Consistently named the best big U.S. city destination for travelers, there’s so much to fall
in love with in Chicago
With a skyline admired worldwide and a river famously dyed emerald green each Saint Patrick’s Day, Chicago blends architectural brilliance, lakefront beauty, global cuisine, and dynamic neighborhoods into one unforgettable urban escape.
Day 1: Art, Architecture, and the Pulse of the City
Morning:
Snap a selfie in Millennium Park at Anish Kapoor’s Cloud Gate (a.k.a. The Bean) with the skyline reflected behind you. Stroll among Lurie Garden’s native plant life before ascending the Renzo Piano-designed Nichols Bridgeway to cross into the Art Institute’s Modern Wing. Here, you’ll find works by Andy Warhol, Jackson Pollock, and Cindy Sherman.
Afternoon:
Meander along the Riverwalk before grabbing a bite at stalls like Tiny Tapp and Chiya Chai or linger for lunch across the river at Pizzeria Portofino for crackly crust pizza. A Chicago Architecture Center river cruise is a great way to learn about the city’s rise as a global powerhouse.
Evening:
The West Loop/Fulton Market District is one of Chicago’s top dining zones. Try gourmet Mexican street food at Taquería Chingón or standout sushi rolls at Noriko Handroll Bar. Cap the night with inventive martinis at Bisous before catching a band at Garcia’s or live jazz at Lazy Bird.
Day 2: Bikes, Boutiques, and Neighborhood Bites
Morning:
The Lakefront Trail from the Gold Coast to Lincoln Park is easily explored using the Divvy Bike cycle sharing system. Visit Green City Market (on Wednesdays and Saturdays in season) for pastries from Bennison’s Bakery, coffee from Kikwetu Kenya Coffee Company, or a gooey grilled cheese sandwich from Gayle V’s.
Afternoon:
Keep pedaling north to “the Friendly Confines” in Wrigleyville to take in a Cubs baseball game and try a famous Chicago hotdog. Another option is to enjoy a sit-down, farm-to-table lunch at Lula Cafe in Logan Square and then browse Milwaukee Avenue’s vintage shops before sampling a flight from Longman & Eagle’s vast whiskey selection.
Evening:
Head south to Pilsen to explore the street murals along 18th Street and the 16th Street railroad embankment, then treat yourself to Mexican fare at 5 Rabanitos followed by a concert at Thalia Hall. Alternatively, head north to Andersonville for an amble along Clark Street (and a detour to Lakewood-Balmoral’s historic homes) before dining on Southern fare at Big Jones. Then catch close-up illusions at Chicago Magic Lounge before closing the night at The Green Mill jazz club.
Day 3: History, Innovation, and Theater
Morning:
In Hyde Park, descend into a coal mine at the Griffin Museum of Science and Industry before strolling the Gothic University of Chicago campus. Grab lunch at French-inspired Plein Air Cafe or Valois, a favorite of former President Barack Obama.
Afternoon:
Find other lunch offerings in West Town at two-Michelin-Starred Kasama, Antique Taco, or Dove’s Luncheonette, then wander the charming boutiques and galleries along Damen Avenue and Division Street.
Evening:
For true Chicago-style pizza (square-cut, thin-crust, tavern style) check out Zarella Pizzeria & Taverna in River North, Pizz’Amici in West Town, or Pat’s Pizzeria in Lincoln Park. End your trip with a performance at one of the city’s world-class theaters: Steppenwolf, the Goodman, Lookingglass, or Chopin.