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


    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


    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


    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


    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


    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


    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


    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


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

  • 12. Shoreline Sightseeing


    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


    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


    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


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

  • 16. Wateriders


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

  • 17. Wendella


    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


    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


    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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