Shannon Shreibak

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. Last updated November 12, 2025: If you’re looking for things to do in Chicago this weekend, welcome—you’re in the right place. There’s no shortage of holiday-themed events this weekend, from the Griffin MSI’s “Christmas Around the World” exhibition to outdoor light displays like Illumination at the Morton Arboretum and Lightscape at the Chicago Botanic Garden. For those who aren’t yet ready to embrace winter in full force (we get it), check out one of many museum exhibitions throughout the city, including a Yoko Ono retrospective, a Peanuts pop-up for kids and the Balloon Museum’s wildly photogenic “EmotionAir” activation. RECOMMENDED: The best things to do in Chicago today RECOMMENDED: The best free things to do in Chicago this month RECOMMENDED: The best cheap eats in Chicago RECOMMENDED: Discover the 50 best things to do in Chicago right now

Thrift stores are more than just treasure troves for great deals on secondhand clothes or vintage furniture finds—shopping secondhand also keeps clothes, home goods and other items out of the landfill a little while longer. You'll find stores all across the city, from Edgewater to Beverly, as well as online storefronts to shop at. Whether you're donating your own gently-used goods at the tail end of a spring cleaning session or browsing through the inventory at some of Chicago's best thrift and secondhand stores for that perfect hidden gem, be prepared to score some serious deals on items you simply can't find at most other clothing stores, furniture stores, record stores or even gift shops. RECOMMENDED: The best streetwear and vintage stores in Chicago

Last updated November 10, 2025: Few sights jumpstart feelings of holiday cheer quite like sparkling Christmas lights—and lucky for us, the Chicago area has plenty of stunning options to choose from. Here in the city, take a stroll down Michigan Avenue or visit Lincoln Park Zoo's famed ZooLights installation, which is free on Mondays. You'll also find impressive lights downtown at the City of Chicago Christmas tree at Millennium Park, which is lit during an annual ceremony that's happening November 21 this year. Once you've had your fill of lights, head over to Christkindlmarket and warm up with spiced glühwein and German-inspired fare, or go ice skating at Maggie Daley Park. So discover some of the best things to do during Christmas in Chicago with our guide to the area's most beautiful holiday lights. RECOMMENDED: Our complete guide to Christmas in Chicago Quick picks: The best Christmas light displays in Chicago ZooLights – Quite literally millions of LED lights scattered across the beloved Lincoln Park Zoo; free on Mondays. Winter Wonderfest at Navy Pier – Lakeside winter light display, plus ice-skating, fire-pits and holiday rides. Illumination: Tree Lights at Morton Arboretum – A walk-through spectacle of LED lights and music set amidst 50 acres of trees. City of Chicago Christmas Tree Lighting – The annual lighting of the city’s main Christmas tree in Millennium Park.

Last updated November 10, 2025: If you’re looking for things to do in Chicago, you’ve come to the right place. Chicago just welcomed its first snow of the season, so you know what that means: it’s time to embrace all things holly and jolly with reckless abandon. If you’re ready to jump headfirst into holiday cheer, don’t miss the kickoff of the Chicago Botanic Garden’s “Lightscape” installation, the Randolph Street Holiday Market or the Griffin MSI’s “Christmas Around the World” exhibition. Whether you’re looking for the best events in Chicago this week, planning a spontaneous night on the town or just exploring what’s new around the city, there’s no shortage of incredible things to do this week. RECOMMENDED: Discover the best things to do in Chicago in November 2025

“At the end of the day, we come into this world with nothing and we leave this world with nothing,” Simone Mitchell-Peterson tells me. She isn’t speaking mournfully—just matter-of-factly, pointing out the parameters we are all given. Within that narrow window between the first nothing and the last, Mitchell-Peterson says, we’re offered a daily invitation: “I’ve learned about the fortitude in choosing joy each day—because I really believe that’s a choice. And if you can’t choose it for yourself, then let somebody help you along the way.” For 21 years, Mitchell-Peterson has been helping older adults choose joy as the CEO of the Chicago chapter of Little Brothers – Friends of the Elderly, a national network of nonprofits that provides companionship and care for the aging community. Through food deliveries, visiting programs and summer getaways at Audrey’s House—the organization’s year-round community center in the western Chicago suburbs in Batavia, IL—Little Brothers supports roughly 1,000 adults aged 70 and over throughout Chicagoland. While Mitchell-Peterson prioritizes celebration year-round—birthday parties, themed events and personalized gifts for older adults—the holiday season holds a special kind of excitement for both her and the community she serves. With the help of volunteers and donors, Little Brothers hosts family-style holiday gatherings complete with music, dancing and, of course, a hearty shared meal. The organization also prepares home-delivered holiday dinner

Last updated November 3, 2025: 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 ice skating and a handful of winter markets. Plus, don't miss out on gallery shows, concerts and other recurring events 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 cheap eats in Chicago

Welcome to November in Chicago! You've got about two weeks of breathing room after Halloween before holiday events begin in earnest, from twinkling Christmas lights displays to the first days of Christkindlmarket in Daley Plaza and Wrigleyville. And of course, don't forget about Thanksgiving in Chicago. Hoping to avoid the holidays altogether? Take a spin on the Maggie Daley Ice Skating Ribbon or huddle away from the wintry weather at one of many Chicago museums as temperatures start to plummet. Say goodbye to fall in Chicago with the help of our list of the best things to do in Chicago this November. RECOMMENDED: Check out our 2025 Chicago events calendar

The official start of fall in Chicago might be in September, but the season doesn't really hit its stride until October—a month replete with crisp air, colorful fall foliage and a heaping helping of spooky fun. Take advantage of everything autumn has to offer by exploring the best pumpkin patches near Chicago, attending an apple-themed neighborhood fest, getting lost in corn mazes or staring up at the changing leaves at your local park or garden. And of course, celebrate Halloween in Chicago with spooky pop-ups, haunted houses, horror movie marathons and even more ghoulish events. Ready to embrace autumn? Check out the rest of the best things do to in Chicago this October.  RECOMMENDED: Events calendar for Chicago in 2026

No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums. Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again. Quick picks: The best things to do in Chicago Millennium Park – See “The Bean” (Cloud Gate) and enjoy free outdoor concerts, workouts and more Art Institute of Chicago – World-class collection with strong Impressionism and modern art wings ($26–$32) Lincoln Park Zoo – Historic zoo in the heart of the city housing over 200 animal species (Free) Willis Tower Skydeck and “The Ledge” – Enjoy sky-high views and step onto glass ledges above the city ($36–$45) Last updated November 1, 2025: The city is shifting gears into full fall mode—and whether you’re looking to explore iconic sights, dive into culture or embrace early holiday energy, there’s no shortage of things to do in Chicago right now. From eyeing masterpieces at the Art Institute of Chicago to cruising down the river in a hot tub boat or settling i

The arrival of December sends the holiday season into full swing—prepare yourself for a jam-packed roster of glittering Christmas lights, festive holiday pop-ups and plenty of glühwein to be sipped at Christkindlmarket locations in both Daley Plaza and Aurora. As the month draws to a close, bid adieu to 2024 at New Year's Eve events and parties happening at Chicago hotels, clubs and other hotspots, where you'll find Champagne towers and other special ways to welcome 2025 in style. So make the most of the final month of the year with our guide to the best events in Chicago this December. RECOMMENDED: Check out our 2025 Chicago events calendar

Last updated October 28, 2025: Fall in Chicago is officially underway, which means it's time to turn your attention to all things spooky, ghoulish and pumpkin-filled. Hoping for a fright? Visit one of Chicago's most haunted places, attend one of the city's many Halloween parades and parties or wander through a ghostly haunted house. No matter your age, embrace the thrills and chills of spooky season with our guide to the best Halloween events in Chicago this year.  RECOMMENDED: Our complete guide to Halloween in Chicago Read more: The 40 greatest Halloween songs for the ultimate spooky party The 12 best Halloween events in the USA for 2025 The 48 best Halloween movies of all time

For the past eight years, we’ve made it our mission to scope out the coolest pockets of the world’s greatest cities in order to create our definitive annual ranking. The places where stuff like nightlife, art, culture, and affordable food and drink can be found on every corner and down every backstreet. Where diversity is championed and independent businesses thrive, from old-school boltholes to the newest avant-garde art space. Put simply, the world’s coolest neighbourhoods are places that represent the soul of our cities, while maintaining their own unique local character that draws people in to live, work and play. So, what are the neighbourhoods that fit the bill this year? To find out, we asked our network of writers and editors across a breadth of cities to nominate the vibiest district in their hometown right now. We then ranked every neighbourhood against criteria including culture, community, liveability, nightlife, food and drink, street life and that hard-to-define sense of ‘nowness’.  On our list this year, you’ll find everything from homely, village-like enclaves with tight-knit communities to revitalised city-centre hubs and formerly dormant, industrial areas transformed into creative districts. Many are underrated spots that sit in the shadow of their commercialised counterparts; others have become unexpected culinary hotspots or magnets for the city’s artists, writers and activists. What they all have in common is a DIY spirit – and an unshakeable proclivity f

Do you like riding your bike? How about delicious Mexican food? Do you want to support local street vendors? If you’ve answered “yes” to all of the above, CyclingxSolidarity’s Street Vendor Bike Tour is the place to be. Organized in partnership with the Street Vendors Association of Chicago, the Bike Tour is designed to build community, one bike and meal at a time. The event will kick off with two stops in Pilsen during which CyclingxSolidarity will highlight its mutual aid efforts and partnerships with local organizations. The bike tour will then move westward toward Little Village, where cyclists will meet street vendors, hear their stories and enjoy delicious food at three different stops. The event is open to cyclists of all skill levels. “I want this tour to act as open arms to welcome people to Little Village and other communities where we have built bridges with local community organizations and introduce them to the people, places and food that make up these beautiful communities,” Rick Rosales, community organizer for CyclingxSolidarity says. “They need our support more than ever and for those of us that love to ride bikes, this seemed like a perfect opportunity.” Rosales hopes that this event will be the first of many Street Vendor Bike Tours. Learn more about CyclingxSolidarity’s mission here.

If Wes Anderson designed a cafe-meets-gift shop, it would probably look a lot like The Center of Order and Experimentation. Step inside and you're greeted by a velvet-upholstered counter, sticker-covered clipboards and sleek, futuristic-font signs declaring that the space is "not a cult." Cake-shaped candles, fluorescent tea boxes and handmade ceramics are artfully arranged on shelves and tables, every detail carefully curated. The space is often buzzing, especially during weekend micro-bakery pop-ups, watercolor workshops and other whimsical events.  

Inspired by the cultural resurgence of Mort Garson’s synth-powered album Mother Earth’s Plantasia, Empty Bottle Presents and Sacred Bones Records have been hosting an annual music festival celebrating plants and people who love them for nearly half a decade. Spread across two days, attendees can enjoy experimental music and on-site activations in the Garfield Park Conservatory's lush confines. This year's Plantasia lineup includes electronic music legend Suzanne Ciani, ambient juggernaut Tim Hecker, Pakistani composer Arooj Aftab and more.

The latest addition to the Salt Shed's sprawling grounds is a pinball palace owned by none other than Jim Zespy of Logan Arcade. Housing over 100 games, 8-bit purists, pinball wizards and casual gamers alike will all find fun ways to collect virtual prize tickets, which can be redeemed at a fully-stocked prize shop. Billed as an all-ages space by day and adult-centric playground—complete with jello shots—by night, there's something for everyone at Elston Electric.

What happens when a grift lands you smack dab in the center-court spotlight during the Chicago Bulls’ legendary 1996 reign? BULL, a two-act comedy following unathletic schemers Scott and Bryce, sets out to answer exactly that. As the duo navigates a grand con and the chaos of unexpected fame, they struggle to hold their friendship together—all against the backdrop of one of the most iconic eras in Chicago sports history.

Stationed on the first floor of the Chicago Cultural Center, Buddy is a one-stop shop for any locavore on the hunt for the perfect gift—whether for a friend or just yourself. The boutique features work from over 400 Chicagoland artists, with options ranging from ceramics and clothing to zines and more. Don't miss their rotating lineup of events, including the “Art 4 Sale” exhibition series, seasonal window installations on Randolph Street and monthly in-store happenings.    

During the summer, spending more time indoors than absolutely necessary feels almost sacrilegious. The Music Box Theatre gets it—and fully embraces the season by inviting movie lovers into its charming outdoor garden. Grab a specialty cocktail (each one cleverly named after an iconic film) and settle in for a night of cinema under the stars. Highlights of this year’s lineup include The Texas Chainsaw Massacre (the 2003 remake, for the horror purists out there), Dirty Dancing and The Goonies.

When Pitchfork Music Festival announced its sudden sunset at the start of 2025, Chicago’s music scene collectively wondered how festival co-founder Mike Reed would fill the sonic void. Turns out, Reed had an ace up his sleeve: Sound & Gravity, a five-day music marathon featuring 48 performances across six venues in Bricktown and Avondale. Lineup highlights include Bill Callahan, Mdou Moctar and Mary Lattimore, with some special sets curated by Electrical Audio—the recording studio founded by the late Steve Albini. Read more about Sound & Gravity's inception here.

There's a new kid joining Chicago's street festival scene, and this one promises to be unlike anything else. Edgewater will be hosting over 35 musical acts—including indie rock mainstays Cloud Nothings, Chicago hip-hop standout Ric Wilson and local drag punk outfit Bev Rage & The Drinks—and 100 vendors for the inaugural Edgewater Music Fest. The fest is open to all ages, with a Kids' Zone activity area for the little ones.

This one’s for the birders out there! Stop by the Newberry Library this August and September for a free guided tour of "Winging It: A Brief History of Humanity's Relationship with Birds,” an exhibit exploring the cultural and environmental resilience of birds across eras and civilizations. The tour ends in one of the library’s cozy reading rooms, where you can chat about what you’ve learned or dive into everything else the Newberry has to offer. (Spoiler alert: it’s a lot.)

Wander into Carol's Pub on the second or fourth Tuesday of the month, and you might not recognize the iconic country dive. No cowboys downing High Life, no two-stepping in sight. Instead, you’ll find a rowdy crowd waving jello shots (proceeds benefit a rotating charity) and gleefully dabbing bingo cards with multicolored markers. Welcome to Cougar Bingo, hosted by comedian Brittny Congleton, who performs as the fabulous Aunt Nance. Throughout the night, Nance calls out bingo numbers with the flair of a tipsy Midwest aunt, mixing in musical interludes, sharp one-liners and the occasional George Michael reference.

The Midwest’s largest free outdoor literary festival returns this September for its 40th year. Book lovers can browse offerings from more than 150 booksellers and exhibitors, while six stages and over 200 presenters deliver programming for all ages. While the full lineup is still under wraps, this year's festival will be headlined by Sandra Cisneros—author of The House on Mango Street and recipient of the 2025 Harold Washington Literary Award.

You can tell it’s the holidays in Chicagoland when even the trains start dressing up: This year, Metra has kicked the seasonal cheer up a notch, expanding its Holiday Train across all five lines so no commuter is spared the tinsel-festooned LED glow of yuletide cheer on rails. And you’d better embrace that wintertime joy quick—tickets for the festive railcars go on sale this Friday. “Our Holiday Trains have become an annual tradition for our riders and their families, and we are happy to be operating them again,” Jim Derwinski, CEO and executive director of Metra said in a press release. “It’s our way to spread a little holiday joy and thank our riders for making Metra part of their lives all year.” RECOMMENDED: The 22 most epic Metra day trips from Chicago Every year, Metra transforms its hyper-neutral railcars into vestiges of a winter wonderland. Stanchions are transformed into candy canes, wreaths crown the glazed glass windows and the whole ride is commandeered by Santa and a crew of trusty elves. Passengers will share a train car with clusters of pint-sized Christmas trees while the sound of holiday music streams through the train's speakers. This year, Metra Holiday Train will appear on all of its train lines—ensuring that every Chicagoan and suburbanite, naughty or nice, can bask in its seasonal sparkle. The holiday train schedule is as follows:  Dec 6: Milwaukee District West and BNSF lines Dec 13: Metra Electric, Rock Island and UP Northwest lines Dec 20: Metra El

Some folks chase Santa during the holiday season. Others chase sales. This week, Chicago bookworms are chasing tickets for the inaugural Chicagoland Bookstore Holiday Trolley like it’s the Polar Express for introverts. With special swag, 10 unique routes and promises of can’t-miss deals and seasonal surprises, it’s the kind of festive outing that reminds you why books still make the best gifts—especially the ones you buy for yourself.  The Chicagoland Bookstore Holiday Trolley is a an endeavor by the Chicagoland Independent Bookstore Alliance, which is comprised of 43 indie bookstores across Chicago and its neighboring bookish suburbs. In hopes of driving sales and promoting a sense of community among book lovers this holiday season, the trolley offers 10 different routes to choose from; and each route includes stops at four to five bookstores. Adding to the variety, each route has a unique starting location and duration. RECOMMENDED: The best bookstores in Chicago This initiative couldn’t have better timing: WTTW reported earlier this month that local businesses are experiencing revenue drops akin to pandemic-era sales slumps. Factors including the onset of “Operation Midway Blitz,” increased ICE presence throughout the city and whispers of a possible recession have all negatively impacted local businesses throughout the city.  “This work serves as a reminder that community third spaces like indie bookstores—and the people who support them—will always have more to offer tha

Every year, as Chicagoans are packing away their Halloween costumes and debating whether it’s too early to cue up the Christmas music, the Maggie Daley Ice Skating Ribbon begins to thaw from its summer slumber—or rather, freezes. The iconic ribbon of ice that winds through downtown Chicago like a frosted racetrack is a welcome event for those who still believe that the trials and tribulations (and dibs) of a Chicago winter can somehow be fun. On Friday, November 14, the Maggie Daley Ice Skating Ribbon’s familiar scene will return: parents lacing tiny skates with military precision, couples testing the limits of romance and balance, and teenagers pretending not to hold onto the rink’s wall for dear life. Whether you’re a seasoned glider or just here for the hot chocolate, here’s everything you need to know before visiting the Maggie Daley Ice Skating Ribbon this winter. RECOMMENDED: The best ice skating rinks in Chicago When does the Maggie Daley Ice Skating Ribbon open? The rink will officially open on Friday, November 14 at 11am. What is the Maggie Daley Ice Skating Ribbon non-holiday schedule? Monday–Friday (non-holiday): 11am–1pm, 2–4pm, 5–7pm and 8–10pm Saturday and Sunday: 8–10am, 11am–1pm, 2–4pm, 5–7pm and 8–10pm What is the Maggie Daley Ice Skating Ribbon holiday schedule? Thanksgiving (November 27): 8–10am, 11am–1pm and 2–4pm Day after Thanksgiving (November 28): 8–10am, 11am–1pm, 2–4pm, 5–7pm and 8–10pm Holiday season (December 12, 2025–January 4, 2026): 8–10am, 11a

As we approach Thanksgiving—or, as I prefer to call it, Planes, Trains and Automobiles season—it’s time to pay tribute to the humble train. Gridlock traffic? Nonexistent. Security lines longer than the wait for a Kasama breakfast sandwich? Not with Amtrak. When it comes to rail travel, it’s as simple as hopping on, tuning out and watching the world go by through a panoramic window. Let’s just hope you aren’t left hauling a trunk full of all your earthly possessions across a muddy field like our beloved transit heroes Neal Page and Del Griffith. If you’re ready to embrace the convoy lifestyle, Chicago happens to be the starting point for one of the most picturesque train rides in the country. In a recent roundup of bucket-list train journeys, The Independent named Amtrak’s Empire Builder the No. 1 most scenic train ride in the U.S. Beginning at Chicago’s Union Station and making its way toward the Pacific Northwest, the route winds through 1,138 miles of rolling vistas and splendid wilderness, even following long stretches of the Lewis and Clark trail. And the best part? Tickets for the life-defining trip can cost as low as $160—granted, it’s a coach ticket. But those views? Priceless. RECOMMENDED: The 22 best Metra day trips from Chicago Amtrak’s Empire Builder has been in operation for 96 years and counting, connecting over 40 communities across eight states. The first westbound Empire Builder trip pulled out of Chicago on June 10, 1929, when the route was helmed by the Grea

When you’re a kid, few things are as delicious as keeping a secret. You steal a cookie, blame the dog, and suddenly you’re living a double life. Secrets make you feel interesting—mystical, even. Then adulthood happens, and secrets start to involve texts you shouldn’t have sent to your ex or some of the darkest moments of your life. The thrill is gone; what’s left is stress over what’s a secret and what’s not, and perhaps a vague sense that you’re being haunted by your own browser history. If you’re feeling the unbearable weight of all things undisclosed, let The Confessions Project lighten the psychic load for you. The pop-up encourages strangers to roll up to a vintage typewriter resting on a wooden podium, anonymously punch out a secret nagging their conscience and deposit it in a steel mailbox enveloped in clanging silver chains. Think of it as a pressure valve for the over-thinkers, over-feelers and mildly guilty. The project, produced by the Chicago art collective Wrath + Love, has been popping up throughout the city—in Logan Square, Hyde Park, Lincoln Park and Wicker Park—all within the past month. The endeavor was inspired by artist Ernest Smith’s time spent as a first responder in Nevada, according to Block Club. Wrath + Love was Smith’s magazine in college, and he returned to Chicago to revive it as a multidisciplinary art collective paying homage to street art. “For months, we’ve been collecting real confessions from strangers across Chicago—transforming them into a

Chicago has been raking in the accolades this year, from being voted the best big city in the U.S. for the ninth consecutive year to being home to one of the coolest neighborhoods in the world, but we’re not done yet: our town was just named the 35th best city in the world by Resonance Consultancy’s 2026 World’s Best Cities ranking. This isn’t just a flattering opinion, though: Resonance Consultancy and Ipsos, a multinational market research and consulting firm, crunched a whole slew of numbers to inform this global ranking. To come up with the report, the agencies surveyed over 21,000 folks across 30 different countries to determine each city's Place Power™ Score, which takes note of three different categories: livability (i.e., walkability, access to green space, air quality, etc.), loveability (i.e., culture, dining, attractions, etc.) and prosperity (i.e., economic indicators of success). London tops the global list for the 11th year in a row and New York lands at number two, the best city in the U.S. In addition to New York and Chicago, three other U.S. cities broke the ranking’s top 50: Los Angeles (number 12), Miami (Nnumber 26) and San Francisco (number 28). "Few cities on the planet are firing on all cylinders like America’s great Midwest metropolis," reads the Chicago section of the report. "The city is leaner and more efficient than ever, boasting the second-highest number of Fortune 500 headquarters in the country, behind only New York." Among the standout qualiti

If you think decorating a Christmas tree is only about tinsel and string lights, the Griffin MSI’s annual “Christmas Around the World and Holidays of Light” exhibition will prove you wrong. Every year, the museum assembles its four-story Grand Tree while hundreds of volunteers decorate more than 50 artificial pines that represent Chicago’s diverse communities and their holiday traditions. These tree decorators are less like Santa’s elves and more like small-scale architects of joy—armed with ladders, handmade ornaments and stories to share one decoration at a time.  I visited the MSI the day after Halloween, while the city was still sleeping off its collective hangover and sugar crash, to witness the construction of these holiday icons. (They’ll open to the public on November 8 and stay on view through early January.) Peppered throughout the museum’s marble rotunda, clusters of emerald pines stood sentinel around the Grand Tree as volunteers worked diligently—but no less joyfully. They fluffed branches, hung ornaments and fussed over every glittering bit and bob like surgeons of seasonal joy. The smell of coffee perfumed the air while children and adults alike nibbled on donuts and admired their handiwork. And from across the hall, the Tesla coil cracked like a whip, its electric snap echoing through the festivities as if to say: science never stops, not even for Christmas.  At the head of the operation, perched at a folding table scattered with meticulous volunteer schedule

Halloween in Chicago is never complete with the Haunted Halsted Halloween Parade, one of the city’s most vibrant Halloween events. Each year, thousands of costumed revelers pack the streets of Northalsted for an unforgettable night of music, performance and community-centered fun. Whether you’re planning a family-friendly Halloween outing or looking to join one of the best Halloween parties in town, Halsted Street is the place to be on Halloween proper.  Here’s your complete guide to this year’s Haunted Halsted Halloween Parade—from start times and street closures to where to park, what to wear and other spooky happenings nearby.  Parade start time, route and street closures The Haunted Halsted Halloween Parade typically steps off from the corner of Halsted Street and Belmont Avenue at 7:30pm on October 31. The parade route runs up Halsted Street from Belmont Avenue to Brompton Avenue. Halsted Street will be closed from Belmont Avenue to Addison Street from approximately 5pm on October 31 until 2am on November 1. Side streets including Aldine, Buckingham, Cornelia, Melrose and Roscoe will also be closed during the same timeframe. Spectators can line the route early to register for a post-parade costume contest or catch the best views of floats, performers and dazzling Halloween costumes.  How to get there No parking will be allowed on the aforementioned closed streets from 5pm on October 31 until 2am on November 1. For transportation to and from the parade, public transit or

At “EmotionAir: Art You Can Feel,” the latest import from the roving Balloon Museum, you’re not so much viewing art as you are being swallowed by it. The space hums with light, color and the faint whoosh of industrial fans—a cathedral of air where the holy sacrament is snapping a selfie before the moment deflates.  Until April 6, 2026, Avondale’s Fields Studios will be packed with nearly 20 soundstage-sized balloon-based installations—like horned sculptures spouting soap bubbles, inflated spheres scrawled with abstract squiggles and, of course, the infamous rose-colored ball pit that was essentially the best supporting actor in season three of Emily in Paris.  True to the exhibition’s name—a play on “emotional,” no doubt—each installation is introduced by a digital screen adorned with an artist statement and the emotion each piece strives to elicit from the viewer. The exhibition’s tagline “art you can feel” certainly rings true—especially if your emotional range tends to hover between wonder, mild disorientation and the irresistible urge to document every waking moment of your life on TikTok.  Photograph: Shannon ShreibakPlayground Love by Michela Picchi I was invited to a press preview of “EmotionAir” a day before its highly anticipated public opening. In lieu of choosing my own adventure as I navigated the exhibition, I was guided through a labyrinth of rooms that built toward catharsis—or something like it—as if the curators were engaging in emotional choreography: fe

There are only so many ways to pass the time in the miserable, liminal space of an airport. You can doomscroll until your eyes twitch, nosh on a $12 bag of chips or stare into the abyss at the Nuts on Clark line. Soon, though, travelers at O’Hare and Midway airports may have a new way to kill time: depleting their life’s savings 20 bucks at a time before boarding the plane. That’s right, along with duty-free liquor and overpriced pretzels, Chicago’s airports may soon house slot machines. On the first day of hearings on Mayor Brandon Johnson’s proposed $16.6 billion budget, Chief Financial Officer Jill Jaworski revealed that Chicago is actively pursuing the installation of slot machines at O’Hare and Midway airports. According to WBEZ, a top mayoral aide confirmed that gambling behemoth Bally’s has even scoped out a slot machine site at Midway Airport.  Ald. Gilbert Villegas (36th)—chair of the City Council’s Committee on Economic, Capital and Technology Development and a longtime champion of the ordinance that would welcome video gaming terminals to sites throughout the city—told the Chicago Sun-Times that airports present the city with a “captive audience” for video gambling. Villegas and his fellow gambling proponents are advocating for exclusive lounge areas stocked with slot machines. Only travelers 21 and older could access these parlors, which would be supervised at all times by an employee aged 21 or over. The miniature casinos would also offer food and drinks for purc

We’ve heard a lot of Halloween talk lately, but this week ushers in another important celebration: Día de los Muertos. Translating to “Day of the Dead” in English, Día de los Muertos is a Mexican holiday that celebrates deceased loved ones with ofrendas (altars), cemetery visits and vibrant festivities. Through offerings like the deceased’s favorite food and drink, the celebration ushers spirits of the departed back to the realm of the living. Día de los Muertos is traditionally observed from October 31 to November 2, and Chicago has no shortage of events, 5K races and more to celebrate.  The best Día de los Muertos celebrations in Chicago Día de los Muertos Ritmo del Mar Shedd Aquarium, 1200 S DuSable Lake Shore DrOct 30 at 6pm Celebrate Día de los Muertos in the Shedd Aquarium’s aquatic confines. The Shedd will be hosting live music, local cuisine and opportunities for community and connection. Event tickets include admission to all aquarium exhibits. Photograph: Courtesy of United Neighborhood Organization La Carrera de los Muertos Benito Juarez Community Academy, 1450 W Cermak RdNov 1 at 8am La Carrera de los Muertos—or “Race of the Dead”—is a fundraising event that began in 2007. With a course weaving through Pilsen, runners and walkers convene to celebrate Día de los Muertos, complete with costumes, entertainment and food. The race’s proceeds benefit UNO, a nonprofit that supports girls’ access to mentorship, mental health, leadership and physical wellbeing. Free publ

We’ve reached the final, flickering weeks of spooky season—a blissful pocket of time before plastic skeletons are replaced by inflatable reindeer and pumpkin spice makes way for all things eggnog (vile) and peppermint (barely acceptable). So, before the city slips into a sleigh bell jingling tizzy, squeeze in a few more scares, boo-zy cocktails (see what I did there?) and chaotic costume decisions. From haunted pop-ups to family-friendly parades, here’s where you can find a little seasonal mischief around the city. RECOMMENDED: The best Halloween bars in Chicago RECOMMENDED: Our complete guide to Halloween in Chicago The best Halloween events, pop-up bars and parties in Chicago Streeterville Doggy & Kitty Halloween Party Museum of Contemporary Art, 220 E Chicago AveOct 25 at 9am Chicago’s most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog and cat owners parade their costumed pets around the grounds. The best-dressed furry friend—chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman—will receive some special prizes. A $10 suggest donation supports the the dogs, cats, kittens and puppies residing at PAWS Chicago. Hallo-Queen! Metro & Smartbar, 3730 N Clark StOct 26 at 9pm Queen!, Smartbar’s weekly LGBTQ+ underground house and disco party, takes over the entire 3730 building in celebration of Halloween. House heavyweights including Derrick Carter and Ralphi Rosario have the tunes covered, while local drag queens