Lauren Brocato

It’s always bittersweet to bid farewell to summer, but don’t let yourself get too down in the dumps—apple picking season is here along with the sunny start of fall in Chicago. The city’s suburbs and surrounding countryside are full of bountiful orchards where you can pick pounds upon pounds of the fruit to take home for snacking or baking (speaking of baking, many of these farms feature bakeries stocked with homemade, apple-filled treats). And that’s not all: Come October, you'll also find some of the best outdoor activities at pumpkin patches near Chicago, plus corn mazes and hayrides at a handful of the farms on our list. Take a look through our roundup of the best apple orchards near Chicago and get excited for all the autumnal fun still to come. RECOMMENDED: Discover the most unique day trips from Chicago

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. Updated August 19, 2026: Clear your calendars because there's a lot to look forward to this weekend. The Lakeview Taco Fest is back with mouthwatering fare and Mexican wrestling, and the West Loop Art Fest transforms Fulton Market into an open-air gallery. There are also plenty of shows to catch, from Kacey Musgraves at the United Center to the Vape! The Grease Parody at the Apollo Theater. Keep scrolling to discover more of the best weekend events across the city. RECOMMENDED: The best things to do in Chicago today

When it comes to dining out, Chicagoans are positively spoiled. As of 2026, the city is home to 20 Michelin-starred kitchens that range from one of the best Mexican restaurants in Chicago to a fine-dining Indian concept. One of the fanciest breweries in Chicago even made the list. And eating at a Michelin-starred restaurant doesn't mean dropping an entire paycheck on a meal—there are a handful of relatively affordable options in this year's lineup. What's the deal with a tire company handing out stars to restaurants? The Michelin Guide (which began as a physical book issued to drivers) evaluates the best restaurants in Chicago on several criteria, but the coveted stars are awarded based on the quality of food alone. Inspectors look for top-notch ingredients, mastery of flavor and cooking techniques, the personality of the chef in his or her cuisine, overall value and consistency. One star represents high-quality cooking that's worth a stop; two stars indicate excellent cuisine that's worth a detour; and three stars denote exceptional cuisine that's worthy of a special journey. With all of that in mind, take a look at the Chicago restaurants that earned Michelin stars for 2026.

September might be here, but don't despair—there are still plenty of things to do in Chicago—whether you're still embracing a summertime state of mind or welcoming fall with open arms. From Oktoberfest celebrations to outdoor festivals (including Riot Fest), we've still got plenty of warm weather fun to take advantage of before the leaves start to turn and the temperature drops. Soak up the sun at the best Chicago beaches and rooftop bars, or spend your weekends checking out the end of festival season at events like the Chicago Jazz Fest and the World Music Festival. And if you really can't wait for fall to arrive, might we suggest some early leaf peeping and apple picking? Whatever your mood, you'll find plenty of ways to keep busy with our roundup of the best things to do in Chicago this September.  RECOMMENDED: Events calendar for Chicago in 2026

Do you feel the warmth in the air? It can only mean one thing—festival season is here. The city's streets and parks will be full every coming weekend thanks to a stacked lineup of fests, fairs and more. You'll find everything from heavy-hitting summer music festivals like Lollapalooza and Sueños to beloved neighborhood block parties on the calendar from May through October. We'll continue to update this list throughout the season as more fests announce lineups and additional details—in the meantime, take a look through some of the best festivals in Chicago this year. RECOMMENDED: The best things to do this summer in Chicago

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, 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 to do in Chicago this October.  RECOMMENDED: Events calendar for Chicago in 2026

We may be savoring our last full month of summer in Chicago, but the fun is far from over. August brings with it some of Chicago’s best seasonal events, from Northalsted Market Days and Grant Park Music Festival to new events like the first Chicago Italian Beef Fest and Malört's attempt to set the world record for the most people to take a shot of the polarizing drink at once. Don't forget to plan a couple of languid afternoons at the best Chicago beaches—Lake Michigan's often-frigid water is at its warmest this month. Looking for even more ways to make the most of the remaining summer days? Scroll through our list of the best things to do in Chicago this August. RECOMMENDED: Events calendar for Chicago in 2026

The annual Oktoberfest celebrations mark the arrival of fall, but even if you can't make it to Munich, plenty of Chicago institutions are throwing bustling, German-themed parties to ring in a new season. From special tappings at Chicago breweries to carnival rides outside neighborhood churches, we've gathered some of the best parties and events during Oktoberfest in Chicago, taking place at amazing restaurants, bars and even zoos. Break out those dirndls and lederhosen and prepare to say "Prost"! What is Oktoberfest?  Oktoberfest is a multi-week beer festival and fair held in Munich, Germany. Originally conceived to celebrate the marriage of Bavarian King Ludwig I and Princess Therese of Saxony-Hildburghausen in 1810, the festival has since evolved into a public event and one of the most important cultural symbols in Bavaria, drawing millions of attendees from across the world each year.  When is Oktoberfest in Chicago? Although Munich's Oktoberfest takes place this year from September 19–October 4, Chicago's celebrations generally take place anywhere from mid-September to late-October.

Each week, our team at Time Out Chicago curates the ultimate weekly event guide, featuring the big events, IYKYK pop-ups and everything in between. Here, you'll find the happenings that are worth your time and money, from family-friendly activities and daytime events to late-night shenanigans and the low-key functions that you won't hear about on TikTok. Updated August 17, 2026: Summer isn't over yet! There's still plenty of time to hit the beach, get out on the lake, and spend time outside before summer ends. This week, you can cheer on athletes (and look for the funniest signs) at the triathlon, or see Sinners under the stars at the final Millennium Park Summer Film Series screening of the year. Keep scrolling for more of the best happenings across Chicago this week. RECOMMENDED: Discover the best things to do in Chicago in August 2026

Welcome to summer, Chicago! We've only got a few precious months of warm weather and long days to enjoy, so let us help you make the most of it with our guide to the city's best season. A few ideas: Maximize your time outside at rooftop bars and restaurants, catch outdoor movies in city parks, sample bites at a street festival and spend your weekends dancing to live tunes at the best summer music festivals in Chicago. And if you're looking for free things to do in Chicago, it's tough to beat a long day at the beach! Summer won't stick around forever—scroll through and get ready to explore the best of the city's warm weather offerings. RECOMMENDED: Discover the best things to do in ChicagoHere are the best boat tours in Chicago

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: The best things to do in Chicago

Last updated August 5, 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 the twice-weekly fireworks show at Navy Pier, ART on THE MART and concerts and movie screenings galore. Plus, don't miss out on the recurring events at Millennium Park 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 RECOMMENDED: The best cheap eats in Chicago

Get ready to bust a move because Chicago SummerDance is back with free dance classes. The instructor-led classes are completely free and open to dancers of all ages and experience levels. This year's lineup is packed with beginner-friendly classes across dance styles, all informed by the city’s rich cultural landscape. From ballroom and Bollywood to Brazilian samba and Chicago steppin’, there’s something for everyone—even those who claim to have two left feet.

Send summer off with a bang at this indoor/outdoor music and arts festival in suburban Bridgeview (7337 W 100th Pl, Bridgeview, IL, 60456), which has been held on the last Saturday of the summer since its debut in 2024. This year, EDM duo Big Gigantic headlines, alongside Saxsquatch, Henry Fong, The Sponges and more. Check out the full lineup here.

Revolve and Cotton are bringing their joint collection to Fulton Market for a four-day pop-up shopping experience. At The Cotton Shop by Revolve, you can browse the pieces, plus participate in a denim recycling program, get custom denim embroidery, snack on free goodies from Lil Sweet Treat, and snap pics in a photo booth. Five people each day will be randomly selected to receive a $100 gift card, and the first 50 guests will get a bag filled with beauty products to bring home.

The inaugural Chicago Art Fair is bringing top galleries from across the globe to THE MART this fall. The four-day event, ideal for collectors, designers, buyers and art enthusiasts alike, will showcase contemporary and modern fine art paintings, sculptures, photography, mixed media and more.

Nearly 20 years after their original Burnin' Up Tour, the Jonas Brothers are hitting rewind with The Burning Up Tour All Over Again, and they're stopping in Chicago. The brothers will headline the Allstate Arena in Rosemont for one night to play nostalgic hits like "Burnin' Up," "BB Good," "Hold On" and more.

The celebration at the DANK Haus German American Cultural Center in Lincoln Square might be the closest you'll get to the actual Oktoberfest without hopping on a plane. The festive evening will have authentic German food and beer, live music, games, a stein-holding competition, a ceremonial keg tapping and even a yodeling contest. Ticket sales support the non-profit organization's mission to preserve German culture, language and traditions in Chicago.

Chicago's largest Oktoberfest celebration is returning to the heart of Fulton Market. Located just behind Restaurant Row at 171 N. Peoria St., this lively six-week German fest is pouring Hofbräu München beer imported directly from Germany. Guests can also expect Bavarian pretzels, brats, live German music, carnival games and more. 

Grab your dirndls and lederhosens and get ready to party at the second annual Old Town Oktoberfest. The three-day German-inspired fest will have brats, pretzels and German beer, plus live entertainment all weekend. Guests can also participate in stein-holding contests, and dance and sing the night away.

What's better than dressing up on Halloween? Dressing up your pups, of course! This spooky season, the Howl-O-Ween Canine Cruise aboard First Lady is back for a limited-time, 90-minute lake and river cruise. Costumed dogs (and humans!) are invited to board the cruise to enjoy a narrated journey complete with pumpkin-flavored dog treats and a canine costume contest. The winners will be entered to receive a grand prize of a $1,000 made by First Lady in the winner's name to a canine organization.

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

The flagship NFL podcast from the New York Times' The Athletic is hosting its second-ever live taping at Lincoln Hall. See hosts Robert Mays, Derrik Klassen and Dave Helman discuss the league's biggest stories, do their signature Wins Pool Draft on stage and talk about why they love the sport. 

A new Latina music festival is debuting this summer, helmed by Chicago creative Kendra Jamaica, who's behind the recurring party series Lipstick Lounge. Nearly 20 local acts will perform across two stages, with sets spanning salsa, cumbia, bachata, R&B and bilingual pop. Guests can also get tooth gems, nail sets, shop and more.

Yes, you read that right. NASCAR just announced that the downtown Chicago street race will not return in 2027. The decision came after the city and NASCAR ran out of time to agree on a 2027 date.   Instead, the Cup Series race weekend will be held at Chicagoland Speedway in suburban Joliet, about an hour outside of the city, from June 25 to June 27, 2027. This marks the second year in a row that the race takes place in Joliet, after NASCAR traded the streets for the Speedway earlier this year. NASCAR first took over the streets of Chicago in 2023 over Fourth of July weekend, notoriously bumping Taste of Chicago out of its signature Independence Day time slot. The debut race weekend was defined by abysmal weather, a truncated race, multiple delays and the cancellation of all three scheduled concerts by The Chainsmokers, Miranda Lambert and Charley Crockett.  RECOMMENDED: Chicago's most iconic street party was cancelled—here's why The following two years brought wet weather and extreme heat, but were far less chaotic than 2023. Despite more favorable conditions and cheaper tickets, Chicagoans weren’t totally sold on the street race. Many residents still complained about things like extensive street closures and parking restrictions, and still-high ticket prices (a single-day ticket went for $99 in 2025). Even the drivers weren’t all in, as they expressed concerns about the possibility for crashes on the track. View this post on Instagram A post shared by NASCAR

Get ready to bust a move because Chicago SummerDance is back with free dance classes in Grant Park for just nine nights this month. The lineup for the series’ final installment, Chicago SummerDance in the Spirit of Music Garden, is packed with beginner-friendly classes across dance styles, all informed by the city’s rich cultural landscape. From ballroom and Bollywood to Brazilian samba and Chicago steppin’, there’s something for everyone—even those who claim to have two left feet. SummerDance classes are completely free and open to dancers of all ages and experience levels. Instructor-led dance lessons kick off at 6pm and are followed by live music performances—with plenty of room to show off your new moves—at 7:15pm.  RECOMMENDED: Chicago's most iconic street party was cancelled—here's why A special edition of SummerDance, hosted by Chicago musician and media personality Dana Divine, will be held during the annual Chicago House Music Festival weekend. BraveSoul Movement will lead a house dance workshop at 6pm before DJs Ron Troupe (6:30pm) and Mark “Flava” Fuller (7:45) take the stage.  “Chicago SummerDance is one of many ways that the Department of Cultural Affairs and Special Events activates and transforms public spaces into vibrant areas for people to connect through culture,” says DCASE commissioner Kenya K. Merritt. “These live performances and free dance lessons celebrate the traditions and communities that define Chicago while making arts and culture accessible in n

Those deafening roars from above are nothing to be afraid of—it’s just the annual Chicago Air and Water Show.  This weekend, the roaring spectacle returns to the skies of Chicago for two days (well, three if you count Friday’s rehearsal) of high-flying stunts, daring tricks and spectacular maneuvers for a crowd of nearly 2 million people. The festivities kick off with a practice on Friday, August 14, followed by the official show on Saturday, August 15 and Sunday, August 16, from 10:30am to 3pm. As always, the show is free to watch—all you have to do is look up.  North Avenue Beach is the central hub, but you’ll still be able to see the show from plenty of other spots along the lakeshore.  View this post on Instagram A post shared by Air Force Thunderbirds (@afthunderbirds) This year’s air show will look a little different as the U.S. Air Force Thunderbirds return for a second year in a row, rather than the typically alternating U.S. Navy Blue Angels due to a scheduling conflict. We’re still in for a remarkable show featuring a lineup of military and civilian performers, including the U.S. Army Parachute Team Golden Knights. Legendary moderator and retired Air Force pilot Herb Hunter will once again voice the show, which you can hear from Oak Street Beach to Fullerton Beach.  Read on for all of the essential information about this year’s Chicago Air and Water Show. Who are the military performers in the Chicago Air and Water Show 2026? U.S. Air Fo

Since 2021, the beloved street party Sundays on State has drawn nearly 1.5 million people to the Loop’s main drag, but, to the disappointment of many Chicagoans, it will not return this year.  The 2026 festival, which took place on September 7 and October 5 last year, was cancelled by The Chicago Loop Alliance, which announced in February that the decision was made as it works to establish the new Loop Arts District, along with revamped arts- and culture-related programming.  Although it’s disappointing that Sundays on State will not take place this year, a new wave of cultural events is on the horizon, and a brand new event called Loop Arts Fest on Saturday, October 17, is slated to replace Sundays on State. The new daylong festival will take over State Street from Jackson to Madison for a celebration of the area's rich arts and culture assets, according to the Loop Alliance. The organization added that Loop Arts Fest will combine on-street activations with amplification of existing offsite programming to showcase the breadth of the Loop’s cultural community. A complete lineup of events and participants is expected to be announced in September. RECOMMENDED: The best festivals in Chicago for 2026, from music fests to street fairs The Loop, and particularly State Street, is still recovering from the effects of the pandemic. But things are looking up: Vacant storefronts on State Street dropped nearly 14% in the fourth quarter of 2025, according to the Chicago Sun-Times, and pe

It’s almost time for Chicago’s biggest event of the year: Lollapalooza.  This year’s lineup is anchored by heavy hitters across genres (more on that below) and a massive roster of official aftershows across the city.  You’ll also want to look out for exciting new additions to the Grant Park festival grounds, including a new—and free—Ferris wheel, courtesy of Motorola. As with any activations at Lollapalooza, whether it’s Ulta Beauty’s Beat Suite or the Coca-Cola Roller Ring, “free” usually means long lines, but there’s plenty of time to explore between sets. Whether you’re ready to relive Brat Summer or are patiently waiting to break out your best moves at Tate McRae or Zara Larsson, we’ve created a complete list of every performance with updated set times and stages below. Bookmark this page, where you’ll find the day-by-day schedules of every performance, both live and on stream, at Lollapalooza this year.  How can I stream Lollapalooza?  You can stream select Lollapalooza sets on Hulu or Disney+. Performances by Charli XCX, Tate McRae, Lorde, Olivia Dean, John Summit, Jennie, Smashing Pumpkins and The xx will be available to stream from home. Check the festival’s website for the latest livestream set times. Photograph: Courtesy LollapaloozaLollapalooza 2026 livestream lineup   What are the Lollapalooza set times and schedule? All four daily schedules are listed below, both in image and text format. There are more than 150 acts, but the biggest ones to watch for are Sombr

I always believed that I, a lifelong Chicagoan, would never succumb to riding a pedicab. That is, until I had no choice but to during a gridlock on State Street—and it completely changed my perspective on them. Chicago pedicabs, AKA cycle rickshaws, bike taxis or tuk-tuks, get a bad rap. A maximum of 200 pedicabs are allowed to operate each year. You can typically find them near major attractions like Millennium Park, Navy Pier, along the Lakefront Trail and around Museum Campus.   To most locals, the music-playing, Christmas-light-clad contraptions are seen as overpriced annoyances that scam tourists, take up space in bike lanes, and weave through pedestrian pathways at risky speeds. While there is a case to be made for staying away from them in some cases, pedicabs are officially licensed operators that can be a genuinely efficient—and fun—mode of transportation. RECOMMENDED: Don’t want to pay for a pricey Chicago River cruise? Book this $10 ride instead. Before you hop on, confirm the price and acceptable form of payment with the driver. Prices vary widely depending on distance, location, time of day and other factors like if a major event is happening. Use your best judgment to decide whether the price is right for you (hint: if there are multiple drivers around, ask a couple to find the best rate).  Photograph: Lauren Brocato for Time OutPedicabs at Navy Pier If you find yourself in one of the situations below, and if the price isn’t egregious, you might be in for a th

Lollapalooza just dropped its official aftershow schedule—and it’s stacked. From Tuesday, July 28, through Sunday, August 2, more than 80 acts are taking over 27 venues across the city. The solo shows offer a chance for fans to see a full set from some of the festival’s most anticipated performers like Zara Larsson, Yungblud and Suki Waterhouse. The best part about the aftershows? $1 from every aftershow ticket sold will support arts education programs for youth across Chicago. RECOMMENDED: The Lollapalooza daily schedule with set times is out When do Lollapalooza 2026 aftershow tickets go on sale? Official aftershow tickets go on sale Friday, May 29, at 10am CT. Visit the Lollapalooza site to score yours. Do I need a festival pass to go to the aftershows? No. You do not need a Lollapalooza festival pass to go to the aftershows. What’s the lineup and schedule?  Check out the poster for the full Lollapalooza 2026 aftershow lineup below, followed by the list of performances by day.  View this post on Instagram A post shared by Lollapalooza (@lollapalooza) Tue, July 28 Paris PalomaMetro Wed, July 29 Evening Elephants w/ The BraymoresBeat Kitchen CMATBottom Lounge Ayybo w/ Inphinity & Rika BCastaways Bad Nerves w/ Flesh PanthersCobra Lounge Bella Kay w/ Claire RosinkranzGarcia’s Blood OrangeHouse of Blues Bixby w/ J.VN.Lincoln Hall Viagra Boys w/ Beau WanzerMetro Between Friends w/ FingyOutset Boris BrejchaRadius Empire of the SunSalt Shed

In case you needed a reminder, the zoo isn’t just for kids. Although it's one of Chicago’s best attractions, the Lincoln Park Zoo might not be the first place you think of when planning a night out, but there’s actually a lot for grown-ups to love about it. First off, it’s free. In this economy, that alone is enough to get almost anyone in the door. It’s a pretty great deal for entry into the wondrous, 35-acre escape into the animal kingdom that makes you forget you’re less than half a mile away from Lake Shore Drive. Whether you’re just passing through on a solo walk or are planning a group excursion, these are the best things for adults to do at the Lincoln Park Zoo. RECOMMENDED: The 44 most iconic Chicago attractions Check out the zoo's 21+ events The Lincoln Park Zoo hosts a series of adults-only events year-round. From themed holiday parties with DJs and drinks to nostalgic functions like `80s vs. `90s Night at the Zoo and Adults Night Out: Crafted, the 21+ events offer a chance to let your hair down, and maybe even see the zoo’s nocturnal animals in action. View this post on Instagram A post shared by Lincoln Park Zoo (@lincolnparkzoo) Take a date here Want to plan a romantic date without breaking the bank? Take them to the zoo. There are dozens of quiet spots for a deep chat, like along the Nature Boardwalk or around the northern edges of the zoo.  Photograph: Lauren Brocato for Time OutLincoln Park Zoo Find zen at a meditation class Start y

Fact: 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.  Also a fact: There’s a lot you can still do here without having a ticket—and much of it is free. Since its opening on June 19, demand for tickets to the Obama Presidential Center museum has been exponentially high. Earlier this month, a second wave of tickets sold out within two hours. The OPC states on its website that it will update ticket availability on the second Wednesday of each month at 10am CT. If you’re hoping to check out the eight-floor museum, which I highly recommend, then it’s probably wise to set your alarm for the best chance at snagging a coveted ticket. RECOMMENDED: Inside the Obama Presidential Center: Celebs, presidents & opening weekend photos But even if you don’t have a ticket, there are still plenty of things to do on the Jackson Park campus. Here are 11 things you can do at the OPC without a ticket. Explore the grounds You can easily spend hours on a walk around the 19.3-acre campus. Green spaces abound here, and there are plenty of benches, water fountains, and walking paths for a day of exploration. Dine at Tafari’s Kitchen Tafari’s Kitchen is the fast-casual on-site restaurant inside the Forum Building, which is open to the public. Named after the Obamas’ late personal chef, the restaurant features an elevated dining room and additional tables in the lobby area.

The FIFA World Cup 2026 Final is almost here. On Sunday, July 19, Spain and Argentina will take the pitch at 2pm CT to compete for the World Champion title—and a portion of the record-breaking $650 million prize fund. Even though Chicago isn't a host city, there are still plenty of ways to get in on the action right here at home. From huge watch parties with a jumbotron to a digital soccer tournament with a $10,000 grand prize, you won't want to miss these World Cup celebrations.  Party at Chicago Fire’s World Cup HQ Photograph: Courtesy RecessRecess Recess and Chicago Fire are going all out for the World Cup. The West Loop bar/event space has installed a massive 360-degree jumbotron and is hosting a lineup of themed watch parties, giveaways, and exclusive merch drops throughout the tournament. Table reservations are completely booked for the remainder of the tournament, but standing room space will be available for walk-ins. Guests should reserve a free mobile pass before coming in. Doors open at 11am—the earlier you arrive, the better chance you'll have of getting in.   RECOMMENDED: The 15 best Chicago sports bars, from Wrigleyville to River North Compete in a Whirl'd Cup tournament at Whirlyball Grab your crew or enter as a free agent and compete in WhirlyBall’s Whirl’d Cup tournament during the World Cup championship match on Sunday, July 19. The Whirl’d Cup will take place while the final match plays out on screen, alongside a shootout competition and other soccer-them

Is it your responsibility to talk a friend out of a risky financial decision? Would you leave if you found out your longtime partner was hiding the fact that they’re in significant debt? And do the ultra-rich owe it to their friends to lend them money in times of dire need? These questions are difficult to discuss even with those closest to us, so naturally, I paid $20 to debate them with people I’ve never met before at The Scout Waterhouse + Kitchen in Old Town. Arguing With Strangers is a new event from the Chicago-based series Let’s Do Fun Things. Founded in 2024 by Sam Mahafzah, LDFT hosts more than 20 events across the city every month, from board game nights and dance classes to lectures on medical mysteries, pickup beach volleyball and even an adult prom night. RECOMMENDED: The best free things to do in Chicago this month As with all of their events, AWS is designed to get Chicagoans out of their homes and into meaningful interactions with new people. This was the second AWS event, both of which sold out, and the theme of the night was Money and Relationships. Not a touchy subject at all, right? View this post on Instagram A post shared by @arguing.with.strangers The idea is to show up alone, which I did, and be paired with a group of other solo strangers. Often, events like this claim to be inviting for solos but end up being filled with cliquey groups who showed up together. This event, though, was, to my surprise, filled with more than 10

As I reflect on my first visit to the newly opened Obama Presidential Center on Chicago’s South Side, I keep coming back to the opening line of Charles Dickens’s A Tale of Two Cities: “It was the best of times; it was the worst of times.” That’s how it feels stepping into the OPC. Outside its bounds, in the real world, chaos, division and unease define many aspects of the moment. But at the OPC, peace, unity and hope swirl throughout the 19.3-acre campus. An overwhelming sense of prosperity offers a beacon of hope for what we can be and a look back at what we once were through archives from Barack Obama's presidency, commissioned artwork, innovative programming and more. Here, visitors gleefully snap selfies outside the towering Museum building; kids run blissfully through the sprawling grounds; and restaurant staff stop by your table to make conversation about nothing in particular even though it’s a counter-service spot. Photograph: Lauren Brocato for Time OutObama Presidential Center RECOMMENDED: Inside the Obama Presidential Center: Celebs, presidents & opening weekend photos Juxtaposing current reality with the utopian-like community that’s alive at this place that feels worlds away from the South Side was jarring, but that's what makes it so special. Since its opening on June 19, sky-high demand has wiped out two rounds of tickets through January 2027. You can still visit much of the campus for free, but if you want a ticket to the Museum, set your alarm because avail