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5 Things to Do Around Chicago This Weekend

Celebrate that you finally made it through the week with five awesome events around Chicago this week! Every week we at Dream Town scour the city and handpick five things we’re excited about.

From culture and history, to weird culture and history, to checking out some art and theatre; you’ll have no shortage of things to talk about next Monday.

Fourteen majestic ships from around the world, including Chicago’s 148-foot tall star attraction Windy, gather at Navy Pier for the annual Tall Ships Chicago Festival. This celebration of classic seafaring includes an appearance from the Draken Harald Harfagre, the world’s largest, most authentic Viking warship.

  • When: Wed Jul 27 – Sun July 31
  • Where: Navy Pier (600 E Grand Ave)
  • Hours: see schedule
  • Admission: Parade of Sail Free, other ticketed events prices vary
  • More Info:

If you are a bookworm, here’s an event you won’t want to miss! Enjoy leafing through more than 200,000 used books at Chicago’s biggest book fair, where prices are low and the selection is vast, including cookbooks, music, fiction, art books, children’s literature, collectibles and much more. The event is hosted at the Newberry Library, a world-renowned independent research library that is home to a collection spanning six centuries.

  • When: Thur Jul 28 – Sun July 31
  • Where: Newberry Library (60 W Walton St)
  • Hours: Thur & Fri 12pm – 8pm, Sat & Sun 10am – 6pm
  • Admission: Free
  • More Info:

Chicago neighborhood Jefferson Park plays host to this popular three-day festival. Grab your djembe and head to Jefferson Park, where a drum circle is just one of the many highlights of this annual community festival. Munch on grub from local food trucks, sip on a beer from local breweries or peruse the juried art show.

  • When: Fri Jul 29 – Sun July 31
  • Where: Jefferson Memorial Park (4822 N Long Ave)
  • Hours: Fri 6pm, Sat & Sun 2pm
  • Admission: $5, Seniors over 65 and kids 12 and younger Free
  • More Info:

Independent retailers and national chains in Evanston both set up shop with too-good-to-resist deals on the sidewalks throughout downtown and Chicago/Dempster district. Expect to find great discounts on apparel, shoes, one-of-a-kind accessories and decorative arts, including the best in specialty and hand-crafted goods. In addition to shopping and art, there will be games and kid-friendly art activities set-up in Fountain Square.

  • When: Fri Jul 29 – Sun July 31
  • Where: Downtown Evanston
  • Hours: 10am – 6pm
  • Admission: Free
  • More Info:

What better way to spend the day lounging with friends listening to original music, sipping on margaritas, dancing, and enjoying food from Chicago’s favorite food trucks next to Lake Michigan? This 21-and-over event celebrating that most festive of beverages will also include an evening fireworks show!

  • When: Sat July 30 – Sun Jul 31
  • Where: South Shore Cultural Center (7059 S South Shore Dr)
  • Hours: 12pm – 8pm
  • Admission: 1 Day + Tasting Ticket $15, 2 Day VIP + 4 Tasting
  • More Info:

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