Things To Do
Restaurant Reservations
Chicago has an incredible dining scene and the most popular spots book up fast, especially on weekends. We'd strongly recommend making reservations before you arrive. Apps like Resy, OpenTable, and Tock make it easy — just don't wait too long!
Local Coffee Recommendations
Fairgrounds Coffee & Tea — Right inside the CAA, so it truly couldn't be more convenient. A great first stop before heading out to explore, with a wide range of craft coffees, teas, and specialty drinks on offer. Intelligentsia Coffee — A beloved Chicago institution and one of the best specialty coffee roasters in the city, just a short walk from the hotel on Randolph Street. Goddess and the Baker — A few steps away on Wabash, this spot doubles as a great breakfast or brunch destination alongside excellent coffee. Open seven days a week and very easy to walk to. Hero Coffee and Bagel Bar — A short walk south on Jackson, Hero is a local favorite known for outstanding bagels alongside great coffee. Perfect for a grab-and-go morning before a day of sightseeing.
The Art Institute of Chicago
Right next door to the CAA, the Art Institute is one of those places that's easy to pop into for an hour or spend an entire day. World-class collection, iconic building, and you really can't get much closer. A great option if you have some time to spare over the weekend.
Cindy's Rooftop
Nestled under a glass atrium on the 13th floor of the Chicago Athletic Association hotel, Cindy's is just an elevator ride away for most of you. Expect sweeping views of Millennium Park, the ever-changing blues of Lake Michigan, and the city skyline beyond. It's one of our favorite spots to bring visitors to Chicago!
Millennium Park
Millennium Park is one of Chicago's most iconic spots and it's right outside the hotel door. Visit the Bean, explore Crown Fountain, and wander the landscaped gardens. It's the park you'll see from the hotel windows all weekend, and well worth a closer look on foot.
Chicago Riverwalk
The Riverwalk runs along the Chicago River right through downtown and is a wonderful way to see the city on foot. Stroll along the water, take in the architecture towering above, and stop at one of the bars or restaurants along the way. Most spots are seasonal, so it's worth checking ahead — but the walk itself is great any time.
Lincoln Park Zoo
A little further north but absolutely worth the trip, Lincoln Park Zoo is a gem right in the heart of the city. Packed with wonderful exhibits and completely free to visit, it's a great way to spend a morning or afternoon and a reminder of why we love this city so much.