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Time Out Best of the City Awards 2021
Time Out

Time Out Chicago Best of the City Awards 2021

Time Out Chicago editors recognize the city's best restaurants, bars, festivals, cultural happenings and sustainable events.

Zach Long
Emma Krupp
Written by
Zach Long
&
Emma Krupp
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The past year in Chicago has been strange, but it has presented plenty of occasions for celebration. In the wake of a year filled with unprecedented events, much of 2021 felt like a slow crawl back to relative normalcy. New restaurants opened for business, summer music festivals welcomed back crowds and Chicago's best museums hosted amazing exhibitions.

While assembling the Time Out Best of the City Awards, our Chicago editors looked back on the past 12 months of food, festivals, exhibitions, shows and innovations in order to highlight our favorites. Some are places and happenings that are veritable Chicago institutions. Others are wonderful new additions to the city. But every Best of the City Awards winner is something that we feel is memorable and impactful in its own way.

Want to heap some recognition on even more of Chicago's best places? You can vote in the Time Out Love Local Awards until December 17 and show some love for spots nominated by Time Out readers.

Time Out Best of the City Awards winners

  • Restaurants
  • Eclectic
  • Logan Square
  • price 2 of 4

“All I can say without choking up is thank you for getting us here safely,” chef Jason Hammel wrote when he announced Lula Cafe’s long-awaited reopening in July. The Logan Square farm-to-table restaurant offered takeout throughout the pandemic, but fans of its seasonal fare know that sitting inside the dining room is an essential part of the Lula experience. Thankfully, not much has changed—the ingredients are still fresh, the breakfast burrito is one of the city’s best and the dinner menu is inventive-yet-approachable (tipping has been eliminated, replaced with a 20 percent service fee). There are more reasons why we love Lula Cafe than we can list here, but the fact that we’ll willingly wait more than an hour to sit down for brunch here feels like one of the highest compliments we can pay.

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Zach Long
Editor, Time Out Chicago
  • Bars
  • Cocktail bars
  • South Lawndale

Since early 2019, Osito’s Tap has been serving top-notch cocktails, draft beer and bites from a space behind the agave-stocked shelves of Moreno’s Liquors in Little Village. The bar’s speakeasy vibes are undeniably cool, but what’s most special about Osito’s is the way it showcases the immigrant-built heritage of the neighborhood, from the Bohemian architectural touches that nod to Little Village’s history as a Czech community (fun fact: the bar once served as an underground bookie joint back in the early 1900s) to the Latinx-inspired sensibilities of its incredibly creative cocktail menu. Pair your drink with an order of tacos or guacamole and settle in for a while, and watch the bar’s social media pages for DJ nights and other special events.

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Emma Krupp
Assistant Editor, Time Out Chicago
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  • Restaurants
  • Coffee shops
  • New City

There’s only one roast on the menu at Sputnik Coffee Company—a roaster and cafe in Back of the Yards—and it’s so good we’re willing to bet you won’t regret the lack of options. Made from a medium roast blend of Brazilian, Colombian and Indonesian beans, Sputnik’s singular coffee is smooth, fragrant and a little chocolatey, with a price point that’s far more approachable than most of its small-batch counterparts. Swing by the Back of the Yards cafe for a cup served in the shop’s signature bright red mugs, or look for bagged coffee at local independent grocery stores (they also sell a bottled cold brew, in case you prefer your coffee on ice).

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Emma Krupp
Assistant Editor, Time Out Chicago
  • Restaurants
  • Hot dogs
  • Grand Boulevard
  • price 1 of 4

Bobby Morelli and his young daughter Brooklyn began slinging sausages out of a shipping container in Bronzeville’s outdoor Boxville marketplace last year, but 2021 was the year they achieved encased meat stardom. After a flurry of favorable write-ups, folks began lining up at the Hot Dog Box to order delicious creations like the Bronzeville Bourbon Filet Mignon Steak Dog, topped with bacon, peppers and a tangy sauce. The Bronzeville stand is temporarily closed as the pair works to open a brick-and-mortar location in Portage Park—and we can’t wait to taste what the Hot Dog Box comes up with next.

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Zach Long
Editor, Time Out Chicago
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  • Restaurants
  • Italian
  • West Loop
  • price 2 of 4

Looking back, 2021 was the year of Italian restaurants in Chicago, as established and rising chefs offered up their takes on the beloved cuisine. Boka chef Lee Wolen was among them, debuting Alla Vita inside the West Loop space that formerly housed Bellemore. The menu is filled with crowd-pleasing Italian dishes that are meant to be shared, including arancini, tender ricotta dumplings, pizzas and an amazing chicken parmigiana. It’s all served in a dining room that feels a little magical, with flowing curtains hanging from the ceiling and a pergola draped in greenery. No wonder it’s still difficult to get a reservation here!

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Zach Long
Editor, Time Out Chicago
  • Bars
  • Breweries
  • Logan Square

When Marz Community Brewing Company first announced a North Side taproom, we knew it’d be something special, and we should have guessed it’d be extremely stylish. Boasting interior design inspired by Polish social clubs, guests sit down among bold blue and green hues, decorative carvings and hanging lamps. The bar’s 14 taps are arranged in the shape of a smiley face—and if you don’t find anything you like, there are canned options in a nearby cooler. If you need a snack with your beer, there’s a menu of local sausages or you can grab ice cream next door at Margie’s Candies.

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Zach Long
Editor, Time Out Chicago
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  • Restaurants
  • Loop

Even after a banner year for outdoor dining in Chicago, the boho chic trappings of Beatnik on the River—a riverside offshoot of the West Town dining destination of the same name—solidify its status as the city’s prettiest place to grab a bite outdoors. Post up beneath a fringe umbrella with a cocktail in hand (we like the Spiked Coconut, a playful rum-based drink served in a young coconut) and admire vintage touches by Chicago design firm Maison Bonhomme on the 80-seat patio, including colorful tile, pillow-topped Indonesian daybeds and plenty of greenery.

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Emma Krupp
Assistant Editor, Time Out Chicago
  • Theater
  • Interactive
  • Uptown
  • price 1 of 4

As live performances came to an abrupt stop last year, the Neo-Futurists quickly launched a Patreon and continued creating miniature plays in the style of its long-running The Infinite Wrench show for online supporters. The ensemble never stopped doing what it does best, which is likely why the Neo-Futurists were still firing on all cylinders when The Infinite Wrench resumed in-person performances in September, presenting hilarious and deathly-serious vignettes that confront a forever-changed world. As topical and unpredictable as ever, the Neo-Futurists are still confronting chaos with creativity (and they could use your help to continue doing so).

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Zach Long
Editor, Time Out Chicago
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  • Art
  • Contemporary art
  • East Garfield Park

Chicago’s an exceptional gallery city, but this year we’ve especially been loving the lush exhibitions at Goldfinch in East Garfield Park, from Hyun Jung Jun’s whimsical, knobby candle creations to “Night Life,” a solo show by the painter Mari Eastman that’s on view through December 18. FYI: Those looking to start an art collection on a budget should check out the gallery’s Flatfiles program, which offers a selection of works from artists like Edra Soto and Anne Harris for relatively affordable prices (usually no more than $1,500, but sometimes as low as $130).

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Emma Krupp
Assistant Editor, Time Out Chicago
  • Museums
  • Art and design
  • Grant Park
  • price 2 of 4

More than a year of closures served as a good reminder of how lucky we are to live near one of the world’s premiere art collections. After moving some of its exhibitions online and creating digital content for folks to interact with during lockdown, the Art Institute of Chicago reopened at limited capacity in February of this year. Since then, the museum has roared back to life with blockbuster exhibitions like “The Obama Portraits” and a so-called “anti-retrospective” of conceptual artist Barbara Kruger’s work, which will remain on view until the end of January. And if you haven’t had a chance to make your way back to the museum’s storied halls, you’ll find that your favorite paintings (and maybe even a couple new favorites) remain just as awe-inspiring as ever.

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Emma Krupp
Assistant Editor, Time Out Chicago
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  • Movie theaters
  • Independent
  • Wrigleyville

After nearly a year without butts in its seats, the Music Box Theatre reopened in February, screening movies for just 50 people in its 750-seat main auditorium. The Southport theater has since expanded its capacity and its options, showing classics by Orson Welles and Akira Kurosawa as well as new films by Julia Ducournau and Edgar Wright. During the summer, the theater’s garden patio even presented outdoor screenings for those who preferred open-air gatherings. The Music Box is Chicago’s anti-multiplex—a communal place to sit down in a dark room and experience cinema’s past, present and future.

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Zach Long
Editor, Time Out Chicago
  • Bars
  • Lounges
  • Wrigleyville
  • price 2 of 4

There were points last year when it felt like we might never be able to crowd onto the cramped dance floor inside Smartbar ever again. But the subterranean Wrigleyville club reopened its doors earlier this year, welcoming revelers back with sets from the likes of Matthew Dear, Machinedrum and RP Boo. Plus, house music party Queen has reclaimed its Sunday night slot, Derrick Carter showed up to spin disco and the venue managed to host a 23-hour party. More importantly, Smartbar remains one of the most inclusive places to cut loose to a beat (just remember that you will need to provide proof of full vaccination before you can hit the dance floor).

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Zach Long
Editor, Time Out Chicago
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  • Bars
  • Lounges
  • Lincoln Park

Technically, Golden Dagger isn’t an entirely new music venue—it’s a renamed and refreshed version of Tonic Room, the venerable Lincoln Park club owned by local promoter Donnie Biggins. Launching over the summer with a coffee program (featuring Anodyne Coffee), a reconfigured stage and a new patio, Golden Dagger has since hosted acts like Kweku Collins, Waltzer and Cordoba, with artists receiving 100 percent of the proceeds from ticket sales. Sadly, the venue was recently damaged by a fire and is currently accepting donations to aid its staff until it can reopen.

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Zach Long
Editor, Time Out Chicago
Best Street Market: Logan Square Farmers Market
Photograph: Wendell Remington

Best Street Market: Logan Square Farmers Market

Chicago has an excellent network of neighborhood farmers markets, but few offer the sheer variety you’ll find every Sunday at Logan Square Farmers Market, where you can browse everything from La Boulangerie’s fresh-baked boules and grass-fed meats from Mint Creek Farm to ethically-sourced coffee beans from newer upstarts like Anticonquista Cafe—not to mention live entertainment and plenty of good people-watching. The market deftly transitioned to a virtual (and then a socially-distanced) format in 2020; this year, it frequently drew lines of shoppers, canvas tote-bearing and eager to stock up on produce. Best of all, because it’s one of Chicago’s few year-round markets, the Sunday fun doesn’t end once winter rolls around: Head to the market’s warehouse space at 2537 N Pulaski Rd to browse winter offerings.

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Emma Krupp
Assistant Editor, Time Out Chicago
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  • Things to do
  • North Lawndale

You can learn a little more about local birds while you try to hit a birdie at Douglass 18, a newly-revamped miniature golf course behind the Douglass Park Cultural Center and Fieldhouse that opened to the public in August after a nearly three-year revitalization effort. Designed by a group of local teenagers, the avian-themed course highlights Douglass Park’s role as an oasis for more than 200 species of migratory birds with colorful installations and informational placards at each of the holes. Come by in the warmer months to hit a round or two—and if you want to get a firsthand look at the park’s many birds, consider bringing a pair of binoculars.

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Emma Krupp
Assistant Editor, Time Out Chicago

The city has been celebrating the Year of Chicago Music in 2021, and Art on theMart got in on the festivities this summer, presenting its best program of projections to date—all set to a soundtrack provided by Chicagoans. The highlight of the display was an animated piece called Footnotes, which projected 25-story-tall images of local footwork dancers on Merchandise Mart, while an original track featuring DJ Spinn, the Chicago Bucket Boys and Angel Bat Dawid played on the Riverwalk. With kinetic animations that channeled the frantic beat of footwork music, Footnotes (the work is by filmmakers Wills Glasspiegel and Brandon K. Calhoun) was a public spectacle that captured the intricacies of a Chicago-born artform in a way that was (quite literally) larger than life.

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Zach Long
Editor, Time Out Chicago
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Best Event of the Year: Hyde Park Jazz Festival
Photograph: Marc Monaghan

Best Event of the Year: Hyde Park Jazz Festival

In 2020, the Hyde Park Jazz Festival adapted to uncertain times by staging a series of outdoor shows. The event took a similar approach in 2021, with only two indoor performances, and lots of sets on the Midway Plaisance, parking lots and courtyards throughout the neighborhood. Bringing together a long list of notable local players—Makaya McCraven, Tomeka Reid, Isaiah Collier, Mike Reed, Dee Alexander—the fest was blessed with gorgeous weather and audiences that seemed ecstatic about seeing music performed in front of them once again. And what better way to close out the summer than with some winding saxophone solos?
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Zach Long
Editor, Time Out Chicago

Even in pre-pandemic times, journeying to the Loop to hang out during the weekend wasn’t exactly a popular pastime for Chicagoans. But the Chicago Loop Alliance managed to provide a great reason to schlep downtown over the summer, introducing a series of events that shut down a large section of State Street and filled the pavement with a variety of vendors, performers and activities. During a trip to Sundays on State, you could see Joffrey Ballet students dancing, watch a movie projected on the side of the Gene Siskel Film Center or purchase new reading material from Open Books. And with a shifting lineup of local entertainment presented during its eight editions, there was always something new to see in the Loop.

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Zach Long
Editor, Time Out Chicago
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With live music returning to the Pritzker Pavilion stage for the first time since 2019, the city’s annual Millennium Park Summer Music Series was an extra-special occasion this summer. Appropriately, the 2021 lineup was packed with local performers that showcased the depth and breadth of the city’s music scene, including contemporary ensemble Eighth Blackbird, avant-garde ensemble Natural Information Society and an evening of ballads curated by singer-songwriter Akenya. As for our favorite moment of the Summer Music Series? That would be a rendition of “Rainbow Connection” performed by NNAMDÏ, Sen Morimoto, Kaina and the rest of the Sooper Records family.

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Zach Long
Editor, Time Out Chicago

A night at the opera doesn't get much more spectacular than this adaptation of The Magic Flute, which the Lyric Opera presented this fall. Originating from the Komische Oper Berlin, the show eschewed sets in favor of a large screen that was bathed in projections of intricate animations. With interludes inspired by the visual language of silent film, a cast of characters caked in white make-up belted out the opera’s dramatic score amid a sea of psychedelic imagery. With any luck, it won’t be the Lyric’s last production that recontextualizes the stage and reimagines what an opera can look like.

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Zach Long
Editor, Time Out Chicago
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Best Exhibition: "Chicago Comics: 1960s to Now"
Photograph: Zach Long

Best Exhibition: "Chicago Comics: 1960s to Now"

Chicago is a city known for the blues, its hot dogs, incredibly cheesy pizza and trains that run above the streets. But the Museum of Contemporary Art’s summer exhibition made the case for Chicago to be known as a city of comics. Showcasing work by Lynda Barry, Daniel Clowes, Kerry James Marshall, Chris Ware and many other artists who blend imagery and narrative, the MCA’s exhibit was a journey from the early days of syndicated newspaper strips to the contemporary world of self-printed zines. With plenty of reading material to soak in, “Chicago Comics” provided a visual history lesson on an often-overlooked component of the city’s thriving art scene.

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Zach Long
Editor, Time Out Chicago
  • Shopping
  • Grocery stores
  • Lincoln Square

Awarded with the help of Luke Dias of Zero Waste Chicago

Got a clean jar at home? You can use it for storing bulk cleaning supplies, pantry staples, beauty products and more household goods from Eco & the Flamingo, Chicago's first-ever zero waste general store. Founded by two best friends seeking to reduce waste in Chicago, the Lincoln Square shop offers helpful accessories (like a stainless steel pump that can turn a jar into a soap dispenser) in addition to its bulk goods, offering lots of easy ways to live a more sustainable day-to-day life. 

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Emma Krupp
Assistant Editor, Time Out Chicago
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Sustainable Event of the Year: Andersonville Homecoming
Photograph: Timmy Samuel/Starbelly Studios

Sustainable Event of the Year: Andersonville Homecoming

Awarded with the help of Luke Dias of Zero Waste Chicago

When Andersonville (one of Time Out's coolest neighborhoods) welcomed an Abba cover band, drag queens and a long list of local businesses to Clark Street for an end-of-the-summer street bash, it did so with sustainability in mind. Coinciding with the neighborhood’s composting pilot program, Andersonville Homecoming partnered with WasteNot to place compost bins throughout the event where guests could deposit food scraps, napkins and more. Local bakery Deflourer used Encora containers, putting baked goods in reuable plastic boxes that customers could return. When the event happens again next year, all vendors will be composting and using Encora containers.

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Zach Long
Editor, Time Out Chicago
  • Attractions
  • Parks and gardens
  • South Deering

At nearly 300 acres, Big Marsh Park—located along Lake Calumet in Southeast Chicago, a historically industrial area of Chicago—is the Chicago Park District’s largest natural area. It’s also one of the city’s most interesting ongoing natural restoration projects, luring visitors with paved paths, BMX jump lines and bike rentals housed inside an expansive bike park. Looking for a slightly more informative approach to experiencing the park’s natural settings? As of this year, Big Marsh is home to the Ford Calumet Environmental Center, an educational hub where visitors can learn about everything from the land’s indigenous heritage to the various native plants, animals and insects that call the area home; public programming and on-site naturalists are also available to supplement the experience.

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Emma Krupp
Assistant Editor, Time Out Chicago
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Social Savior: Shermann 'Dilla' Thomas
Photograph: Courtesy Shermann Thomas

Social Savior: Shermann 'Dilla' Thomas

When did deep dish pizza become synonymous with Chicago? Why are there so many bungalows around here? And what’s the deal with dibs, anyway? Late in 2020, when COVID-19 restrictions kept us cooped up indoors, public historian Shermann “Dilla” Thomas took to TikTok as @6figga_dilla to share the stories behind questions like these, quickly gaining a following of folks eager to share in his wholehearted enthusiasm for Chicago history and trivia. This year, with appearances on The Today Show and other national outlets under his belt, the Auburn Gresham native has taken his knowledge to the streets, hosting walking tours throughout Chicago neighborhoods and offering up his historical acumen to quiz Governor J.B. Pritzker during a trivia event at the Hideout in November. And there’s even more good news on the horizon for fans of everything Dilla- and history-related: He has plans to crowdfund money for a tour bus and start his own nonprofit to offer free tours across the South and West Side in the near future.

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Emma Krupp
Assistant Editor, Time Out Chicago
Innovation of the Year: Divvy e-bikes
Photograph: Zach Long

Innovation of the Year: Divvy e-bikes

E-bikes officially joined the Divvy fleet in the summer of 2020, a time when many folks were understandably more focused on social distancing than trying out the latest bike-share options. But the jet black bikes with electric motors quickly became the preferred option for Divvy riders in 2021—according to bike-share operator Lyft, e-bikes received two to three times as many rides per bike as the classic blue bikes over the past year. Whether you’re using them to quickly cover the last mile from a train station or for a longer journey, the e-bikes are an innovation that make Divvy rides faster and easier. And you’ll see even more e-bikes in the coming months, thanks to the launch of Lyft’s latest model.

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Zach Long
Editor, Time Out Chicago
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Weird and Wonderful: Joe Swanberg's Analog Video Store
Photograph: Emma Krupp

Weird and Wonderful: Joe Swanberg's Analog Video Store

If you happened to find yourself at Borelli’s in Ravenswood this summer, you may have stumbled across what appeared to be a vintage video rental store operating out of the pizza shop’s back room. That’s where Joe Swanberg—director of Drinking Buddies and other mumblecore staples—briefly ran Analog Pizza and Video Store, a computer-free service that allowed subscribers to rent Swanberg’s collection of some 275 VHS tapes (including odd and hard-to-find picks, like a college project from Lars von Trier) and catch screenings on the pizza shop’s rooftop. The DIY Blockbuster effectively shuttered due to permitting issues once the city caught wind of its dealings back in August, but Swanberg says he’s hopeful rooftop screenings will return next summer—a potential silver lining for film buffs without VCRs at home.

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Emma Krupp
Assistant Editor, Time Out Chicago
Green Star: Urban Rivers
Photograph: Courtesy Urban River

Green Star: Urban Rivers

The folks at Urban Rivers want you to stop thinking of the Chicago River as a dirty, disease-ridden waterway from the pages of an Upton Sinclair novel. For years, the environmental nonprofit has been planning what’s been dubbed the Wild Mile: a mile-long, floating eco park—the first of its kind in the world—where visitors can get a closer glimpse of the river’s thriving ecosystem along the North Branch. The organization completed the first 400 feet of the walkway this fall, a stretch flanked by 10,000 square feet of gardens filled with native plants like Joe-Pye weed and swamp milkweed, and plans to devote time to educational outreach, fundraising and additional conservation-minded projects next year before continuing with construction. You can check out the first section of the Wild Mile in the meantime; and if you’re interested in lending a helping hand, consider applying for the organization’s River Ranger program, which sends volunteers out on kayaks to assist with trash collection and other tasks.

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Emma Krupp
Assistant Editor, Time Out Chicago
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