TOP 15 Things to Do This Weekend in Chicago – July 20-22

Looking for things to do this weekend of July 20-22 in Chicago?  There’s no shortage of things to do for this weekend in and around Chicago! But if you’re in need of ideas, we’ve got you covered.  Here would be our picks for the weekend.


Without a doubt, one of the best deals of the city is its free Chicago Greeter program. A local volunteer will take up to six people (more if it is one family) on a tour of whatever interests them. There are more than 40 themes to choose from (including antiques, churches, public art to the zoo.) Or, if a specific neighborhood interests your group, that’s fine, as well.

Whether it’s Little Italy, North Michigan Avenue or The Loop, or anywhere in between, there’s a local waiting to take you. Reservations can be made as much as a week in advance (877-244-2246 or If that’s too much trouble, visit the Chicago Cultural Center (78 E. Washington St., 312-744-6630), and see if an InstaGreeter is available. You can get a one-hour, free tour of the downtown area, which is a great get-acquainted-with-the-city tour.



The skinny: The Chicago Human Rhythm Project (CHRP) is celebrating Rhythm World, the 28th annual festival of tap and percussive dance, with performances at Navy Pier, Studebaker Theater and other locations, as well as intensive educational programs.

  • WHEN: July 16-22
  • WHERE: Various Locations
  • COST: Free-$55



  • Divvy is offering free Explorer Passes, good for an unlimited number of 3-hour rides within a 24 hour period, this Saturday. Enter code NOOSA18 in the Divvy app on Saturday, July 21. (Noosa Yoghurt is sponsoring the passes.)



This three day fine art festival takes place on Chicago’s famous Michigan Avenue at the base of the iconic Chicago Tribune building overlooking the Chicago River. Admission to the festival is free and open to the public.  About 120 juried artists will be featured at this “all art” show.

  • WHEN: July 20-22
  • WHERE: Near North Side
  • COST: Free



  • Rising nearly 18 feet above street level, The 606 (which takes its name from the common numerals for all Chicago ZIP codes) officially opened in June 2015 on Chicago’s west side, bringing together nature, science and culture and significantly adding to Chicago’s urban playground.    The 2.7-mile elevated park and trailway provides bike and jogging paths, as well as ample green space, while connecting neighborhoods through the reuse of an old industrial rail line and re-purposed bridges.
  • The opening of The 606 is a big win for the expansion of Chicago’s open green spaces, motivating visitors to get active and also to explore hip neighborhoods along The 606 — the park and trail system connects the vibrant communities of Wicker Park / BucktownLogan Square and Humboldt Park.   Get above traffic and discover this year-round city treasure with a walk or picnic in one of the street-level parks. Run the dog or take a family bike ride. Snap selfies from the numerous scenic look-out points, visit the seasonal observatory and take in colorful public art murals and sunsets.


  • A playful sprinkling of four ground-level parks make for abundant pit stops to relax, toss a Frisbee or enjoy a picnic. Julia de Burgos Park whimsically includes a flower-filled poetry garden and will host poetry readings.   The 606 Trail is a beautiful way to spend a quiet (if busy) tree-lined stroll the city this weekend, but if you’re up for some exploring, part of the 606 is the southern boundary of the Logan Square neighborhood. Ji Suk Yi has explored Logan Square for our ‘The Grid’ series.   Special note: there’s a free concert along the 606 on Thursday, June 19th starting at 7:30pm at the Milwaukee and Leavitt park area.
  • WHEN: Open every day from 6 a.m. to 11 p.m.
  • WHERE: The 606 in Chicago
  • COST: Freefree walks on the 606 trail



Whether or not one has a green thumb, the iconic Sheffield Music Fest & Garden Walk, celebrating its 50th year in 2018, is inspirational, dreamy and motivational. It’s a unique way to savor a summer weekend in the city! There’s also a fantastic music lineup on two stages.

More than 80 of the neighborhood’s lush residential gardens will again be open for the public to explore. There are both self-guided garden tours, and guided architecture tours. Visitors are always amazed at the creativity of urban green spaces on splendid display.   Presented by the Sheffield Neighbors Association, the weekend also includes food, and plenty of nifty afternoon activities for kids and families.

Another exciting component of Sheffield Music Festival & Garden Walk is its partnering with the sixth annual Chicago Craft Beer Festival. This stand-alone microbrew fest will be held in tandem with the Garden Walk throughout the weekend and definitely enhances the crowds.

  • WHEN: July 21-22
  • WHERE: Lincoln Park
  • COST: $10 suggested donation



The Logan Square Farmers Market opens at 10 a.m. Sundays. It’s always a great place to get local produce, talk with farmers and get to know the neighborhood!  While you are at it, take a self-guided walking tour of Logan Square using our neighborhood guide “The Grid: Logan Square.” 



Come check out the Taste of River North this weekend, now in its 17th year as a foundational event in this north side neighborhood. Try some new beers and flavors, or listen to one of the dozen bands play at the event. Like Taste of Chicago, plenty of people are expected to go and try some amazing food; unlike the Taste of Chicago, the Taste of River North is dog-friendly.

  • WHEN: Friday, July 20, 5-10p.; Saturday, July 21, noon-10p.; Sun, July 22, 11a– 8p.
  • WHERE: Ward Park, 630 N. Kingsbury St.
  • COST: $10 Friday; $5 before 3 p.m. Saturday, $10 after; $5 Sunday



This weekend, scores of athletes will take over the city to celebrate the 50th anniversary culminating in a Special Olympics Concert at Northerly Island. If you would like to check out an event or two see the list below to help guide you through the weekend’s activities.

Concert Date: July 21
Location: Northerly Island
Start Time: 5:40PM CT

Join Chance the Rapper, Usher, Francis & The Lights, Daya, Smokey Robinson, Jason Mraz, and O.A.R. on July 21 at the 50th Anniversary Celebration Concert! Dedicated to empowerment and inclusion, the concert will inspire an #InclusionRevolution.



St. Benedict Parish’s annual BenFest is one of the north side’s longest-running family festivals and is quite unique compared to other community events. Hosted during the weekend of July 20 – 22, this renowned Northcenter neighborhood celebration offers live entertainment, craft beer, a mouthwatering menu and fabulous family fun for every age group!

For nearly 40 years as “Chicago’s best family-friendly summer festival” (Chicago Tribune), BenFest is legendary for its family element but caters to all age groups; from tots to teens to the young-at-heart, there’s a variety of activities and entertainment on two stages suitable for all.   Clear the calendar and join friends and neighbors for a huge weekend of camaraderie, great music, fabulous food options and tons of activities.  For more information, visit

  • WHEN: July 20-22
  • WHERE: North Center
  • COST: $5 suggested donation




The Art Institute of Chicago is hosting its first-ever block party, a 12-hour celebration of the museum with tons of different activities and events, indoor and outdoor. Festivities run the gamut, including workshops, conversations with artists, analytical and historical discussions, a picnic and an Instagram scavenger hunt. Evening activities include music, dance and reading performances in the Modern Wing. Everything begins at 10:30 a.m. Saturday at the Art Institute (111 S. Michigan Ave.). Tickets: $10, free for members.


Grab your kids and show them how a community can band together to do something good that benefits all.  There’s a clean-up on Saturday hosted by the Discovery Channel. Bring your own reuseable water bottle. Gloves and trash bags will be provided but you are encouraged to bring your own gloves and a bucket if you can.  You can find out about other beach clean-ups and how to host your own from the The Alliance for the Great Lakes, through the Adopt-a-Beach program. It organizes and coordinates beach cleanups across the Great Lakes shorelines, including in and around Chicago.

  • WHEN: Saturday, July 21st starting at 9:45 am
  • WHERE: Hollywood Beach (also known as Kathy Osterman Beach) in Edgewater



The Midwest’s largest celebration of Colombian music and culture, Colombian Fest / El Gran Festival Colombiano, moves to the spacious grounds of Kelvyn Park, 4438 W. Wrightwood Avenue in Chicago, July 15 and 16 from noon until 10:00PM. In doing so, they are renaming the gathering Chicago’s Colombian Fest Al Parque. The Festival coincides with Colombian Independence Day. In addition to presenting a wide variety of Colombian music from international and local artists, the family-friendly festival will feature food, artisans, games, dancing and a kid zone designed especially for younger attendees.

The expanded park space will be put to good use with a carnival featuring 25+ attractions consisting of family orientated and kiddy amusement rides as well as exciting games. The Carnival Experience will open the previous night on July 14 from 5 to 10PM when the festival hosts a community day at the park for area residents and Chicago Summer Camp programs with rides, games and family entertainment in which portion of the proceeds from Carnival and donations at the gate to benefit community partners. The Carnival Experience will remain open during the entire festival.

Daily general admission tickets are just $10. Children 12 and under are free when accompanied by a ticketed adult. Advance general admission tickets are available online at or by calling 1-800-668-8080. Advance tickets along with official festival merchandise will also be available beginning June 9 at the Colombian

  • WHEN: July 20-22
  • WHERE: Hermosa
  • COST: $7-$25



Tacos y Tamales Festival

This  street fair is inspired by tianguis, outdoor Mexican markets, and includes authentic Latin American and Mexican food, art installations, local vendors, music and dance performances, and a beer garden.  he Tacos y Tamales Festival returns, kicking off July 20, in Pilsen for three days of handmade tortillas, stuffed masa and more.   Food vendors announced so far include Cemitas Puebla, Churro Factory, DeColores, Dia De Los Tamales, Don Pedro Carnitas, Taqueria Los Comales, Yvolina’s Tamales, plus food trucks Aztec Dave’s and El Patron. A beer garden will serve Modelo, an event sponsor.

Organizers of the third annual festival promise a modern day tianguis, a traditional Mexican and Central American open-air market, with not only shopping but also art installations plus a stage for Latin music and dance.   A $5 suggested donation will benefit the Frida Kahlo Community Organization, a nonprofit that serves the Latino community with immigration services and after school programming for children.  The event will be held July 20-22, from noon to 10 p.m. daily, at 16th and Peoria streets.
  • When: July 20-22
  • Where: Lower West Side
  • How much: $5 suggested donation




Chicago Craft Beer Festival

  • When: July 21-22
  • Where: Lincoln Park
  • How much: $35



Chicago Whiskey & Wine Beach Festival

  • When: July 21
  • Where: Uptown
  • How much: $30-$39


Silver Room Block Party

  • When: July 21
  • Where: Hyde Park
  • How much: Free


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