The Drag Swap

Two-route food and drink crawl through Chicago's most iconic LGBTQ+ neighborhood. Sample bites and sips from over 20 restaurants, bars, and local businesses along Halsted Street. Choose Route A (noon–3pm) or Route B (3pm–6pm), or grab a discounted two-route ticket to hit them all. 21+ with ID.

Northalsted's luxury wellness showcase brings together the neighborhood's best health, beauty, and self-care businesses for an evening of discovery. Browse interactive booths featuring personalized skin consultations, aerial hammock demos, mobility assessments, and on-site spa services. Each $50 ticket includes champagne, a service sample, three raffle tickets for over $5,000 in prizes, and a participation passport to guide your experience. Light bites and desserts from Silver Fork, plus complimentary beverages from local breweries.

The 12th annual Halloween Pup Crawl turns Northalsted into a trick-or-treat paradise for dogs and their people. Walk the neighborhood from Aldine to Cornelia, collect swag and treats from local vendors, snap photos with Miss Foozie, and cap off the morning with an after-party brunch at the Lark Patio at 2pm. Costumes encouraged—for you and your pup. $5 advance registration includes a tote bag, raffle entry, and pup swag.

The 29th annual Haunted Halsted Halloween Parade is Chicago's most spectacular All Hallows' Eve street party—free to watch, ranked in Fodor's top ten US Halloween celebrations. Hundreds of costumed revelers compete for $4,000 in cash prizes across five categories (Character, Creative, Scary, Youth, and Group), with live performances from the Chicago Full Moon Jam fire performers, Lakeside Pride Marching Band, Windy City Rollers, and more. The parade winds through Northalsted, the city's landmark LGBTQ+ neighborhood, and concludes with an awards celebration that's become a Halloween tradition.