Things to do in Chicago
The unmissables
Most booked
Chicago River Architecture Cruise: 40+ buildings from the water★ 4.84 (17,014) · 1h–1h 30m
Top rated
Chicago: Architecture River Cruise & First Lady Boat Tour★ 4.93 (7,138) · 1h 30m
Best value
Chicago River: 90-Minute Architecture Boat Tour★ 4.71 (10,970) · 1h 30m
Recommended (7)
Chicago River: 45-Minute Architecture Boat Tour★ 4.65 (3,600) · 45mUS$ 28View ›
Chicago Crime Mob Bus Tour: Al Capone, Massacre★ 4.60 (3,558) · 1h 30m–2hUS$ 49View ›
Chicago Skyline Boat Tour: River & Lake Michigan views★ 4.69 (2,443) · 1h 30mUS$ 45View ›
Chicago: Food Walking Tour with Deep Dish Pizza & Hot Dog★ 4.85 (2,314) · 3hUS$ 85View ›
Chicago River: 90-Minute Architecture Cruise & Three Branches★ 4.84 (1,899) · 1h 30mUS$ 37View ›
Chicago Loop: Architecture Interiors Tour & Art Deco★ 4.96 (1,809) · 2hUS$ 35View ›
Chicago: Lake Michigan Sunset Cruise from Downtown★ 4.51 (1,694) · 1h 30mUS$ 45View ›Top rated (10)
Chicago RIB Boat Tour: Navy Pier & Skyline from the waterYou board a small-group RIB boat at Navy Pier and cruise past the Willis Tower, Soldier Field, the Adler Planetarium, and the Vietnam Memorial. Life jackets are included, and the fast-moving vessel keeps the skyline constantly changing as you photograph it. The route covers over 50 acres of waterfront sights in a few hours without requiring a full day.Is it for me?Right for travelers who want to see Chicago's skyline from a perspective you can't get from the street, with photography time built in and a small group keeping the pace manageable. Expect wind and water spray — that's what makes the boat fast and the views unobstructed.
Chicago: Art Institute Private Tour with Skip-the-Line EntryYou’ll walk through Chicago’s Art Institute with a private guide who brings famous works like Nighthawks and America Windows to life. Skip-the-line entry means more time exploring masterpieces (and less waiting). Expect personal stories, unexpected details, and space to linger in front of art that might surprise you.
Chicago: Murder Mystery Walking Tour & True Crime GameYou’ll dive into Chicago’s true crime legends as you play detective on foot, solve clues with your group, interrogate “suspects,” and wander historic neighborhoods from Water Tower Place to Gold Coast. Expect laughter, surprises, and real stories that stick with you long after your mugshot photo goes home with you.
Chicago: Architecture & True Crime Walking Tour HalloweenYou’ll step inside historic landmarks like the Palmer House Hilton and follow your local guide through Chicago’s streets as real-life crime tales unfold around you. Listen for unexpected details and pause at places most tours skip, ending at Chase Tower with its strange architectural twist. This Halloween edition blends eerie stories with city sights — you might catch yourself glancing over your shoulder afterward.
Art Institute Chicago: Skip-the-Line Tour & Impressionist MasterpiecesYou arrive, skip the entry line, and spend 2.5 hours with an expert guide moving through the Art Institute's Impressionist and modern galleries. All entrance fees are covered, the group stays small (max 8 people), and you see the masterpieces that made the museum's reputation without the usual wait or the usual crowd. Bring only a small bag and wear appropriate dress for entry.Is it for me?Book this if you want to see the Art Institute's masterpieces without losing your morning to the entry line, and you'd rather have a guide explain the connections between the paintings than wander the galleries alone.
Chicago Walking Tour: Loop Architecture & Picasso SculptureYou walk 2 miles through Chicago's Loop district with a guide who knows the architecture and history of each building. You enter the Rookery, see the Picasso sculpture, visit the Cultural Center and Chicago Theatre, and learn how the city's most important structures came to be. All fees are included, and the tour takes 2 hours with moderate physical activity required.Is it for me?Book this if you want to understand Chicago's architecture and history without arranging your own walking route — the guide's knowledge of why each building matters is what transforms a walk into an education, and the 2-hour pace keeps it focused enough to actually absorb it.
Chicago: Art Institute Private Tour & Skip-the-Line EntryYou’ll walk straight into the Art Institute of Chicago with your private guide (no waiting in line), hear stories behind masterpieces from Monet to Chagall, and see sunlight spill through Tiffany glass. Expect small surprises, quiet moments, and a chance to really look at art — not just pass by it.
Chicago: Art Institute Early Access Tour & Skip-the-LineYou’ll slip into Chicago’s Art Institute before the crowds, guided by an art historian who shares both famous works and hidden details. See masterpieces like Seurat and Chagall up close in near silence, enjoy skip-the-line access with all admission included, and leave with moments you’ll keep replaying long after you step outside.
Chicago: Gangster & Ghosts Walking Tour with Speakeasy BarsYou’ll walk Chicago’s streets after dark with a local historian as your guide, hearing true crime tales and ghost stories right where they happened. Step inside old speakeasy bars and explore hidden spots like the Pedway while learning about Capone and haunted landmarks. You might not believe everything you hear — but you’ll feel it.
Chicago: Downtown Pizza Tour & Deep Dish vs. Italian StylesYou'll taste four distinct pizza styles—deep dish, Roman, Neapolitan, and artisanal—while walking through River North, Gold Coast, and the Loop with a guide who explains how each one evolved and what makes the ovens and techniques different. Lunch is included, and the whole thing takes about two hours. Come hungry.Is it for me?A good fit if you want to understand Chicago's pizza culture and eat a real lunch without planning which restaurants to hit—the guide's route and the fixed stops take that off your hands. Expect to walk steadily for two hours and eat at four places, which is what makes tasting four different styles possible in one afternoon.
Lowest price (10)
Chicago: American Writers Museum Ticket & Guided TourYou’ll step right into the world of American writers in downtown Chicago—touching vintage typewriters, hearing local guides share stories behind famous names, and playing creative games in interactive galleries. Your ticket includes flexible entry, a free bookmark gift, and the chance to join a complimentary guided tour at 3pm if you want extra context or just someone friendly pointing things out.
Chicago Navy Pier Centennial Wheel: Skip-the-Line TicketYou board the Centennial Wheel with a mobile ticket, skipping the line. From an enclosed gondola 200 feet up, you rotate slowly through 360-degree views of Lake Michigan and Chicago's skyline. Multiple rotations are included, and the enclosed design keeps you comfortable year-round. The ticket gets you straight to the wheel without stopping at the box office.Is it for me?Pick this if you want the Chicago skyline and lake view without standing in a ticket line — the mobile entry is what saves you 15 to 20 minutes and gets you straight into a gondola.
Chicago: Griffin Museum of Science & Industry AdmissionYou get admission to the Western Hemisphere's largest science museum, housed in an 1893 World's Fair building. Walk through a 40-foot tornado chamber, board a WWII submarine, descend into a simulated coal mine, and climb a human-sized hamster wheel — all included in your entry. The museum is hands-on by design, wheelchair accessible, and offers underground parking near downtown Chicago.Is it for me?Pick this if you want a full day of hands-on learning without planning multiple stops — everything is under one roof, admission covers all exhibits, and the museum is built for doing, not just looking.
Chicago Ghost Tour: Lincoln Park Haunted HistoryWindy City Ghosts runs a nightly walking ghost tour through Lincoln Park, Chicago's North Side neighborhood built atop a Civil War burial ground. A live English-speaking guide takes you through five stops—Julia Porter Park, the Alphawood Foundation Building, the Red Lion Pub, the Biograph Theater and Oz Park—sharing documented accounts of hauntings, paranormal encounters and the city's gangster past. The tour lasts about an hour and covers intensely researched true stories tied to each location.Is it for me?Book this tour if you have a free evening and want to learn Chicago's hidden history through the paranormal stories tied to real sites—the 60-minute walk stays in one neighborhood, so you're not traveling far from Lincoln Park.
Chicago: Flyover at Navy Pier 30-Min Flight SimulationYou spend 30 minutes in a motion-enabled theater at Navy Pier watching drone and helicopter footage of Chicago's skyline, lakefront and architecture while scents and surround sound pull you into the experience. Admission and an immersive audio guide are included. It's a short, high-intensity experience that works best if you're comfortable with motion and want a different angle on the city without leaving downtown.Is it for me?Book this if you want a concentrated, high-sensory look at Chicago's architecture and geography without spending hours on a tour — the 30-minute format and motion design are what pack the experience into a single stop at Navy Pier.
Field Museum Chicago: SUE T. Rex & Egyptian Mummies TicketsYou get admission to all permanent exhibitions—SUE, the Egyptian mummies, the Gem Hall, Dinosaur Hall, and the Ancient Americas—plus access to free daily docent-led tours. The museum spans nearly half a million square feet of gallery space, is fully wheelchair accessible, and opens at 9am daily. Arrive early to avoid crowds and secure a spot in the 3D theater if that interests you.Is it for me?Right for anyone visiting Chicago who wants to see major natural history collections in one place without planning multiple stops—the Field Museum's scale and range mean you get everything from dinosaurs to mummies to gems under one roof, and the free tours help you understand what you're looking at if you want that context.
Chicago: Drunk Shakespeare Show Tickets & Craft CocktailsYou’ll laugh hard as one actor braves five shots of whiskey before tackling Shakespeare live in Chicago’s Loop. Expect improv chaos, real audience interaction, and a special treat on arrival. The whole thing feels part party, part play — you might even forget you’re at the theater until you’re quoting lines on your walk home.
Chicago Theatre: Behind-the-Scenes Tour & Stage AccessYou get a fully guided 60-75 minute walk through the Chicago Theatre's grand lobby, auditorium, and stage, with access to backstage areas and dressing rooms where performers left their signatures. Your guide explains the French Baroque architecture and the theatre's history from 1921 onward. The tour doesn't happen on concert days, so book around event schedules.Is it for me?Book this if you want to see inside one of Chicago's landmark theatres without arranging your own research or timing — the guide handles the history and the backstage access, which is what makes the artist signatures and the stage itself feel like more than just a room.
Chicago Skyline Boat Tour: 30–45 minute Lake Michigan cruiseYou board a Lake Michigan sightseeing cruise and listen to pre-recorded commentary about Chicago's skyline, major skyscrapers, and lakefront landmarks as the boat moves along the water. The cruise lasts 45 minutes in warmer months and 30 minutes from November through April. An onboard bar serves drinks, you can bring your own food, and the boat is dog-friendly with restrooms available.Is it for me?Book this if you want to see Chicago's skyline from the water without arranging separate transportation or timing — the boat handles the route, the narration covers the history, and you just show up and look.
Chicago: Mob & Ghost Walking Tour in the Loop at NightYou’ll walk Chicago’s Loop as night falls, tracing mobster footsteps under the “L,” hearing chilling stories outside haunted hotels, and exploring infamous alleys with your local guide. Expect laughter, shivers, and details you won’t forget—the city feels different after this tour.
