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
Food & Drink
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
Enjoy free Chicken Shack Sandwich or Lettuce Wrap at Shake Shack every week
Shake Shack is definitely known for its juicy burgers and creamy shakes, but there is also a delicious option for chicken sandwich fans on the menu. And, for a limited time, customers can enjoy big savings on a Chicken Shack Sandwich or Chicken Shack Lettuce Wrap every week at the popular … [Read more...] about Enjoy free Chicken Shack Sandwich or Lettuce Wrap at Shake Shack every week
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
Cheap Eats Lakeview
Chicago ranks as one of the top foodie towns in the country but sometimes all that flavorful excellence comes at a price. The Lakeview neighborhood is filled with chic and trendy restaurants that can be a little pricey but don't worry. This community also hosts eateries for folks … [Read more...] about Cheap Eats Lakeview
Old Town Chicago Happy Hours
The historic Old Town neighborhood is noted as the birthplace of modern improv but the area's Victorian area structures are also filled with classic neighborhood bars and hangouts. Visit these bars for Happy Hour deals and specials. Deals are subject to changes so check the … [Read more...] about Old Town Chicago Happy Hours
