As a native Chicagoan, Lauren Brocato is still awed by her hometown, so much so that she’s dedicated her career to telling the stories of the people and places that inspire her each day. 

Lauren is the Things To Do Editor at Time Out Chicago. She previously served as Time Out Chicago’s Food and Drink Editor, contributed to Eater, and edited nearly a dozen Modern Luxury publications across the country, helping people from New York City to the Bay Area discover the best of their cities. 

When she’s not out exploring the city, you can find her biking along the lake, taking bar trivia way too seriously or planning her next trip. 

Follow her on Instagram (@laurenbrotaco) and pitch her at lauren.brocato@timeout.com.

Lauren Brocato

Lauren Brocato

Things To Do Editor, Time Out Chicago

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Articles (73)

Lollapalooza 2026 lineup, headliners & schedule: everything you need to know

Lollapalooza 2026 lineup, headliners & schedule: everything you need to know

Lollapalooza, one of the biggest events of the summer, is almost here. Chicago’s annual music festival returns to Grant Park July 30–August 2 with over 150 bands across eight stages. Headlining this year’s summer spectacle are Charli XCX, Tate McRae, Lorde, Olivia Dean, John Summit, Jennie, The Smashing Pumpkins and The xx. Along with the sensational lineup, Lollapalooza has some new amenities in store for attendees, including the Northside Suites, a private, air-conditioned experience with a private rooftop viewing deck, complimentary food and drinks and more. The exclusive space will accommodate up to 15 guests per day. There's also a new—and free—Ferris wheel, courtesy of Motorola. Other highlights in the lineup include Sombr, Turnstile, Geese, Freddie Gibbs, Lil Uzi Vert, Blood Orange, Hot Mulligan, The Chainsmokers, Finn Wolfhard, Beabadoobee, Ethel Cain and DJ Trixie Mattel. The Chicago Youth Symphony Orchestra will also be performing. And if you’re on the hunt to see the next breakout artist, this year will feature up-and-comers like Pearly Drops, Case Oats, Love Spells and more. Most tickets are sold out, but there are limited General Admission and Platinum Sunday passes available.  RECOMMENDED: Check out photos and coverage of Lollapalooza RECOMMENDED: Lollapalooza drops official aftershow lineup with 80+ acts The Lollapalooza 2026 lineup The festival will be headlined by Charli XCX, Tate McRae, Lorde, Olivia Dean, John Summit, Jennie, The Smashing Pumpkins and The
The best things to do in Chicago this weekend

The best things to do in Chicago this weekend

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 July 29, 2026: It's Lolla weekend! If you're headed to the festival, check out our coverage, from the lineup and updated schedules to aftershows and more. If you're planning on staying far away from the festival crowds, there are a lot of other things to do, like the inaugural Chicago Italian Beef Fest, which kicks off on Friday. On a budget? No problem. We've rounded up some of the best free events in Chicago, like Live on the Lake concerts at Navy Pier and free movie screenings in the parks, too. Keep scrolling to discover more of the best weekend events across the city. RECOMMENDED: The best things to do in Chicago today
The 28 best museums in Chicago

The 28 best museums in Chicago

Last updated July 13, 2026: Some of the world's most famous collections and exhibits can be found in Chicago. Want to see premier pieces from famous artists? Book your tickets for The Art Institute or the Museum of Contemporary Art. Obsessed with the deep unknown of the sea or space? Take a trip to the Shedd Aquarium or Adler Planetarium, which just so happen to be two of the city's best children's museums. Whether you enjoy art, science, history or architecture, Chicago's many museums are some of the top Chicago attractions and provide a great way to spend an afternoon.  RECOMMENDED: Discover the best things to do in Chicago
The best free things to do in Chicago this month

The best free things to do in Chicago this month

Last updated July 8, 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 street fairs galore. Plus, don't miss out on film screenings and other 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
The 24 best record stores in Chicago

The 24 best record stores in Chicago

When you want some fresh tunes for your turntable, tape deck or CD player, there's no better place to find them than at Chicago's best record stores. Whether you're trying to prepare for a concert coming up at a Chicago music venue or are feeling an old-school vibe, these shops have what you're looking for. Many have been in business for years, selling new and used vinyl, CDs and tapes—and making recommendations when you need them. From the latest albums in indie rock, hip hop and contemporary R&B to vintage jazz, blues and Chicago house records, Chicago's best record stores have it all. RECOMMENDED: The best thrift stores in Chicago
The best things to do in Chicago this week

The best things to do in Chicago this week

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 July 27, 2026: Get ready, Chicago: It's Lollapalooza week! The four-day festival kicks off on Thursday, so if you're going, check out our ultimate guide to Lollapalooza. If you're planning to stay away from the chaos around Grant Park, there are a lot of other events this weekend, like Chicago's first Italian Beef Festival and concerts at Ravinia Festival. And if you're thinking of fleeing the city altogether, check out the best day trips from Chicago. Keep scrolling for more of the best happenings across Chicago this week. RECOMMENDED: Discover the best things to do in Chicago in July 2026
36 Chicago slang words that only real Chicagoans know

36 Chicago slang words that only real Chicagoans know

Every city has its own lingo, so if you're spending some time in Chicago, you might as well get acquainted with the local vernacular. From unique Chicago delicacies to nicknames for interstates, there's plenty of Chicago slang that might elicit a bit of confusion if you haven't spent much time in the Midwestern metropolis. While most folks are familiar with “The Bean” and nicknames for other iconic Chicago attractions, we've gathered some more essential Chicago slang—including terms you can use during your next visit to a Chicago hot dog stand or pizza joint. Boystown (n.): A Lakeview neighborhood technically named Northalsted. It was the first officially recognized gay village in the U.S. Bungalow (n.): One-story, single-family homes with sloped roofs that are found in neighborhoods throughout the city, primarily in the "Bungalow Belt," an arc-shaped zone containing almost 80,000 of the unique houses. Photograph: Courtesy Just Dance/ShutterstockA classic Chicago bungalow Chicago handshake (n.): The local version of a boilermaker, typically comprising a pint (or can) of Old Style and a shot of Malört. Chicago Mix (n.): The salty-sweet combination of cheddar and caramel popcorn. You'll find it at Garrett Popcorn Shop (where the scent usually wafts into the street) and pretty much every popcorn shop worth its salt in the city. Coach house (n.): A small, separate dwelling located in the rear of a property. The construction of new backyard houses was formerly prohibited under
The absolute most beautiful gardens in Chicago

The absolute most beautiful gardens in Chicago

Back in the 19th century, Chicago's government picked the phrase "urbs in horto"—Latin for "City in a Garden"—as its motto, employing landscape architects like Daniel H. Burnham, Jens Jensen and Frederick Law Olmsted to beautify the budding city over the course of several decades. Today, thanks in part to that rich tradition of landscape architecture, Chicago is home to more than 8,800 acres of green space. Want to take advantage of warm weather and explore the best of the city's greenery? From nature preserves tucked into the Chicago parks to the city's massive conservatories, you don't have to go far to find gardens teeming with flowers and plant life native to Chicago and (far) beyond. Whether you're an amateur naturalist or you're just looking to explore some new Chicago attractions, take a minute to unwind in these beautiful gardens throughout the city. RECOMMENDED: Discover more of the best things to do in Chicago
Ravinia Festival 2026: Full lineup, schedule and ticket info

Ravinia Festival 2026: Full lineup, schedule and ticket info

Beloved summertime tradition Ravinia Festival returns to Highland Park this season with a jam-packed schedule of shows, featuring artists ranging from jazz and blues acts to classic rockers like Billy Idol and Deep Purple. Tickets are on sale now. This year, Ravinia debuts the revamped, 2,850-seat Hunter Pavilion. And although there's plenty of seating, many people opt to bring lawn chairs, blankets and food and beverages for a picnic spread on the lawn instead. Highlights for this season include a grand opening performance by Lizzo (July 11), Billy Idol (July 12), two nights of Paul Simon (July 17-18), Chance the Rapper (August 8) and Ricky Martin (August 20). Classical music lovers can catch a variety of performances from special guest conductors and soloists accompanied by the Chicago Symphony Orchestra, which takes up residence at Ravinia Festival every summer.  Take a look through the full Ravinia Festival lineup for 2026 below. When is the Ravinia Festival? Ravinia Festival 2026’s summer season runs from June 3 through September 23. Where is the Ravinia Festival? Ravinia takes place at Ravinia Park (418 Sheridan Road) in Highland Park, Illinois. The easiest way to make the trip from inside Chicago city limits is to take I-94 north and get off at the Lake Cook Road or Clavey Road exit, or ride Metra's Union Pacific North Line to the Ravinia Park stop, which drops passengers off directly in front of the venue's gates. All trains on the Union Pacific North Line will honor
The best free things to do in Chicago

The best free things to do 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
The best cheap things to do in Chicago for fun on a budget

The best cheap things to do in Chicago for fun on a budget

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 $25. And for even more cost-effective options, check out the best free things to do in Chicago. RECOMMENDED: The best cheap eats in Chicago
The best things to do in Chicago this summer

The best things to do in Chicago this summer

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

Listings and reviews (143)

Shark Week

Shark Week

Immerse yourself in the exhilarating underwater world where sharks swim freely at the Griffin Museum of Science and Industry's Giant Dome Theater. Every 60 minutes for one week, guests can see Shark Kingdom, which follows conservationists on a journey into the kingdom of sharks, on the museum's five-story, wrap-around dome screen. Entry to Shark Kingdom screenings is not included with a general admission ticket.
Christmas in July

Christmas in July

It's never too early to get into the holiday spirit. The Griffin Museum of Science and Industry is celebrating early with its Christmas in July weekend. Enjoy holiday music in the Rotunda, a liquid nitrogen show, holiday photo-ops and the annual family-friendly Naught or Nice after-hours events. Guests can also snag discounted tickets and membership offers, and get a sneak peek at the museum's beloved Christmas Around the World and Holidays of Light exhibit.
Sunday Jazz Cruise

Sunday Jazz Cruise

Set sail with Chicago Line Cruises for an evening of jazz on the river. On the last Sunday of each month through September, the cruise line is partnering with the Jazz Institute of Chicago for 90-minute cruises featuring live performances, an on-board bar, open-air decks and a prime view of the sunset.
Red Bull Setlist

Red Bull Setlist

Red Bull is bringing its Setlist experience to the U.S. for the first time for a one-night show at Radius. Headlined by Lil Yachty, Red Bull Setlist lets fans vote on elements of Lil Yachty's set, from the songs and performance style to surprise moments. Plus, in the weeks leading up to the show, Red Bull is giving local artists a chance to open for Lil Yachty by auditioning in a mobile recording studio.
Lee Miller: Fearless

Lee Miller: Fearless

From model to battlefield correspondent—and with many other titles in between—Lee Miller was a complex figure, and this year, the Art Institute of Chicago is showcasing works from her career in an expansive exhibit titled Lee Miller: Fearless. The first comprehensive survey of Miller's photographs in more than 25 years, Lee Miller: Fearless will feature nearly 150 works and will explore her life and approach to creativity, both behind and in front of the camera.
Grant Park Rose Garden

Grant Park Rose Garden

4 out of 5 stars
The Grant Park Rose Garden is a popular location for weddings and proposals and is a peaceful sanctuary to enjoy the park's scenery. On the north end of the park, you can walk between beautifully manicured rose bushes of all kinds. We recommend stopping to smell the roses—literally.
Theater on the Lake

Theater on the Lake

5 out of 5 stars
Situated at Fullerton Avenue on Lake Shore Drive, Theater on the Lake is a year-round event venue with an on-site restaurant. A range of events are hosted here, from a roaring St. Patrick's Day celebration to the annual Air and Water Show viewing party, plus theater performances. Thanks to its location on the east side of Lake Shore Drive, it offers some of the best lake and skyline views in the city.
Navy Pier Beer Garden

Navy Pier Beer Garden

4 out of 5 stars
Navy Pier's seasonal beer garden features a rotating slate of live performances from local musicians, trivia nights and a prime view of the fireworks on Wednesday and Sunday nights throughout the summer. The menu features a large selection of beers, cocktails and frozen drinks, as well as tasty pub grub.
Chicago & Styx

Chicago & Styx

STYX is hitting the road with Chicago this summer, and they're stopping at Allstate Arena in Rosemont for the final show of the "Chicago & Styx: The Windy Cities Tour - All The Hits...Your Kind of Tour." STYX will be playing, of course, the hits, plus tracks from their latest album Circling From Above, which dropped last summer.
Huntington Bank Pavilion at Northerly Island

Huntington Bank Pavilion at Northerly Island

5 out of 5 stars
In addition to O’Hare and Midway, Chicago used to have a small third airport called Meigs Field right along the lakefront. It got bulldozed, and since 2005, it's hosted hundreds of concerts along the lake. With a capacity of up to 30,000 people, the mid-size, open-air venue offers some of the most picturesque views you can get at a concert in Chicago.
Purple Pickle Party

Purple Pickle Party

Head to Big City Pickle in Fulton Market to compete in a pickleball tournament to support the Alzheimer's Association. The fifth annual Purple Pickle Party raises funds for Alzheimer's research, care and local support services for the Association's Illinois chapter. Players of all levels are welcome to join the tournament and enjoy live music, lawn games, food and drinks, and a silent auction.
40th Slamiversary of the Poetry Slam

40th Slamiversary of the Poetry Slam

The Newberry Library is celebrating its recent acquisition of the Marc Kelly Smith Poetry Slam Collection, an archive of documents on the artform's history, and the 40th anniversary of slam poetry with an afternoon of performances at the Newberry Library. See slam poetry heavyweights take the stage to deliver powerful spoken-word performances and browse memorabilia from the library's collection.

News (88)

Lollapalooza 2026 lineup, updated set times and streaming schedule: the full list to keep track of

Lollapalooza 2026 lineup, updated set times and streaming schedule: the full list to keep track of

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
The only 5 times when a Chicago pedicab is worth it

The only 5 times when a Chicago pedicab is worth it

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 drops official aftershow lineup with 80+ acts: Zara Larsson, Empire of the Sun, Ethel Cain and more

Lollapalooza drops official aftershow lineup with 80+ acts: Zara Larsson, Empire of the Sun, Ethel Cain and more

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
A grown-up’s guide to the Lincoln Park Zoo

A grown-up’s guide to the Lincoln Park Zoo

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
11 things you can do at the Obama Presidential Center without a ticket

11 things you can do at the Obama Presidential Center without a ticket

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.
Where to celebrate the World Cup in Chicago: Watch parties, specials and freebies

Where to celebrate the World Cup in Chicago: Watch parties, specials and freebies

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
I paid $20 to argue with strangers in Old Town—and it was surprisingly heartwarming

I paid $20 to argue with strangers in Old Town—and it was surprisingly heartwarming

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
Prosperity is palpable at the Obama Presidential Center

Prosperity is palpable at the Obama Presidential Center

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
Don’t want to pay for a pricey Chicago River cruise? Book this $10 ride instead.

Don’t want to pay for a pricey Chicago River cruise? Book this $10 ride instead.

One of the best ways to see the city is by cruising down the Chicago River. There are plenty of options for a proper sightseeing tour, like the Chicago Architecture Center's River Cruise Aboard First Lady and Shoreline Sightseeing’s rides, all of which offer rich insights into the architectural history of the city’s most iconic buildings. Those cruises are essential experiences—beloved by both tourists and locals—but they can be pricey. So next time you’re in the mood to get out on the water but don't want to shell out more than $10, consider one of the most overlooked forms of transportation: a water taxi. Water taxis, by design, are intended to provide a traffic-free alternative to other modes of transportation. Are they practical? Not always. Are they more efficient than other forms of public transit? Usually not. Are they a great deal, though? Indeed.  RECOMMENDED: The 14 best boat tours in Chicago  For just $10, you take the same ride you'd take on one of the more expensive river cruises for a fraction of the price. There’s no narration on the water taxi, but it makes for a peaceful journey with the same views through the city’s most iconic waterway.  Chicago Water Taxi’s route runs from March through the end of December, between Michigan Avenue (at Rush Street) and Chinatown (at Ping Tom Park) with a stop at Ogilvie and Union Stations. These bright-yellow, double-deck boats offer indoor and outdoor seating, plus bike racks, luggage storage, restrooms and drinks for purc
The World Naked Bike Ride returns to Chicago this weekend: Date, route and how to join

The World Naked Bike Ride returns to Chicago this weekend: Date, route and how to join

Yes, you read that correctly. The 22nd annual World Naked Bike Ride is rolling through the streets of Chicago again this weekend.  Despite its name, the ride is actually clothing-optional. Bare as you dare, as they say.  World Naked Bike Ride is a national tradition that celebrates “freedom from oil” in transportation. As the organizers say, “Even when clothed, we cyclists are virtually naked, exposed to the dangers and pollution imposed by cars. By cycling naked, we show our confidence in the beauty and individuality of our bodies and the bicycle's place as a catalyst for change to a future of ecologically responsible transport and healthy and humane communities.” Here’s everything you need to know about the 2026 World Naked Bike Ride in Chicago. When is the World Naked Bike Ride 2026 happening in Chicago?  The World Naked Bike Ride is on Saturday, July 11. Check-in starts at 6pm, and the ride kicks off at 8pm. Do I need to sign up, and how much does it cost?  The ride is free, and you don’t need to sign up. Just show up at the check-in point, which will be announced shortly before the ride on the event’s Facebook page. Where does the Chicago Naked Bike Ride start?  The exact route will not be announced until the day of the race. But here’s what we know so far: The ride kicks off from Kinzie Street, between Halsted Street and Desplaines Street in Fulton Market. Bikers will head east before circling back to the starting point.  Organizers have also said that Union and Ogilvie
Chicago was just named the 4th most beautiful city in the world, beating Paris, Lisbon and Rio de Janeiro

Chicago was just named the 4th most beautiful city in the world, beating Paris, Lisbon and Rio de Janeiro

It’s official: Chicago is the most beautiful city in the U.S. In fact, it’s the fourth most beautiful city on earth, according to a new ranking of the world’s most beautiful cities. Our team at Time Out asked more than 24,000 city dwellers across the globe if they’d describe their city as “beautiful.” Unsurprisingly, Chicago earned a 77% beauty score, preceded only by Sydney (78%), Edinburgh (84%) and Cape Town (86%). Of the 19 cities on the list of the world’s most beautiful, Chicago beat out some heavy hitters. Lisbon came just after Chicago with a 74% beauty score, followed by Paris (68%), Stockholm (68%), Porto (67%) and Medellin (66%). RECOMMENDED: The world’s best cities in 2026, according to Time Out Factors like an abundance of green spaces, walkability, architectural significance and waterfront views all played into the ranking. Luckily, Chicago has all of them in spades. Earlier this year, the Windy City was also named the second best city in the world for green spaces, earning an 89% green space score for its more than 600 parks spread out over 8,800 acres.  But wait, that’s not all! Chicago was ranked the world’s 41st best city overall in March. Lauded for its diversity, inclusivity, neighborhood pride and deeply rooted loyalty to the arts, it ranked higher than urban hotspots like San Francisco, Dublin and Buenos Aires.  An influx of major cultural openings, including the Obama Presidential Center and the PokĂ©mon Fossil Museum at the Field Museum, certainly helpe
14 things to do over Fourth of July weekend in Chicago

14 things to do over Fourth of July weekend in Chicago

The sound of firecrackers, the smell of grill outs and the sight of people dressed in red, white and blue can only mean one thing: Fourth of July weekend is here.  Whether you’re in the city or the suburbs, there are plenty of ways to celebrate America’s 250th anniversary this Independence Day weekend.  For family-friendly fun, head to Brookfield Zoo for a patriotic America 250 celebration. Don’t want to spend money? Check out one of the free concerts at Navy Pier or Grant Park. And, of course, cap the night by seeing one of Chicagoland's many fireworks shows. Read on for the best Fourth of July weekend events in Chicago. RECOMMENDED: Where to see Fourth of July fireworks around Chicago 1. See a fireworks show Fri, Sat One of the best parts of summer in Chicago is watching fireworks light up the sky on the Fourth of July. You've got plenty of options for catching a show this year, whether you'd rather head out to the suburbs for weekend-long festivals and parades or stick to Chicago to see Navy Pier's iconic display along the lakefront from beaches or boat cruises. 2. Get festive at the 4th on 53rd Parade Sat Celebrate the Fourth of July with a parade in Hyde Park that steps off at 11am. Afterwards, stick around for a free festival featuring performances, games, bouncy houses, face painting, a petting zoo, magicians and more. 3. Learn about iconic American species at Brookfield Zoo Sat The Brookfield Zoo is celebrating the country's 250th birthday with a lineup of America-the