The Chicago Guide
Fresh off the heels of our Chicago goop pop, we can’t seem to shake the feeling that Chi town is our spirit city. In the two weeks we were lucky to call the Waldorf Astoria our home-away-from home, we’ve explored countless boutiques, bars, bakeries, and eateries, taking note of the ones that made our hearts skip a beat along the way. And while some may still see Chicago as the Second City, as evidenced by the deep list of restaurants we’ve amassed, the ever-expanding food scene is second to none.
Chicago Athletic Association Hotel12 S. Michigan Ave., The Loop | 844.312.2221
Over a century ago, this Michigan Avenue landmark served as home base of the Chicago Athletic Association. The building had been vacant since 1997, so it was a pretty big deal when design firm Roman and Williams stepped in to re-imagine the massive building as a slick 241-room hotel. Sport is still a prominent theme here, as evidenced by a tricked out game room and walls of museum quality athletic memorabilia. And while the stained glass windows, grand ballroom, and general clubbiness were left intact, the brass lighting fixtures and leather furniture (both in-room and throughout the hotel) are welcome additions. There's also the sexy rooftop restaurant, Cindy's, a Shake Shack, and three more places to eat and drink. Incidentally, the cozy library at Cindy's is an excellent place to host a private event—it doesn't feel at all like a corporate hotel space, and the views of Lake Michigan are jaw-dropping.
The Langham Chicago330 N. Wabash Ave., Magnificent Mile | 312.923.9988
At barely two years old, this 300+ room hotel takes up the first 13 floors of the Mies van der Rohe-designed IBM building (it’s actually the architect’s final work) but feels more like a boutique operation rather than a corporate-y behemoth. That said, it’s well equipped to host both business and leisure-minded travelers: spacious rooms, a choice of on-site restaurants, and a killer spa. It also offers all the thoughtful extras one might expect from a Langham, including afternoon tea service and a mini fleet of the signature pink taxis.
The Peninsula108 E. Superior St., Magnificent Mile | 312.337.2888
For many years this was GP's all time favorite city hotel. The rooms and suites are spacious and beautifully turned down with great views of central Chicago. It’s definitely more of a traditional hotel with everything you’d expect—a great big pool, a wonderful spa, and perfect service.
Soho House Chicago113 N. Green St., West Loop | 312.521.8000
Scoring a membership here is like hitting the Soho House jackpot: There’s a rooftop pool, a killer house restaurant (and a separate white-tablecloth option), Cowshed spa, tricked-out gym with boxing ring, and a 40-room hotel. Including the two public restaurants on the ground floor (Chicken Shop and Pizza East), this is the largest space on the roster. And while it’s been a long time coming (nine years since Nick Jones first set his sights on Chi town), this outpost looks and feels like it fits right in with its cool West Loop surroundings.
Waldorf Astoria Chicago11 E. Walton St., Gold Coast | 312.646.1300
The Waldorf’s massive, elegantly appointed guestrooms—a good portion of which have working fireplaces—are just one of the many reasons why we chose it as our home away from home during the Chicago goop pop (it actually used to be the Elysian, another goop fave). Here, a heated porte-cochère (a godsend during those brutal Midwestern winters) gives you the sense that comfort is taken very seriously before you even step through the doors. Balsan, the on-site bistro, has a solid selection of classic American fare (burgers, salads, and super fresh oysters), so leaving the grounds for a great market-driven meal isn’t a necessity.
Freehand Chicago19 E. Ohio St., River North | 312.940.3699
The second Freehand outpost (the first is in Miami) refers to itself as a hotel-slash-hostel, meaning they've made their beautifully appointed shared and private rooms exceptionally tourist and wallet-friendly. Designed by goop favorites Roman & Williams, it's all understated, eclectic comfort through and through: Public areas are set up like living rooms with a pool, cafe, and bar right on property—that's all in addition to a 24/7 communal kitchen.
Longman & Eagle2657 N. Kedzie Ave., Logan Square | 773.276.7110
This is easily the hippest hotel in town, and at only 6 rooms strong, it’s also the tiniest. But what it lacks in size and fancy amenities (there’s no concierge or room service) it totally makes up for in fun and food. For one thing, the open-plan rooms are exceptionally designed (terrariums, freestanding tubs, custom furniture handmade by the owners) with hilarious little details like vintage Fisher Price tape decks and PBR in the mini fridge. The guesthouse sits directly on top of its namesake Michelin star restaurant, which means that wild boar sloppy joes and over 150 varieties of whiskey are literally steps away. Understandably evenings tend to get rowdy, so keep that in mind when booking.
Hotel Palomar505 N. State St., River North | 877.731.0505
Located in the hub of the art and design district, the Palomar is a modern, pet-friendly, eco-friendly, organic-oriented hotel that caters to active city visitors. The hotel organizes fun group exercise classes that include guided runs along Lake Michigan and ballet barre workouts on the hotel’s sundeck. Other novel perks are the in-room massages and yoga sessions. And, if you travel with your pets, you’ll be pleased with all the amenities that they’ll enjoy. Sable, one of the best bars around, is just down the stairs.
The James55 E. Ontario, Magnificent Mile | 312.337.1000
Simply put, this downtown hotel's proximity to some of the city's best sites can't be beat: Millennium Park, The Museum of Contemporary Art, and Michigan Avenue are all just steps away. It offers all the comforts and amenities you'd need (bike rentals, a great gym), in addition to a sleek, modern design that makes it nothing short of a city oasis.