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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.
Chicago: 90-Minute River & Lake Cruise with Skyline ViewsYou board at the dock, spend 90 minutes on the Chicago River and Lake Michigan with a live guide pointing out Marina City, the Wrigley Building, Grant Park, Soldier Field, and the Field Museum from the water, then return to shore. No walking required, all ages welcome, and the commentary is included. Discounted parking is available nearby if you're driving in.Is it for me?Right for families or anyone wanting to see Chicago's main landmarks without walking or arranging transport between sites. The 90 minutes is enough to cover the river and lake sections without feeling rushed, and the fixed schedule means you don't have to plan the route yourself.
Chicago Small Group Tours: Museum Campus skyline viewsYou ride in a 13-person minibus with an expert guide who handles the driving and the stories. You stop at four photo spots including The Rookery, Museum Campus (for the skyline view), Buckingham Fountain (seasonal), and either Millennium Park or Lincoln Park depending on the time of year. The whole tour takes about three hours, and you can ask the driver to drop you at Millennium Park at the end if you want to explore The Bean on your own.Is it for me?A good fit if you want Chicago's main landmarks and skyline views without navigating the city yourself — the minibus and guide handle the route, timing, and stories. Expect about three hours out, which is what fits all the major stops and photo time into one morning or afternoon.
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: 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.
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: Pedway Underground Tour & Loop ArchitectureYou'll navigate Chicago's underground Pedway tunnel system with a local guide, moving through 40 blocks of downtown while ducking in and out of buildings like City Hall, the Chicago Cultural Center, and the old Marshall Field's. You'll see the Chicago Picasso from street level, learn the routes most locals don't use, and finish with the knowledge to keep exploring the city's hidden passages on your own. The tour runs rain or shine and takes a few hours of steady walking.Is it for me?Book this if you want to see downtown Chicago's architecture and hidden spaces without arranging your own route through the tunnels — the guide handles the navigation and the building access, which is what makes it possible to see interiors most visitors never find.
Chicago Night Crimes Tour: St Valentine's Day Massacre & Gangster SitesYou ride a climate-controlled bus through Chicago's mob neighborhoods, stopping to walk the sites where Al Capone, John Dillinger, and Hymie Weiss operated and died. The tour includes entry to Nitti's Vault, historic video footage, a crime quiz, and a keepsake pamphlet with photos. It runs 2 to 2.5 hours and departs from Michigan Avenue and Pearson Street, so arrive fifteen minutes early.Is it for me?Book this if you want Chicago's mob history told on the actual streets where it happened, with stops to walk the crime scenes themselves — the fixed 2.5-hour schedule and included guide mean you don't have to research the stories or navigate the neighborhoods alone.
Chicago: Historic Fireboat River & Lake Cruise with ArchitectureYou board a working 1937 fireboat and cruise Chicago's river and Lake Michigan while a guide walks you through the city's fire history and architecture from angles you won't see from land. Onboard bathrooms, expert narration, and memorabilia from the boat's 44 years in service are included. Parking is steps from the dock.Is it for me?Book this if you want Chicago's river and lake in one outing without arranging separate boat tours, and you're interested in the city's working history rather than just its buildings—the fireboat angle is what sets this apart from standard architecture cruises.
Chicago: Neighborhood Pizza Bus Tour & Historic PizzeriasYou’ll ride through Chicago’s neighborhoods with a local guide, tasting everything from classic deep dish at Pizano’s to caramelized-crust pies at Pequod’s and coal-fired slices near United Center. Expect stories, laughs, and a full stomach as you discover why pizza means so much here — plus bus transport and four generous slices included.
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.
Chicago Architecture Walking Tour: Burnham & Sullivan LandmarksYou walk Michigan Avenue and State Street with a certified guide, stopping at six major buildings from Chicago's 1890–1930 boom: the Wrigley Building, Palmer House, Carbide and Carbon Building, Reliance Building, and Chicago Cultural Center. Admission to the Architecture Center galleries is included. The tour takes about two and a half hours and covers the architects—Burnham, Sullivan, Holabird and Roche—who defined the city's look.Is it for me?This tour works well if you want to understand Chicago's architecture and the architects behind it without arranging your own research or transport between sites—the guide handles the history and the route, so you just walk and listen.
Escape Room Chicago: 5 Themed Puzzle Games in River NorthThe Escape Game Chicago is a live-guide escape room experience in River North with five themed adventures—Prison Break, Mission: Mars, Special Ops, The Heist, and Legend of the Yeti—where teams of up to eight work together to find clues and solve puzzles within 60 minutes. Each game is family-friendly and non-scary, with a dedicated guide on hand to help. An adult must accompany anyone 14 and under, and the location sits steps from Michigan Avenue with restaurants and bars within walking distance for a full night out.Is it for me?Book this if your group wants to solve puzzles together in a single room rather than wander a building hitting multiple locations—the locked-door format and one-hour time limit keep everyone focused on the same mission. The five different themes mean you can pick based on whether you want sci-fi (Mission: Mars), heist (The Heist), espionage (Special Ops), survival (Legend of the Yeti), or prison escape (Prison Break), so the same venue works for repeat visits with different games.
Paint your own street art in Chicago: Spray paint workshopStudio W.I.P. in Chicago is a 90-minute street art painting workshop where you learn spray paint, stencil and graffiti techniques from local artists, then create your own work on canvas to take home. The class is BYOB, suitable for ages 10 and up, and all materials and instruction are included; you bring the drinks and the willingness to get paint on your hands.Is it for me?If you have a free afternoon in Chicago and want to make something instead of watching someone else make it, this workshop puts a spray can in your hand and sends you home with proof you did it. The 90 minutes is short enough to fit into a day without planning around it, and the BYOB setup means you control the vibe.
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 Lakefront Segway Tour: Grant Park & Museum CampusYou arrive early, train for 15 minutes, then spend two hours gliding 6–8 miles past Buckingham Fountain, the Field Museum, Shedd Aquarium, and Soldier Field with a guide who keeps groups to eight people. You get the lakefront and Museum Campus without arranging transport or walking the whole distance, and you stop long enough to actually see things instead of just passing them.Is it for me?Book this if you want to cover Chicago's main lakefront attractions in two hours without renting a car or walking the whole distance — the Segway does the distance, the guide does the knowledge, and the small group size means you're not lost in a crowd.
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: Haunted Pub Crawl & Ghost Stories Walking TourYou’ll follow a costumed local through Chicago’s most storied bars on this haunted pub crawl & ghost tour. Sip drinks where gangsters once hid out, walk past shadowy alleys near Biograph Theater, hear chilling tales in Lincoln Park, and end up swapping laughs (and maybe shivers) with fellow travelers under city lights.
Chicago Bike Tour: Lakefront, Museum Campus & City IconsYou’ll pedal along Chicago’s Lakefront Trail with a local guide, stopping for stories at places like Millennium Park and Soldier Field. Feel lake breezes as you pass Grant Park and catch glimpses of Cloud Gate up close. This city bike tour includes your bicycle and helmet—just show up ready for an easygoing ride full of real-life moments and local color.
Chicago Lakefront Bike Tour: Neighborhoods, Trail & Local GuideYou’ll ride through Chicago’s north side neighborhoods with a local guide, see Gold Coast homes, pedal beside Lake Michigan on the Lakefront Trail, and pause for moments at Lincoln Park Zoo and Old Town’s historic corners. Expect laughter, unexpected details, city sounds—and maybe a squirrel sighting or two.
