Chicago’s Old Town was originally called “Cabbage Patch” for the farms that sprung up in the mid-19th century. By the 1960s it was the Windy City’s answer to New York’s Greenwich Village, with funky shops and nightclubs. These days, the independent vibe remains with modern boutiques and restaurants amid the old houses and narrow streets. It’s also the home of the world’s most famous comedy club. And it’s all just a quick trip from the heart of the city.
Day 1: Shopping & Laughs
Breakfast: Kick off your trip with breakfast from Nookies, a family-owned staple since 1973. Enjoy the cozy atmosphere as you savor innovative dishes like the pesto scramble or the crunchy French toast.
Midday: Take a stroll down Wells Street, the beating heart of Chicago’s Old Town. This bustling street is home to shops where you can find quirky gifts (Judy Maxwell Home), something new to read (Slant of Light Books) and contemporary fashion (Sara Jane). Stop by Adobo Grill for margaritas and tableside guacamole along the way, or eat a sweet, hand-made treat from The Fudge Pot.
Evening: Start your night with drinks and dinner at Corcoran’s, where the brisket grilled cheese on Texas toast comes with a tomato bisque for dipping. Then, cross the street and take in a show at The Second City, Chicago’s legendary comedy club. This spot, known for launching the careers of some of the most famous American comedians ever, including John Belushi, Tina Fey and Steve Carell, offers nightly performances of improv and sketch comedy.
Day 2: Explore Art & History
Breakfast: Fuel up for a day of exploring at La Fournette, a charming French bakery. Order the chocolate croissant or ham and cheese croque monsieur and feel yourself being transported to France.
Morning: Enjoy a peaceful start to your day by visiting St. Michael’s Church. Built in 1852, it’s one of the few buildings to survive the Great Chicago Fire. With its towering spires and stunning interiors, it’s an impressive landmark and a tranquil place to visit.
Midday: Spend the afternoon at the Chicago History Museum, where you’ll discover the city’s rich history through informative exhibits and family-friendly activities. For lunch, go to Dog House Grill and sample classic Chicago street food, like the “dragged through the garden” hot dog or the Italian beef sandwich, as made famous by The Bear.
Evening: Try delicious chicken katsu or fresh rainbow rolls from Kamehachi, Chicago’s original sushi bar. After your meal, enjoy a nightcap at Old Town Ale House. Known for its quirky artwork and relaxed dive bar feel, this 1950s local watering hole is a late-night favorite.
Day 3: End With a Bang
Morning: Head a few blocks north into Lincoln Park and grab a quick bite or pick-me-up from Bourgeois Pig, a literary-themed café. Try a scratch-made scone or muffin with a coffee or latte and settle into one of the cozy, book-filled corners.
Midday: Return to Wells Street and comb through keepsakes at one-of-a-kind specialty shops, like The Spice House. The store, which has been in Chicago’s Old Town since 1957, offers high-quality, hand-mixed spices, herbs and blends. Spend happy hour at The Vig, a stylish and trendy spot for dinner and drinks in a casual setting. Try the old-fashioned or take a chance with the featured cocktail of the day. Enjoy happy hour deals on small plates like lobster deviled eggs, oysters and blistered shishito peppers.
Dinner: End your stay the right way at Topo Gigio Ristorante. Toast to your travels with a blend from the extensive wine list and savor classic, warm dishes like the conchiglie alla sarda (seashell pasta in a tomato-cream sauce) or the veal chop alla sassi (veal chop sautéed in wine, mushrooms, artichokes & sage sauce). Finish on a sweet note with the zabaglione chocolate mousse cake or a classic affogato.
