Collected by Ryan Cirkles
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
26 W Randolph St, Chicago, IL 60601, USA
A combination of sugar and salt, sweet and savory, there's nothing like Garrett's "Chicago Mix"—a combination of caramel corn and cheese popcorn. It's the kind of thing I crave in such a way that it's a good thing I don't live in Chicago....
1616 N Wells St, Chicago, IL 60614, USA
The Second City has come a long way since the small cabaret theater that launched in 1959. As a sketch comedy and improvisational performance theater, the venue has been keeping people laughing for over 50 years. Situated in the historic Old Town...
6836 N Sheridan Rd, Chicago, IL 60626, USA
Ask any local where to try your first real deep-dish pizza and they'll say "Giordanos." It's obviously the best in town. Chicago-style pizza is unique and totally different than what you'll find in Italy. More like a pie, the crust is tall and...
111 S Michigan Ave, Chicago, IL 60603, USA
909 W Belmont Ave, Chicago, IL 60657, USA
Chicago, IL 60626, USA
Pick up your morning coffee at one of the many local coffee shops, and walk to Rogers Beach (known by locals as Lighthouse Beach). The sunrise over Lake Michigan is stunning! Locals fish off the lighthouse pier in the early morning semi-darkness....
220 E Chicago Ave, Chicago, IL 60611, USA
The interior architecture of Chicago’s MCA building is worth the price of admission. Four floors of exhibit halls branch off the central staircase pictured above, and the East and West facing glass walls have unparalleled views over Lake Michigan...
1655 W Cortland St, Chicago, IL 60622, USA
To find the Trap Door Theatre, you walk down a narrow walkway between two white brick walls. A steel door opens onto the kitchen of Jane's Restaurant. A second door leads to a small black box theater. There, for the last 15 plus years, the Trap...
51 W Jackson Blvd, Chicago, IL 60604, USA
Chicago’s beloved South Side hat shop, Optimo, recently opened a downtown location in the historic Monadnock building. A favorite of Johnny Depp and former Mayor Richard Daley, the new shop sells handmade felt fedoras and porkpies that appear to...
565 W Jackson Blvd, Chicago, IL 60661, USA
Lou Mitchell’s diner has been open in the same location since 1923; so long, in fact, that diner patrons witnessed the heyday of Route 66, which started right here next to Union Station. The Chicago city council renamed Jackson Street “Lou...
401 N Franklin St, Chicago, IL 60654, USA
I have two pieces of advice for you regarding the Doughnut Vault: 1. Go early. They open at 8am Tuesday-Friday and 9:30am on Saturdays and if you want a breath of a hope of a chance of getting a doughnut before they sell out, you want to be there...
50 W Randolph St, Chicago, IL 60601, USA
A perfect buttermilk old fashioned donut is fresh and hot with crispy crunchy edges underneath a melting sugary glazy and the minute I’ve eaten one, I’m already dreaming about the next one. Do-Rite hits all these marks with room to spare, which...
4802 N Broadway, Chicago, IL 60640, USA
Open and thriving since 1907, the Green Mill Cocktail Lounge survived both prohibition and ownership by Al Capone in the 20’s. That alone should make you want to visit. Additionally, the plush restored interior hearkens back to its speakeasy roots...
700 S Wabash Ave, Chicago, IL 60605, USA
Buddy Guy’s Legends is a legendary blues bar in Chicago and Buddy Guy himself is still alive, making music and appearances on his own stage. Legends has been open since 1989 and the stage has seen the eclectic likes of Eric Clapton, Keith...
1462 N Milwaukee Ave, Chicago, IL 60622, USA
The “Back to the Future” Delorean in the window is your first indication that this place is awesome. I mean, it has a flux capacitor! Just like it should. If that’s not enough for you, here are a couple more reasons to visit the...
1747 N Damen Ave, Chicago, IL 60647, USA
Hot chocolate isn’t the only thing Mindy’s has going for it, although the varieties are epic. Mexican chocolate with spicy cinnamon, French chocolate made with 72 percent cacao, and Belgian chocolate mixed with mint, chai, and...more...
812 W Belmont Ave, Chicago, IL 60657, USA
Hollywood Mirror is my favorite vintage, retro, tchotchke-filled store of randomness in Boystown. It’s incredibly crowded but amidst the clutter you’ll find Halloween costumes, vintage lunch boxes, Mardi Gras beads, feather boas, 60’s style...
1564 N Milwaukee Ave, Chicago, IL 60622, USA
A good used bookstore is a glorious thing and Myopic is one of the great ones. They have a giant selection of new, used, rare and out of print books on 3 floors, they’re well organized, they're open until 11pm and there’s a store cat! There's also...
Lower, 430 N Michigan Ave, Chicago, IL 60611, USA
Billy Goat Tavern achieved international fame in the 1970’s with a Saturday Night Live skit that mocked the order process and the lack of options. No Pepsi… Coke! No Fries… Chips! The tavern’s been open since 1934 on the lower level of Michigan...
77 E Adams St, Chicago, IL 60603, USA
Russia isn’t the first place that springs to mind when I think of tea but despite my ignorance Russian Tea Time offers a fantastic afternoon tea service. This elegant restaurant offer all the things I’d expect for an afternoon tea like scones with...
738 W Fullerton Ave, Chicago, IL 60614, USA
If you want a quiet chill place for a cup of tea, a sandwich and a book, Bourgeois Pig is your place. Big wood tables, jazz music playing and the largest loose leaf tea selection in Chicago makes this the ideal afternoon destination. The Bourgeois...
1379 N Milwaukee Ave, Chicago, IL 60622, USA
Reckless Records specializes in DVDs, vintage vinyl and used CDs of all kinds from Top 40 music to every obscure band that ever put out an album. The workers at Reckless have a reputation for being the tiniest bit elitist and because of that...
1900 W North Ave, Chicago, IL 60622, USA
Rapid Transit’s bike mechanics are awesome, friendly and helpful and everyone with a bicycle knows that that’s a rare combination in a bike mechanic. They’re dedicated to helping you find the bicycle that fits you and your lifestyle the best,...
1960 N Western Ave, Chicago, IL 60647, USA
Old school ice cream parlor and soda shop with homemade candy and ice cream since 1921 in the same location in Bucktown. I wish the little jukeboxes on the tables worked but clearly it’s not hampering their business as there’s a line out the door...
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