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Top picks in Chicago

Historical sites with views

Standing before a piece of the past while taking in the expanse of the horizon provides a rare moment of perspective.

Based on 628 Opinions
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Updated May 2026
01
DuSable Bridge image 1
DuSable Bridge image 2
DuSable Bridge image 3
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Bascule bridge spans a busy river channel, offering stunning views of the city skyline and riverwalk. The atmosphere is lively and bustling, with street performers adding a vibrant energy. It serves as a key connection between city parts and a popular spot for walking and photography.

A landmark bridge connects the Magnificent Mile to the Loop, showcasing Chicago's rich architectural heritage with elegant design and stunning river views. A monument honors Jean-Baptiste Pointe DuSable, highlighting his legacy as the city's founder.

The DuSable Bridge offers magnificent views of the Chicago River and the surrounding skyline. It provides a great spot for scenic photos and feeling immersed in the heart of the city.

People are saying

"The views from the bridge are stunning, especially of the river and skyline."

"The historical sites offer amazing views of the river and cityscape."

"The views here are amazing, offering a unique look at the city's architecture."

Good to know

1

The DuSable Bridge hosts various events and festivals throughout the year.

2

The bridge is always accessible with no tickets or restrictions.

3

It connects the Magnificent Mile to the Loop, making it a key landmark.

02
Tribune Tower image 1
Historical landmark

Neo-gothic skyscraper stands with historic fragments embedded in its walls, creating a unique facade. Public plaza offers breathtaking views of the city and river, blending history with urban energy. Indoor amenities include a rooftop terrace and pool with sundeck, adding modern comfort to a timeless landmark.

Walls feature fragments of monuments from famous landmarks worldwide, creating a unique architectural story. A public plaza offers views of the river and skyscrapers, enhancing the site's historical presence.

Spectacular views of the city and river stand out, especially from the public plaza and upper levels. The combination of breathtaking architecture and skyscraper vistas creates a memorable sight.

People are saying

"It's amazing how much history these historical sites hold."

"I loved exploring the outdoor space, finding artifacts from around the world."

"I loved the amazing Chicago city views from up high."

Good to know

1

Make sure you use Spot Hero to find parking.

2

The closest parking location is below, where the Museum is on 401 N Lower Michigan Ave.

3

Once you park there, you take an escalator to the floor leading to Michigan and it's not that far from there.

03
Thalia Hall image 1
Live music venue

Historic opera house converted into a modern music venue offers intimate concerts with great acoustics and vintage architecture. Spacious layout includes a balcony and multiple bars, creating a cool atmosphere with excellent views from all angles.

Unbelievably beautiful with historic charm and pleasing acoustics, this concert hall blends cozy ambiance with a rich story and history.

Phenomenal sound and views fill the space with no bad seats. Spacious opera-style seats and the balcony offer great views from all angles.

People are saying

"It's an intimate venue with awesome sound and good acoustics."

"It's a beautiful historical venue with gorgeous architecture."

"The views from the balcony were amazing."

Good to know

1

Parking in the area can be rough; add time for street parking.

2

The coat check costs $5.

3

Food is reasonably priced, with popcorn at $4 and hot dogs at $5.

04
The Old Post Office image 1
Historical landmark

Massive Art Deco building offers a spacious, elegant interior with grand yet purposeful design. Rooftop features a wild garden urban oasis and stunning views of the city and river. Lounge areas provide comfortable seating and extended wifi, creating a peaceful atmosphere despite occasional loud events.

Extensive size and art deco elements highlight the building's historical value. The restored lobby features architectural details that have appeared in major films, showcasing its cultural significance.

Massive rooftop features beautiful gardens and views of Chicago skyscrapers including the back of the Sear's Tower. The terrace and second floor offer amazing views of Downtown Chicago and the Chicago River alongside spaces like a basketball court and a bar.

People are saying

"The historical sites here blend old and new beautifully."

"The renovation blended history with a surprisingly modern, elegant interior."

"The views from the terrace and rooftop are amazing."

Good to know

1

Access to the Old Post Office is through the Van Buren Street side.

2

The food hall offers a variety of dining options for visitors.

3

The venue is suitable for large gatherings and private events.

05
South Shore Cultural Center image 1

Elegant space with historic architecture offers beautiful lake views and a large, comfortable layout. Vibrant yet calm atmosphere includes music, beach access, nature trails, and golf. Setting blends natural beauty with cultural charm.

A beautiful, historic building with incredible architecture inside and out. The space carries a strong sense of historic charm and significance.

Spectacular lake views dominate the scene, visible from every major room and ballroom. The setting offers peaceful water scenery and great views of the city and ocean.

People are saying

"It's a beautiful place with a nice view of the lake."

"The historical sites here are beautiful and ornate."

"The house music was on point and the DJ was killing it."

Good to know

1

Parking is limited and can be challenging on busy event days.

2

The parking lot charges $7 for a full day of parking.

3

Events are often scheduled simultaneously, leading to crowded conditions.

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