The Rest Is History: Hip Chicago Hotels in Charming Old Buildings

Downtown Chicago boasts many nice hotels, but we especially love the LondonHouse and the Chicago Athletic Association, both located in beautiful buildings reclaimed from other uses

From the cool W Chicago and the relatively recently arrived Virgin Hotel Chicago in the Loop to the storied Drake and ultra-elegant Peninsula along the Magnificent Mile, the heart of Chicago is plentiful in upmarket hotels that offer just enough luxury for a business trip, as well as solid customer reviews and good (or at least reasonable) value for money.

Having scouted a number of nicer hotels in downtown Chicago, Billy is especially keen on a pair that successfully demonstrate how to convert an old building into a new hotel.

Here, then, are the first accommodations you should try to book if you’re looking for something in the four star/upper mid-price range, and you want to stay within walking distance of both the Loop and the Magnificent Mile.

Chicago Athletic Association Hotel

Across from Millennium Park on Michigan Avenue, you’ll find the Chicago Athletic Association Hotel, whose solemn, creaky beauty makes it a refuge from the bustle of street life below and Millennium Park across the street.

Having served as a gentlemen’s indoor sporting club from 1893 to 2007, the building was renovated and reborn in spring 2015 as a 241-room luxury hotel. The Chicago Athletic Association is cleverly unapologetic about its old-fashioned nature, wearing it with pride to attract lovers of nostalgia and eccentricity.

Imagine someone handed The Royal Tenenbaums director Wes Anderson a bunch of scrap pieces from Victorian gentlemen’s clubs and high school gyms and told him to mash them together to make a hotel. The result might be something like the atmosphere you encounter at the Chicago Athletic Association.

Courtesy Chicago Athletic Association Hotel

The drawing room (Cognac not included)

Witness, as you step out of the elevator, the Gothic Revival splendour of the grand, gloomily lit reception area. Luxuriate in the majestic fireplaces, leather seating and beautifully tiled mosaic floors. Once you tire of the Hollywood-slash-Hogwarts “drawing room," proceed the Game Room (which doubles as a bar) and play a round on the indoor bowls court. Even the wooden tokens the hotel supplies to guests to exchange for cups of coffee feel like materials salvaged from an imaginary boarding school.

To add credibility to the whimsy, the dining and drinking outlets are handled by respected local restaurant group Land and Sea Dept., a fact that has generated curiosity and traffic from in-the-know locals since the reopening.

The rooms continue the boyish paradise theme. Masculine fixtures in wood, leather and brass could have been assembled from pieces of an old-timey workout room. Gleaming white-and-black tiled bathrooms mimic the style of a century ago, and the robes are made of sweatshirt material. The minibar is impressively stocked with local beers and spirits, and even coupe cocktail glasses for those who dare attempt a bit of in-room mixology.

Views vary from room to room. Some of the windows face ugly roofs and other windows, which is typical and understandable for a building constructed some 125 years ago. For a decent view, you may need to upgrade your room.

Courtesy Chicago Athletic Association Hotel

Take it from us: In the middle of the night, remember there's that pommel horse at the foot of the bed


There are two broad schools of Chicago visitors: The downtown crowd who swear by the Loop and everything contained therein, and the Magnificent Mile folk who relish the shopping and dining choices arrayed on and around North Michigan Avenue between the Chicago River and Oak Street. To enjoy the best of both worlds, we urge visitors to consider the Wacker Triangle, an area that’s home to no fewer than seven hotels.

Courtesy LondonHouse

At left, the former London Guarantee building, now the LondonHouse by Hilton

On the northern edge of the Loop there’s a triangle formed by East Wacker Drive, East Wacker Place and Michigan Avenue. That’s the Wacker Triangle, and it presents what is arguably the best possible jumping off point for Chicago explorations. Of all the accommodation experiences available within that triangle, we’re especially fond of the new kid on the block, the LondonHouse Hotel. Well, it’s not exactly new – built in the early 1920s, the 22-storey structure was an early Chicago skyscraper. Called the London Guarantee building, it served as an office tower before the redevelopment into a hotel began in 2013.

Today LondonHouse is part of the Curio Collection by Hilton (they’re a grab-bag of four- and five-star Hilton properties that are too idiosyncratic to fit into any of the chain’s other brands; most are older buildings with an established history and local reputation).  

We visited while the hotel was still suffering through some teething pains. Minor irritations were led by a semi-transparent frosted glass bathroom door (hello? A little privacy, please!) and a rather needlessly complicated elevator system that requires entering a floor number into a computer bank and then being assigned an elevator. LondonHouse nonetheless impressed with its sleek lobby, luxurious if somewhat spatially challenged rooms with superbly comfortable beds, Chicago River views and the LH Rooftop bar, already established as a place to be seen. Above all it was the generally high standards of service that will make us eager to book another stay.

Courtesy LondonHouse

The lobby at the LondonHouse

This article was originally published Feb. 6. 2017.

Published Tuesday, September 19th 2017

Header image credit: Courtesy Chicago Athletic Association Hotel



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