“Totally new to the event this year,” Rogers said of the 1917 building. “This historic department store building was repositioned as new offices with an enormous rooftop amenity.” Visitors will be able to walk out on that rooftop, which features a bar, fireplace, lounge, and garden. You’ll also see a mural, which is a tribute to its former tenant, the Boston Co. department store.

Open Saturday, October, 19, from 10 a.m. to 5 p.m. and Sunday, October 20, from 10 a.m. to 5 p.m.

This address is a two-fer: you’ll have access to the Central Standard Building and Wintrust’s Grand Banking Hall. A mix of neoclassical and Gothic Revival architecture with Art Deco influences, the Central Standard Building is directly across from the Federal Reserve Bank of Chicago. It is also worth noting that in 1883, this is the site where the United States was divided into time zones in what was the former Grand Pacific Hotel. At OHC you’ll be able to see Grand Banking Hall and the expansive basement vaults.

Open Saturday, October, 19, from 10 a.m. to 5 p.m. and Sunday, October 20, from 10 a.m. to 5 p.m.

“An Art Deco tower at Michigan and Wacker,” Rogers said. “We listed the building for its fourth-floor amenities space. Visitors can also go to Eastlake Studio Architecture firm.” People like Frank Lloyd Wright, Carl Sandburg, and William Wrigley would once frequent the building’s Tavern Club,

Open Saturday, October, 19, from 10 a.m. to 5 p.m. and Sunday, October 20, from 10 a.m. to 5 p.m.

Headquarters for OHC, the Chicago Architecture Center will offer free access to visitors during the weekend. Head inside the nonprofit’s doors to find the Chicago City Model Experience and the Building Tall exhibit with large-scale models of notable skyscrapers, and more.

Open Saturday, October, 19, from 10 a.m. to 5 p.m. and Sunday, October 20, 10 a.m. to 5 p.m.

Visitors to this once-vacant Art Deco gem will have access to the historic building’s restored and modernized lobby. The building, which is currently undergoing a $600 million adaptive reuse project, was built in 1921 and is set to become 2.8 million square feet of office space for companies like Walgreens and Uber.

Open Saturday, October, 19, from 10 a.m. to 5 p.m.

In this new residential tower designed by Hartshorne Plunkard Architecture, visitors will get a chance to see its four-story winter garden, which boasts an indoor infinity pool and balcony overlooking Grant Park. This is also the first building in Chicago to receive WELL Certification for healthy living.

Open Saturday, October, 19, from 10 a.m. to 5 p.m. and Sunday, October 20, from 10 a.m. to 5 p.m.

Rogers called this space, “very idiosyncratic and a lot of fun.” This 1883 warehouse was formerly owned by Chicago architect Harry Weese and is now the studio where Ross Barney Architects designed the Chicago Riverwalk and McDonald’s Chicago flagship store. Visitors will get to see 3D models, building fragments, and other exhibits related to past projects.

Open Saturday, October, 19, from noon to 4 p.m. and Sunday, October 20, from noon to 4 p.m.

If you are headed to OHC for the views, this might be the place for you. “This is a really exciting site and very popular,” Rogers said. “It’s a private club on top of the Old Republic Building on Michigan Avenue. It has an outdoor terrace with a good view and an old-world, homey and comfortable atmosphere.” The old world description is quite literal—the pub was deconstructed and brought over from the Sussex region of England.

Open Saturday, October, 19, from 10 a.m. to 4 p.m. and Sunday, October 20, from 10 a.m. to 4 p.m.

This 176-unit apartment building in the Loop will be available to CAC members only. “They will be showing model units and letting members go to the rooftop amenity level and lounge. It’s a treat to see it.” The building opened as offices in 1925 and much of it was preserved in this recent adaptive reuse project.

Open Saturday, October, 19, from 10 a.m. to 4 p.m. and Sunday, October 20, from 11 a.m. to 3 p.m. (members only)