Things to Do In Chicago This September (2022)

We don’t know how it’s September already, but that’s fine — because September only means beers, football season, picnic and leaf-watching, and tons of other fun stuff to do! Make some noise: have you been waiting for our list of things to do in Chicago this September? Yes? Well, here you go!

Dine at Bambola

A romantic voyage along the Silk Road as imagined through the travels of a bon vivant and connoisseur, Bambola is a 175-seat restaurant and cocktail bar from Bonhomme Hospitality that tells the story of trade, travel, and culture. The restaurant opens on Tuesday, September 13, and reservations are now available through Resy.

Bambola is a journey for the senses, an expedition to the East that weaves through a diverse cultural tapestry stretching from Italy to Xi’an. Led by Chef de Cuisine Alisha Elenz and Bonhomme Group’s Michelin-starred Executive Chef Marcos Campos, Executive Pastry Chef Shannah Primiano, and Culinary Director Erwin Mallet, Bambola is inspired by the rich traditions, ancestral techniques, exciting products, and flavorsome spices widely exchanged and mastered by Eastern and Western cultures since the 13th century.

Image Credit: Tzuco

Celebrate Mexican Independence Day at Tzuco

Tzuco, located at 720 North State Street in River North, is celebrating its third anniversary and Mexican Independence Day by hosting a ticketed five-course dinner and wine pairing on Thursday, September 15. The dinner is $180, and a wine pairing can also be added to the experience. Head chef and owner, Carlos Gaytán has invited a variety of reclaimed chefs, including Chef Claudette Zepeda of San Diego, Chef Yvan Mucharraz of Cabo San Lucas, Chef Javier Plascencia of San Diego, and Chef Juan Gutierrez of Chicago, to prepare a course with their own unique ingredients and flavor profile sure to excite the palate from start to finish.

Capture the Last of Patio Season

Look out! A wave of cold weather is steadily approaching, and September is your last chance to enjoy the beautiful outdoors at your favorite patio! Grab a few friends, or have a work meeting in the early autumn sun. We truly cannot think of anything more delightful.

Explore Fall Happy Hours

The holiday season craze hasn’t arrived, but the summer maniac has passed. Fall is usually the calmer season to catch up with friends and colleagues. Then, what’s a better occasion than one of the many brilliant happy hours across town? From $1 oysters to $5 shots, Chicago is big enough to have a happy hour offering for everyone.

Dine at FARE

The brainchild of Kasia Bednarz and Brini deLeon, the dine-in and takeaway spot’s bright herbaceous menu is rich in plants and environmentally sustainable with robust vegan and gluten-free options. Originally launched at Wells Street Market and closed during the pandemic, FARE now has an outpost with a limited menu at From Here On food hall at the Old Post Office.

The coffee program features Passion House coffee, espresso and nitro cold brew, Rishi single origin matcha, tea, and chai. The menu also features Publican Quality Bread’s Honey Wheat Croissant, Kouign Amann, seasonal Danish and Chocolate Brioche Morning Bun.

Check Out HIDE + SEEK

Restaurant Row now has a new chic resident. HIDE+SEEK, taking over the former Vivo space fuses comfortable elegance, and a Creative-American shared plates menu drawing inspirations from Spain, France, and Italy. HIDE+SEEK embodies laid-back luxury and a sense of connection, encouraging guests to stick around, order another drink, and focus on the people you’re with in a beautiful setting.

Watch College Football

What’s your color? It’s time to get those school hoodies back out, because the college football season is here! Find a bar showing your home game with specials and viewing parties, and you might as well make it an alum reunion. Celebration shots, pizza deals… Check out our list of best sports bars in Chicago with college football specials and make your reservations now!

Oktoberfest in Chicago

This one’s for you, beer lovers! Later in the month, we’re publishing a list of Oktoberfest celebrations across Chicago and in nearby suburbs, so you better stay tuned! Meanwhile, check out the fall beers from your favorite local breweries and get a taste ahead of time.

Prince Brunch at Hub 51

In partnership with The Prince Experience on Michigan Avenue, Hub 51 is hosting a Prince-themed brunch featuring a Purple Rain Cocktail, themed food and DJ blasting Prince’s greatest hits. Guests will have the opportunity to win passes to visit the Prince Experience and other giveaways. To reserve your spot, make a reservation at Hub 51. The Prince Brunch experience is available on September 25, one day only!

Take Your Date to The Green Tie Ball

Get fancy and do something good at this year’s Green Tie Ball — one of Chicago’s biggest and longest-running gala events!

The Green Tie Ball, benefiting Chicago Gateway Green, returns Saturday, September 17, at the Chicago Sports Museum. The event delivers the best in venues, decor, and live entertainment each year. This year’s attendees will include Chicago’s top VIPs, beloved sports figures, and notables, including gala emcees Cortney Hall (Host of NBC5 CHICAGO TODAY & former Chicago Bulls In-Arena Host) and Chris Petlak (Host of The Morning Mix on 101.9).

Tickets are available here.

wine rival
Image Credit: Francis Son

Get Buzzed at Wine Rival

After a two year hiatus, The 4th Annual WINE RIVAL (formerly Somm Madness) returns on Thursday, September 22, 2022, to award the 2022 title of WINE RIVAL Champion at Venue West. At 6pm, the event kicks off with an over-the-top Tailgate Tasting. Ticket holders will have access to more than 300 luxury wines in a walk-around tasting as well as a grand display of endless bites. At 7 pm, the WINE RIVAL Tournament begins. All ticket holders can watch the tournament while the 64 registered competitors try their luck at the tasting tournament led by renowned judges.

A portion of the proceeds will benefit The Balance Project. Tickets can be purchased here.

Chicago Gourmet

The biggest foodie event is back! This year’s Chicago Gourmet schedule is reaching a whole new level, including a unique Oktoberfeset celebration called Prost! In the Park. Other highlights include Tacos and Tequilas, an all-day wine tasting event, and a late-night after party. The tickets are going fast, so you better hurry!

Have a Romantic Cruise Date

Before it’s too cold to get onto the water, grab your date for a romantic cruise ride!

Locally-owned and operated Chicago Electric Boat Company offers self-guided cruises along the beautiful Chicago River, with docks in both the concrete jungle of the city and the tree-filled banks of Avondale. Their cruising season goes through October, allowing couples an extra opportunity to take in the fresh air & sights from the comfort of a cozy, intimate vessel. Their bright and colorful Retro boats can hold four people, making them perfect for double dates or extra spacious couple adventures. All of their vessels come equipped with Bluetooth speakers, coolers, and are BYO food + drink friendly, allowing you to set the exact vibe for you and your lover.

Visit the RNDD Fall Art Walk

Where can you find all the best interior design and fine arts in one? The famous River North Design District! This September, check out their biggest art walk of the year where the best of the best showcase their brilliant pieces across multiple disciplines from drawing, painting, sculpture, and installation. You’ll also get to see all these pieces coming together after the interior designers do their magic!

Chicago Artist Coalition’s Annual Benefit

Join artists, art supporters, and enthusiasts at the Chicago Artists Coalition’s annual benefit, WORK IN PROGRESS 2022. The benefit includes a lively party, art auction, art activations, and music. This year’s party is designed to honor artist Candida Alvarez and art dealer Monique Meloche. Proceeds from the benefit support CAC’s programs to ensure that artists and curators continue to live, work and thrive in Chicago. Get your tickets here!

secret wall art battle
Image Credit: Griffin Gher

Secret Walls Art Battle

Los Angeles-based live arts entertainment brand Secret Walls is proud to announce the first-ever Support Your Local Artist North America Tour (SYLA Tour). The tour kicked off in mid-August in Southern California, bringing Secret Walls’ high-energy physical illustration and design battles to cities across North America. Each stop will spotlight local talent, delivering an unforgettable battle event as the next generation of superstar artists compete for Secret Walls glory.

The SYLA Tour heads to the Subterranean in Chicago on September 21, 2022, and will feature local street muralist Sentrock, street artist Lauren Asta, multi-media artist Emmy Star Brown, visual artist EDO and more to be announced. Grab your tix and come support our local artists!

Flourish at Chicago Botanic Garden

Fall is the perfect time to visit a botanic garden as trees begin to change color and summer flowers bloom for one last time. However, if you want another reason to pay the lovely Chicago Botanic Garden a visit, here you go. September is your last chance to see Flourish, their 50th-anniversary celebration featuring multi-artist installations across the garden, a gallery exhibition, and interactive performances.

Check Out Architectural Artifacts

How does six floors of antiques sound? That’s Architectural Artifacts for ya! We fell in love immediately with this treasure building, and spent a whole hour just going through their basement gallery! Therefore, now is the time to grab your antique nerd friend, and set out to the newly opened Architectural Artifacts for an exploration.

RSM chicago june
Image Credit: Randolph Street Market

Visit the Randolph Street Market

Chicago’s most beloved treasure hunt returns to the West Loop where the world-famous event first began at 1341 W. Randolph for the second installment of its 19th season Saturday, September 24 through Sunday, September 25.

The European flea-market style experience and family-friendly event will bring together 175 of the top independent vendors, makers, and designers across North America. Here, you’ll find an ultra-curated, high-quality selection of antiques, vintage and modern goods ranging from designer fashion to art, jewelry, décor, retro home furnishings, global goods, and more!

yoga awareness chicago things to do september mariott
Image Credit: Marriott Mag Mile

Celebrate Yoga Awareness Month

To celebrate International Yoga Awareness Month, all of the classes will feature a Yoga Flow led by one of the amazing instructors from Mariott’s Summer Series. Unwind to gorgeous skyline views as the sun begins to dip low, followed by light bites and cocktails using ingredients from the rooftop garden. All classes are from 6pm – 7:30pm. There are two remaining dates to enjoy rooftop yoga: Thursday, September 15th with Jodan Hana and Thursday, September 29th with Bridget Murphy.

Long Grove Apple Fest

The Midwest’s biggest tribute to apple season will return to the historic streets of charming downtown Long Grove when the 31st annual Apple Fest takes place September 23rd through 25th.  The 2022 edition features countless apple delicacies, everything from apple wine to apple tempura. In addition, as always, there will be live music stages in multiple areas, family activities, and a classic carnival offering “bushels of fun” for everyone.

beefstake things to do in chicago this september leye
Image Credit: RPM Steak on Tock

6th Annual Beefsteak

Join the Beefsteak tradition on Saturday, October 8

, a meat-centric banquet dating back to mid-19th century New York City. This year’s event – a “”Degustation of RPM Beef”” – features RPM Steak’s collection of boutique, signature and classic butcher cuts. Enjoy steaks from around the world. RPM Wine Director, Richard Hanauer, showcases Russian River Valley Pinots from George Wine Company – one of the country’s greatest and rarest Pinot Noir houses . This event is $195 per person, plus tax (gratuity not included; premium add-ons are additional) and takes place on Saturday, October 8, starting at 12:00 PM.

Honig Wine Dinner

Alongside Honig Vineyard & Winery, Summer House invites you to a night of decadent food and delightful wine on Tuesday, October 4th from 6:00 PM – 9:00 PM. The evening will kick off with welcome wine and appetizers followed by a three-course menu curated by Chef Ben Goodnick. Each course features a globally inspired yet California fresh dish and is perfectly complemented by a Honig wine pairing. The dinner is priced at $120 per person, plus tax (not including gratuity). Purchase tickets on Tock to save your seat!

Featured Image: FARE