Things to do in Chicago
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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: Segway Tour Grant Park, Museum Campus & LakefrontYou’ll glide through Chicago’s best-known sights by Segway with a small group and an easygoing local guide. Expect hands-on training first (don’t worry if you’re new), stops at Grant Park’s Buckingham Fountain, Soldier Field, Museum Campus and Shedd Aquarium — plus plenty of stories and laughs along the way. There’s something about seeing the skyline from a Segway that stays with you.
Chicago Architecture Walking Tour: 90 Minutes Through TimeYou walk through 90 minutes of Chicago's architectural evolution with a certified guide, starting at the Chicago Architecture Center and moving through downtown's most significant buildings from the 1800s to today. The tour includes admission to the Center's galleries, so you can revisit what you learned indoors if you want. Small groups keep the pace manageable, and the entire route is wheelchair accessible.Is it for me?Choose this if you want to understand Chicago's skyline as a timeline rather than just a collection of tall buildings — the certified guide and chronological route do the organizing for you, so you're not trying to remember which era each building belongs to.
Chicago Street Art Tour: Murals and Graffiti on the 606You’ll walk Chicago’s 606 trail with a local guide who knows the city’s street art inside out—expect hidden murals, real stories from artists, and even a surprise coffee stop. The tour ends in Logan Square over food and drinks if you want them. You’ll leave seeing Chicago differently—and maybe noticing colors everywhere after.Is it for me?Book this for an afternoon when you want to see what locals know about Chicago's art scene without spending hours in a museum — the guide takes you straight to the pieces and the stories behind them.
Chicago Private City Tour: Millennium Park & Lincoln Park with PickupYou're picked up at your downtown hotel by a driver and guide who stay with your group for 3-4 hours, stopping at Millennium Park, Lincoln Park, the University of Chicago, and historic neighborhoods while they share Chicago's architectural and cultural history. The car holds up to five passengers, and you're dropped at your preferred downtown location when the tour ends.Is it for me?Right for groups or families who want to see Chicago's main neighborhoods and architecture without managing public transit or following a tour bus schedule—having your own driver and guide means you move at your pace and stop where you choose.
Chicago: Gangsters & Ghosts Walking Tour with HistorianYou’ll walk with a historian through Chicago’s South Loop, hearing gritty gangster stories and ghost legends where they actually happened. Step inside Palmer House’s grand lobby, snap photos under the famous theatre sign, and end outside Congress Plaza Hotel—the city’s most haunted spot. The city feels different when you know what happened beneath your feet.
Chicago: Art Deco Skyscrapers Loop Walking TourYou walk past five Art Deco landmarks in downtown Chicago's financial district with a certified guide who explains the style's origins and geometric details. The ninety-minute tour includes admission to the Chicago Architecture Center galleries, where you can review what you've seen. All stops are wheelchair accessible and the route stays on flat, urban streets.Is it for me?Right for anyone who wants to understand Chicago's 1920s architecture without arranging their own research or navigation — the guide handles the history and the route, so you just show up and look up.
Chicago Gangster Tour by Bus: Prohibition Era SitesChicago's Original Gangster Tour is a guided bus tour through Prohibition-era sites including the St. Valentine's Day Massacre location, Biograph Theater, and Holy Name Cathedral, led by an actor guide who takes on a gangster character. The tour runs roughly two hours and covers the exploits of Capone, Moran, Dillinger and other figures from the 1920s and 1930s. Reservations are strongly recommended.Is it for me?Your gangster guide performs the era's history as you ride past the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral—covering major sites without the walking.
Chicago Walking Tour: 90 Minutes, 12+ BuildingsYou walk past a dozen of Chicago's most recognizable buildings in ninety minutes with a certified guide who explains the architecture and history. Admission to the Architecture Center galleries is included, and the pace leaves room for photos at each stop. Plan for steady walking on city streets—it's the kind of tour that covers ground, which is what fits everything in.Is it for me?A good fit if you want a quick overview of Chicago's most famous buildings without arranging your own route or spending hours in a museum. Ninety minutes is exactly what it takes to see the major landmarks and understand how they fit together on the street.
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 Lakefront Segway Tour: Parks, Skyline & Museum StopsYou’ll roll along Chicago’s lakefront trail on a Segway with a local guide, stopping at Millennium Park for photos, cruising past Grant Park’s fountain, and pausing outside Soldier Field and the Field Museum. Expect laughter, city stories, and a new angle on Chicago’s skyline — all with helmet included.
Chicago Helicopter Tour: 45 Minutes, 3 Passengers, One PriceYou and two others board a helicopter for a 45-minute flight over Chicago's skyline, passing the United Center, Soldier Field, Millennium Park, Navy Pier, and the lakefront museums. Noise-cancelling headsets let you hear the pilot's live commentary, and you get free professional photos before landing. The price is fixed for all three passengers, and parking is included.Is it for me?Right for three people who want a view of Chicago you can't get from the ground and want to split the cost evenly. Plan for the weight requirement—each passenger needs to be under 260 pounds—and know that 45 minutes is enough to see the main landmarks without the flight feeling rushed.
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 Loop Food Tour: Deep-Dish, Hot Dogs & Local GuideYou taste three signature Chicago dishes—hot dog, deep-dish pizza, Italian beef—at local spots in the Loop with a guide who knows the food and the city's history. The walk between stops covers about 1.5 miles at a relaxed pace with regular breaks. Vegetarian options are available if you request them ahead of time. You're back where you started in roughly three hours, full and oriented to one of Chicago's most walkable neighborhoods.Is it for me?A good fit if you want to understand Chicago's food culture through the dishes that built it, guided by someone who actually knows the spots and the stories. Plan for about three hours of walking and eating at a comfortable pace—that's what lets you taste three iconic meals and see the Loop without rushing.
Chicago Architecture: Art Deco Interiors Walking TourYou'll walk inside Art Deco lobbies and corridors in Chicago's Loop and along the Chicago River that most tourists never enter, guided by someone who knows the architectural story behind the geometric details and gleaming materials. The tour covers multiple stops across the 1920s–30s buildings, some recognizable from boat tours, some completely hidden. You skip the sidewalk view and get the real thing.Is it for me?Book this if you've done the Chicago River boat tours and want to actually step inside the buildings you've only seen from the water — the guide takes you where most visitors never go, and the walk works for any fitness level as long as stairs and standing aren't a problem.
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.
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 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 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.
