Erika Davis
Summer may be winding down, but Chicago is still buzzing with activity. August and September bring what locals call “shoulder season”—when the crowds ease, the weather turns golden, and some of the city’s most vibrant events unfold. For those working near TAWANI-managed office spaces, it’s the perfect time to enjoy everything downtown Chicago has to offer—right outside your door.
Dining al Fresco
Whether you’re grabbing lunch to-go or lingering by the Riverwalk with friends, August and September are ideal months for outdoor dining. Check out these downtown favorites for picnic-ready bites, dine-in options, and unbeatable views:
- Café Crèmerie (615 N State) for a European vibe, including gelato, macarons, and pizza
- The Goddess and the Baker (33 South Wabash) for grab-and-go treats. Don’t miss their icy-cool specialty drinks to go, such as spicy watermelon lemonade, Thai Iced Tea, and Iced Yuzu Matcha Americano.
- Beatnik On the River (180 N Upper Wacker) channels retro global glamour with eclectic dishes, vibrant decor, and a lush 80-seat patio perched along the Chicago River.
Free Outdoor Fitness Classes Across the City
Chicago offers plenty of ways to stay active outdoors—and many of them are free! Whether you’re near Millennium Park or River North, here are top picks for staying energized.
Millennium Park Summer Workouts
- Click here to see the schedule.
- Saturdays May 17-August 30 (except on July 5)
- 8-11:45 a.m. in Millennium Park
- Series of 45-minute workouts including Pilates, yoga, cardio kickboxing and Zumba
165 W. Superior Lawn Series (Free Coffee Included!)
- Tuesdays, 8 a.m. – Yoga (Yoga Now)
- Thursdays, 9:30 a.m. – Mat Pilates (Motus Fitness)
- Saturdays, 9 a.m. – Yoga (Motus Fitness)
- Attendees get a complimentary coffee from Goddess and the Baker. Just bring a mat and water!
Lakeside Pilates by The Friendwork Collective
- Sunrise classes at 7:30 a.m., Sunset at 6:30 p.m.
- Held at Oak Street Beach Concrete
- View updated class dates and sign-up here
Rise Pilates Club by Olivia Santelli
- Friday mornings from May 30 – Aug. 8,
- 6-7:45 a.m. at Oak Street Beach
- Pilates classes for all levels. Sign up here
Jazzin’ at the Shedd Indoor Series (through August 27th)
For a midweek wind-down, check out Jazzin’ at Shedd Aquarium! These evening events combine live music with aquarium access and skyline views—perfect for a post-work cultural escape.
Wednesdays, 5–10 PM | Shedd Aquarium, 1200 S. DuSable Lake Shore Drive
Live jazz, skyline views, and aquarium access—all indoors. Food and drinks available for purchase.
Millennium Park Events Not to Miss
Nothing says summer in the city like a Millennium Park event! Join in the remaining dates of these festive activities:
- Summer Film Series – Catch the last movie of the season (Pride & Prejudice) on August 19. Gates open at 5 PM, show starts at 6:30 PM.
- Public Art Walking Tours – Explore Chicago’s vibrant art scene on docent-led tours every 1st and 3rd Saturday through October 18.
- Chicago SummerDance: At Grant Park, Taste of Chicago, and neighborhood parks across the city, residents can dance their cares away with the SummerDance series. A packed calendar of events offers something to fit every schedule, and dance genres span the globe.
Work Near the Action
TAWANI Property Management’s commercial spaces—like the beautifully restored Monroe Building on Michigan Avenue—put tenants at the heart of downtown Chicago’s cultural and business life. Whether you’re grabbing a quick lunch, fitting in a morning workout, or staying late for an event, you’re never far from the best of what downtown Chicago offers.
