Experience Chicago Like a Local
No matter what kind of vacation vibe you want, the Windy City can cater to it. Chicago is filled with iconic sites such as the Art Institute of Chicago and Navy Pier, as well as quieter areas like Andersonville on the North Side. You will feel at home in Chicago before long.
If time permits, aim to spend about three days in Chicago to enjoy a variety of activities without feeling rushed. The city offers experiences for every price point, from luxury dining to numerous free activities like exploring beautiful parks or attending live music events.
However, with so much on offer, where should you begin? Listen to the locals and explore via bus or L train. Here are 15 fantastic ways to experience Chicago like the locals.
1. Take Yourself Out to the Ball Game
Chicago is home to two baseball teams: the Chicago Cubs at historic Wrigley Field and the Chicago White Sox at Guaranteed Rate Field, making a baseball game a must for sports fans. There are also plenty of opportunities to catch football, basketball, hockey, and soccer events throughout the year. Chicago is undeniably a sports town, and attending a game can be an exhilarating experience.
On any given day, sporting events draw fans to arenas and stadiums. It’s important to plan ahead, as tickets for popular games can sell out quickly, and hotel prices may surge during peak tourism seasons.
2. Take an Architecture River Cruise
One of the best ways to appreciate the skyline and learn about the history of Chicago’s urban landscape is by taking an architecture river cruise. This experience offers insights into some of the city’s most iconic buildings and their developers. Cruises are available throughout the day and offer both indoor and outdoor seating options.
3. Dive Into Chicago’s Cocktail Scene
Chicago’s cocktail scene is vibrant and diverse. The Violet Hour is renowned for its craft cocktails, and enjoying a drink there feels like stepping back in time. For something more contemporary, The Aviary offers innovative molecular drinks paired perfectly with small plates. If you’re eager for unique experiences, explore speakeasies like The Drifter and Lady Bird, which provide an exciting twist on a night out.
4. Find Chicago’s Magic
Chicago boasts a thriving magic scene with talented magicians performing in various venues. For an upscale experience, attend an intimate show at the Palmer House Hilton with renowned magician Dennis Watkins. Alternatively, the casual Chicago Magic Lounge features magic alongside cocktails in a unique setting that’s perfect for families or casual outings.
5. Groove to the Blues and Rock
Chicago has a rich musical heritage, particularly known for its electric blues. Enjoy live performances at iconic venues like Buddy Guy’s Legends or Rosa’s Lounge, which showcase the city’s blues scene. The annual Chicago Blues Festival draws top talent and is a fantastic way to immerse yourself in the music culture.
6. Shop Local in Chicago’s Cool Neighborhoods
To truly experience Chicago, venture beyond the Loop and explore its eclectic neighborhoods. From the nostalgic shops of Andersonville to the hipster havens of Wicker Park, there are treasures to be found everywhere. Little Village and Hyde Park also offer unique shopping experiences, making each neighborhood worth the visit.
7. Dine at Award-Winning Restaurants
Chicago’s culinary scene has gained recognition for its innovative chefs and diverse offerings. From high-end dining in the West Loop to classic favorites, there’s something for every palate. Don’t miss famous spots like Giordano’s for deep-dish pizza or upscale locations like Alinea for an unforgettable dining experience.
8. Make the Most of Millennium Park
Millennium Park is a vibrant public space renowned for its art installations and hosts a variety of free concerts during the summer months. Explore Cloud Gate, also known as “the Bean,” and enjoy the beautiful surroundings while soaking up local culture.
9. Take a Windy City Tour
Discover hidden gems in Chicago by taking a guided tour to explore different neighborhoods and their unique stories. Local historians offer fascinating insights that can enhance your understanding of the city.
10. Laugh Out Loud at Local Comedy Shows
Chicago is the birthplace of improv comedy, and there are numerous venues where you can catch a show, including the famous Second City. Enjoy a night of laughter and entertainment as local comedians take the stage with their unique twists.
11. Stroll Along Navy Pier
Navy Pier offers a fun and engaging experience for visitors of all ages. With its rides, restaurants, and cultural activities, the Pier is a destination worth exploring, especially with the stunning backdrop of Lake Michigan.
12. Discover African American History at the DuSable Museum
The DuSable Museum of African American History is an essential stop to learn about the rich history and culture of African Americans. The museum hosts a variety of exhibits celebrating notable figures and significant events in history.
13. Explore the Sea and the Stars
Near Lake Michigan, the Shedd Aquarium and Adler Planetarium provide unique educational experiences. From underwater wonders to celestial exploration, they are perfect destinations for family outings.
14. Get Cultured at the Art Institute
The Art Institute of Chicago is not just a museum; it is a cherished cultural institution featuring remarkable collections that captivate art lovers. Even a short visit can be rewarding, so be sure to stop by if time allows.
15. Enjoy the Outdoors at Grant Park
Grant Park offers beautiful gardens, spacious lawns, and plenty of open space for relaxation. It serves as a perfect venue for a picnic or a leisurely stroll, especially when the iconic Buckingham Fountain puts on a dazzling display at night.
Plan Your Trip to Chicago
Chicago is a city brimming with activities and experiences that showcase its unique character. Start planning your visit to the Windy City and get ready for an unforgettable adventure with iBestTravel’s tips to navigate the city’s best offerings.
