Erin Yarnall

We’re probably not alone in saying that the weekend is always on our minds here at Time Out Chicago HQ. Like you (probably), we spend the workweek daydreaming about the next restaurant to obsess over and obsessively updating our concert calendars. Whether you’re museum-hopping, plotting a day trip to escape the city, or ready to ghost your original plans for something spontaneous, you’ll find plenty of ways to make the most of your weekend in Chicago. Every week, we curate a Chicago weekend itinerary packed with the city’s best concerts, culture and cuisine. Start the weekend on a sweet note by visiting the just-opened Van Leeuwen Ice Cream shop in Wicker Park—the cult favorite’s first Midwest outpost. Admire some local art at Ravenwood ArtWalk or Lakeview East Festival of the Arts, or head down to Little Village to celebrate Mexican Independence Day. For those itching to squeeze in one last rooftop hang before chillier climes arrive, swing by Time Out Market Chicago for La Vita Spritz. RECOMMENDED: Discover the 50 best things to do in Chicago right now

There’s no surer sign that fall is coming than seeing pumpkins everywhere—whether used in fancy coffee drinks, recipes or just as decorations, pumpkins are the ubiquitous symbol of autumn. Maybe you don’t love pumpkin spice lattes or pumpkin pies, but it’s hard to deny the appeal of choosing your own perfect-to-you gourd at a pumpkin patch. All of the farms and pumpkin patches on this list are within a two hour drive from the city (one is even in Chicago), and bursting with fall fun. After you’ve picked out a jack-o’-lantern, spend the day exploring creative corn mazes, eating apple cider donuts and checking out fall foliage. RECOMMENDED: Your complete guide to fall in Chicago

September in Chicago started off strong in terms of things to do, and there are no signs of it slowing down. This weekend, the 26th Street Mexican Independence Day Parade returns to Little Village with the theme “Pride and Power: Our Strength, Our Legacy,” celebrating the resilience of the Mexican community. If you're hoping to enjoy the week's balmy temperatures, run for a good cause at the PAWS Chicago 5K or stroll around the Ravenswood ArtWalk. To no surprise, Chicago’s music festival scene is still firing on all cylinders: Sound & Gravity, a new five-day music festival from Pitchfork co-founder Mike Reed, debuts this weekend and Plantasia, a two-day experimental music festival taking over the Garfield Park Conservatory, kicks off on Sunday. RECOMMENDED: Discover the best things to do in Chicago in September 2025

These days, even the simple act of stepping outside feels like it siphons money from your wallet. Prices for minor luxuries like concerts, a fancy latte or trendy bars are climbing higher and higher, but that doesn't mean that everything in Chicago will wreck your budget. There are plenty of activities around the city that don't cost a penny. Give your bank account a rest by exploring captivating Chicago museums during free museum days, checking out a beautiful park or laughing out loud during a free show at a comedy club. Our list of the best free things to do in Chicago is here to save you some dough. RECOMMENDED: Our complete guide to the best things to do in Chicago

Summer in Chicago is fun, but the city really stands out in the fall when the trees start to change colors, a slight chill permeates the air and there's an abundance of autumnal activities to take part in. One of the most fun ways to celebrate the season? Visiting a corn maze. It’s nearly impossible to find one in the city, as you need a pretty large field, but we've traveled just outside of Chicago to nearby suburbs to find find a wide array of farms and orchards that have creative and sometimes daunting corn mazes to get lost in (plus apple picking). Open through the end of October, some of them serve as a festive way to get into the Halloween spirit as well. So make the most of the season with a fun-filled day at the best corn mazes near Chicago. RECOMMENDED: Find the best pumpkin patches near Chicago

As a chill runs through the air and the leaves begin to change, it’s not just fall that’s upon us, but spooky season. Autumn is the perfect time to watch horror movies, tell scary stories and walk through haunted houses. If you’ve ever wanted to have a real paranormal encounter, though, Chicago has plenty of destinations to try and make that happen. Historic buildings aren't the only places that have reported hauntings—music venues, cemeteries and hotels all have ghost stories surrounding them as well. So for those who are looking for more than pumpkin patches and corn mazes this fall, we’ve put together a list of some of the most haunted spots in Chicago that offer a truly chilling experience. RECOMMENDED: Our complete guide to Halloween in Chicago

Often defined by its amazing restaurants, beautiful beaches, lively jazz scene and culturally significant architecture, there's another side to Chicago that most tourists don't get the opportunity to delve into ...  The city has a notorious history of Prohibition-era organized crime and violence, which you can explore by signing up for one of the best Chicago crime tours. Learn the nitty gritty details of the city's dark past as your guide unearths stories that will leave you shocked. While the tours may be a bit eerie, some can be experienced on your own schedule, whether in-person or virtually. Certain tours even make stops at the most haunted places in Chicago to help set the mood. RECOMMENDED: 📍 Check out the full guide to the best Chicago tours🏠 The best Airbnbs in Chicago 🏨 The best hotels in Chicago

Between the amazing restaurants to try, swankiest bars to visit and best things to do, having a good time in Chicago can be expensive. However, there are still plenty of options for fun on a budget. Chicagoans have access to affordable museums around the city, theater shows that don't break the bank and even a cat cafe. Here are some of the best cheap things to do in Chicago for under $20. And for even more cost-effective options, check out the best free things to do in Chicago. RECOMMENDED: The best cheap eats in Chicago

Dating can be tough, but picking out what to do on a date doesn’t have to be. Thankfully, Chicago offers plenty for a fun date night. From the incredible lineup of romantic restaurants to the abundance of romantic things to do, there are tons of exciting and intimate options (including cheap date ideas). The following ideas combine dinner and drink recommendations with interesting activities all around the city. To make it convenient, we’ve kept each pairing close together, so you won’t have to travel too far between destinations. Whether it’s your first date or your 50th anniversary, here are some of the best date night ideas in Chicago for an unforgettable evening. RECOMMENDED: Find more of the best unique date ideas in Chicago

Sometimes, the trickiest part about a date isn’t working up the nerve to someone out—it’s figuring out what you’re going to do for date night. Sure, you could go the classic route and get dinner at a romantic restaurant or see the latest blockbuster at a bougie movie theater, but why not mix it up with a truly unique date idea? Learn more about each other while simultaneously getting the hang of a new skill at classes for every interest, or spend the day exploring each other’s musical tastes at a concert to see if you’re compatible. You also can’t go wrong with just getting a drink at one of the city’s riverfront breweries or distilleries. So here are some of our favorite date ideas in Chicago to help ignite your love life. RECOMMENDED: Check out the most romantic things to do in Chicago

Over the years, Chicago has served as the backdrop for films like The Dark Knight, The Blues Brothers and just about every movie made by John Hughes. While it’s always thrilling to see a movie being filmed, it’s just as fun to see the finished product put together at the movie theater. Thankfully, the city’s home to a wide array of great theaters, from multiplexes with massive recliner seats and in-theater dining service to art houses where you can catch up on all of the latest indies or an international flick at one of the city’s film festivals. And, like any respectable Chicago institution, many of them come with fully stocked bars, offering extensive beer and cocktail options. No matter what movie you're looking to see, you’ll find the perfect place to watch among our list of the best movie theaters in Chicago. RECOMMENDED: The best drive-in movie theaters near Chicago

In the thick of winter in Chicago, it can be easy to bundle up and lay low (we see you, Netflix and chill)—but let us not make a habit of hunkering down in this town, where world-class cultural attractions cues us into action. Case in point with Chicago Theatre Week, a multi-day celebration of local musicals, comedies, operas and beyond. With more than 100 performances at theaters across the city—all featuring tickets at $30 or less—there’s never been a better time to round up your fellow arts enthusiasts for an evening out. And this year's Theatre Week coincides with Chicago Restaurant Week, so you can enjoy dinner and a show without breaking the bank. From a reimagined production of Hamlet to a Bob Marley-scored musical, here are some of the best Chicago Theatre Week performances to catch now. For tickets, dates and shows, check out the CTW website. What is Chicago Theatre Week? More than 100 participating productions at the best theaters in Chicago, the suburbs and everywhere in between will offer tickets at discounted price points of $15 or $30 (or less) during the promotion. When is Chicago Theatre Week 2025? Chicago Theatre Week is February 6-16.

There’s a good chance that you’ve heard of A Raisin in the Sun. If you’re a fan of theatre, maybe you’ve even seen it or read it. The play, written by Lorraine Hansberry, depicts the experience of a black family on Chicago’s South Side as they try to improve their financial circumstances after the death of the family’s patriarch. The plot deals with still-relevant issues, like housing discrimination and racism. A Raisin in the Sun is being performed at Court Theatre in Hyde Park, the professional theatre of the University of Chicago.

You’ve probably seen Hamlet. Now it’s time to see Fat Ham, a reimagining of the Shakespeare tale. The Pulitzer Prize-winning and Tony-nominated play by James Ijames tells the story of Juicy, a queer Black man whose widowed mother has married his uncle. When his father’s spirit shows up for revenge during a backyard cookout, Juicy must grapple with his identity. Fat Ham is showing at the Owen Theatre, part of the Goodman Theatre in the Loop.

A musical based on the 2007 film of the same name, Waitress follows Jenna, a waitress at a cafe who’s in an abusive relationship with her husband, Earl. After becoming pregnant, Jenna starts an affair with her doctor and enters a pie-baking contest, hoping to win the grand prize in order to fund her escape.

Betrayal isn’t structured like a traditional play. The events move in reverse chronological order, showcasing the demise of an affair and going back in time as it occurred and ultimately to the beginning. The play stars Academy Award- and Emmy Award-winner Helen Hunt as Emma, who is having an affair with Jerry, her husband’s friend and coworker. Betrayal, which is playing at the Goodman Theatre, was first written by British playwright Harold Pinter in 1978.

At a motel in the Mojave Desert, two lovers, or fools as the play would suggest, meet up and clash. With just three main cast members, Fool for Love is a haunting drama that explores the deeply complex relationship between the trio. The play was written in 1983 by noted playwright Sam Shepard, whose works also include A Lie of the Mind and Buried Child, for which he won the Pulitzer Prize for Drama in 1979.

The song “Three Little Birds” by Bob Marley and the Wailers is almost 50 years old but its enduring message lives on, most recently in the children’s musical Bob Marley’s Three Little Birds, which is playing at The Greenhouse Theatre Center. The reggae classic is just one of many Bob Marley hits featured in the production, which centers around Ziggy and his three avian friends. The musical is inspired by the children’s book Every Little Thing, written by Marley’s daughter Cedella.

During its original Broadway run in 2015, Fun Home won seven Tony Awards, including Best Musical, Best Original Score and Best Leading Actor in a Musical. Now, the award-winning musical has moved on from New York and is playing in Chicago during Chicago Theatre Week. Fun Home was based off of the graphic novel memoir of the same name written by Alison Bechdel. Both the novel and musical follow Bechdel as the writer comes of age: Bechdel’s experience of coming out as a lesbian and her relationship with her father, who was a closeted gay man.

Sam Shepard is one of the most highly-regarded American playwrights for good reason—his works are a masterclass in writing about bleak situations and infusing them with black comedy, like in A Lie of the Mind. The play, which is also a part of Chicago Theatre Week at the Raven Theatre, is centered around spousal abuse and how it impacted two families.

On the last night of Frida Kahlo’s life, viewers of Frida…A Self Portrait are transported to La Casa Azul, the famous Mexican artist’s home. The one-woman production is written and performed by Vanessa Severo, and sees the artist reminisce about her life. Throughout the 75-minute play, Severo connects her own life’s experience to the famed artist’s, and explores Kahlo’s works, addiction, physical limitations and romances. The play is running at Writers Theatre, a non-profit theatre company, in suburban Glencoe.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

DePaul University students use The Ray to help avoid the freshman 15, but it’s not just for students. Undergraduate students have the membership cost included in their tuition, but graduate students, staff, faculty and members of the community can purchase memberships with community memberships costing $91 per month. The 12,000-square-foot open fitness area has more than 100 pieces of cardio equipment, free weights and strength equipment. The gym also offers up a six-lane swimming pool, a banked jogging track, racquetball courts and more than 40 group classes each week.

If you’ve ever craved a private space to work out beyond your home office or living room, The Gym Pod, a cluster of repurposed shipping containers in Fulton Market, is ideal. The Gym Pod offers five different types of pods, each equipped for various types of workouts—the gym pod, which comes equipped with free weights and a cardio station; the spin pod, where spin classes are available; the flow pod, which offers yoga, dance barre and martial arts classes; the rumble pod for anyone looking to improve their boxing or MMA; and the grit pod, which has three weight training stations.

Before she started working with My Block, My Hood, My City, Ashanti Marshall says that, despite living in Chicago, she and many teenagers like her hadn't actually seen much of the city. Marshall, who's currently a sophomore at the University of Illinois Urbana-Champaign, first started working with the Chicago-based nonprofit four years ago and is now much more familiar with the city's 77 neighborhoods—including her own, North Lawndale. My Block, My Hood, My City aims to provide educational programs and field trips to underprivileged youth communities throughout Chicago (which, by the way, was just named the second best city in the world according to Time Out readers). It was founded in 2013 by Jahmal Cole after he spent time volunteering at Cook County Juvenile Detention Center. According to Ernesto Gonzalez, the nonprofit's marketing manager, while working at Cook County Cole heard young people talk about their blocks and their hoods, but never the city as a whole. From there, Cole started an after-school program and the organization grew from there. "We're one of the fastest-growing nonprofits in the city," Gonzalez says. It's very local work, but with a loud purpose For the past five years, My Block has been hosting youth-led community walks through neighborhoods like Marshall's native North Lawndale. She's one of many young people leading community walks through their own Chicago neighborhoods, giving historical context and sharing what makes their blocks special. "I rea

One of the distinctive features of the West Loop is its vast collection of street art created by numerous artists, present amid the streets lined with restaurants and on the side of overpasses and railway embankments. Painter and muralist Jenny Vyas is one of those artists whose work has helped to shape the former industrial area, adding splashes of color and creativity to the trendy destination for nightlife and dining that it has become. A self-taught artist, Vyas first became inspired to paint while recovering from a breakup in 2013. She said that much of her work is inspired by “a lot of the darkness in life that we don’t really talk about.”. Her latest show, “Awaken,” opened last month and is on display at Pilsen Yards through October 31. The show features 15 of Vyas’ paintings, all of which center on themes of vulnerability and finding strength through exploring one’s own demons. “It’s the show I’ve been working toward for the last five years so it’s been really great to bring it all together,” Vyas said. “It’s my largest body of work, ever.” Although she’s originally from India, Vyas has lived in Chicago for more than two decades and considers the city to be her home. “I love the inclusivity and different cultures in Chicago,” Vyas said. “I’ve been to so many cities in America and the feeling of home that you get, it’s very much integral in Chicago. You can go to a bar and make friends that night.” One of the painter and muralist’s favorite neighborhoods in the city is