Chicago, Illinois, is one of the largest cities in the United States. It’s known for its stunning architecture, rich history, and windy weather. Chicago is also home to 77 vibrant neighborhoods, each of which boasts its own unique feel and flavor. Here’s one way to spend a day exploring a few of the most iconic.

neighborhood downtown
A Downtown Neighborhood in Chicago.

Late Morning: Wrigleyville

As the name suggests, Wrigleyville is home to Wrigley Field. When the Chicago Cubs won the World Series in 2016, this neighborhood erupted and became the scene for celebration hours and even days after the game. Wrigleyville also boasts exciting nightlife with bars lining Sheffield, Clark, and Addison Avenues.

During the day, the area is calm and quiet with casual restaurants and shops selling Chicago souvenirs. Grab a bite at Chen’s Chinese & Cuisine, D’Agostino’s Pizzeria & Pub, or Rockit Burger Bar. On game day, the streets are crammed with people walking to and from the stadium as well as those celebrating a win or lamenting a loss.

The Chicago Riverwalk.

Midafternoon: The Loop

The Loop is Chicago’s downtown business district. During morning and afternoon rush hour on weekdays, this area is busy, so wait to visit until the crowds die down. It’s home to Millennium Park, a 24.5-acre oasis in the middle of the city that houses the famous “Bean” sculpture. The neighborhood also has impressive buildings designed by famous architects such as Louis Henri Sullivan and Jeanne Gang. Several outdoor spaces, such as the Chicago Riverwalk and Maggie Daley Park, are within walking distance. It is also home to the world-famous Art Institute of Chicago and the Chicago Theater District.

north avenue beach
North Avenue Beach.

Evening: Wicker Park/Bucktown

Wicker Park sits between Western Avenue East and Ashland Avenue as well as North Avenue South and Division Street. It’s often described in the same breath as Bucktown since it sits so close. Many years ago, goats grazed and lived in what is now one of the trendiest neighborhoods in Chicago.

The area includes a diverse mix of housing, from studio apartments to multimillion-dollar homes. It’s fun to check out the exciting nightlife and relaxing outdoor spaces in the evening. Residents looking to flip homes often flock to Wicker Park. When visiting the area, stop by The Violet Hour for a nightcap, a spot known for its mixologists. High-end boutiques and vintage shops line Damen, Division, North, and Milwaukee Avenues.

Chicago and its 77 neighborhoods offer unique flair for visitors and locals alike. Explore these three to get a feel for life in the city.