The Sky Room at The Obama Presidential Center Museum
Photograph: The Obama Foundation | The Sky Room at The Obama Presidential Center Museum
Photograph: The Obama Foundation

The best free things to do in Chicago this month

No need to break the bank—check out all the fun (and free) stuff happening throughout the city this month.

Lauren Brocato
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Last updated October 1, 2026: As it turns out, some of the best things in life—or at least, some of the best things to do in Chicago—are free. There are plenty of free ways to spend your time over the next few weeks, including ART on THE MART, Halloween parades, live shows and much more. Plus, don't miss out on all the things to do at the Obama Presidential Center without a ticket that won't cost you a dime. Ready to save some money without sacrificing any fun? Check out more of the best free things to do in Chicago this month.

RECOMMENDED: The best free museum days in Chicago

Best free things to do in Chicago this month

  • Things to do
  • Festivals
  • East Garfield Park
  • Recommended

This annual (and free) arts-centric Halloween parade returns to Columbus Drive for an evening of colorful, family-friendly flair. Watch as participants from major cultural organizations, youth programs and aspiring artists march from Balbo Drive to Jackson Boulevard. Arts in the Park is bringing back its "Upside Down" parade in Washington Park on Halloween night, where attendees can walk through a route thronged by costumed performers and puppeteers. 

  • Things to do
  • Festivals
  • Washington Park
  • Recommended

In addition to the regular Arts in the Dark parade on State Street, the arts organization LUMA8 is hosting a "reverse" parade—in which attendees pass through a stretch of costumed performance groups lining Russell Drive in Washington Park. Bonus: At the end of the route, attendees will get a complimentary candy bag and other goodies. Come wearing your best Halloween costume!

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  • Things to do
  • Quirky events
  • Streeterville
  • Recommended

Chicago's most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog and cat owners bring their costumed pets for a parade around the premises. The best-dressed furry friend—chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman—will receive prizes. Donations support the dogs, cats, kittens and puppies residing at PAWS Chicago.

  • Kids
  • Lincoln Park
  • Recommended

Take the little ones trick-or-treating in Lincoln Park for some Halloween fun this spooky season. Businesses along Lincoln Avenue from Diversey Parkway to Webster Avenue on Saturday; and along Clark Street from Armitage Avenue to Diversey Parkway, and on Diversey Parkway from Lakeview Avenue to Orchard Street on Sunday will hand out candy to trick-or-treaters, so come dressed in costume. There will also be a special Halloween celebration at Lincoln Common Plaza on Saturday with a DJ, face painting, a photo booth, a balloon artist and more.

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  • Museums
  • Art and design
  • Loop
  • 4 out of 5 stars
  • Recommended

On any given day at the Chicago Cultural Center, you might find a free classical concert being performed, an art exhibition on display in one of the building’s many galleries or tourists marveling at the world’s largest stained glass Tiffany dome. Don’t worry about paying for admission—nearly everything that happens in this building is free and open to the public.

  • Things to do
  • Conventions
  • Loop
  • Recommended

Explore limited-edition comics, artist books, zines and art by more than 100 artists and independent publishers at Pretty Good Fest. The free fair features exhibitors, readings and other events, plus programming with special guests and acclaimed cartoonists Chris Ware, Michael DeForge and Tara Booth.

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  • Comedy
  • Stand-up
  • Recommended

Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.

  • Things to do
West Town First Fridays
West Town First Fridays

Explore a host of galleries and programming at this monthly event that showcases West Town’s dynamic arts community. On the first Friday of every month, galleries and arts-based businesses stay open until 8pm.

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  • Things to do
  • Lincoln Park
  • Recommended

See some 1,100 animals—from apes to zebras to flamingos—at one of the last free zoos in the country. The 35-acre attraction connects visitors with animals from all over the world, and a variety of seasonal events and special programming keep locals coming back again and again. Admission to Lincoln Park Zoo has been free since it opened in 1868. There's even a lineup of adults-only events throughout the year.

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  • Things to do
  • City Life

You don’t need a ticket to visit the Obama Presidential Center. You do, however, need a ticket to get into the museum inside the campus’ towering granite building. But there’s a lot you can still do here without having a ticket—and much of it is free. From exploring the 20-acre grounds and picknicking on the Great Lawn to checking out the Presidential Reading Room in the on-site Chicago Public Library branch and visiting the eight-floor Sky Room, you could spend a full day here without spending a dime.

  • Attractions
  • Parks and gardens
  • Millennium Park
  • 5 out of 5 stars
  • Recommended

One of the latest additions to the Chicago Park District, Maggie Daley Park pays tribute to the late first lady of the city with 20 acres of recreational opportunity. Walk across the BP Pedestrian Bridge from Millennium Park and you’ll be greeted by a 40-foot climbing wall, a quarter-mile skating ribbon and one of the most whimsical playgrounds in the city. With facilities fit for kids and adults, this is a park where the entire family can spend the day having fun outdoors.

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  • Art
  • Film and video
  • Recommended

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running for 30 minutes on Thursdays through Saturdays, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Museums
  • Museum Campus

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm–10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

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  • Things to do
  • Exhibitions
  • Loop

This exhibition poses a devastatingly powerful question: What if Emmett Till had not been brutally lynched in Mississippi in 1955? Through photography, the exhibition imagines an alternate history in which Till lived—moving from images inspired by the last meal his mother packed before his trip south to meditations on the life he might have experienced, from the rise of the Chicago Bulls to the ongoing fight for civil rights.

  • Things to do
  • Festivals
  • Boystown
  • Recommended

Wanna see some of the best Halloween costumes in the city? Head to Northalsted, where hundreds of people show off their creations at this spooky festival and procession. During the day, a street fest features food, drinks, live entertainment and more. At 7pm, you'll find drag queens, kids, parents and pets marching in the 30th annual Halsted Halloween Night Parade, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller." Stick around afterwards for the costume contest awards ceremony.

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  • Things to do
  • Loop
  • 4 out of 5 stars
  • Recommended

If you're looking for breathtaking views of some of Chicago's most gorgeous architecture, take a stroll along the Riverwalk, which hugs the main branch of the Chicago River and provides a continuous walkway with restaurants, bars and urban attractions at every turn. Clever design features throughout offer areas to lounge around and enjoy the city from a stellar angle.

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  • Things to do

Experience the wealth of public art decorating the city through the eyes of an expert. Each walking tour—spanning anywhere from 45 minutes to an hour—is led by a docent and covers a half-mile, beginning outside the Chicago Cultural Center and ending in Millennium Park. Throughout the tour, the docent offers context about each piece and its artist. The tour is free, but keep in mind that advance registration is required.

  • Attractions
  • Streeterville
  • Recommended

This tourist hot spot—which is free to visit—features shops, eateries, an IMAX cinema and a bevy of sightseeing boat tours. Pier Park is home to a 200-foot-high Ferris wheel, a beer garden and public art exhibitions galore. Beyond its year-round offerings, the Pier's seasonal events, indoor activities and great people-watching provide plenty of entertainment, no matter the weather.

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  • Attractions
  • Parks and gardens
  • Millennium Park
  • Recommended

This 24.5-acre park might be one of the most popular gathering spots in the city, known for its free concerts, famous public art installations and its proximity to the Loop. The centerpiece of Millennium Park is the Jay Pritzker Pavilion, a flowing Frank Gehry-designed structure that hosts of the city’s biggest outdoor festivals and concerts. You’ll also find the serene Lurie Garden, al fresco dining destination the Park Grill and pedestrian bridges that lead to the Art Institute and Maggie Daley Park.

  • Music
  • Latin and world
  • Loop

Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 

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  • Things to do
  • Cultural centers
  • River North
  • Recommended

Housed in an airy, sun-soaked building in the heart of downtown, The Poetry Foundation is a hidden gem perfect for remote working, perusing its 40,000-volume library, or attending a workshop. If you're game to brave the elements, you can stroll through the tree-lined plaza to savor the snowy vistas.

  • Museums
  • Art and design
  • Lower West Side
  • Recommended

You don't have to look any further than Pilsen to find one of the largest Latino cultural organizations in the U.S. Visit the National Museum of Mexican Art and explore a 6,000-piece permanent collection, rotating exhibits, performing-arts showcases and educational programming that represents an illustrious Mexican culture.

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  • Music
  • Latin and world
  • Lincoln Square

Every Wednesday, the Old Town School of Folk Music hosts a showcase of world music and dance. Featuring both local and touring talent, you're sure to hear something new and exciting at this long-running series. Before the show, be sure to peruse the Old Town School of Folk Music Store, where you can rent instruments, learn about lessons and peruse a wide selection of books.

  • Comedy
  • Uptown
  • Recommended

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

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  • Things to do
  • South Shore
  • 5 out of 5 stars
  • Recommended

Stretching 18.5 miles from Edgewater’s Hollywood Avenue down to 71st Street, the Lakefront Trail is the ultimate way to experience Chicago’s shoreline. Edged by sparkling blue water, the path serves as a scenic reminder of why the city is such a spectacular place to live. Whether you walk, run, blade or bike, the trail makes it easy to spend a day by the lake, passing through four major parks and iconic landmarks like Navy Pier and the Museum Campus.

  • Art
  • Arts centers
  • Kenwood

With a mission of making contemporary art more approachable, the Hyde Park Art Center offers engaging exhibitions, as well as community programming of all varieties, including artist talks, a residency program, studio classes and more. Established in 1939, it's the oldest alternative visual arts center of its kind in Chicago, a place where visitors can experience art free of charge.

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  • Things to do
  • Literary events
  • Logan Square

The Whistler’s monthly lit series pops up on the second Wednesday of every month, bringing an evening of readings, workshopping and discussion to the Logan Square cocktail bar. Each show is followed by an installment of the Relax Attack Jazz Series, a free event with a constantly rotating bill.

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  • Things to do
  • Literary events
  • Washington Park
  • price 1 of 4

When this institution opened in 1961, African-American history was suffering serious neglect at the hands of the city’s—and for that matter, the nation’s—cultural institutions. The Hyde Park cultural hub is now one of the oldest African-American–focused museums in the country. Admission is free for all every Wednesday.

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