Five unique places to stay in Chicago
The hotel is usually the least exciting part about planning a trip, but it doesn’t have to be. In a place as rich in history as Chicago, you can find amazing places to stay that are unique to the city and make your lodging as memorable as the rest of your visit. Skip the rental car and spend time in the neighborhood around your accommodations for a more authentic experience—Uber makes it easy to get to and from the airport when you need to.
Villa D’Citta With uberX, typically $28-36 from O’Hare International Airport and Midway International Airport.
Villa D’ Citta is not your usual bed and breakfast. This almost 150-year-old greystone is located near Lincoln Park, and inside it’s more Tuscany than Illinois. The Italian-style courtyard, wrought-iron staircases, and sundeck add up to a small oasis from the buzz of activity outside. On top of museums and a zoo, Lincoln Park also houses the restaurant North Pond, where you can get innovative seafood dishes in as natural a setting as you can find in the city. Or you can grab takeout at Sultan’s Market and have a picnic in nearby Oz Park, dedicated to The Wizard of Oz.
Freehand Chicago Typically $30-39 from O’Hare, and $24-30 from Midway.
In recent years, hostels have risen in prestige (if not in price), and more and more cities are boasting affordable yet swanky lodging. Freehand Chicago is one of the newest, in a renovated building from 1927 and featuring the well-appointed Broken Shaker bar and chic-but-cozy lounge and rooms. In River North, it’s near some of the city’s best galleries and restaurants, including the jazz era-inspired French steakhouse, Bavette’s, and the Bohemian House, showcasing Czech and Eastern European cuisine. You can pass your evenings at the Green Door Tavern, or hit up FTW Chicago, a steampunk arcade that hands out actual prizes.
Longman & Eagle Typically $25-32 from O’Hare, $28-36 from Midway.
A couple years back, the popular Longman & Eagle restaurant branched out and got into the hotel game. Now the site of one of Chicago’s best farm-to-table, nose-to-tail brunches is attached to six rooms for travelers looking for a unique vibe. (The rooms are above the sometimes raucous tavern, so it’s ideal if you’re planning for late evenings.) From Logan Square, it’s not far to the inland beach at Humboldt Park or, if it’s too cold for that, there’s always the Bang Bang Pie Shop—which you should head to regardless of the weather, actually.
Wicker Park Inn Typically $28-36 from O’Hare, $26-33 from Midway $26-33.
You can get a more domestic experience in trendy Wicker Park, where the Wicker Park Innoffers an actual three-bedroom apartment (including dining room and kitchen) along with more standard doubles. The quiet residential area adds to illusion of living like a local, while it’s only a short walk to a slough of dive bars like Danny’s Tavern and Estelle’s, as well as The Violet Hour, the cocktail lounge named for T.S. Eliot. Wicker Park is also a great place for events year-round, but in July you can catch indie musicians at the Wicker Park Fest. This is also the neighborhood of tacos: Antique Taco is a standout, as is the Korean taco joint, En Hakkore.
Chicago Athletic Association Hotel Typically $32-41 from O’Hare, $24-30 from Midway.
History and luxury exist side by side all over Chicago, and in the Chicago Athletic Association Hotel, you can get both at the same time. The 1893 building has been converted into a stellar boutique hotel with a gothic exterior, stained glass, and a beach house-inspired rooftop restaurant. Its downtown location gives easy access to Millennium Park and the Art Institute of Chicago, as well as the high-end shopping of the Magnificent Mile. If you’re looking for some lower-key browsing, check out Graham Crackers Comics or Reckless Records.
Claire