Visiting Chicago in September - Tripshepherd
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Visiting Chicago in September

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Adler Viewpoint at Adler Planetarium Skyline Walk in Chicago

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Best of Chicago History & Architecture Walking Tour

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Adler Viewpoint at Adler Planetarium Skyline Walk in Chicago

Best of Chicago Tour

$229

Side view of Chicago Skydeck & The Ledge

Private Tour of Chicago

$909

Best of Chicago History & Architecture Walking Tour

$49

Adler Viewpoint at Adler Planetarium Skyline Walk in Chicago

Best of Chicago Tour

$229

Side view of Chicago Skydeck & The Ledge

Private Tour of Chicago

$909

Best of Chicago History & Architecture Walking Tour

$49

Ammara Younas2024-09-10

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Chicago, also known as Windy City is famous for its sports and deep-dish pizzas. The nightlife, shopping districts, sporting events, museums, and iconic buildings in Chicago have no match. It is also home to one of the World’s tallest buildings, the Willis Tower. 

You can relax at Lake Michigan, watch the Hancock Skyline, be in awe of the marvelous Montrose Point Bird Sanctuary, or walk down to Southport Avenue where you can see the beautiful Music Box marquee - Chicago has the power to make you forget about everything else in the world.

Embark on the Best of Chicago Small-Group Tour to See the City's Top Attractions!


Is September a good time to visit Chicago?

Yes, September is a great month to visit Chicago. From Grant Park Music Festival to Woody’s Orchard Fall Fest, where you can enjoy delicious apple cider donuts, there’s something for everyone in this beautiful city. You’ll love Chicago Gourmet where you can savor the delicious gourmet food, finest cocktails, lively music, and much more. 

What’s more? Immerse yourself in some natural history at the Field Museum. Lastly, the Taste of Chicago, the largest food festival, hosted in September in various Parks across the city with diverse cuisine is a must-visit special event. 

Lincoln park Chicago

(Credit: Megan Ruth / Unsplash)

Reasons to Visit Chicago in September

There are many reasons to visit Chicago, one of the most important ones is to soak in the beauty of Chicago by taking an architectural tour of the City. In September, go for a river cruise tour, because from the river you can get to see lots of the main architecture of the city. 

Also, Chicago, in many ways, looks like New York. The downtown area of Chicago, also known as The Loop, feels like an endless path with lots of skyscrapers. Walking from one end of the Loop to the other one feels like forever and takes around half an hour. Moreover, there are tons of local eateries influenced by the immigrants.

Moreover, Chicago is located on the vibrant Lake Michigan that feels like an Oceanside city. The neighborhoods around the central part of Chicago feel like towns making it look magnificent. 

Embark on an Architecture + History Tour of Chicago featuring a Boat Cruise!


Things to do in Chicago in September 

Chicago is home to some of the most popular museums and parks. The heart of Chicago comprises over 77 neighborhoods. So, just staying in The Loop when there are tons of places to explore is a sin. There are so many things to do and the metro and bus can be accessed very easily. Some of the things you can do in Chicago in September are:

Labor Day Weekend 

Summer may be winding down, but Chicago in September is still full of festivals to enjoy. And Labor Day Weekend is great to enjoy the last of the summer. You can enjoy the remaining warm weather with scenic boat tours, the Chicago Jazz Festival, the ARC Music Festival, live sports, dinner on a patio, and a lot more.

Labor Day Weekend in Chicago is incomplete without Chicago's annual music festivals, where the events include hip-hop and rock acts, art installations, food vendors, and more. Also, the festival features house music, which is a Chicago-born genre, and Chicago’s free lakefront music. 

Moreover, you can go for a ride at Lake Shore Drive, which is shut down for cars one day every year. You can wander around in the Chicago Riverwalk where you can find waterfront restaurants and bars. Catch the Chicago White Sox and Chicago Cubs game at Wrigley Field. Or see the gorgeous fireworks at the Navy Pier - there are endless things for you to do! 

The Art Institute of Chicago

One of the World’s greatest art museums, where you can find a unique collection of objects, cultures, time, and a lot more. The institute is ranked consistently as the number 1 travel destination. The Michigan Avenue Building with iconic bronze lions was constructed for the World’s Fair in 1893 and now it houses over 300,000 works of art. Millions of people visit this place every year from around the world. 

Located next to Millennium Park, the museum is a perfect place to spend your day. Apart from all the art collections, it hosts around 40 exhibitions each year. The events include the demonstration of the museum's unique history and identity which is a window to the world. Lastly, there’s a dining place offered by the museum where you can enjoy your lunch or grab some dessert and a refreshing drink. 

Chicago Illinois

(Credit: Raf Winterpacht / Unsplash)

Lincoln Park

This gorgeous, picturesque park is a perfect place to visit in September. It has beautiful lush green gardens, a hidden lily pond, an indoor botanical garden, great lakefront green space, and the country’s oldest free zoos. If you’re into music, head over to the Kingston Mines which is home to the Chicago-style blues, and enjoy live music there till 4 in the morning. 

If you love shopping, this place will be a paradise for you. You can find the best boutiques here, make a customized leather bag at Laudi Vidni, shop for snacks at Foxtrot Market, and find decor items. There is also a great dining place with lots of delicious food. With stunning views of Lake Michigan, enjoy your drinks at the J. Parker Rooftop or have a delicious relaxing dinner.

Chicago History Museum

An excellent museum in Chicago, Chi Town which highlights the contributions this city has made to the world. There are tons of artifacts for you to see with a gorgeous view of Chicago. It can also be an educational visit as you can learn a lot here. One of the most amazing things to do in this museum is to see objects that survived the Great Fire in 1871.

The museum also has a cafe and bookstore. Although the fire of 1871 destroyed a lot of the stuff, the museum rose from the ashes. It shares the story of Chicago over the years, serving as a place for learning and inspiration. If you are interested in the city’s past, present, and future, this place should be on your bucket list.

Hyde Park

The park is mostly residential but a great place to explore. The Frederick C. Robie House, a work of Frank Lloyd Wright, and the University of Chicago reside in this park, which is home to the most beautiful neo-gothic buildings, including a very famous cathedral. Also, it’s very easy to walk around the university area and explore different sights.

You can find lots of cafes, restaurants, coffee shops, museums, bookstores, and parks here in this place. It’s a culturally diverse neighborhood and the food is heavily influenced by the local community. You can find some great art museums in the Park known as the Smart Museum of Art and Hyde Park Art Center. Lastly, there is Promontory Point on Lake Michigan for you to see. 

Chicago September Weather

September in Chicago means the end of the summer and the start of Autumn- where you can enjoy the last bits of the warm weather. The weather in Chicago in September reaches around 23 degrees Celsius at day-time and drops to 17 degrees Celsius at night-time. It is better to pack mid-season clothing and some warm jackets with you because it gets quite chilly at night. 

Wrapping Up:

To wrap it all up, September in Chicago offers a sweet spot for tourists with perfect weather. The city has so much to offer - from museums to parks to amazing skylines, there’s something for everyone to enjoy. So, book your tour to Chicago now without further ado!