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Local picks in the Loop

Hotels with historical sites

Made for those who prefer to sleep within the walls of a building that holds a significant place in local history.

Based on 690 Opinions
+687
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Updated May 2026
01
Staypineapple, An Iconic Hotel, The Loop Chicago image 1
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Historic building blends modern amenities with charming style and comfortable rooms featuring exceptional views. Atmosphere stays fun and welcoming with a calm, chill vibe throughout. Complimentary treats and a friendly bar add to the inviting experience.

Rooms feature very comfortable beds that stand out for quality. Staff members like Marshay provide kind and helpful service. The hotel offers a pet-friendly environment near major shopping and park areas.

The building stands out for its rich history and unique, historical design that blends old charm with modern updates. It retains an old feel through thoughtful restoration and decor.

People are saying

"This hotel's location is great for walking everywhere."

"The beds here are so comfortable and the rooms are clean."

"This historic building is a delightful place to stay."

Good to know

1

Happy hour offers a burger and beer or soda for $10 from 4-6 pm.

2

Every afternoon, enjoy a cookie hour with complimentary beverages.

3

Valet parking is expensive and can be problematic during busy events.

02
Chicago Athletic Association - The Unbound Collection by Hyatt image 1

Venetian-Gothic architecture shapes a stylish hotel with ornate woodwork and intricate carvings. Lively atmosphere fills public game rooms and a rooftop bar with great views of the lake and park. Athletic-themed amenities include basketball, bocce, and yoga, blending historic charm with active recreation.

Rooms combine historic charm with modern comfort, supported by attentive staff who handle situations with care. The hotel offers a central location and a memorable stay experience.

A historic building with a storied history offers a stay in a beautifully preserved and updated setting. The hotel combines rich heritage with attentive staff.

People are saying

"It's a striking historical site with authentic charm and artistic details."

"The rooftop bar has an awesome view of Millennium Park."

"This hotel's stunning design blends old-world charm with modern comfort."

Good to know

1

Happy hour runs daily from 4-6pm with discounted drinks.

2

Expect wedding crowds on weekends due to the hotel's wedding venue status.

3

Reservations are required weeks in advance for dinner at Cindy's Rooftop.

03
University Club of Chicago image 1

Building showcases early 20th century architecture with historic character and beautiful views. Atmosphere blends classy, elegant charm with modern exclusivity, creating a harmonious and inviting setting. Amenities include squash courts, gym, library, and bar, supporting both relaxation and active pursuits.

Early 20th century style blends with elegant simplicity and well-maintained facilities. The hotel includes a sport room with 8 squash courts and a library and bar with great views.

Historic character shines through the stunning architecture and thoughtful design. The library holds a large selection of historical volumes on topics like religion and government.

People are saying

"The views of Lake Michigan from the club are great."

"This historic building is fascinating and stunning."

"I found the hotel staff to be really great."

Good to know

1

The club hosts various events, including weddings and corporate gatherings.

2

Expect high costs for events, with weddings starting around $50,000.

3

Reservations are recommended for dining, especially during peak hours.

04
The Blackstone, Autograph Collection image 1

Historic hotel with classic charm and artistic decor creates an elegant and lively atmosphere. Rooms offer spacious layouts and great views, though noise from hallways and street is noticeable. Fitness center shows signs of wear but remains a notable feature.

Historic architecture and art displays create a unique atmosphere. Staff share the hotel's rich history eagerly, adding to the experience.

Historic architecture and ornate design stand out in the lobby and mezzanine. Staff share details about the building's history and architectural changes, blending rich history with modern updates.

People are saying

"The hotel rooms here are spacious and impeccably clean."

"It's a beautiful historical site with a timeless elegance."

"You get a nice view of Lake Michigan from your room."

Good to know

1

Parking is available at a garage across the street, but no valet service is offered.

2

The hotel charges a nightly resort fee that is not disclosed at check-in.

3

Breakfast and snacks are served Monday through Friday at the hotel restaurant.

05
Pendry Chicago image 1

Historic building with Art Deco design offers spacious rooms featuring city views and luxurious amenities. Lobby and rooftop lounge provide a resort-like atmosphere with music and entertainment. Downtown location brings loud street noise at all hours, affecting room quietness.

Rooms include a legit wet bar. Staff greet guests warmly, creating a welcoming vibe. This hotel serves as a reliable choice for stays in the city.

A historic building with a luxury atmosphere stands out here. Renovations keep the architectural gem feeling alive while offering a resort vibe.

People are saying

"The hotel staff were so friendly and helpful."

"The bar has rare liquors and a delicious cocktail menu."

"This historic building is an architectural gem with amazing art-deco style."

Good to know

1

The Cadillac experience is available only on select days and hours.

2

Escalade service operates on Fridays and Saturdays for rides within a two-mile radius.

3

Happy hour is offered daily at the restaurant.

06
Hampton Inn Majestic Chicago Theatre District image 1

Hotel occupies a beautiful building with high ceilings and a vintage vibe. Rooms are quiet, spacious, and equipped with microwaves and mini fridges. Atmosphere feels friendly and business-oriented, with easy access to nearby restaurants and cafรฉs.

Friendly and courteous staff provide stellar service with hotel and valet teams going above and beyond. The hotel offers high quality, clean accommodations at a reasonable price in a great location.

The building shows historic charm with many original features on its facade. It stands as part of the Majestic Theatre complex, adding to its old character.

People are saying

"The breakfast staff here is incredibly friendly and helpful."

"This hotel's location is great for exploring downtown Chicago."

"It's so easy to explore the city's historical sites from here."

Good to know

1

Breakfast is served from 6 am to 10 am with a variety of options.

2

Check-in before 4 pm incurs a $25 charge.

3

The hotel does not have its own parking lot; valet can take a long time.

07
Hampton Inn Chicago Downtown/N Loop/Michigan Ave image 1

Historic building showcases art deco style and original lobby with high ceilings and wonderful views. Rooms feel spacious and cozy but street noise and HVAC sounds create a loud atmosphere at night. Lobby bar adds a fun social spot amid a busy downtown setting.

Location stands out with walking distance to major attractions like Millennium Park, the Magnificent Mile, and the theater district. The hotel features a spectacular art deco style and staff are consistently friendly and helpful.

A beautiful historic building houses the hotel with an original lobby that reflects its past. The space blends modern amenities with historic details throughout.

People are saying

"The breakfast location is great, right in the city center."

"This hotel's location is unbeatable, right in the city center."

"This place's historical sites are right in the middle of downtown attractions."

Good to know

1

The hotel is conveniently located downtown, within walking distance of major attractions.

2

Breakfast is served until 10am daily.

3

Only one of the three elevators was operational during the weekend.

08
Silversmith Hotel Chicago Downtown image 1

Historic building blends modern comfort with classic design in a quiet atmosphere despite city noise. Spacious rooms feature floor-to-ceiling windows and high-quality amenities. Lobby bar offers a chill vibe with excellent service and drinks.

Centrally located just a block from Millennium Park, the hotel offers easy access to main attractions and is right by the orange line train from the airport. Staff provide fantastic service and the overall experience is consistently wonderful and memorable.

Building shows historic charm with updated interiors reflecting the area's jewelry trade past. Location sits close to landmarks and tours, making it easy to explore local history on foot.

People are saying

"The Hotel staff made my stay feel welcoming and personal."

"I was surprised how quiet it was, even near the metro."

"It's so easy to walk to all the historical sites from here."

Good to know

1

The hotel charges a $30 historic preservation fee at check-in.

2

Happy hour at the bar features discounted drinks and appetizers until 7pm.

3

The bar closes at 10pm, so plan your evening accordingly.

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