Moon 52 Things to Do in Chicago

THIS IS MY CHICAGO

The streets of Chicago crackle with energy and history. Vibrant personalities, softened by Midwestern warmth, flow through its 77 neighborhoods. Chicago isn’t showy like L.A. or worldly like New York; it’s a big city wrapped in small-town sensibilities, both grounded and passionate. Living here grants you hustle and heart. Though this is a place where people still say hello when walking down the street, it requires real contact and honest effort to connect with the essence of Chi-Town. But if you spend some time interacting with locals and picking up the lingo, you will be rewarded.

I grew up on a placid South Side street, lined with wide lawns and laughter, called Avalon. It was here that I learned essential Chicago lifestyle standards: how to get the best seat on the “L” (shorthand for “elevated train”), how to represent the city’s best baseball team (go White Sox!), and how to glide across the floor in the Steppin’ dance (a quintessential Chi-Town dance that has had couples swaying since the ’50s). Since then, I’ve lived all over the city, from Chatham, to Lakeview, to Rogers Park.

What I love about my city is that each neighborhood is like its own little village, with its own rules, main squares, and even unofficial mayors. While Chicago is famed for the glossy architecture of the Loop and the bikes, beers, and Cubs flags of the North Side, its lesser-known neighborhoods are where its spirit really shines. There’s Pilsen, where Mexican heritage and street art create a warm community; Hyde Park, where the city’s love of arts and culture takes center stage; and Rogers Park, where the raw energy of a diverse population lends a free-wheeling open-mindedness.

This is my Chicago and I’d love to take you there.

TO DO LISTS

Chi-Town Essential

4 Savor South Side barbecue

6 Groove to the Chicago blues

8 Roller-skate Chicago style

13 Listen to classic Chicago jazz

14 Get out to Grant Park

18 Chow down on classic Chicago eats

22 Get inspired by Black art at the South Side Community Art Center

23 Take a trip down LSD

24 Ramble the Riverwalk

25 See world-class Impressionist art at the Art Institute of Chicago

29 Laugh out loud at Second City

37 Learn about labor history at the Pullman National Monument

Food and Drink

1 Wander the world in Rogers Park

4 Savor South Side barbecue

7 Drink in local flavor at neighborhood cafés

12 Feast on Senegalese cuisine

15 Enjoy the cultural feast of Chinatown

18 Chow down on classic Chicago Eats

21 Eat your way down 53rd Street

32 Scoop up sweet treats

35 Enjoy greens with a side of soul food in Garfield Park

41 Taste sweet candy history

49 Indulge in brats and brews in Milwaukee, Wisconsin

51 Dine lakeside in Madison, Wisconsin

Arts and Culture

3 Go gallery-hopping in Bronzeville

5 Stroll the street art in Pilsen

6 Groove to the Chicago blues

9 Celebrate music and history at Black Ensemble Theater

13 Listen to classic Chicago jazz

16 Browse community bookstores

20 Celebrate Borinquén culture at the National Museum of Puerto Rican Arts & Culture

22 Get inspired by Black art at the South Side Community Art Center

25 See world-class Impressionist art at the Art Institute of Chicago

28 Wander the urban canvas at the Wabash Arts Corridor

29 Laugh out loud at Second City

34 See a play (or two) at the historic Biograph Theater

38 Tune in to live local music

40 Appreciate Indigenous culture at the American Indian Center

Get Outside

2 Bike the Lakefront Trail

10 Kayak the Chicago River

14 Get out to Grant Park

19 Hop a water taxi from the Loop

24 Ramble the Riverwalk

26 Paddle and play in the water at Montrose Beach

27 Catch the views from Promontory Point

31 Find peace at Garden of the Phoenix

36 Amble along the elevated 606 trail

39 Explore the Burnham Wildlife Corridor

45 Walk in the woods at Morton Arboretum

46 Hike in Starved Rock State Park

48 Hit the beach in St. Joseph, Michigan

50 Relax at Elkhart Lake, Wisconsin

52 Enjoy the bounty of Door County, Wisconsin

Black Chicago

3 Go gallery-hopping in Bronzeville

4 Savor South Side barbecue

6 Groove to the Chicago blues

8 Roller-skate Chicago style

9 Celebrate music and history at Black Ensemble Theater

12 Feast on Senegalese cuisine

21 Eat your way down 53rd Street

22 Get inspired by Black art at the South Side Community Art Center

33 Appreciate Chicago’s Black roots at the DuSable Museum of African American History

37 Learn about labor history at the Pullman National Monument

Neighborhoods and City Streets

1 Wander the world in Rogers Park

3 Go gallery-hopping in Bronzeville

5 Stroll the street art in Pilsen

7 Drink in local flavor at neighborhood cafés

11 Admire the amazing architecture of Beverly

15 Enjoy the cultural feast of Chinatown

16 Browse community bookstores

17 Hang out in happening Hyde Park

21 Eat your way down 53rd Street

28 Wander the urban canvas at the Wabash Arts Corridor

Family Fun

9 Celebrate music and history at Black Ensemble Theater

14 Get out to Grant Park

26 Paddle and play in the water at Montrose Beach

32 Scoop up sweet treats

35 Enjoy greens with a side of soul food in Garfield Park

36 Amble along the elevated 606 trail

41 Taste sweet candy history

45 Walk in the woods at Morton Arboretum

48 Hit the beach in St. Joseph, Michigan

50 Relax at Elkhart Lake, Wisconsin

Get Out of Town

43 Explore the eclectic in Evanston

44 Retrace Hemingway’s footsteps in Oak Park

45 Walk in the woods at Morton Arboretum

46 Hike in Starved Rock State Park

47 Go back in time in Galena, Illinois

48 Hit the beach in St. Joseph, Michigan

49 Indulge in brats and brews in Milwaukee, Wisconsin

50 Relax at Elkhart Lake, Wisconsin

51 Dine lakeside in Madison, Wisconsin

52 Enjoy the bounty of Door County, Wisconsin

1 Wander the world in Rogers Park

Neighborhoods and City Streets • Food and Drink • Arts and Culture

Language is the music that floats through Rogers Park. Other neighborhoods might have hip-hop or salsa booming from windows, but in Rogers Park, it’s the lilt of Gujarati, the punch of Polish, or the rhythm of Yoruba that form the area’s soundtrack. Perched on Lake Michigan, this is a beachfront community with an artsy, gritty vibe. Some consider this a college neighborhood since Loyola University dominates a major portion along Sheridan Road, where you’ll see students milling around the Starbucks and Loyola Beach and Park. But this is also a place of immigrant dreams, of tree-lined streets and green landscapes, of ramshackle shops and indie theaters. Elegant courtyard buildings, sprawling 19th-century homes, and high-rise apartments might all share space on a single block. As the northernmost neighborhood in Chicago, Rogers Park is often overlooked; frankly, it’s a hike to get here—almost 10 miles from the Loop—but its under-the-radar treasures make it the perfect place for itchy-foot culture lovers.

The first time I stepped into Rogers Park was to visit an underground Ethiopian restaurant in someone’s apartment (my friend knew the owner). I remember the thrill of eating fresh injera and lentil stew while sitting in an easy chair. After sipping tej, a heady honey wine, I strolled out onto a bustling sidewalk filled with people selling jewelry and incense. Arabic music blared, and the smell of roasting elote (grilled Mexican street corn) filled the air. There was an atmosphere of surprise around every corner and colorful revelry, similar to the sensation you might get at open-air markets in Latin America or the Caribbean. I remember thinking, “How come I’ve never visited this cool neighborhood?” I now live in Rogers Park, and those initial feelings of enchantment I first experienced decades ago still surge through me every time I stroll through my eclectic surroundings.

Rogers Park used to be the land of the Potawatomi, Chippewa, and Ottawa people. Indian Boundary Park (2500 W. Lunt St.), just west of the neighborhood’s borders proper, is an oasis and reminder of the area’s original residents, who were driven out by various treaties in the early 19th century. By the early 20th century, wealthy business owners lived in Rogers Park—until WWI, when waves of immigrants from Eastern Europe, Italy, Ireland, and Russia arrived. From then on, each decade brought new groups of immigrants, hailing from regions including Southeast Asia, Africa, the Caribbean, and the Middle East, creating the global mix that the neighborhood is noted for.

Start your exploration of Rogers Park at Howard Street, the boundary between Chicago and Evanston, and terminus of the L’s Red Line. You’ll glimpse lots of activity in front of the station, from vendors selling cell phone plans to evangelists peddling saved souls. A walk east from the L past a wig store and a leafy community garden brings you to the Caribbean American Bakery (1539 W. Howard St., 773/761-0700, www.caribbeanamericanbakery.com), a community outpost. The smell of Jamaican hard dough bread baking floats through the air, and on weekends, locals line up for the bakery’s jerk chicken dinners. But most people come for the patties—savory pastries filled with seasoned beef, curried chicken, spinach, or vegetables. If there’s a wait, pop into Lady B Boutique (1547 W. Howard St., 312/714-2485), a couple of doors down, where you can browse an assortment of vibrant island-style dresses, shirts, and shorts while grooving to a reggae soundtrack.

Make your way south on Clark Street, one of the neighborhood’s primary thoroughfares. It’s lined with cafés, shops, taquerias, panaderías (bakeries), and even a quinceañera boutique. Stop at Taste of Peru (6545 N. Clark St., 773/381-4540, http://tasteofperu.com) to try delicacies like fried yuca with cheese sauce or Peruvian-style tamales, and wash them down with chicha morada, a tasty purple corn drink. Or try some injera for yourself at the nearby Denden Restaurant (6635 N. Clark St., 773/973-4752), a family-owned diner that’s the city’s only Eritrean eatery.

East of and parallel to Clark Street is Glenwood Avenue. Head here to view the Mile of Murals (http://mileofmurals.com/home.html), along the L’s Red Line track between Estes and Pratt. The community-based initiative features the faces and symbols of Chicago’s most diverse neighborhood as interpreted by a range of artists, including beginners, art students and teachers, art collectives, and well-known local artists like Hebru Brantley. You’ll spot murals of rainbow-colored bikers representing the open-mindedness and active nature of the community; local leaders like Charlotte Goldberg and Tobey Prinz, both of whom fought against high-rises and worked to preserve public beach access; and Barack Obama—gazing off into the distance with circles of red and white framing his head like a halo—who kicked off his senate campaign at a former Rogers Park community anchor, the now-shuttered Heartland Cafe.

Heading south on either Clark Street or Glenwood Avenue, you’ll eventually arrive at Devon Avenue, the neighborhood’s southern border. Head west past Ridge Boulevard into the adjacent neighborhood of West Ridge, also called West Rogers Park. Just strolling down this street, nicknamed Little India for its plethora of Indian stores and eateries, is transporting, with Bollywood tunes streaming out of shops and glistening displays of sarees and gold jewelry in every other window. Drop by Sona Chandi Boutique (2659 W. Devon Ave., 773/262-6787) for well-priced salwar kameez (traditional tunic and trouser sets) or Shop N’ Help (6377 N. California Ave., 773/819-9233), a community nonprofit offering handmade purses, jewelry, and kitchen goods. Top off your journey with a visit to Sukhadia (2559 W. Devon Ave., 773/338-5400, www.sukhadiasweetschicago.com), an Indian candy shop with flavors like chickpea, cardamom, and carrot.

Connect with . . .

30 Learn about leather at the Leather Archives & Museum

2 Bike the Lakefront Trail

Get Outside • Neighborhoods and City Streets

Striking landmarks cap off Chicago’s skyline, but nothing defines the city’s landscape more than Lake Michigan, and nothing is more beloved by Chicagoans. Sure, we adore our pizza and sports, but the lake is the pride of the entire city. No matter what political or economic turmoil pops up to bother us, just gazing at the blue waves lapping the coastline brings joy and peace, even knocking off some of the pain of the seemingly endless winter months. One of the best ways to appreciate the lake’s breadth and diverse offerings is to bike or walk the Lakefront Trail, which links many of the city’s neighborhoods, parks, beaches, and attractions.

Summer is peak season, when the roughly 18-mile Lakefront Trail is thronged with an average of 30,000 walkers, joggers, bikers, skaters, e-scooters, wheelchair users, and more daily. Fortunately, in 2018 the trail was separated into parallel two-way biking and walking paths, which eases the congestion. The trail is mostly flat and paved for easy traction. Go midmorning or midweek to avoid the biggest crowds in summer. I prefer to head out on the trail in fall, when the trees lining the path turn gold and red, and people are fewer and farther between. Although the Lakefront Trail is accessible year-round, the winds and waves licking at the edges of the path can be vicious in winter.

My favorite parts of the trail are along its southern half, and I love gliding down the paved pathway on my bike; it’s much easier to maneuver through the throngs on two wheels. Divvy bike rentals (www.divvybikes.com, $15 day pass) are available via the city’s bicycle-sharing program at convenient spots along the Lakefront Trail, including the starting and ending points described here.

Start at tiny Ohio Street Beach (E. Ohio St. and N. Lake Shore Dr.), a pocket of sand tucked just northwest of Navy Pier’s tourist bustle. While the trail runs through lots of beaches, this one is more secluded, has lovely skyline views, and is home to Caffè Oliva (550 E. Grand Ave. 312/612-0734, www.caffeoliva.com, Memorial Day weekend-Sept.), known for offering “sustenance on the sand”; situated right on the beach and surrounded by a small park, it’s a scenic setting in which to fuel up for your ride. My go-tos are the fish tacos and parmesan truffle fries. The café also supplies a restroom, which is a big deal as there are only a handful scattered along the trail in park field houses and beaches.

Head south from here to begin rolling through the leafy scenery of Grant Park and past the landmark Beaux-Arts beauty of the Buckingham Fountain and the Museum Campus. It’s especially fun to ride by Soldier Field, with its distinctive, neoclassical colonnades and expanse of parking lots; the stadium is like its own contained village. Soon after passing it, you’ll ride through Burnham Park, and on the horizon see long lines of boats bobbing at 31st Street Harbor.

That’s my signal that I’ll soon need to turn briefly off the trail at the 47th Street Bridge to ride through the Burnham Nature Sanctuary, part of the Burnham Wildlife Corridor. Bicyclists are allowed to ride through the sanctuary, which hosts different habitats and numerous birds. I like to follow the paved path (veer left upon entering) that connects to the boardwalk, which runs through grassland and a butterfly garden, and pause to watch the colorful insects flutter around wildflowers and native shrubs.

I tend to get so taken with the scenery in the sanctuary that I rarely ride much farther. But it’s worth it to make the extra effort and hop back on the Lakefront Trail. Pedal another mile and a half south to reach a sublime end goal: Promontory Point (at 55th St.), a parkland offering the most rewarding panoramas in the city.

Connect with . . .

14 Get out to Grant Park

27 Catch the views from Promontory Point

39 Explore the Burnham Wildlife Corridor

3 Go gallery-hopping in Bronzeville

Black Chicago • Arts and Culture • Neighborhoods and City Streets

Bronzeville’s streets vibrate with echoes of history and culture. In the exodus between 1916 and 1970 known as the Great Migration, more than six million African Americans relocated to northern cities from the Jim Crow South, and this neighborhood, along with Harlem in New York, became a beacon for Black creativity and enterprise, earning the nickname the “Black Metropolis.” Signature strains of blues, gospel, and jazz, as well as fine art and literature, were nurtured here. Gwendolyn Brooks and Lorraine Hansberry created literary classics, and Nat King Cole and Louis Armstrong established their musical genius here. This was also the neighborhood where Daniel Hale Williams, an African American cardiologist, completed the world’s first open-heart surgery. Today, the Bronzeville art scene is still thriving, and three vibrant Black-owned galleries offer great insight into it.

Known for its exciting displays of work from across the African diaspora, Gallery Guichard