It’s hard to believe a new month has arrived! August brings with it plenty of exciting opportunities to explore Chicago.
Whether you’re seeking hidden gems, new restaurants, or outdoor experiences, Secret Chicago has everything you need. Check out this list of the best things to do in Chicago this August, and start planning your month!
Lollapalooza 2026 turns Grant Park into a four-day music takeover — here’s what to know. One of the biggest ways to “Attend Lolla” this year is by heading to Lollapalooza 2026, now underway in Grant Park, Chicago. The festival features headliners including Lorde, Charli XCX, Olivia Dean and more; the post covers headliners, brand activations, street closures, and transit updates including Metra and CTA service and fares.
If you need a quick break from the heat, swing by Dunkin’s “Refresherland” at Lollapalooza 2026. Dunkin’ has declared it a Pink Summer—and this immersive, high-energy oasis lets festivalgoers cool down, recharge, and sip on the newest pink drinks all weekend long, including the Pink Pineapple Lemonade and Double Strawberry Daydream Refresher.
Five days of Ferris wheels, monster trucks, live music, and livestock competitions in Grayslake. If you’re building out your festival calendar beyond Lolla, the 97th Lake County Fair returns for five days in Grayslake with rides, monster trucks, Motocross, a demolition derby, Pro Bull Riding, 4‑H livestock shows, and a full live-music lineup. The festivities kick off with a Demolition Derby at 6:00 PM on Wednesday, July 29, 2026.
Sample Chicago’s iconic Italian beef and vote for the best! If you’re planning to attend Lolla but want to add another classic Chicago festival to your weekend, Jefferson Park’s longtime Jeff Fest is rebranding as Italian Beef Fest, taking over Jefferson Memorial Park from Friday, July 31 to Sunday, August 2, 2026. The three-day festival features Italian beef vendors (including Byron’s Hot Dogs, Bust Outs, and Frannie’s Beef), two stages of live music, craft vendors, a kids zone, and a fan vote for best Italian beef.
Grab $15 passes for a two-day wellness festival with yoga, spa treatments, and complimentary smoothies. Need a pre- or post-festival reset? A two-day Summer Wellness Weekend takes place August 7–8 at Guinness Open Gate Brewery in Fulton Market, featuring group yoga (mats provided), spa experiences, complimentary Pure Green smoothies and wellness shots, plus 20% off brunch.
Explore 2,100 authentic artifacts and chilling crime-scene recreations at Chicago’s Serial Killer: The Exhibition. If you’re looking to round out your plans beyond the festival crowds, Serial Killer: The Exhibition arrives in Chicago showcasing over 2,100 authentic artifacts across more than 21,500 sq ft, with crime-scene recreations, VR experiences and narratives on 140 serial killers backed by forensic science and criminologists.
The Mahjong Society is hosting a beginner-friendly Mahjong 101 class at Sushi-san – Lincoln Park to teach the fundamentals of American mahjong, from understanding the tiles and rules to confidently playing your first hand
The event includes all necessary materials for Mahjong play, 2.5 hours of instruction, a selection of Sushi-san’s signature dishes such as maki and edamame, and a 2026 Mahjong League Card for you to take home.
Head to The St. Regis Chicago to celebrate Miru during their third annual Yatai festival! This incredible summer event showcases the rich flavors and beloved traditions of Japanese street food. Treat yourself to mouthwatering delights, including premium A5 Wagyu, freshly made handrolls, and classic favorites like Okonomiyaki and Chicken Karaage. Plus, enjoy a thoughtfully curated selection of Japanese beers, wines, Takanome sake, and delightful cocktails infused with Kagoshima green tea.
Explore a summertime selection of wines from Bordeaux and Burgundy, France, led by seasoned experts. You’ll sip refreshing rosés, crisp whites, and bold reds, alongside passed bites and charcuterie, with featured bottles available for retail purchase; banquette seating available, first-come, first-served.
An exclusive, immersive Michelin-star chef dinner inside WNDR Museum—only for Mastercard cardholders. If you’re looking to add a standout culinary moment to your Lolla plans, Chef Norman Fenton of Michelin-starred Cariño hosts an exclusive, one-night immersive dinner at WNDR Museum on Saturday, August 22 from 6:00–9:00 PM, with progressive bites and a seated multi-course meal. Tickets are available only to Mastercard cardholders via Priceless.com.
Don’t miss Chicago’s biggest Asian street festival — tickets start at $14! For a can’t-miss stop while you attend Lolla weekend events around the city, Panda Fest 2026 takes over Grant Park from August 28–30. The three-day event features 300+ Asian food vendors, live music and cultural performances, kawaii merch, giant inflatables, and family-friendly attractions.
A little piece of Paris is hidden beneath Ogilvie Transportation Center. When you need a quick (and delicious) stop downtown, head to this underground, year-round market beneath Ogilvie Transportation Center. Featuring dozens of small independent vendors serving French and local foods—everything from handmade macarons to bite-sized loaves—it’s been a go-to since it was founded in 2009, with weekday and weekend hours for visitors.
Watch 35+ hot air balloons light up Fairview Park during Centralia Balloon Fest. As part of your “Attend Lolla” plans, consider a quick detour to Centralia’s annual Balloon Fest at Fairview Park, featuring about 35 hot-air balloons, evening flights, tethered rides, Balloon Glows, and a Free Family Fun Day — admission and parking are complimentary.
Chicago’s beloved Ann Sather is back in Wicker Park serving its famous cinnamon rolls. If you’re planning to attend Lolla and want a classic Chicago breakfast stop, Ann Sather—the 81-year-old Chicago Swedish restaurant famous for its cinnamon rolls—has reopened a flagship in Wicker Park at 1819 W. Division St., taking over the former Yolk site and continuing to serve breakfast and lunch.
Race iconic F1® tracks in Chicago starting August 14 with 61 full-motion simulators and a rooftop terrace. If you’re looking to add a high-speed activity to your plans, F1® Arcade Chicago opens August 14 in River North, featuring 61 full-motion racing simulators, Chicago-inspired food and cocktails, private event spaces and the brand’s first rooftop terrace. Reservations are open for simulator racing at 1 W. Grand Ave., with special introductory ticket pricing for the first 1,000 guests.
If you’re building out your “Attend Lolla” plans with another must-see Chicago-area set, Chance the Rapper plays Ravinia’s rebuilt Hunter Pavilion on August 8 — tickets from $65. Chance the Rapper will perform at Ravinia Festival’s newly reconstructed Hunter Pavilion on Saturday, August 8, 2026, as part of his Coloring Book Ten Year Anniversary Tour; tickets start at $65. The set will include hits from Coloring Book and Acid Rap plus material from his 2025 album Starline.
Chicago will experience a microscopic partial solar eclipse on August 12, 2026, peaking at 12:28 p.m. local time. A very small partial solar eclipse will be visible over Chicago on August 12, 2026, peaking at 12:28 p.m. local time with a magnitude of 0.010.
A storybook 19th-century town perfect for a weekend trip. If you’re looking to tack on a quick getaway after Lolla, Galena—about three hours northwest of Chicago—is a well-preserved 19th-century town known for its Helluva Half Mile of independent shops, the Ulysses S. Grant Home (tours Wed–Sun), the historic DeSoto House Hotel, and the 8.8-mile Galena River Trail.
