11 More Things to Do in Chicago in the Second Half of September

There are only two weeks left of September events and activities, but we still have plenty of events going on. If you’re in the mood for a music festival, a food lover’s event, or simply want to try something new, we’ve got you covered. Below are 11 more things to do in the second half of September.

All these events are filling up quickly. So don’t hesitate, grab your ticket, and let’s finish out September strong! Say… how does breakfast with animals sound?



Credit: The Dearborn

‘Halfway To St. Patrick’s Day’ at The Dearborn 

145 N Dearborn St, Chicago, IL 60602


Are you looking for the ultimate end-of-summer celebration or the perfect reason to get excited for St. Patrick’s Day? Look no further because The Dearborn has got you and your guests covered!

On September 17th, The Dearborn is celebrating the halfway mark to St. Patrick’s Day with a variety of specials, including Corned Beef Sandwich, Shepherd’s Pie, Teeling Irish Whiskey cocktails, and more. Additionally, The Dearborn will be hosting a raffle for 2 Notre Dame football tickets!


Riot Fest 

Riot Fest is a multi-day music festival specializing in punk, rock, alternative, metal, and hip-hop. Founded in 2005 in Chicago. Carnival Rides, amazing food vendors, sideshow performers, and more add to the atmosphere of this independent music fest. If you’re an avid music lover, then you know this year’s lineup is worth every dollar for the ticket. So, what are you waiting for?


You can purchase your tickets here.


Posted by Chicago Blues Festival on Wednesday, September 1, 2021

Chicago’s Blues Festival 

Millennium Park, Chicago, IL 60601


The annual Chicago Blues Festival is the largest FREE blues festival in the world and remains the top Chicago music festival, and now you can join us on Sept 18th, 2021 for a special Chicago Blues evening as part of Chicago In Tune.

Four special evenings at Jay Pritzker Pavilion presented with the Millennium Park Foundation will honor music born and innovated in Chicago, including Chicago In Tune–Blues (September 18 at 5:30–8:30 pm). Additionally, DCASE and its partners will celebrate blues music with community concerts in the Bronzeville and Austin neighborhoods, on historic Record Row, and in music venues across the city.

Chi-Town Movies in Pilsen 

2343 S. Throop St, Chicago, IL 60608

Looking for more things to do this month? Let’s all enjoy some blockbusters and classic movies under the stars at our drive-in located in Chicago’s Pilsen Neighborhood. Order food and beverages from ChiTown Grille. They will deliver delicious popcorn, tacos, wings, pizza, kid’s meals, and more to your vehicle as you enjoy the movie.  

Purchase tickets here

360 Sky Yoga

875 N Michigan Avenue, 94th Floor Chicago, IL 60611

We can’t talk about things to do in Chicago without mentioning some yoga events, you know? This month, 360 Sky Yoga welcomes yoga enthusiasts to a one-hour weekly class led by 360 CHICAGO’s professional instructor. Participants will be led through movements perfect for all ages and skill levels in front of breathtaking views of Chicago.

Registration is $20 (plus taxes and fees) and includes a General Admission ticket to the observation deck, so feel free to stick around after the class and take in the full experience! 

Register here.

Brews n ‘Baahhs’ 

450 N. Waller Ave, Chicago, IL 60644

This is not your average city experience! Spend an hour hanging out with some gentle, sociable mama and baby goats in a pasture setting. This is a private experience just for groups of 2-6 people. You will get an up-close and personal goat experience – and plenty of pictures to prove it! And then, after an hour with the goats, it’s beer time! Head down the street to One Lake Brewing for a rooftop beer tasting experience!

Your first 2 flights are included and let you taste all 8 of their house-made rotating craft beers! Purchase tickets here

Lakeview Taco Festival

3500 N. Southport, Chicago, IL 60657

The Southport Corridor is arguably one of the hottest commercial strips in Chicago with its eclectic mix of stores, boutiques, and restaurants. And it’s about to get even more sizzling this September when the glorious taco is again in the spotlight as we welcome back the Lakeview Taco Festival.

Back for its eighth flavor-filled year in 2021, the festival is also a celebration of seasonal beers as well as the start of autumn. Whether you prefer your shells filled with traditional chicken, steak, chorizo, and beef, or stuffed with imaginative ingredients such as mushrooms, seafood, goat, and duck, there is something for you at the festival.

This year, more than eight local eateries challenge themselves to make the tastiest tacos. The fest also features special beer and taco pairings, two music stages, crowd-pleasing Mexican wrestlers, and activities for kids. But most importantly, visitors can text vote for Chicago’s “Best Taco!”

Breakfast with The Animals Presented by Nutella

2234 North Cannon Drive, Chicago, IL 60614

This special series brings back a guest favorite event and pairs it with a menu featuring the family favorite hazelnut spread. Guests get exclusive access and information about animals with each intimate breakfast limited to 100 people. Therefore, this is your chance to ask questions of our curators and experience the zoo in a special way at a special time of day, as mornings are one of the most active times for animals!

Both breakfasts run from 9 a.m. to 11 a.m. and feature a one-hour program and Q&A with a zoo curator. The menu is vegetarian-friendly. Also, all guests will receive a complimentary sample of Nutella® hazelnut spread and recipes to try at home.

Tickets are $50 per person. Reservations are limited. Secure your seat today!

The Little Mermaid Cocktail Experience

3014 W Irving Park Rd., Chicago, IL 60618

Dive deep into a submersive tale of tails! Relive the centuries-old fairytale as you witness the human world collide with ocean life in a theatrical cocktail experience. Meet fellow seafarers on the shores of a stormy sea before diving deep down into a secret underwater cave, where you’ll find walls of coral and pearls that glimmer as the water passes. Will you drink the nefarious sea witch’s draught? Surrounded by the stunning decor, talented actors and secrets to be uncovered, get ready to discover the mysteries hidden beneath the surface!

Tickets are for 1 person to a 1.5 hour-long submersive theatrical cocktail experience including 3 bespoke themed cocktails based on the Hans Christian Anderson Fairytale

Purchase tickets here

Chicago Drag Brunch 

1132 W Grand Ave, Chicago, IL 60642

Muffy Fishbasket and the Grand Cabaret present the Chicago Drag Brunch! Every Sunday, head on over for a delicious brunch served up with a heaping helping of camp and sass from Muffy Fishbasket and a rotating cast of Chicago’s Queens & Kings of drag entertainment. Comedy, songs, dance, and so much more await—it’s the most fun you can have on a Sunday morning! Tickets for 1 person and include a full brunch meal and a drag show full of comedy, song & dance. 

Purchase tickets here

pizza bus chicago

Pizza City USA Bucktown-Wicker Park Pizza Crawl

2010 N Damen Ave., Chicago, IL, 60647

Created by 13-time James Beard Award-winning food journalist Steve Dolinsky, this Sunday-only series of tours is based on his book, “Pizza City, USA” and features four different styles of pizzas in less than three hours. No doubt, this is one of the coolest things to do in the remainder of this month.

Learn about Chicago’s 10 pizza styles, and discover why there’s more to The Windy City than just deep-dish. You will also get to go back in the kitchens to see how pizzas are made, talk to the owners, and taste the differences. Expert “doughcents” will share the history of Chicago pizza as well other interesting tidbits about the neighborhood you’re exploring.

Purchase tickets here

Featured Image Credit: The Dearborn