What to Eat, Drink, See & Do in September

Kayak Chicago

It’s hard to believe that it’s already September… but it’s here! Don’t worry though, there are plenty of warm sunny days still ahead for you to take advantage of! From this year's NEW Culinary Guide launch to charity events and outdoor activities, there is plenty to do before that first evil cold front hits. Check out our list of the best things to do in September 2022.. 

Buy the NEW 2022/2023 Dine-It-4ward Culinary Guide

Need a way to tour Chicago’s food scene without breaking the bank? Well, we have the answer to your prayers! Our NEW 2022/2023 Culinary Guide features BOGO offers on carryout and dine-in dishes at 90+ Chicago restaurants, bakeries, and more! It will help you get the best bang for your buck while you support local restaurants, small businesses and charitable organizations. It doesn’t get better than that!

Drink up at WineRival  {September 22}

This one’s for all the oenophiles in your life (that’s a “connoisseur of wines” for the uninitiated) 🍷 After a two-year hiatus, WineRival is back and better than ever! Spend your evening walking around Venue West as you try from more than 300 luxury brand wines and spirits. While you’re there, you also have to check out the blind wine tasting competition open to anyone who thinks they can win. Cheers to a fun night!

via Rooftop Cinema

Visit the Rooftop Cinema for their Fall Movie Line-Up

Spend one of your last warm weather evenings at the Rooftop Cinema Club in Fulton Market. Watch iconic movies as you lounge in comfy deck chairs and munch on food and drinks from the Emily Hotel (we strongly recommend the nachos) with views of the city in the background. Upcoming movies include Legally Blonde, Black Panther, Hocus Pocus and more! This was so popular over the summer that they’ve extended into spooky season and we can’t wait to make the most of it!

Take in all the fun of Chicago Gourmet {September 22-25}

Want a way to try some of Chicago’s best gourmet food, all in one weekend? Check out the many events of Chicago Gourmet! Starting Thursday, September 22, try everything from gourmet tacos and burgers to some of the world's finest wines and spirits. The event will commence with a “Tacos & Tequila” event, hosted by one of Chicago’s favorite chefs, Rick Bayless and really hits it’s stride with the Grand Cru all-day event on Saturday at the Harris Theater Rooftop. Don’t miss out on a single bit!

Take Advantage of Epic Thursdays at EPIC Burger {Every Thursday in September}

Epic Burger is celebrating their 14th anniversary the RIGHT way - with deals all September long! Every Thursday, you can get one of their delicious sandwiches like the Honey Hot Chicken or the Garden Veggie for only $5! The sandwich special changes every week so you can come back again and again. To make it even better, they also have $2 fries on Thursdays PLUS a special Birthday Cake Shake available all month 🍔 Head to one of their spots to get yours!

Treatyoself to the Prime & Provisions Wagyu Card 

This special menu is a MUST try for steak-lovers in Chicago 😍 Prime & Provisions is now sourcing and serving three different cuts of Japanese Wagyu beef including Omi Princess, Sanuki Olive-Fed Beef and Hokkaido, which all have an A5 marbling score, the highest score on the Japanese scale. You can order a tasting of one of the cuts of steak, or indulge in a flight of all three cuts. This steak is literally the best of the absolute best, and even though the portion looks small, it’s so rich in flavor that you can order it to share with your table and still be full 🥩

Support The Simple Good “City of Big Dreams” Event at Chop Shop {September 29}

For their 10th anniversary, The Simple Good, a Chicago non-profit that focuses on empowering youth through mindfulness and social emotional learning (SEL) based art programming, is hosting their City of Big Dreams Fundraiser. Spend the evening of September 29 at an immersive arts experience as you view live art and a curated gallery, join in on a silent auction, listen to an unforgettable DJ, all while sipping on specialty cocktails. There’s no better way to give back to your community!

Kayak the Chicago River 

Get views of the city like never before with Kayak Chicago. Grab your friends, hop in a kayak and experience one of Chicago’s most unique ways to view the city and the Chicago River. With architectural tours, a late night paddle filled with all the city lights glistening off the river and more, this is an experience you’ll never forget!

By Madison Freeman | Special Correspondent