Ana Dominguez’s Chicago Staycation

The creator of @TheCitySidewalks escapes winter in Chicago


The City Sidewalks' Ana DominguezChicago-native Ana Dominguez of The City Sidewalks paid us a visit to escape the winter cold on a downtown staycation. Scroll through the gallery below to see how Ana spent a snowy weekend with us and her tips on making the most of your stay!

Processed with VSCO with a6 preset

A glamorous welcome to the Chicago Athletic Association Hotel! Built in the 1890s, this building used to be a historic – and exclusive – men’s club. After the club closed, the building was restored and converted into a boutique hotel in 2015! I can’t wait to check in.

Not sure if I’m in the hotel lobby or Hogwarts! The lobby’s Drawing Room is so cozy and inviting; plus it’s open to the public (something that wasn’t the case historically when the building was a members-only club), so you can come down here just to enjoy it even if you’re not a hotel guest! What a cool spot for local Chicagoans to escape to.

I loved this guest room, hidden right behind the building’s Venetian Gothic facade facing Michigan Avenue and Millennium Park. A great staycation calls for a comfy bed that you never want to get out of and plenty of blankets to keep warm. This wool throw reads “I miss everything about Chicago, except January and February” …and I couldn’t agree more! It’s a hot item for guests looking for souvenirs – luckily you can buy your own blanket onsite at the Madison Hall boutique shop downstairs!

One of my favorite things about staying at Chicago Athletic Association Hotel was that I really didn’t have to leave the building, for anything! Between Shake Shake (did you know they do room service?!), Drawing Room, Cherry Circle Room, Game Room, Milk Room and Cindy’s Rooftop, I had plenty of options for spots to eat, drink, work and play (even to shop at Madison Hall) – without having to face winter outside.

The city of Chicago is notorious for its speakeasies and it only seems fitting that Chicago Athletic Association Hotel has its very own! A coffee shop by day, check out Milk Room Chicago – a small but vibrant bar on the lobby level of the hotel. This hidden watering hole only seats 8 people, so make sure you get a reservation ahead of time if you’re coming to visit. Once you’re in there, get ready to indulge on some of the tastiest drinks in the Midwest – made with rare vintage liquor bought at auction. Make sure to ask about the history of the room to hear the cool story!

Cherry Circle Room transported me to the Mad Men era – it’s so easy to imagine power meetings and three-martini lunches happening in here! This is where breakfast is served to hotel guests (and the public!), with phenomenal brunch, lunch, dinner and cocktail options as well.

Game Room, also open to the public, is a great space to catch up with friends over bites and booze and play games in a low-key environment – foosball, pool, shuffleboard, chess and more are free to play. Did you know they have an indoor bocce ball court too?

Cindy’s Rooftop is like the jewel in the crown of Chicago Athletic Association Hotel. Killer city views, an incredible specialty cocktail and food menu, and plenty of sunlight make this place a great hangout day or night. This rooftop is open year-round thanks to a glass atrium over the space. You can also step out onto the outdoor patio year-round – fire pits in the cooler months are always roaring. Make sure you pay your respects to Cindy herself, who is immortalized on the back wall thanks to the legendary Andy Warhol.

There’s a ton of artistic and cultural details throughout the hotel – from Drawing Room artwork (take a close look at the trophy cases and gallery wall) to the guest rooms! Bibliophiles can grab a book and chair near a fireplace while audiophiles can curl up with a pair of Master & Dynamic headphones checked out from the front desk – there’s a record-listening station with curated tunes right in the library!

I’ve fallen in love with this city all over again thanks to this hotel and all the history that’s tied to it! Really can’t wait to come back soon and get cozy, especially with all these holiday details!

Follow Ana on Instagram at @TheCitySidewalks and visit her blog at

From The Vault

Go Back to Chicago: 1948 Spend Thanksgiving With Us! Bowie Book Signing at the MCA Labor Day in Chicago Over Time Guarding the Emperor For Eternity Fireworks Throughout Chicago History Hello, Fall & Winter: November in Chicago Explore Chicago's Taco Scene