Collected by Anna
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...
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...
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...
909 W Belmont Ave, Chicago, IL 60657, USA
800 N Michigan Ave, Chicago, IL 60611, USA
Outfitted in turquoise and chocolate patterned decor with a stellar view from the Park Hyatt Hotel’s 7th floor, NoMI is a cool tranquil oasis in the midst of the shopping extravaganza that is Michigan Avenue. And yes, it’s just as chic and swanky...
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...
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...
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...
1138 W Bryn Mawr Ave, Chicago, IL 60660, USA
Lovely, Too is a delightful little bakery up in Andersonville. They serve Intelligensia coffee, a Chicago brand, and their pastry case is drool worthy with incredible scones, cookies and cupcakes. It's rarely crowded and there are plenty of tables...
951 Chicago Ave, Oak Park, IL 60302, USA
Frank Lloyd Wright built 700+ houses all over this nation but he lived and worked in Oak Park, just a 45 minute train ride from the city center of Chicago. His house and studio are now a museum with guided tours that let you see the playroom he...
78 E Washington St, Chicago, IL 60602, USA
Chicago's art scene is often overshadowed by the ever-increasing foodie scene but the Windy City offers just as much contemporary and historical art as pizzas and gourmet doughnuts. The Chicago Cultural Center is one of my favorite art-focused...
4839 N Western Ave, Chicago, IL 60625, USA
Tucked away behind an unassuming storefront you will find a shop with a misnomer of a name: Ravenswood Used Bookstore (it's located in Lincoln Square, not Ravenswood). Our hero and proprietor, Jim, has gathered such an incredible collection of...
517 Market St, Metropolis, IL 62960, USA
DC Comics proclaimed Metropolis, IL the official hometown of Superman; so, if you or your kids are fans of this superhero, you definitely want to get in the car and spend a day in Metropolis. Visit the Super Museum to see comics, Hollywood props,...
Picnic Rd, Herod, IL 62947, USA
Get everyone outdoors and spend a day hiking, climbing and picnicking in one of Illinois’ most beautiful parks. Garden of the Gods is part of the Shawnee National Forest and has 5.5 miles of interconnected trailways meandering around beautiful...
875 N Michigan Ave, Chicago, IL 60611, USA
Watch the Chicago city lights come up as the sun goes down at the the Signature Lounge. While the Observatory on the 97th floor is a popular spot, you'll have an even more memorable experience lounging, cocktail in hand, overlooking the same...
Old Town, Chicago, IL, USA
Located a short train ride from the Loop, this wrought-iron doorway marks the entrance to Chicago’s Old Town. You'll find plentiful shopping and restaurant options in the neighborhood, as well as St. Michael’s Church, one of the city's oldest...
4803, 505 N State St suite 101, Chicago, IL 60654, USA
I had one of the most delicious drinks I've yet had the pleasure of experiencing at Sable. Chicago knows its mixology, and I was lucky to have insiders lead me to this bar located inside the swank Palomar Hotel on North State Street. Their head...
1633 N Halsted St, Chicago, IL 60614, USA
Balena offers hand-made Italian food and delicious cocktails in a prime location right next to the Royal George and the Steppenwolf theatres. Recently voted one of the top 21 Italian restaurants in the US by Thrillist, all of Balena’s pasta...
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