 bus): stop off at 57th St for Powell's Books, Salonica, and/or the Med.

Also Valois (pronounced "va-LOYS") which is a diner that has a strong "unchanged since the 60s" vibe, and Woodlawn Tap (pronounced "Jimmy's") which is a bar that is similar. In fact, if 70s counts, I was just talking to someone who was there in the 70s and confirmed the unchanged-ness. And walk out to Promontory Point for one of the most amazing distance views of downtown Chicago. Visit the Museum of Science and Industry too, and wander around the lower levels for some pure retro Chicago goodness.

I was in town recently and spent most of my time in Andersonville which definitely hit a lot of those magical, offbeat notes pretty strongly. There are kitschy antique shops, an awesome feminist bookshop (yes, the name is the inspiration for the Portlandia sketch), pancakes, a Dala Horse, and many other neat things that I enjoyed. More neighborhoods you should check out include Wicker Park, Logan Square, and Belmont, though my memories of specific attractions/activities are more rusty since I last lived in Chicago 5+ years ago.

Hmmmmm what else. Oh, go to an Al's Beef and/or a Harold's Chicken Shack and/or a Portillo's. You could go to Wiener's Circle if you're into that sort of thing. And Wrigley Field is the real deal, it is as retro as they come.
posted by capricorn at 1:51 PM on August 17, 2017 [2 favorites]

People have really good recommendations re: neighborhoods, but the Loop is not lacking for this stuff either.

1) It's cheesy and I probably wouldn't put it in "take a special person" category, but the Macy's (formerly Marshall Field's) on State Street is a Chicago icon. It's the most impressive at Christmas, but architecturally it's cool any time of year.

2) Monk's Pub has not materially changed since the late 70s.

3) And seriously, eating a sandwich under the Picasso is an extremely Chicago thing. Like, when you live here and work downtown, this is what you do on our 7 nice days per year. ;)

4) I would take a special person to Cindy's any day of the week. But make a res!
posted by We put our faith in Blast Hardcheese at 5:15 PM on August 17, 2017 [2 favorites]

Thirding Promontory Point. Bonus points, ride there on the Lakeshore Trail.

Seconding a CAF boat tour - talk about sense of place!

Also the Swedish Museum is tiny and adorable.
posted by raspberrE at 6:47 PM on August 17, 2017

tivalasvegas: "the Billy Goat Tavern, which is itself a quirky chicago cubs place of legend and lore."

A little more on that.
posted by WCityMike at 7:40 AM on August 18, 2017

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