Gardens & Street Art: October Order of Events 2021

October is the perfect time to visit Chicago! It is a temperate climate with beautiful foliage. Often, even the most iconic of attractions are a bit less crowded. It is recommended to come well prepared as the weather can switch on a dime. Every day could be a new season. Sometimes, a fall morning, a summer afternoon, and a wintery evening allows all of them in just a day! It is the perfect time to gather outside or see outdoor exhibits. There are also plenty of fun events in the area! From festivals and architecture cruises to gardens and street art, take a look at what is happening in Chicago this October!

Spend Some Time Outdoors

Because of the generally gorgeous weather, it can be a wonderful time to stroll around Chicago. Classics like Millennium Park and the Chicago Riverwalk will be less packed and great places to see the autumn colors. Places like the Morton Arboretum, which boasts 4,000 different types of trees, or the Chicago Botanical Garden with its 385 acres of immaculately landscaped parks, are amazing places to take in the fall splendor. At the time of writing, the Arboretum requires visitors to reserve their spot ahead of time on their website.

If you do find yourself wandering the streets enjoying yourself and the views, keep your eyes open for Chicago’s famous street murals.

And check out the Banksy Exhibit running through October. It is the largest touring collection of Banksy’s works in the world.

Explore Local Architecture

The Banksy Exhibit is just a couple blocks from the Chicago Architectural Museum. Besides being a great place to visit on its own, for two days (October 16-17), the museum allows the public access to a great deal of architecturally significant buildings and spaces that are generally closed off from the public.

If architecture is your thing, you can follow up with a trip to the museum via the Chicago Architecture River Cruise. These cruises are narrated by the architecture center’s own guides and are open as long as the river isn’t frozen. These cruises as a must as there is no better way to get such a widespread glimpse of the city. Additionally, they are often much more pleasant in October due to smaller crowds and pleasant temps.

On top of those listed above, there are a great many other events happening as well.

Other Events this October: 

  • Looking to celebrate? Join two of the biggest and longest running Pride events in the nation in the home of the first recognized LGBTQ community at Chicago Pride Fest and Parade (October 1-3, 2021).

  • Celebrating is generally better with some imbibements. Chicago Wine Fest (October 2, 2021) features night and day servings of rare varietals and stellar musicians to keep the party going.


Whether it’s gardens & street art, music festivals & architecture, or beer & wine — for whichever part of October you find yourself in Chicago, The Windy City always has something to catch your sail.


Stay safe this October! To stay updated on the latest and most accurate information related to COVID-19, please refer to

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Jane Goodall to Jazz: July Events in Chicago this Summer

As vaccinations continue to climb, we continue to see event spaces opening up. There are many new and fun ways you can spend your social nights now. There are many spaces starting up consistent shows again, right in time for the music festivals so popular around this time of year. These spaces are consistently conscious of attendee safety, meaning you can go out without too much stress. Whether you’re itching for live music or wanting to nerd out at an arboretum, we have events for you and your date! From Jane Goodall to Jazz, July events in Chicago this summer are off to a great start!

Enjoy Outdoor Live Music

Grant Park Music Festival

Grant Park Music Festival is going forward this year with an impressive line up throughout the summer including the New World Symphony, the William Tell Overture, Grieg Piano Concerto, and Prelude to the Afternoon of a Faun. Along with the many shows, there are a ton of family-oriented events like Carnival of the Animals and Classic Broadway. Of course, masks will be required unless eating or drinking, and all seats within the seating bowl are free of charge. The Great Lawn has also been modified to allow for “pods” for groups of 2 to 6! 


Lollapalooza is also back, including headliners like the Foo Fighters, Post Malone, Tyler the Creator, Miley Cyrics, DaBaby, and Megan Thee Stallion. The event will take place from July 29th-August 1st in Grant Park. In accordance with local public health guidance, attendees must provide proof of COVID-19 vaccination or negative test results to attend. 

MCA’s Anna & John Kern Terrace Garden

For a smaller venue, MCA’s Anna and John Kern Terrace Garden is opening up to free music focusing on Chicago’s jazz community. This event will be outdoors and will require masks unless seated in your socially-distanced spots. Food and beverages will be available through the upper part of the terrace, making this a great dinner and drinks date spot! A few upcoming shows include acts such as Edwin Sanchez and Papo Santiago, Twin Talk, Junius Paul/Tomeka Reid Duo, and The Fred Anderson Legacy Band featuring Tatsu Aoki. While advanced free tickets are claimed, sign up for their waiting lists and join their mailing list as they expect the potential for more tickets to be available!

Check Out some Science-Themed Events

The Field Museum

Looking for an event to nerd out about? There are a few awesome science-related exhibits throughout the Chicago area that are currently running! One we suggest is Becoming Jane: The Evolution of Dr. Jane Goodall at the Field Museum. This event runs through September 6th, and details Jane’s inspiring life and experiences. You will get to interact with features such as a projection of Dr. Goodall, who shares memories in a biographical format; augmented reality interactive activities; and a projection of Tanzania’s Gombe Stream National Park complete with virtual chimpanzees.

The Morton Arboretum

Looking for something outdoors? Check out The Morton Arboretum’s Human+Nature exhibit. The artist Daniel Popper shows his 15 to 26-foot-tall sculptures beautifully set in the landscape, inspiring attendees to rethink their relationship to nature and trees.


Stay safe socializing with friends! To stay updated on the latest and most accurate information related to COVID-19, please refer to

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