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Cindy’s

While we were in Chicago for Christmas, my family and I headed to Cindy’s, the rooftop bar everyone in the city is talking about.

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

It’s located on the roof of the Chicago Athletic Association Hotel, which despite its name is actually an upscale hotel (think the equivalent of NYAC in New York City).

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

While Cindy’s has food, we were a little late in the game to get reservations (you must book early)! So instead we stopped by for a drink (or two…ish).

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy’s has a selection of unique cocktails, and our favorites were the Pillar of Hercules (bruichladdich, manzanilla sherry, Mallorca melon shrub, hibiscus, mint and lemon) and the Aperitivo (cynar, campari and aperol).

While the drinks were delicious, I do have to admit we picked them mostly based on the names. We were headed to Italy the following week, so the Aperitivo seemed appropriate, and the Pillar of Hercules just sounded badass!

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

But the best part about Cindy’s isn’t its drinks, but its outdoor area.

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Yes, the fire pit is awesome.

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

But the views of Millennium Park and Lake Michigan are what make it so special. It’s worth braving the cold to take a peek (and a picture)!

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

After we finished our drinks there was only one thing left to do: head out to the park to take pictures in front of The Bean! Because sometimes it’s fun to be tourists in your home city, no matter how many years you lived there.

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

When Cloud Gate (the actual name for what we all call “The Bean”) was first erected, it seemed like a waste of $23 million dollars (yes – that’s how much it cost)! If you wanted to see the city skyline, why not just turn around (for free)?!

But The Bean has since grown on me. While I wouldn’t necessarily say it’s worth the price tag, since it’s here we may as well have fun taking pictures in its reflection.

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

And for the best pictures, stand between The Bean and Michigan Ave so you can see the entire city skyline reflected in The Bean.

Cindy's Rooftop Restaurant - Chicago travel and dining tips - Wanderlust in the City

We had fun in the park despite the cold (and possibly because of those cocktails)!

To find out more information about Cindy’s, or to make a reservation to eat, click here.

Cheers to you, Chicago (the city, not the new Kardashian-West baby)!

~A

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