Visitors from Australia

Question

Hi all

Visiting in September

What are the things not to miss we will be there about 5 days

Thanjs

Answer

Chicago is an exciting city with a lot to offer, and you’re in for a great time during your 5-day visit! September is a wonderful time to explore the city as the weather is typically pleasant, with warm days and cooler evenings. Here are some must-see attractions and activities to help you get the most out of your trip:

1. Millennium Park & Cloud Gate ("The Bean")

One of Chicago’s most iconic landmarks, Millennium Park is a must-visit. It’s home to the famous Cloud Gate sculpture, affectionately known as "The Bean." You can take fun photos with your reflection in the shiny surface, and it's also a great spot to relax and enjoy the public art. While you're there, be sure to check out the nearby Jay Pritzker Pavilion, designed by Frank Gehry, and the Crown Fountain.

Location: Millennium Park (Michigan Ave between Randolph St and Monroe St)
Highlight: Cloud Gate and the surrounding park, great for photos and people watching.

2. Navy Pier

Navy Pier is a lively waterfront area offering entertainment, dining, and great views of Lake Michigan. You can take a ride on the Ferris wheel, explore the shops, or relax by the water. It’s also a hub for boat tours and has a variety of seasonal events, making it a great place to visit for a bit of fun and sightseeing.

Location: 600 E Grand Ave
Highlight: The Centennial Wheel offers amazing views of the city and lake.

3. Art Institute of Chicago

If you enjoy art, the Art Institute is one of the top museums in the world. You’ll find works from renowned artists like Van Gogh, Picasso, and Grant Wood’s famous "American Gothic." The museum is massive, so plan for a few hours to explore. The museum is also home to the beautiful bronze lion statues out front, which make for great photos!

Location: 111 S Michigan Ave
Highlight: The collection of Impressionist and American Art.

4. Architecture Boat Tour

Chicago is famous for its architecture, and an architecture boat tour is one of the best ways to see the city’s stunning skyline and learn about its history. These tours typically run along the Chicago River and offer insights into the city's famous skyscrapers, bridges, and iconic buildings. You'll get a unique perspective of the city’s architectural gems.

Location: Chicago Riverwalk (various departure points)
Highlight: Learn about Chicago's innovative architecture while enjoying views from the river.

5. The Magnificent Mile

Chicago’s premier shopping district, the Magnificent Mile, stretches along Michigan Avenue and is home to luxury boutiques, department stores, and popular shopping centers. Even if you’re not shopping, it’s a great place to explore with lots of restaurants, cafes, and stunning historic buildings.

Location: North Michigan Ave (from the Chicago River to Oak Street)
Highlight: Great for shopping, dining, and exploring Chicago’s architecture.

6. Willis Tower Skydeck (formerly Sears Tower)

No visit to Chicago would be complete without going to the top of the Willis Tower Skydeck. The glass ledge at the top gives you an exhilarating view of the city from over 1,300 feet in the air! It’s one of the tallest buildings in the Western Hemisphere, so the views are spectacular, and it's a must-do for any first-time visitor.

Location: 233 S Wacker Dr
Highlight: The Skydeck and The Ledge (glass boxes you can stand in for a clear view straight down).

7. Chicago's Food Scene

Chicago is famous for its deep-dish pizza, hot dogs, and Italian beef sandwiches. Be sure to visit one of the classic pizzerias like Lou Malnati’s, Giordano’s, or Pequod’s for a true Chicago-style deep-dish pizza. For hot dogs, you can’t go wrong with Portillo’s or The Original Chicago Hot Dog Stand. If you’re into food tours, consider booking one to experience a variety of local dishes in one go.

Food Must-Try: Deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches.
Suggested spots: Lou Malnati's, Portillo’s, The Purple Pig.

8. Lincoln Park Zoo & Conservatory

If you’re a nature lover or just looking for a peaceful escape, the Lincoln Park Zoo is a great spot. It’s free to visit and has a lovely variety of animals, plus beautiful gardens. You can also visit the Lincoln Park Conservatory, which is a short walk from the zoo and is full of lush tropical plants, making it a nice, relaxing stop.

Location: 2001 N Clark St
Highlight: Free admission and great for a more relaxed, natural experience in the city.

9. Chicago Riverwalk

Walk along the scenic Chicago Riverwalk to enjoy stunning views of the city’s architecture and the Chicago River. You can grab a drink at one of the riverside cafes, rent a kayak, or just enjoy the walk. It’s a lovely spot to spend a relaxing afternoon and take in the city’s vibe.

Location: Along the Chicago River from Lake Shore Drive to Lake Street
Highlight: Riverside restaurants, beautiful views, and public art installations.

Conclusion: With 5 days in Chicago, you’ll have plenty of time to explore the highlights. Be sure to check out the must-see attractions, enjoy some delicious local food, and take in the city’s vibrant culture and stunning architecture. September is a great time to visit, with lots of outdoor activities available and fewer crowds than the summer months. Have a fantastic time!

Visitors from Australia

More Chicago Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions