The 6 Best Historic Hotels in Chicago

The Publishing House

Windy Chicago is renowned for its striking architecture where neo-Gothic buildings lie next to sleek glass and steel towers. This mix of the old and new makes for a particularly impressive skyline. However, the grandeur of the city's historic buildings is something that must be admired, which is why our hotel experts recommend booking a historic hotel. The best historic hotels in Chicago range from all-out luxury stays to craftily reimagined boutiques. Our collection has a range of properties from great value hotels to truly decadent choices. With something for everyone, why not browse through our guide to start planning your next break?

For city style

The Blackstone

  • Once the tallest building in the city when it opened The Blackstone is a historic grand dame updated to the 21st Century. Expect wood-panelling, chandeliers and double-height ceilings combining with buzzing restaurants, an extensive art collection and quirky modern furniture. Having hosted many presidents and celebrities, you can be sure of a very luxurious stay.

For luxury

LondonHouse

  • LondonHouse is a luxury hotel, in downtown Chicago, on Michigan Avenue; one of the city's original high-rises, which dates back to the 1920s. Pick this property for the indulgent rooms with floor-to-ceiling windows and marble bathrooms. With a chic rooftop bar and superb seafood and steak restaurant — this is a spoiling choice.
  • Chicago Athletic Association was a Gentleman's club in the early 1800s which now opens its Venetian Gothic doors to all. Boasting large, retro rooms with Millennium Park views. Cherry Circle Room catches the essence of its former dining glory while the rooftop bar completes the picture.

For great value

Staypineapple Chicago

  • Set in a grand building dating back to 1895, the Staypineapple Chicago offers a fun and youthful stay in a prime downtown location. Iron filigree staircases and exquisite tiled floors remain but the rooms are whitewashed and modern. Complete with a locally popular restaurant and with rooms starting at below $100 — this is a very alluring choice.

For a boutique

The Robey

  • The Robey is a chic modern boutique hotel set in a striking art-deco building dating back to 1929, in Wicker Park. Pick this property for the chic whitewashed rooms (many of which have epic city views) and the French-American restaurant. However, the real pull is the rooftop pool and bar.
  • The Publishing House is a stylish boutique B&B set in a 110-year-old brick building with a literature theme. Complete with a heaving library and author-themed rooms, this is geek-chic territory. Breakfasts are home-cooked and there is a pantry available for guests all day.

Still not sure where to book?

The 6 Best Historic Hotels in Chicago

Chicago Athletic Association
Chicago Athletic Association

Chicago (The Loop)

Gentleman's club in the early 1800s now opens its Venetian Gothic doors to business travellers, leisure seekers and city slickers. Large, retro rooms boasting Millennium Park views. Cherry Circle Room catches the essence of its former dining purpose. Remember the bar up on Cindy's Roof Top Terrace.

  • Sights nearby - Millennium Park is in close proximity to the hotel.
  • Restaurant -
  • Views -
  • Lively
from $190 for 1 room, 1 night including taxes & fees
Check availability on Expedia Check availability on LateRooms
The Robey
The Robey

Chicago (Wicker Park)

Situated in Chicago's Wicker Park, The Robey is set in the art-deco former Northwest Tower building and provides boutique, upmarket accommodation. Expect fresh and contemporary design. Café Robey serves up French-American fusion cuisine and cocktails are served on the rooftop lounge. Superb!

  • City Style - Chic accommodation in a historic building evoking memories of bygone years
  • Local exploring - Make the most out of The Robey's location to truly get to know Chicago
  • Sights nearby - Head over to Wrigley Field and enjoy a Cubs game or give the Lioncoln Park Zoo a visit
  • Views - For great views book either a Corner Suite or Panorama Suite
from $135 for 1 room, 1 night including taxes & fees
Check availability on Expedia Check availability on LateRooms
The Publishing House
The Publishing House

Chicago (West Loop)

A boutique B&B offering hip design in the trendy West Loop. Featuring a heaving library and author-themed rooms with books to match. A home-cooked breakfast feast is provided for each guest and there's a round-the-clock pantry. A charming and central base to explore the city from.

  • Local markets - Check out Randolph Street Market, the West Loop’s monthly vintage bonanza. Its food-focused rival is Chicago French Market
  • Hideaway - With plenty of books to choose from in the hotel library, curl up in one of the reading nooks
  • Restaurant - Complimentary breakfast
  • Views - Stunning city views
from $225 for 1 room, 1 night including taxes & fees
Check availability on Expedia Check availability on LateRooms
LondonHouse
LondonHouse

Chicago (The Loop)

A luxury hotel, in downtown Chicago, on Michigan Avenue. Rooms are modern and spacious with marble showers and floor-to-ceiling windows facing the Chicago River. Enjoy a handcrafted cocktail on the sophisticated rooftop bar and delicious seafood and steaks at the restaurant. A spoiling central stay.

  • City Style - With a cool rooftop bar and its location right on Michigan Avenue, the hotel is the perfect Chicago city break spot
  • Families - There is a children’s menu for afternoon tea and the hotel is near many kid-friendly tourist attractions
  • Great walks - Walk to Millenium Park and explore the sights
  • Restaurant -
from $172 for 1 room, 1 night including taxes & fees
Check availability on Expedia Check availability on LateRooms
The Blackstone
The Blackstone

Chicago (The Loop)

Historic grand-dame updated for the 21st-century. Built in the Beaux-Art era, this city-centre luxury hotel is the epitome of boutique glamour. Wood-panelling, chandeliers & double-height ceilings combine with buzzing restaurants, extensive art collection & quirky modern furniture to great effect.

  • City Style - A Chicago institution dripping in history which feels cool, chic and on the pulse
  • Great walks - Grant Park is literally on the doorstep. Explore Millenium Park, world-famous Cloud Atlas and Buckingham Fountain
  • Views - Many rooms have views of Lake Michigan and Grant Park
  • Restaurant -
from $187 for 1 room, 1 night including taxes & fees
Check availability on Expedia Check availability on LateRooms
Staypineapple Chicago
Staypineapple Chicago

Chicago (The Loop)

Fun and great-value luxury hotel for those who don't take themselves too seriously. Iron filigree staircases, endless ceilings and exquisite tiled floors combine with contemporary style in pineapple-themed rooms; expect pet-friendly touches & fluffy duvets. The superb restaurant is a city favourite.

  • Value chic - Entry-category rooms are incredible value; the great location, historic building, fun vibe & excellent dining come at a steal
  • Local exploring - Everything you want from central Chicago is here; Lake Michigan, Millenium Park, designer shops, restaurants and sites
  • Great walks - Stretch your legs; it's a very short walk to Millenium Park - home to famous Cloud Gate - and the shores of the lake
  • Views - For views of Millenium Park and Michigan Lake you'll need to book the Millenium Park View Suite
from $110 for 1 room, 1 night including taxes & fees
Check availability on Expedia Check availability on LateRooms
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Written by Katie Harris

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