Bar
Cindy's Rooftop
Cindy's RooftopSome booking links are affiliate links. If you book through them, we may earn a small commission at no extra cost to you. We never let this influence which places we recommend.
Cindy's Rooftop is a stylish bar and restaurant perched atop the historic Chicago Athletic Association hotel on Michigan Avenue. It offers one of the best vantage points in the city, with floor-to-ceiling windows and a spacious outdoor terrace overlooking Millennium Park, the Art Institute, and Lake Michigan. The interior blends vintage charm with modern elegance, featuring a marble bar, cozy seating, and a fireplace. The menu focuses on craft cocktails, local beers, and seasonal American fare, with dishes like oysters, burgers, and shareable plates. The atmosphere is lively yet refined, making it a popular spot for both tourists and locals. At sunset, the views are spectacular as the skyline lights up. Reservations are recommended, especially for prime window seats.
Don't miss
- Panoramic views of Millennium Park and Lake Michigan
- Craft cocktails and seasonal small plates
- Outdoor terrace with fire pits and lounge seating
- Historic setting in a landmark building
- Sunset views over the Chicago skyline
Tickets & tours
Ways to visit Cindy's Rooftop
You can visit on your own (No cover charge; pay for food and drinks. Reservations recommended). A tour adds transport and a guide, or combines nearby sights into one day.
Cheapest way inEmbers of the Windy City: Chilling Chicago Ghost Tours4.4★ · 122 travelers~1 hourFree cancellationFrom$26 per personSee dates →
Most bookedChicago Architecture River Cruise4.8★ · 16,571 travelers1-2 hoursFree cancellationFrom$39 per personSee dates →
Top ratedOriginal Chicago Architecture Interiors Tour: Dazzling Interiors5★ · 1,725 travelers~2 hoursFree cancellationFrom$35 per personSee dates →Getting there
Know before you go
- Reservations are strongly recommended, especially on weekends and during summer.
- Dress code is smart casual; no athletic wear or flip-flops.
- The outdoor terrace closes in inclement weather; check forecast.
- Photography is welcome, but avoid using flash at night.
A bit of history
The Chicago Athletic Association building opened in 1893 as a private social club for athletes and businessmen. It was converted into a hotel in 2015, with Cindy's Rooftop named after the building's original architect, Henry Ives Cobb's daughter.
Common questions
Is there a minimum spend?
No minimum, but reservations for prime tables may have a food/drink minimum.
Can I bring children?
Yes, it's family-friendly until late evening; after 10 PM it's 21+.
Do I need a reservation?
Highly recommended, especially for sunset and weekends.
Is there a dress code?
Smart casual; no gym wear, swimwear, or offensive attire.
What are the hours?
Typically open from late morning to late night; check official site for current hours.
Is there parking?
Street parking and nearby garages; valet available at the hotel.
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