Chicago weather may be getting chilly but there are plenty of activities to lend some heat. The second annual Andersonville Autumn Restaurant Week runs from November 1-15, 2026. The two-week event features 13 restaurants serving prix fixe deals. The popular Andersonville … [Read more...] about Food and Drink Deals at Andersonville Autumn Restaurant Week
Food & Drink
Chipotle’s Boorito 2026 scares up $6 entrée on Halloween night
Back in 2000, Chipotle celebrated its very first Boorito giveaway with a burrito-themed costume contest on Halloween night. In the following years, customers who showed up dressed in any costume on Oct. 31 received a discounted entrée. Over the years, the giveaway has evolved with various … [Read more...] about Chipotle’s Boorito 2026 scares up $6 entrée on Halloween night
Shake Shack celebrates Halloween season with 3 free sandwiches in October
Ding-dong! Trick-or-burger! Shake Shack is shaking up the spooky season with three juicy deals for a FREE sandwich in October. The chain’s burgers are made with a custom 100% Angus beef blend, never frozen, no hormones or antibiotics ever, humanely raised and grazed in the U.S. Fans and hungry … [Read more...] about Shake Shack celebrates Halloween season with 3 free sandwiches in October
Ravenswood Costume Crawl
Dive into the joy of the season with a visit to the Ravenswood Costume Crawl, filled with Halloween-themed fun, seasonal goods, treats and drinks on October 28, 2026. This thrill-filled event will transform Ravenswood's Montrose Avenue of shops and restaurants into a spooky space for sipping, … [Read more...] about Ravenswood Costume Crawl
Chicago Free and Cheap Fall Events
After the close of the beloved Summertime Chicago season, the fun continues with a hearty lineup of activities that celebrate the flavors, scents and visions of fall. As the red and gold foliage reflects off the lake, the city vibrates with autumn fests, apple-picking events, Oktoberfest and artisan … [Read more...] about Chicago Free and Cheap Fall Events
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 19 to November 1, 2026. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
Riverwalk Fall Fest
Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 19- October 31, 2026. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along … [Read more...] about Riverwalk Fall Fest
Cheap and Chic: $7 Cocktails at Cache 310
Chicago is filled with bars and lounges that deliver tasty but pricey drinks and cocktails. Patrons at downtown bars can expect to spend $14-$20 for basic mixed drinks but there's a new bar in town that offers style, a charming atmosphere and elevated cocktails for only $7. Inspired by … [Read more...] about Cheap and Chic: $7 Cocktails at Cache 310
Get Free Stuff on Your Birthday
It's your special day so you deserve a gift. Lots of companies offer free stuff for your birthday. In some cases, you will be required to sign up to receive emails, download an app, or sometimes join a dining or other club for free or for a fee in order to receive birthday freebies. All … [Read more...] about Get Free Stuff on Your Birthday
Free Pasta Dishes with Barilla Connection Kitchen Food Truck
Enjoy delicious pasta dishes while making a difference at the Barilla Connection Kitchen Food Truck, which will partner with Meals on Wheels to encourage volunteer sign-ups at the Merchandise Mart on December 6, 2024. Chase the freezing temperatures away with a warm bowl of pasta and consider … [Read more...] about Free Pasta Dishes with Barilla Connection Kitchen Food Truck
Free Time Out Market Fifth Anniversary Party
Join the all-day celebration for five years of food, drinks and events during the Fifth Anniversary Celebration of Time Out Market, on November 16, 2024. Enjoy food and drink specials and live DJs in the West Loop neighborhood. Head to Time Out Market for festivities filled … [Read more...] about Free Time Out Market Fifth Anniversary Party
Andersonville Viking Pub Crawl
The Andersonville neighborhood's historic Swedish roots will be on full display during the sixth annual Viking Pub Crawl down Clark Street on November 17, 2024. Hundreds of revelers will don viking gear and grab a commemorative glass as they visit a dozen bars and restaurants offering specials … [Read more...] about Andersonville Viking Pub Crawl
