Things To Do

These are a few of our favorite things...

The City of Chicago requires masks to be worn in indoor spaces, regardless of vaccination status. Remember to bring a mask!

In the Hotel

The Chicago Athletic Association has stellar restaurants. Reservations are strongly recommended and can be made through Resy.

  • Cindy's (Resy) - Rooftop restaurant with spectacular views

  • Cherry Circle Room (Resy) - Old school vibes won this place with classics a James Beard Award for Outstanding Design

  • Shake Shack - Burgers, fries, shakes

  • The Game Room - Eat, drink, and play shuffleboard, bocce, darts, and more!

  • Milk Room (Resy) - A small speakeasy hidden away serving up delicious cocktails

Within a Block or Two

Even a short trip outside of the hotel and you can get to some great places

Millennium Park and The Bean

Also called "Cloud Gate", but nobody calls it that.

Chicago Cultural Center

The Chicago Cultural Center is an 1897 building featuring two magnificent stained-glass domes, including the world's largest stained-glass Tiffany dome. Admission is free. Open daily from 10 AM to 5 PM. More information here.

Restaurants and Bars

  • The Gage (American, $$$) The best Old Fashioned in town.

  • Pizano's Pizza & Pasta (Italian, $$) Get your deep dish here.

  • The Goddess and the Baker (Cafe, $$)

  • Acanto (Italian, $$$) Fantastic Italian food with a great view and a solid wine list.

  • Wildberry Pancakes and Cafe (Brunch, $$) Third date brunch before we went to the Art Institute. Doesn't take reservations, but you can 'get in line' virtually via Yelp.

  • Oasis Cafe (Mediterranean, $) Hidden at the back of a jewelry store, this cafe serves up a great lunch.

  • Nando's Peri-Peri (South African, $$) BBQ with a South African twist.

The Art Institute of Chicago

Nighthawks by Edward Hopper
One of Nick's Favorites

The Banquet by Rene Magritte
One of Nick's Favorites

Paris Street; Rainy Day by Gustave Caillebotte
One of Carolyn's Favorites

The South Garden

One of Carolyn's Favorites

More of Nick's Favorites

Within a Mile

Chicago Architecture Tour

For more than 25 years, the Chicago Architectural Center's expertly trained docent volunteers have led the river cruise, sharing fascinating stories behind more than 50 buildings along the Chicago River. Hear how Chicago grew from a small settlement into one of the world's largest cities in less than 100 years. In just 90 minutes, you'll get the best overview of Chicago’s architecture and its history.

We highly recommend the CAC's tour, as it is the gold standard. Accept no substitutes!

The Riverwalk

Enjoy a 1.25-mile long path from Lake Street to the lake front with art, restaurants, events, and more. Featured on our save-the-dates and also where Nick proposed to Carolyn! chicagoriverwalk.us

Buckingham Fountain

May be drained by November, but still an impressive sight, and the surrounding park is superb.

The Sears (Willis) Tower

It's the Sears tower, RIP department stores.

Restaurants and Bars

  • Gibson's Italia (Italian, $$$) The best Italian steakhouse around.

  • The Dearborn (American, $$) One of Carolyn's favorite spots for lunch, brunch or a solid cocktail.

  • Portillo's (Fast Food, $) Chicago chain where you can get a hot dog "dragged through the garden" (the Chicago Dog) and a shake with a whole slice of cake blended in.

  • Lou Malnati's (better than Giordiano's).

  • Brown Bag Seafood (Woman-owned Healthy Fast Food, ) Carolyn's go-to for a quick and healthy bite.

Within Half an Hour

Lincoln Park Zoo

Museum Campus

  • The Field Museum

  • Soldier Field

  • Adler Planetarium

  • Shedd Aquarium

West Loop & Fulton Street Market

  • The Hoxton

    • Cabra

    • Lazy Bird

Wherever

The Blues Brothers

Imagine going 100 MPH under the L tracks. The movie ends at Daley Plaza, which is blocks from the hotel.

Ferris Bueller's Day Off

Featuring many notable Chicago landmarks, including The Art Institute.