Chicago and architecture go together like Hollywood and entertainment. From record-setting steel skyscrapers to Gothic Revival and Prairie style masterpieces, the buildings that make up Chicago’s skyline are some of the most significant structures in the world. At Must Do Travels, we love scouting little-known treasures and underrated activities. However, Chicago architecture tours are world-famous for a reason. If you’re planning a trip to the prettiest city in the Midwest, don’t miss your chance to experience the details of its architecture up close.

So, which buildings should be on your list? While you’re in the Windy City, make time to hop on a boat and tour the downtown’s iconic buildings and bridges from the perspective of the Chicago River. Enjoy unique views of Marina City’s circular parking spots, the Tribune Tower’s ornate peaks, and the gleaming white Wrigley Building. But when you’re done (or if the water’s frozen)? Make some individual stops of your own.

Some Chicago buildings are so historic and unique, and you should really step inside them to get the full experience. Here are a few of our favorite examples of Chicago architecture:

Chicago Cultural Center

78 E Washington St

There’s history behind every brick and beam in this city, but if you want to soak up some artistic detail, spend an afternoon in the Chicago Cultural Center. For a free tourist attraction right across from Millennium Park, this former library is surprisingly quiet, clean, and rich with well-preserved history.

For example, the largest Tiffany glass dome in the world arches over Preston Bradley Hall, casting gorgeous sunlit patterns across the usually-empty marble floor. And if you enter or exit through the Washington Street entrance, you’ll walk past a three-story mosaic and climb a Venetian staircase made of smooth Irish marble.

Palmer House Hilton

17 E Monroe Street

Want to travel back in time to the decadence of the Roaring Twenties? Just duck into the Hilton Hotel on Monroe Street. The lobby alone is one of the most ornate and awe-inspiring spaces in the city, with ceilings dripping in gold chandeliers and covered in hand-painted, Renaissance-style angels.

While you’re there, don’t be afraid to walk around and experience the fixtures, furnishings, and artwork up close. For example, you can explore the first few floors of rooms from the lobby, making it easy to follow in the footsteps of a century’s worth of movers and shakers.

The Dorchester Projects

6916 S. Dorchester Avenue

And now for something a little different: a sustainable home on the South Side. Good architecture anticipates the demands of the future, after all, and this structure is one of the city’s best examples of that. Bringing high-dollar prestige to a neglected neighborhood, this house on Dorchester Avenue is made of discarded materials like fire hoses and fragments of other buildings.

Of course, the strategy is both artistic and political. By turning unused properties and unused materials into a contemporary new South Side structure, designer Theaster Gates used architecture to boost and rebuild a part of Chicago that needed it.

Which buildings are you most excited to explore during your time in Chicago? Whether you’re an architecture buff or you just want cool angles for Instagram, this visit won’t disappoint.