The Best Places To People Watch In Chicago

Where To People Watch And Soak Up Local Culture In Chicago

Chicago is a city filled with personality. The people are diverse and the settings are interesting. Whether you want to rest, or enjoy some basic people watching, these are some of the more interesting areas.
Lincoln Park
This neighborhood and park area offers a beautiful setting with nicely landscaped gardens, a quaint lily pond, and lakefront green space that has nice views of the city. The Lakefront Trail, the Lincoln Park Trail, Lincoln Park Zoo, North Avenue Beach, and Peggy Notebaert Nature Museum are all in the area. There is also plenty of shopping in Lincoln Park with many boutique shops spread among the row houses.
Chicago, IL
Jay Pritzker Pavilion
Jay Pritzker Pavilion is a stage in Millennium Park that hosts regular concerts and events including the Grant Park Orchestra during the summer months (a series of free concerts). The Chicago Jazz Festival, the Chicago Blues Festival, and Grant Park Music Festival are all held here as well.
201 E Randolph St, Millennium Park, Chicago, IL, 60601
Interested in more travel advice for Chicago? Check out The Best Places to Enjoy the Water in Chicago and The Best Places to Run in Chicago.
Washington Park
Washington Park has a number of attractions including the DuSable Museum, a bird and butterfly sanctuary, The Fountain of Time, and several lagoons.
5531 S. Martin Luther King Dr., Hyde Park, Chicago, IL, 60637
Burnham Park
Burnham Park follows the banks of Lake Michigan for six miles from 14th Street to 56th Street. It spans 600 acres and includes the Burnham Harbor, Soldier Field, and McCormick Place. The Lakefront Trail passes through the park as well. Skateboarders will appreciate Burnham Skate Park, but there are also tennis courts, a fishing pier, and several beaches. For kids, there is a playground.
South Loop, Chicago, IL
Logan Square
Logan Square is a trendy neighborhood that is popular with artists, musicians, and anybody with a creative vibe. The neighborhood is home to the Logan Theatre, which hosts the Chicago Underground Film Festival. It's also a popular nightlife area with its cool cocktail bars and local music scene. There are also a number of breweries in the neighborhood. For foodies, there are a few Michelin star rated options, as well as more casual pizza and noodle shops. Near Logan Square there's a Sunday Farmers Market that's held year round.
Chicago, IL
TheMART
25 stories high and spanning two city blocks, this unique marketplace sits at the intersection of the North, South, and Main branches of the Chicago River. The architects sought to bring together the concept of a warehouse, a department store, and an office building. Within the building you'll find a number of home furnishing showrooms and a large number of tech companies.
222 N. Merchandise Mart Plaza, Near North Side, Chicago, IL
The Gateway
Situated on a wide median on State Street between Wacker and Lake is this park area with seating, public art, and nice areas to relax, meet with friends, or have a meal.
State and Lake, Loop, Chicago, Illinois
Wrigleyville
Wrigleyville is where you'll find the famous Wrigley Field, which is the second oldest ballpark in the country and home to the Chicago Cubs. Near the stadium you'll find a number of sports bars, souvenir stall, and restaurants. Clark Street is the main drag where you'll find locals and Cubs fans. Also outside of the stadium is Gallagher Way, which is a popular meeting spot for fans, locals, and tourists. There are often farmers markets, outdoor concerts, film screenings, and even a holiday winter wonderland here.
Chicago, IL
Planning a trip to Chicago? You might also be interested in Things to Do in Chicago's Grant Park & Millennium Park and Places to Bike in Chicago.
Edgewater
Set right by the lake, this neighborhood has a number of nice beaches and green spaces. It's a family-friendly area with great antique shopping and a thriving theater scene. There are also a diversity of restaurants and markets that are fun to explore.
Chicago, IL
Maggie Daley Park
Maggie Daley Park
Maggie Daley Park is an impressive park with a 1/4 mile long ice skating/roller skating ribbon. There's also a 40 ft tall climbing wall and a play garden for kids. The playground includes a pirate ship play structure with slides, rope bridges, and climbing areas. There's also a 18 hole mini golf course in the park.
337 E Randolph St, Millennium Park, Chicago, IL, 60601
Jackson Park
This is a 600 acre park that sits on the edge of Lake Michigan on the South Side of Chicago. It has a variety of facilities including basketball, tennis courts, and playgrounds. The Osaka Garden is also on the grounds, which is a Japanese style garden that's on an island in the park's east lagoon. There are also several beaches and a running track that visitors can take advantage of.
6401 S Stony Island Ave, South Shore, Chicago, IL, 60637
The 606
This renovation project has turned an elevated railway track into a 2.7 mile path that weaves through the North Side of the city, passing through Logan Square, Humboldt Park, Wicker Park, and Bucktown. It connects a handful of parks and is the perfect place to enjoy a walk, bike ride, or short run.
Humboldt Park, Chicago, IL
Michigan Avenue and the Magnificent Mile
The Magnificent Mile is one of the most famous shopping neighborhoods in the world. It's lined with brand name retail shops, boutique designers, historic hotels, luxury brands, large shopping centers, one-of-a-kind stores, and unique attractions. This neighborhood also has the original American Girl Place, Water Tower Place, and The Drake Hotel where you can enjoy high tea at the historic Palm Court.
Chicago, IL
Garfield Park
Garfield Park is a popular city park on the West Side of the city in the Garfield Park neighborhood. It has a number of recreational facilities including baseball, boxing, basketball, tennis, and swimming. There's also a playground and trails for running, walking and bike riding. When the weather isn't cooperating, you can head inside to the Garfield Park Conservatory, which has about 120,000 plants from 600 different species in a 1.6 acre indoor space.
300 N. Central Park Ave., Garfield Park, Chicago, IL, 60624
Interested in more travel advice for Chicago? Check out A Fashion-Lovers Guide To Chicago and A Nature Lover's Guide to Chicago.
Lakefront Trail
The Chicago Lakefront Trail is a 18.5-mile long trail that is great for running, walking, biking, and even skateboarding. It runs alone the western shore of Lake Michigan and it's popular with locals, tourists, athletes, and commuters. From the trail you can access the lake at different points and the trail passes by a number of different recreational areas including Lincoln Park, Grant Park, Burnham Park, and Jackson Park.
Chicago, IL
Andersonville
Andersonville offers a truly unique personality with a vibrant bar scene and an energetic atmosphere. This neighborhood is home to one of the city's largest LGBTQ+ communities and it hosts annual Pride celebrations. The neighborhood also has beautiful architecture and a charming urban atmosphere, particularly along its main street. There are a large number of independently owned shops here and the "shop local" movement runs deep. Head to Clark Street for the most restaurants including diners, dives, and pastry shops.
Chicago, IL
West Ridge
West Ridge is where you'll find Chicago's Little India, along Devon Avenue. The area has a number of Indian and Pakistani restaurants, shops, bakeries, and grocery stores. West Ridge is also a very diverse neighborhood with a mix of cultures and a strong sense of community. Jewish, Middle Eastern, and South and Southeast Asian populations are all common here.
Chicago, IL
Daley Plaza
In the center of Daley Plaza, visitors will find the famous Picasso sculpture. This public square hosts a variety of events including live music, food trucks, festivals, markets, and more. In fact, almost every day of the year at noon some sort of performance art event takes place here in the plaza.
50 W. Washington Street, Loop, Chicago, Illinois
Chase Promenade
Chase Promenade is a tree-lined pedestrian walkway in Millennium Park. It spans 8 acres and hosts regular exhibitions and festivals.
Chase Promenade Central, Loop, Chicago, Illinois
Crown Fountain
Crown Fountain
Crown Fountain is a video sculpture and work of art that's located in Chicago's Millennium Park. It opened in 2004 and has a black granite reflecting pool between two glass brick towers that display digital videos. The water is turned on between the months of May and October.
Crown Fountain, Loop, Chicago, Illinois
If you're looking for more information about Chicago, read Best Places To Enjoy A Picnic In Chicago and The Best Gardens in Chicago.
Ping Tom Memorial Park
Ping Tom Memorial Park
Located in Chicago's Chinatown, this park has a pagoda-style pavilion, bamboo gardens, and a playground. The waterfront park spans 17 acres and there are places nearby where you can rent kayaks. The Field House is a recreational area in the park that has a pool with slides and a fitness center. From here you can enjoy great views of the Chicago skyline. Throughout the year there are a number of events held here including Shakespeare in the Park. Runners and walkers will appreciate the trails through the park as well.
300 West 19th Street, Chinatown, Chicago, Illinois, 60616
Dearborn Station
Dearborn Station is the oldest of the six train stations in downtown Chicago. It currently has a shopping mall with retail and entertainment space.
66 West 9th Street, Printer's Row, Chicago, Illinois, 60605
Grant Park
Grant Park
Grant Park is a large and impressive public space in the city's central business district. This large park is where you'll find the famous Millennium Park, Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus. There are a number of gardens, sport fields, and performances venues found in the park as well.
Printer's Row, Chicago, Illinois
Millennium Park
Millennium Park
Millennium Park is a famous public space that's located in Grant Park. The 24.5 acre park is near the Lake Michigan shoreline and includes a number of famous attractions such as Cloud Gate, Crown Fountain, Lurie Garden and a number of outdoor performance areas.
Loop, Chicago, Illinois, 60601
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Prices for activities, things to do, and tours range from $5 to $498. The average cost for a tour or tickets is $93. A few of the best options are below.

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Chicago has plenty more to offer, so see also our other articles: The Best Outdoor Activities in Chicago and The Best Parks in Chicago.
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