DjangoCon US 2026 is coming back to Chicago from August 23–28, and we at Caktus couldn’t be more thrilled, not only to be returning as a Silver Sponsor, but also because I (Keanya) have the privilege of chairing the conference once again!
As a Chicago native, welcoming the Django community to my hometown will be a high point of my year. While you’ll be busy soaking in all things Django, connecting with peers, and catching incredible talks during conference week, there’s no reason you can’t experience the city like a local while you’re here. Whether you’re looking for great food, late-summer festivals or places to unwind, here are some top recommendations straight from a born-and-raised Chicagoan.
This is the first in a two-part series of posts leading up to the conference, stay tuned for Part 2, where we’ll dive deep into Chicago’s best-kept hidden gems and unique local experiences!
Classic Chicago Bites
- Tavern-Style Pizza – Deep dish gets all the tourist fame, but thin, square-cut tavern-style is what locals actually eat every week. Check out Lou Malnati’s, which serves up a delicious thin-crust tavern pie alongside their iconic deep dish.
- Italian Beef – Try Mr. Beef on Orleans (the real-life inspiration for The Bear) for an iconic downtown dive experience, or Al’s Beef if you’re willing to venture out for the gold standard.
- Garrett Popcorn Shops – An undeniable Chicago staple. Grab a bag of the famous “Garrett Mix” (a sweet-and-salty combination of cheddar cheese and caramel crisp) for the ultimate conference snack.
- Wax Vinyl Bar & Ramen Shop – One of my personal favorites! If you love two of my favorite things—ramen and vinyl records—this West Town listening bar is a must. Inspired by Japanese jazz kissas, Wax pairs fantastic ramen and craft cocktails with DJs spinning everything from jazz and house to hip-hop and funk on vinyl. It’s the perfect spot to unwind after a day of conference talks.
After-Hours & Group Hangouts
- Electric Shuffle (Loop) – Perfect for group outings after conference talks! This tech-enabled shuffleboard bar serves up custom craft cocktails, tasty bites, and high-tech custom tables that automatically track score so you can focus on the fun.
- Brando’s Speakeasy (Loop) – Looking to blow off some steam after a long day of talks? Head to this vintage cocktail lounge tucked away in the Loop for vintage vibes and late-night, on-demand karaoke.
- Offshore Rooftops – Sitting at the tip of Navy Pier, Offshore holds the record as the world’s largest rooftop venue. It offers panoramic glass windows and unmatched skyline and Lake Michigan views.
- Reggies (South Loop) – A legendary South Side music institution. Featuring a live music venue, a rock-and-roll record store, a classic music joint, and a lively rooftop deck, it’s a staple for music lovers wanting an authentic local vibe.
Events & Entertainment (Late August Specials)
Since DjangoCon is taking place in late August, you’re visiting during peak Chicago summer event season!
- Chicago House Music Festival (Aug 27–30) – Chicago is the birthplace of house music! Overlapping directly with the second half of DjangoCon week, this free festival at Millennium Park features legendary DJs, local icons, and soulful beats right on the lakefront.
- Chicago Video Game Music Fest (Aug 22) – Arriving a day early for the conference? Head over to Beat Kitchen on Saturday night for this live celebration of video game music featuring local artists, live bands, and VGM cover sets.
- Chicago SummerDance Grant Park – One of Chicago’s favorite summer traditions, SummerDance transforms Grant Park into an open-air dance floor with free dance lessons and live music.
Cultural & Art Spots
- Field Museum – Located on the scenic Museum Campus, this world-class natural history museum features ancient Egyptian mummies, stunning gemstone collections, and SUE—the largest and most complete T. rex fossil ever discovered.
- Shedd Aquarium – A staple for marine life enthusiasts right next to the Field Museum, featuring incredible aquatic habitats and a stunning oceanarium looking out over Lake Michigan.
- Harold Washington Library Center – The central hub of the Chicago Public Library system, famous for its massive roof-mounted owl gargoyles. Ride the elevators up to the 9th floor Winter Garden for a stunning, glass-domed architectural sanctuary that’s perfect for quiet reading, remote work, or taking in public art installations throughout the building.
Outdoor & Scenic Views
- Architecture River Cruise – Unanimously agreed by locals and visitors alike as the best tour in the city. Hop on an open-top boat down the Chicago River to learn about the engineering and design behind our world-famous skyline.
- FlyOver Chicago – Located right on Navy Pier, this immersive flying theater attraction uses motion seats, wind, and mist to sweep you across Chicago’s neighborhood culture and skyline.
- The Riverwalk – Walk along the Chicago River for amazing views, outdoor bars, and great people-watching.
Neighborhood Vibes
- Chinatown – Easily accessible via a short ride on the CTA Red Line or a fun Water Taxi trip down the river. Wander through Chinatown Square, sample unbeatable dim sum, sip boba tea, and take in the iconic Nine Dragon Wall.
- Fulton Market District – Once an industrial meatpacking hub, this vibrant West Loop pocket is now Chicago’s premier culinary epicenter, packed with world-class dining, cobblestone corridors, and high-energy rooftop lounges.
- Pilsen – A vibrant neighborhood with incredible street murals, art galleries, and some of the best authentic Mexican food in the city.
- Andersonville – Known for its charming local shops, independent dining, and rich Scandinavian heritage.
Final Tips
- Public Transit – The CTA (L trains and buses) is your best friend. A Ventra card or contactless payment (Apple Pay/credit card) makes getting around seamless.
- Weather Check – Late August in Chicago brings peak summer vibes! Expect warm, sunny days (70s–80s°F) and pleasant evenings along the lake. Pack sunglasses, comfortable walking shoes, and lightweight clothing.
- Hidden Gems – Ask locals! Chicagoans love sharing their favorite neighborhood spots.
DjangoCon US 2026 is going to be an unforgettable week. As both Conference Chair and a proud member of the Caktus team, I can’t wait to welcome you to my hometown! I hope Part 1 of this guide helps you get excited for your trip. If you have extra time before or after the conference, explore beyond downtown,you won’t regret it!
Got any favorite Chicago spots? Drop them in the comments, come say hello during the conference, and stay tuned for Part 2, where we’ll cover Chicago’s Hidden Gems & Unique Experiences!