The Chicago Classics Tour
Our most popular private Chicago tour hits every must-see icon — Millennium Park and Cloud Gate (The Bean), the Magnificent Mile from the Wrigley Building to the John Hancock Tower, Willis Tower (Sears Tower) Skydeck, Navy Pier and its Ferris wheel, Buckingham Fountain, the Museum Campus (Field Museum, Shedd Aquarium, Adler Planetarium), and Soldier Field. 4–6 hours, fully chauffeured, with stops timed so your group has room to explore each site without the parking, traffic, or tour-bus crowds. Flat-rate pricing for up to 14 passengers.
Chicago Architectural & Neighborhood Tours
Chicago is the birthplace of the skyscraper, and our architectural tour takes you past every legendary building — the Tribune Tower, the Rookery, the Monadnock, the Wrigley Building, the Marina City corncobs, and dozens more — paired with drives through the city's most distinctive neighborhoods: the Gold Coast's historic mansions, Lincoln Park and its DePaul campus, Wicker Park's boutique-lined streets, Pilsen's vibrant murals, the Loop's Art Deco towers, and Bucktown / Logan Square for the foodie scene. Perfect for first-time visitors, architecture enthusiasts, and history buffs.
Chicago Sports & Stadium Tours
Headed to Wrigley Field for a Cubs game, Soldier Field for the Bears, the United Center for Bulls or Blackhawks, or Guaranteed Rate Field for the White Sox? Our stadium tour and game-day car service covers every Chicago venue with flat-rate pickup and drop-off, tailgate-friendly Sprinter party buses for groups, and a chauffeur who knows where to park (and where to pick you up after the seventh-inning stretch). Combine with a stop at Harry Caray's, Gibsons, or any classic Chicago pre-game institution.
Chicago Food, Brewery & Pizza Tours
Chicago's food scene deserves a day of its own. Our private food tour hits deep-dish classics (Lou Malnati's, Pequod's, Giordano's), Italian beef stops (Al's #1, Portillo's), hot dog shrines (Portillo's Char-Dog, Superdawg), and for drinks: craft breweries (Revolution, Half Acre, Goose Island taproom), cocktail bars in River North, and the speakeasies of Logan Square. Chauffeur included, designated driver guaranteed, and no missing the 30-minute-wait-for-pizza ordeal.
Family Tours: Zoos, Museums & Kid-Friendly Attractions
Traveling with kids? Our family Chicago tour loops through Lincoln Park Zoo (free!), the Museum of Science and Industry, Shedd Aquarium, the Field Museum, Navy Pier's Children's Museum, the Lincoln Park Conservatory, and Maggie Daley Park. Car seats available on request, and our chauffeurs keep the day stress-free so parents can actually enjoy Chicago with their family.
Custom Chicago Tours — Weddings, Bachelorettes, Corporate Events
Hosting out-of-town wedding guests? Our wedding guest tour packages bring the whole party together. Planning a Chicago bachelorette weekend? Our Sprinter party bus tours of rooftops, wineries, and Wicker Park nightlife are unforgettable. Corporate retreat or client entertainment? Our executive tour option pairs a luxury SUV or Sprinter with a curated route — architectural cruise on the river, dinner at Alinea, drinks at the Signature Room. Every Chicago tour is fully customizable.
