Chicago

We’ve compiled the best of the best in Chicago - browse our top choices for the top things to see or do during your stay.

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  • 1. Chicago Architecture Foundation

    Tour–Sight

    The foundation conducts excellent docent-led boat, walking, and bus tours of the Loop and beyond. To get a panoramic view of Chicago's magnificent...Read More

  • 2. Chicago Food Planet Food Tours

    Tour–Sight

    Sample local delicacies like deep-dish pizza, Polish pastries, Chicago-style hot dogs, and Szechuan cuisine on a Near North, Bucktown–Wicker...Read More

  • 3. Chicago Greeter

    Tour–Sight

    Savvy local volunteers run free two- to four-hour walking tours of the city's neighborhoods and areas of interest, such as fashion, film, and...Read More

  • 4. Chicago River Canoe and Kayak

    Tour–Sight

    This company offers a wide variety of trips, from floats among the skyscrapers to sunset paddles to a nearby island. ...Read More

  • 5. Chicago Trolley and Double Decker Co

    Tour–Sight

    This hop-on, hop-off ride takes visitors to many downtown and Loop highlights and allows you the flexibility to stop at attractions that catch...Read More

  • 6. Ernest Hemingway Museum

    Museum/Gallery

    How did the author's first 20 years in Oak Park affect his later work? Check out the exhibits and videos here to find out. Don't miss his first...Read More

  • 7. Federal Reserve Bank of Chicago

    Loop | Tour–Sight

    The facility processes currency and checks, scanning bills for counterfeits, destroying unfit currency, and repackaging fit currency. A visitor...Read More

  • 8. Goose Island Brewery

    Lincoln Park | Tour–Sight

    Follow a brewer on a tour of this well-known Chicago brewery producing handcrafted lagers, ales, and vintage ales. During the tour you'll sample...Read More

  • 9. Graceland Cemetery

    Far North Side | Tour–Sight

    A comprehensive guide available at the entrance walks you by the graves and tombs of the people who made Chicago great, including merchandiser...Read More

  • 10. Kayak Chicago

    Tour–Sight

    Tours focusing on everything from the city's varied architecture to the nighttime skyline are available at this well-regarded outfit. ...Read More

  • 11. Mercury Chicago's Skyline Cruiseline

    Tour–Sight

    This company does Canine Cruises, where dogs are welcome, and a Chicago by Night tour at sunset. ...Read More

  • 12. Shoreline Sightseeing

    Tour–Sight

    Shoreline's been plying these waters since 1939, and has tours of both the river and Lake Michigan. ...Read More

  • 13. Tall Ship Adventures of Chicago

    Tour–Sight

    Adventure and education meet on lake tours that illuminate Chicago's maritime history, the life of lake sailors, and environmentalism. Former...Read More

  • 14. Untouchable Tours: Chicago's Original Gangster Tour

    Tour–Sight

    Your guides, in character as Prohibition era goons, take you on a bus tour through Chicago's checkered mafia past. Though the kitsch factor...Read More

  • 15. Urban Kayaks

    Tour–Sight

    At this popular outfitter you can join 90-minute tours of the main branch of the Chicago River. ...Read More

  • 16. Wateriders

    Tour–Sight

    A "Ghosts and Gansters of Shadytown" tour is one of the unique offerings at Wateriders. ...Read More

  • 17. Wendella

    Tour–Sight

    See the city at dusk on the Chicago at Sunset tour. There's also a river architecture tour and a combined river and lake tour. ...Read More

  • 18. Willie Dixon's Blues Heaven Foundation

    Prairie Avenue | Tour–Sight

    A cadre of music legends, including Etta James, Bo Diddley, Aretha Franklin, Koko Taylor, and John Lee Hooker, recorded here in the former Chess...Read More

  • 19. Chicago Neighborhood Tours

    Tour–Sight

    Get out of downtown to experience Chicago the way the locals do. Combining bus rides and walking, these guided trips introduce visitors to the...Read More

  • 20. Chicago ShopWalk

    Tour–Sight

    Chicago ShopWalk. Shop 'til you drop on one of these specialized trips focusing on local designers and boutiques. Personalized itineraries...Read More

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