Drinks The Loop & Chicago River
Cindy's
A place for a drink in The Loop & Chicago River, pricey ($$$) and worth about 1.5 hours. Best time to go: Sunset.
Why go
Rooftop bar atop the Chicago Athletic Association with views over Millennium Park and Lake Michigan.
It is one of 9 curated places we feature in The Loop & Chicago River, alongside 3 places to eat, 3 sights and 1 activity. 6 more of our picks sit within about half a mile in a straight line, so it pairs easily with McCormick Tribune Ice Rink and Millennium Park.
- Type
- Drinks · Nightlife
- Neighborhood
- The Loop
- Price
- $$$
- Time needed
- 1.5 hr
- Best time
- Sunset
Nearby
Our closest curated picks, including 6 beyond The Loop & Chicago River. Distances are straight-line, not walking or driving.
- 1McCormick Tribune Ice Rink
Free outdoor rink in Millennium Park next to Cloud Gate, open from mid-November into March; skate rental extra.
Activity · Chicago · 0.1 mi straight-line - 2Millennium Park
Cloud Gate, Crown Fountain and free summer concerts at Pritzker Pavilion.
Sight · Chicago · 0.1 mi straight-line - 3The Walnut Room at Macy's
Marshall Field's 1907 dining room on State Street, where a Great Tree rises through the room each Christmas.
Food · Chicago · 0.2 mi straight-line - 4Art Institute of Chicago
Huge collection including Nighthawks, A Sunday on La Grande Jatte and the Thorne Miniature Rooms.
Sight · Chicago · 0.2 mi straight-line - 5The Berghoff
German restaurant on West Adams Street since 1898, with schnitzel, sauerbraten and its own root beer and lager.
Food · Chicago · 0.2 mi straight-line - 6Christkindlmarket
German-style Christmas market in Daley Plaza since 1996, with wooden stalls, ornaments, bratwurst and Glühwein.
Shopping · Chicago · 0.3 mi straight-line
On these curated routes
Cindy's is a stop on our Chicago New Year's Eve route. Open it to see the full day-by-day plan.
More to do in The Loop & Chicago River
Cindy's is our only drinks pick in The Loop & Chicago River; here is what else we recommend there. See the full The Loop & Chicago River guide.
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Chicago River NYE Fireworks
The city's free midnight show, fired from the river bridges between Orleans Street and Columbus Drive; held in 2024 and 2025.
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Art on the Mart
Large-scale projections across the Merchandise Mart's river facade; on Dec 31 it becomes the countdown clock for the fireworks.
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Navy Pier New Year's Eve Fireworks
Free midnight fireworks over Lake Michigan, visible from inside and outside along the mile-long pier; held in 2024 and 2025.
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Chicago Riverwalk
A 1.25-mile promenade along the main branch of the river, lined with cafes, boat docks and the city's architecture.
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Gibsons Bar & Steakhouse
Gold Coast steakhouse open since 1989, known for huge cuts, martinis and a packed bar on big nights.
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Shaw's Crab House
River North seafood house since 1984, with an oyster bar and a formal dining room for crab legs and lobster.
When to go: weather by month, based on Chicago
Our climate figures for The Loop & Chicago River come from nearby Chicago. Average daily highs in Chicago run from 32°F in January to 77°F in July; May is usually the wettest month. For Cindy's itself, we suggest: Sunset.
Modelled monthly averages for Chicago from NASA POWER, not a forecast. Chicago weather by month (covers The Loop & Chicago River).
Getting there
Map links open a live search for Cindy's, so hours and directions come straight from the map app.
- Coordinates
- 41.88189, -87.62522
- Destination
- The Loop & Chicago River, Illinois
Cindy's: quick answers
How much time do you need at Cindy's?
Plan on about 1.5 hours at Cindy's. That is our curated estimate for a typical visit; groups that linger will want more.
When is the best time to visit Cindy's?
Our pick: Sunset. Insider tip: NYE is ticketed; on a normal night go just before sunset for the park and lake views.
Which TripsCircle routes include Cindy's?
Cindy's appears on Chicago New Year's Eve, a curated route you can open on TripsCircle and plan with your group.
Add Cindy's to your crew's plan
Save it to a shared TripsCircle itinerary, settle the timing with a quick poll, and split the costs with everyone going to The Loop & Chicago River.
Plan The Loop & Chicago River
- The Loop & Chicago River travel guide 9 places
- Chicago weather (covers The Loop & Chicago River) weather by month
Lists & regions
Also in The Loop & Chicago River
- Chicago Cut Steakhouse Food
- Art on the Mart Sight
- Chicago Riverwalk Activity
- The Langham, Chicago Stay
Curated recommendation, not live listing data. Confirm hours, prices, bookings and access before you go.

