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New Yorkers 1st Choice
Local picks in Chicago

Historical sites with outdoor space

Made for those who prefer to absorb the weight of history while remaining under the open sky.

Based on 825 Opinions
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Updated May 2026
01
Colvin House image 1
Colvin House image 2
Colvin House image 3
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Event venue

Historic mansion blends classic architecture with vintage decor and intimate rooms, including a basement speakeasy. Atmosphere feels bohemian and romantic, lively with music and diverse energy. Outdoor patio offers a warm, inviting space ideal for gatherings and cocktail hours.

Historic charm shines through layered textures and a moody, romantic atmosphere blending speakeasy, library, and mansion vibes. The site honors the neighborhood's rich architectural history with well-maintained spaces and 19th-century jazz influences.

A warm, inviting outdoor patio sets a great scene for cocktail hour with vintage energy. The courtyard works well for ceremonies, and outdoor events like concerts and art fairs happen here too.

People are saying

"The venue's unique character and beautiful spaces made our wedding magical."

"The outdoor seating feels warm, inviting, and full of vintage energy."

"The historic charm and layered textures create a moody, romantic atmosphere."

Good to know

1

Concerts at Colvin House now have an admission fee.

2

Recitals occur every Tuesday, providing a regular event option.

3

Colvin House hosts outdoor concerts and art fairs.

02
National Museum of Puerto Rican Arts & Culture image 1

Museum occupies a stunning 1890s building with authentic Puerto Rican art displayed across two floors. Atmosphere feels tranquil and welcoming, suited for slow roaming and deep appreciation. Grounds include a beautiful garden with natural sounds enhancing cultural experience.

The museum showcases a unique collection of art that tells the story of Puerto Rican history and culture. It offers a deep dive into Puerto Rican heritage through stunning artwork and historical exhibits.

Outdoor areas feature a beautiful park setting with a large mural. Speakers play Coqui sounds, adding a unique and recognizable atmosphere. The grounds complement the experience with thoughtful installations and natural elements.

People are saying

"I thought the museum was a must-see."

"You'll feel the spirit of Puerto Rican heritage and culture here."

"The outdoor space has amazing coqui sounds and a beautiful mural."

Good to know

1

Admission to the museum is free for all visitors.

2

Free parking is available on-site for museum guests.

3

Tickets are required for special events and can be purchased online.

03
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.

Beautiful architecture surrounds the area with an outside wall decorated by fragments of world-famous architectures. Historical bricks and blocks are placed sporadically, and a courtyard near the back hosts a few other businesses.

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.

04
Garfield Park Field House image 1

Building features 1800s architecture, a two-story rotunda, and a gold leaf dome. Atmosphere stays quiet and peaceful, with community classes and an outdoor pool for all ages. Large park area offers city views and easy access by public transit.

Building showcases phenomenal 1800s architecture and retains its historical character well. Offers beautiful city views from the landmark.

An outdoor pool hosts water activities for all ages. The space includes community-centered classes and fitness options. The architectural structure stands out inside and out.

People are saying

"The park is a beautiful place with great views."

"The historical sites here feel like a step back in time."

"The architecture here is phenomenal, a step back in time."

Good to know

1

The field house hosts roller skating nights with free skate rentals available.

2

Parking is available right outside the Garfield Park Field House.

3

The park is conveniently located near the Green Line stop at the conservatory.

05
Epiphany Center for the Arts image 1

Historic church converted into an event venue offers intimate acoustics and rotating art displays. The atmosphere blends inviting neighborhood vibe with diverse live music, including jazz and DJ sets. Outdoor terrace and garden spaces complement the indoor bar and dance floor areas.

A former church restored into a historic venue filled with galleries and alcoves. The space holds deep history and elegance visible in its architecture and design.

Courtyard hosts live music and sick bands creating a lively vibe. Outdoor areas include a large balcony with shade, a grassy space with tables, a fire pit, and a patio perfect for gatherings.

People are saying

"I found the renovated church space really cool and artsy."

"This historic church is beautifully renovated into an art and music venue."

"The outdoor courtyard is beautiful, with a fire pit."

Good to know

1

Happy hour runs from 4-7pm in the main bar with discounted drinks.

2

Free or low-cost events are available all weekend long.

3

Parking is limited; nearby street and garage options are available.

06
Café Brauer image 1

Venue combines historic charm with stunning skyline and pond views through grand windows and outdoor patios. Atmosphere balances relaxing natural surroundings and lively indoor energy without feeling crowded. Space suits events with versatile indoor/outdoor layouts and elegant brick architecture.

Stunning architecture and historic charm define the space. It holds a rich history that stands out clearly.

Outdoor space features a charming patio overlooking a pond with native flowers. The indoor/outdoor layout offers great views and a vibe suited for large-scale entertaining.

People are saying

"The food here is amazing, and they handled every detail with care."

"The outdoor space offers a charming patio with a nice pond view."

"It's a stunning historical site with amazing architecture and charm."

Good to know

1

Café Brauer is a full-service restaurant, not fast food.

2

Reservations are recommended for large groups, especially for events.

3

The venue can be chilly in winter; consider bringing a coat.

07
Pullman Coffee Club image 1

Historic home with beautifully restored interior offers a quiet, community-centered vibe and charming ambiance. Spacious layout includes rooms for chatting or working and a section to watch short movie clips. Outdoor patio adds a pleasant option on nice days.

A coffee shop inside an 1880 historic building offers a rich view of the area's past. Staff share videos and stories about the site's history and the restored kitchen on the grounds.

Patio offers a nice outdoor space on good weather days with plenty of seating both inside and outside. Outdoor areas provide a comfortable spot to enjoy the weather.

People are saying

"The staff at these historical sites are incredibly friendly and knowledgeable."

"This cafe offers a view of the park and historical videos."

"It's nice to have outdoor space when the weather is good."

Good to know

1

Pullman Coffee Club offers interesting programming like presentations and tours.

2

The coffee shop provides a great chance to learn about the history of Pullman.

3

The staff is knowledgeable about the neighborhood and its history.

08
Murphy's Bleachers image 1

Sports bar with historic baseball decor and electric game day energy draws a lively crowd of fans. Indoor and outdoor seating offer bird's-eye views and ample space despite crowds. Atmosphere captures classic ballpark vibe and deep ties to local baseball culture.

Decades of deep history and cultural significance shape the atmosphere here. The place feels like a living tribute to the city's sports passion.

A patio offers a spot to enjoy drinks outdoors during warm evenings. The space blends indoor and outdoor bar vibes for a casual hangout.

People are saying

"You have to grab a beer here before or after a Cubs game."

"I felt like I stepped back in time at this historical site."

"It's the perfect pre- or post-game ritual for Cubs fans."

Good to know

1

Expect long wait times during Cubs games.

2

Reservations are recommended for winter eve dinners.

3

The bar accepts credit cards and mobile payments.

09
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.

Outdoor space includes a beach patio with live music and a public lawn used for events like weddings. Visitors can bring their own food and drinks to enjoy the open-air ambience.

People are saying

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

"The historical sites here are beautiful and ornate."

"The outdoor space is gorgeous, especially on the lakefront."

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.

10
New Sound Cafe image 1
Coffee shop

Space inside a renovated soul record label building features old skool vinyl record theme and bright second-story windows. Atmosphere feels warm and inviting with cozy workspaces and a dedicated kids play area. Spot suits both casual hangouts and focused work sessions.

The space preserves the history of an old record shop and celebrates local gospel heritage. Thoughtful preservation of the site's past creates a welcoming atmosphere.

A nice patio offers a great spot for summer hangouts. The outdoor area includes a back patio and spaces that accommodate kids and private meetings.

People are saying

"This cafe has a gorgeous, bright interior with plenty of seating."

"The historical sites here thoughtfully preserve the old record shop's heritage."

"The outdoor space is a great hangout spot in the summer."

Good to know

1

Parking in the lot connected to the cafe may result in booting your car.

2

Expect longer wait times due to the cafe's recent popularity.

3

There are plenty of laptop outlets available for remote work.

11
Frank and Mary's Tavern image 1

Classic dive bar with a fishing theme and historic charm updated through thoughtful renovations. Atmosphere stays relaxed and cozy, attracting an older crowd who share stories in a lively yet low-key setting. Features include outdoor seating, multiple TVs, and a jukebox system, with music leaning toward pop country and hip-hop rather than punk or metal.

Historic neighborhood bar with recent renovations done carefully. Updates follow guidance from prior owners and longtime regulars.

Outdoor seating offers good sunlight in spring and summer. The patio sees active bartender interactions, including moving customers outside even in rain.

People are saying

"It's a great old neighborhood bar with a cool dive feel."

"It's a great neighborhood bar, a real historical site."

"The patio gets great sunlight in the spring and summer."

Good to know

1

Lunch is served from 11 AM to 2 PM on weekdays.

2

They host a Monday Night Foodball pop-up event.

3

Expect a rotating selection of local cooks at food pop-ups.

12
Pittsfield Cafe image 1

Old diner inside an elegant 1930s building offers a cozy atmosphere with a quiet morning vibe and architectural charm. Seating is ample, including outdoor spots with an amazing view. The setting feels like a calm oasis amid a bustling city.

A historic building with architectural grandeur sets the scene. Seating in an indoor courtyard adds to the old-school vibe and rich history.

Outdoor seating features a cozy patio feel with a terrace facing an interior patio. Tables offer an amazing view of the Pittsfield Building, and pets or service dogs must stay outside.

People are saying

"I found this diner to have delicious, classic American food."

"You have to see the restored vault doors and ornate plaster details."

"The outdoor seating has a beautiful view of the Pittsfield Building."

Good to know

1

They have early bird specials until 11am every day.

2

Credit card payments incur a 3% charge without prior notice.

3

The bathrooms require a key from management for access.

13
Goose Island Taproom image 1

U-shaped bar made from reclaimed local wood creates a communal vibe in a sleek, modern space with indoor and outdoor seating. Atmosphere feels laid-back and playful, attracting people who enjoy quality beer and relaxed socializing. Specialty brews and exclusive offerings add a unique touch to the experience.

Tours include a quick history lesson on brewing and the area's past. Guides share fun anecdotes and detailed knowledge about Bourbon County and local history.

Outdoor seating includes sidewalk tables and spots along the riverwalk. The space looks inviting and suits warmer weather well.

People are saying

"The beer tour guides are knowledgeable and share great stories."

"The historical sites tour guides are so knowledgeable and funny."

"You can sit at the bar, a table, or enjoy the outdoor patio seating."

Good to know

1

The brewery tour costs $15 per person and lasts over an hour.

2

Bingo events are held regularly, providing a fun community experience.

3

Participate in March Madness promotions for a chance to win prizes.

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