THE AUTHOR
Lauren Viera has called Chicago home for more than 20 years. After visiting on a whim during a college break, she was drawn to the city’s thrilling music scene, fantastic Mexican food and friendly people, and fell for the historic architecture, cultural diversity and beautiful show of seasons.
While on staff at Time Out Chicago and the Chicago Tribune, and contributing to publications including Chicago Magazine, the Chicago Reader and Crain’s Chicago Business, Lauren has been fortunate to dig deep into the city’s culture from a reporter’s point of view. With assignments ranging from the opening of the Art Institute’s Modern Wing to discovering the loudest bands in the Ukrainian Village, she has grown to know and love the people, places and things that make Chicago so wonderfully unique.
Beyond writing, Lauren’s passion for the city extends to teaching, gardening, preservation, volunteering, and advocating for representation from a diverse cross-section of residents. There are so many things she loves about Chicago, narrowing them down to 500 was a challenge.
The author wishes to thank all of the people who shared their secrets to grow and diversify the list of treasures that made it into the book. Special thanks to Sam Landers at Trope for the referral, Dettie Luyten at Luster for editing and advice, photographer Giovanni Simeone for lovingly capturing the city, and Rick Kogan for embodying Chicago through and through.
CHICAGO community areas overview
Map 1–3 Central
Near North, The Loop, Near South
Map 4 West Side
Humboldt Park, West Town, West & East Garfield Park, Near West Side, North & South
Lawndale, Lower West Side
Map 5 North Side
North Center, Lakeview, Avondale, Logan Square, Lincoln Park
Map 6 Northwest Side
Portage Park, Irving Park, Dunning, Montclare, Belmont Cragin, Hermosa
Map 6 Far North Side
O’Hare, Jefferson Park, Forest Glen, North Park, Albany Park, West Ridge, Lincoln Square, Rogers Park, Edgewater, Uptown
Map 7 South Side
Bridgeport, Armor Square, Douglas, Fuller Park, Grand Boulevard, Oakland, Kenwood, Washington Park, Hyde Park, Woodlawn, Greater Grand Crossing, South Shore
Southwest Side
Garfield Ridge, Archer Heights, Brighton Park, McKinley Park, West Elsdon, Gage Park, New City, West Lawn, Chicago Lawn, West Englewood, Englewood
Map 8 Far Southeast Side
Chatham, Avalon Park, South Chicago, Burnside, Calumet Heights, Roseland, Pullman, South Deering, East Side, West Pullman, Riverdale, Hegewisch
Far Southwest Side
Ashburn, Auburn Gresham, Beverly, Washington Heights, Mount Greenwood, Morgan Park
SIDE
FAR SOUTHEAST SIDE
Chatham, East Side, Pullman, South Deering
8 KIMSKI
954–960 W 31st St
Bridgeport ➆
+1 773 823 7336
9
MEDICI ON 57TH
1327 E 57th St
Hyde Park ➆
+1 773 667 7394
medici57.com
10 MANNY’S CAFETERIA & DELI
1141 S Jefferson St
South Loop ➁
+1 312 939 2855
mannysdeli.com
Borne of its owner (and unofficial mayor of Bridgeport) Ed Marszewski’s Korean and Polish heritage, Kimski features signature flavors from each cuisine in delightfully unique dishes. Try the veggie potskis filled with sauerkraut and mushroom, herb salad and pickled onion; or the sweet-and-spicy ‘Ko-Po’ wings. Dishes are relatively small and affordable, perfect for sharing.
A comforting all-day restaurant in the heart of University of Chicago’s retail district, Medici on 57th has been feeding town and gown alike since the early 1960s. Serving coffee all day (and into the night), pizzas, burgers, hearty soups, several salads, and an array of fried finger-food staples, Medici has something for everyone.
No frills, 80-year-old institution serving all-day staples. Established as a workingclass cafeteria doling out generous portions of Jewish cooking, Manny’s offers lunchroom classics: corned beef sandwiches, liver & onions, meatloaf, matzo ball soup, and more. A favorite of local politicians and lawmakers, it’s still a go-to lunch spot for former president Barack Obama.
11 SUGAR MOON
3612 W Wrightwood
Avenue
Logan Square ➄
sugarmoonchicago.com
There’s a long queue on most mornings, and for good reason. From crusty, savory tarts to its famous tahini chocolate chip cookies and tiramisu-flavored Cloud Cookies, Sugar Moon has earned fans since it opened in 2021. Grab a coffee down the street at Necessary & Sufficient Coffee for the wait.
11 SUGAR MOON
5 cafes for SITTING A SPELL
96
PLEIN AIR CAFE
5751 S Woodlawn Avenue
Hyde Park ➆
+1 773 966 7531
pleinaircafe.co
97 HEXE COFFEE CO.
2000 W Diversey Avenue Parkway ➄
+1 312 525 2099
hexecoffee.com
Located adjacent to Frank Lloyd Wright’s famed Robie House, this charming French-inspired cafe knows its espresso drinks, but there’s so much more. Stay for hearty sandwiches, yummy hand pies, perfectly flakey pastries, and a nicely curated list of wines. If it's nice out, find a spot outside at the lushly landscaped communal table to people watch.
Though it opened with the intent of focusing on cold brew for afternoon pick-me-ups, this unique spot has been embraced for its all-day espresso (and coffee cocktails), down-to-earth service, and housemade pastries and sandwiches. The indoor cafe is cozy, and the vast patio space accented with native perennials buzzes with pollinators in the summer months.
96 PLEIN AIR CAFE
148 RICHARD’S FABULOUS FINDS
148 RICHARD’S FABULOUS FINDS
2545 W North Avenue
West Town ➃
+1 773 943 0710 richardsfabulous finds.com
149 DIAL M FOR MODERN
1818 W Grand Avenue
West Town ➃
+1 708 268 2069 dialmformodern.com
150 LOST GIRLS VINTAGE
1947 W Chicago Avenue
West Town ➃ lostgirlschicago.com
Richard Biasi has been in the menswear business since his days at high-street retailers like Ralph Lauren and Neiman Marcus. At his neatly organized secondhand shop, dove-grey walls and vintage mirrors lend the space the air of a gentleman’s dressing room, with racks of ties, stacks of caps, and a collection of vintage barware.
Even casual mid-century modern fans get sucked into this sexy shop with tastefully arranged furniture. Walnut, oak, and leather-based pieces are polished to showroom quality, then put on display alongside vintage accessories like cameras, one-of-a-kind artwork and eye-catching accent lighting. Nothing stays on the floor for long, inspiring frequent returns.
Launched from a trusty 1976 Winnebago gutted and kitted out as a pop-up vintagemobile, Lost Girls does not take the traditional route to selling retro threads. The shop’s two brick-and-mortar locations are each painted as colorful as the wares for sale, and the Logan Square location features a bonus store dedicated solely to housewares.
SKYLANDING BY YOKO ONO
5 NATURE OUTINGS
256 LABAGH
WOODS
West Foster Avenue at N Cicero Avenue
North Park ➅
+1 800 870 3666 fpdcc.com
257 SNORKELING NEAR THE SILVER SPRAY SHIPWRECK
E 49th St at
Lake Michigan
Kenwood ➆
Some 80 acres of dense canopy cover lend the combination of wetlands, savannas and meadows a genuinely rural feeling, and plenty of resident wildlife – from deer and mink to a range of birds and waterfowl – call it home. These woods mark the southern anchor of the North Branch Trail, a popular spot for biking.
Chicago isn’t exactly a diving mecca, but there are a handful of spots near the city to snorkel and scuba dive. The closest to shore is the shipwreck of the Silver Spray, which sank without fatalities in the summer of 1914 after hitting a shallow underwater rock terrain. Rusted in about 10-foot-deep water, it’s easily accessible for exploration.
256 LABAGH WOODS
368 PEACH FUZZ
368 PEACH FUZZ
1005 N California Avenue
West Town ➃
+1 312 881 9971
littlepeachfuzz.com
369 KIDO
1137 S Delano Court
South Loop ➁
+1 312 285 2957
kidochicago.com
This playfully pastel shop with thoughtful details (curious little ones will love discovering the secret nook) is a dream come true for parents looking for pretty yet practical finds. Inclusiveness of all stripes is a running theme, and there are occasionally kids’ playtime events in the sweet little backyard.
Kido bills itself as a diverse kids boutique, prioritizing representation and inclusivity across families of all shapes, sizes, colors and traditions. That rings especially true in this welcoming shop’s impressive library, overflowing with must-reads recommended by educators and artists in the know. A charming collection of sustainable toys and sweet, comfy clothing round out the wares.
370 TOYS ET CETERA
1502 E 55th St
Hyde Park ➆
+1 773 324 6039
toysetcetera.com
This long-running Hyde Park toy shop with confetti-patterned carpet carries more than 10.000 toys in its roomy storefront. There’s always been an emphasis on educational and STEMcentric toys (even before STEM was a thing), and the incredibly well organized shelves – and helpful staff –make shopping fun.