Bar · West Town
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"Run by father-daughter duo Charlie and Jenny Solberg, Rhine Hall specializes in eau de vie, or fruit brandy. In addition to a tasting room, the West Town distillery offers classes, tours, and private events." - Adam Rothbarth
Bar · Andersonville
Nestled in Andersonville, Simon's Tavern is a beloved dive known for its cozy, vintage vibe, extensive beer selection, and the standout seasonal glögg—your go-to for warmth and cheer during those chilly Chicago nights.
9 Postcards
Bar · Bucktown
Royal Palms Shuffleboard Club in Bucktown is a vibrant spot with 11 shuffleboard courts, tropical cocktails, food trucks, and a breezy rooftop bar for laid-back fun.
15 Postcards
Lemon is your cozy neighborhood cocktail bar with a lively vibe, expertly crafted drinks, and a welcoming space for live music and good times.
7 Postcards
Restaurant · Streeterville
Monarch & Lion is a chic new British pub in Streeterville, blending pub classics like fish and chips with Indian twists in a cozy, elegant setting.
10 Postcards
State government office · Loop
The Thompson Center is an architecturally striking government hub in Chicago, featuring a vast rotunda and a lively food court packed with fast-casual dining options and retail shops, making it an active spot for both locals and visitors alike.
1 Postcard
Blues club · South Loop
Dive into Buddy Guy's Legends for blues-infused nights, where you can catch iconic acts, chow on Cajun bites, and sip unique brews in a vibrant atmosphere.
6 Postcards
Hot dog stand · Logan Square
Red Hot Ranch is your go-to spot for delicious smash burgers and Chicago-style hot dogs, all at wallet-friendly prices, served under the L train's clatter.
13 Postcards
Restaurant · Near North Side
New American fare, wines by the glass, cocktails & happy hour in a chic, relaxed dining room.
4 Postcards
Art museum · Streeterville
Nestled just off the Magnificent Mile, the Museum of Contemporary Art dazzles with ever-evolving exhibits, local talent, and a Michelin-worthy café, making it a must-visit for art lovers.
11 Postcards
American restaurant · Near West Side
At the Billy Goat Tavern, a beloved Chicago institution, you can savor thin but satisfying cheeseburgers and hot dogs in a lively, sports-loving atmosphere before heading to the nearby United Center.