Top 10 Things to Do in Chicago

The Art Institute of Chicago is consistently ranked among the world's top five art museums, housing an encyclopaedic collection of over 300,000 works including Georges Seurat's A Sunday on La Grande Jatte, Grant Wood's American Gothic, and Edward Hopper's Nighthawks. The Modern Wing designed by Renzo Piano is a masterpiece of museum architecture. Admission is $35 for adults; free on most Thursdays evenings. Allow at least four hours — the Impressionist and Post-Impressionist galleries alone deserve two.

Chicago invented the skyscraper and its riverine cityscape is a living textbook of architectural history. The Chicago Architecture Center runs 90-minute boat tours along the Chicago River that pass over 40 landmark buildings with expert commentary from volunteer docents. Tours run from May through November and cost around $55. The view of the canyon of buildings from water level is completely different from street level — you see facades, water gates, and bridges invisible from the sidewalk. Book in advance for summer weekends.

Chicago's deep-dish pizza is not merely food — it's a civic institution. The thick, buttery crust is layered with cheese first, then toppings, then crushed tomatoes on top, and baked in a round steel pan until the crust is golden and the filling is bubbling. The three essential stops for a proper tasting: Lou Malnati's (the purist choice, Butter Crust), Giordano's (stuffed style, extra deep), and Pequod's (caramelised crust, the cult pick). Expect a 45-minute wait for a pie to bake — it is worth every second.

Navy Pier is Chicago's most visited attraction — a 1 km pier jutting into Lake Michigan with a 196-foot Ferris wheel, a Shakespeare Theatre, an IMAX cinema, the Chicago Children's Museum, a beer garden, and restaurants with panoramic lake views. Entry to the pier is free; individual attractions cost extra. The Centennial Wheel at night, with the skyline behind it, is one of Chicago's most photogenic sights. Free fireworks launch from the pier every Wednesday and Saturday night in summer.

Wrigley Field is the second-oldest Major League Baseball park in America, opened in 1914 and home to the Chicago Cubs. The ivy-covered brick outfield walls, the hand-operated scoreboard, and the rooftop bleachers on Waveland Avenue are beloved American sports traditions. Even if you're not a baseball fan, attending a Cubs game for the atmosphere is a bucket-list experience. Tours of the park run year-round; game tickets range from $20 for bleacher seats to $200+ for premium sections.

The 606 is an elevated rail trail converted from an abandoned freight line — Chicago's answer to the New York High Line, running 4.5 km through the Wicker Park, Bucktown, and Humboldt Park neighbourhoods. It's beloved by cyclists, runners, and dog walkers and lined with public art installations. The western end in Humboldt Park gives access to Puerto Rican cultural restaurants and the beautiful lagoon. Rent a bike from a Divvy station and ride the full length; the elevated perspective through the tree canopy is beautiful.

The Field Museum houses one of the most extensive natural history collections in the world — over 40 million specimens across anthropology, botany, geology, and zoology. Its most famous resident is Sue, the largest and most complete T. rex skeleton ever discovered. The Egyptian collection with its genuine mummies, the Underground Adventure shrunken-world exhibit, and the Pacific collection are all exceptional. Admission is $30; the Experience Chicago pass combines it with the Shedd Aquarium and Adler Planetarium at a discount.

Chicago electric blues — the amplified, urban sound developed by Muddy Waters, Howlin' Wolf, and Little Walter after the Great Migration — is one of America's defining musical traditions, and the South Side still carries its living flame. Buddy Guy's Legends in the South Loop is the best-known venue, with Buddy himself often appearing unannounced. Rosa's Lounge in Logan Square is the authentic neighbourhood pick. Multiple clubs host live blues seven nights a week; cover charges typically run $10–20.

The Chicago Riverwalk is a beautifully designed pedestrian promenade running along the south bank of the Chicago River from Lake Street to Lake Michigan — about 1 km of cafes, kayak rentals, river tours, and architectural views from water level. It's one of the best free public spaces in any American city. Kayak Chicago rents stand-up paddleboards and kayaks here; grabbing a drink at the outdoor beer garden while watching tour boats pass beneath the skyscrapers is a quintessentially Chicago experience.

The Art Institute of Chicago is consistently ranked among the world's top five art museums, housing an encyclopaedic collection of over 300,000 works including Georges Seurat's A Sunday on La Grande Jatte, Grant Wood's American Gothic, and Edward Hopper's Nighthawks. The Modern Wing designed by Renzo Piano is a masterpiece of museum architecture. Admission is $35 for adults; free on most Thursdays evenings. Allow at least four hours — the Impressionist and Post-Impressionist galleries alone deserve two.

Chicago invented the skyscraper and its riverine cityscape is a living textbook of architectural history. The Chicago Architecture Center runs 90-minute boat tours along the Chicago River that pass over 40 landmark buildings with expert commentary from volunteer docents. Tours run from May through November and cost around $55. The view of the canyon of buildings from water level is completely different from street level — you see facades, water gates, and bridges invisible from the sidewalk. Book in advance for summer weekends.

Chicago's deep-dish pizza is not merely food — it's a civic institution. The thick, buttery crust is layered with cheese first, then toppings, then crushed tomatoes on top, and baked in a round steel pan until the crust is golden and the filling is bubbling. The three essential stops for a proper tasting: Lou Malnati's (the purist choice, Butter Crust), Giordano's (stuffed style, extra deep), and Pequod's (caramelised crust, the cult pick). Expect a 45-minute wait for a pie to bake — it is worth every second.

Navy Pier is Chicago's most visited attraction — a 1 km pier jutting into Lake Michigan with a 196-foot Ferris wheel, a Shakespeare Theatre, an IMAX cinema, the Chicago Children's Museum, a beer garden, and restaurants with panoramic lake views. Entry to the pier is free; individual attractions cost extra. The Centennial Wheel at night, with the skyline behind it, is one of Chicago's most photogenic sights. Free fireworks launch from the pier every Wednesday and Saturday night in summer.

Wrigley Field is the second-oldest Major League Baseball park in America, opened in 1914 and home to the Chicago Cubs. The ivy-covered brick outfield walls, the hand-operated scoreboard, and the rooftop bleachers on Waveland Avenue are beloved American sports traditions. Even if you're not a baseball fan, attending a Cubs game for the atmosphere is a bucket-list experience. Tours of the park run year-round; game tickets range from $20 for bleacher seats to $200+ for premium sections.

The 606 is an elevated rail trail converted from an abandoned freight line — Chicago's answer to the New York High Line, running 4.5 km through the Wicker Park, Bucktown, and Humboldt Park neighbourhoods. It's beloved by cyclists, runners, and dog walkers and lined with public art installations. The western end in Humboldt Park gives access to Puerto Rican cultural restaurants and the beautiful lagoon. Rent a bike from a Divvy station and ride the full length; the elevated perspective through the tree canopy is beautiful.

The Field Museum houses one of the most extensive natural history collections in the world — over 40 million specimens across anthropology, botany, geology, and zoology. Its most famous resident is Sue, the largest and most complete T. rex skeleton ever discovered. The Egyptian collection with its genuine mummies, the Underground Adventure shrunken-world exhibit, and the Pacific collection are all exceptional. Admission is $30; the Experience Chicago pass combines it with the Shedd Aquarium and Adler Planetarium at a discount.

Chicago electric blues — the amplified, urban sound developed by Muddy Waters, Howlin' Wolf, and Little Walter after the Great Migration — is one of America's defining musical traditions, and the South Side still carries its living flame. Buddy Guy's Legends in the South Loop is the best-known venue, with Buddy himself often appearing unannounced. Rosa's Lounge in Logan Square is the authentic neighbourhood pick. Multiple clubs host live blues seven nights a week; cover charges typically run $10–20.

The Chicago Riverwalk is a beautifully designed pedestrian promenade running along the south bank of the Chicago River from Lake Street to Lake Michigan — about 1 km of cafes, kayak rentals, river tours, and architectural views from water level. It's one of the best free public spaces in any American city. Kayak Chicago rents stand-up paddleboards and kayaks here; grabbing a drink at the outdoor beer garden while watching tour boats pass beneath the skyscrapers is a quintessentially Chicago experience.