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Things to do in Chicago

Even the most world-weary traveler will find countless cool things to do in Chicago. The Windy City is renowned for its great urban landscape (elevated train, soaring skyscrapers, historic parks, and storied waterfront), but there are also a host of attractions and activities to enjoy—shopping on Magnificent Mile, walking trails along the shores of Lake Michigan, concerts at Millennium Park, baseball games at Wrigley Field, the comic improv stylings of Second City—from Downtown and the Gold Coast to Lakeview, Lincoln Park, The Loop, and Logan Square.

Don’t know what to do in Chicago? Check out T+L’s travel guide, which features listings for everything from docent-led tours by boat with the Chicago Architecture Foundation and cooking classes to funky design boutiques, old-fashioned apothecaries, even a bakery devoted to savory cupcakes. Chicago is a big drinking town; T+L also points you to the city’s best watering holes—classic bars, brew houses, and places where mixology is elevated to high art. If you go for cutting-edge cuisine, vibrant neighborhood scenes, or world-class art and architecture, our travel guide is your resource for planning the ultimate Chicago getaway.

  • 2nd Fridays Gallery Walk

    What could be better than spending a Friday evening exploring the eclectic galleries of the Chicago Art District? How about socializing with the ar... More
  • 57th Street Books

    The non-academic sister store to the Seminary Co-op, 57th Street Books is located underground in an unassuming red-brick building in Hyde Park. Ins... More
  • Alternatives Shoes

    Located in a very popular shopping area along North Michigan Avenue, Alternatives not only stays ahead of current trends, but has been know to insp... More
  • Andrea Sertoli

    Whether you are hoping to hit the “Big 3” (Rome, Florence and Venice) with tots in tow, sample phenomenal wines in the alluring region of Apulia, o... More
  • Apartment Number 9

    Style-savvy men frequent this Bucktown clothing boutique to find the latest fashions from both established and emerging designers. Owned by sisters... More
  • ArchiCenter

    Housed in the 1904 Santa Fe Building designed by Daniel Burnham, the Chicago Architecture Foundation’s ArchiCenter features temporary exhibits as w... More
  • Arts Club of Chicago

    In operation since 1916, the Arts Club of Chicago hosts three public art exhibits each year in its gallery space on East Ontario Street. The buildi... More
  • Beansprout

  • Belly Dance Maternity

    Even celebrities like Julia Roberts and Naomi Watts have relied on this boutique for stylish, non-frumpy maternity clothes. Located in Wicker Park,... More
  • Big City Swing

    Whether you’re hoping to master complicated dance floor dips or simply tame your two left feet, Big City Swing has you covered with well-priced dan... More
  • Binth

  • Blake

    Eleven months out of the year, this unassuming River North storefront goes unadorned, with no signage, no merchandise displays and a hard-to-find e... More
  • Book Cellar

    Quality over quantity is the rule of thumb at this small, independently owned bookstore in Lincoln Square. Behind a glass storefront brightened by ... More
  • Carole Cambata

    Top tip: Don’t miss early morning prayers at the Thiksey monastery, near Leh, in northern India. “When the prayers end, the younger monks suddenly ... More

Explore things to do in Illinois for more options.

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