You don’t have to go far to have an awesome vacay. Here are the best Hotels, Airbnbs and Bed & Breakfasts for your Chicago staycation.
Hotels
Longman & Eagle
Photo Credit: Longman & Eagle Instagram
L&E is a boutique hotel like none other in the city. This Logan Square lodge adopts the ages-old inn archetype, offering its guests a place to eat, drink and sleep all in one. The creators behind The Eagle pride themselves on providing Chicago’s urban transients a place to lay their head and whet their whistle in this hip and cozy hotel. The first floor of L&E features a grand whiskey-based bar and inviting public space, whereas the second breaks off into six individually and uniquely designed rooms in which overnight visitors can make themselves at home. A pub, hostel and diner rolled into one, this hotel is well worth a relaxing weekend stay.
Chicago Athletic Association
Photo Credit: Chicago Athletic Association Instagram
Though best known for their bars, The Chicago Athletic Association is also home to one of the city’s coolest hotels. With an old-world style and undeniable sportsman theme, this exclusive boarding house is guaranteed to make any Chicago staycation. The CAA’s bluesy vibes and vintage feel are perfect for anyone trying to escape the doldrums of their everyday life. I mean, just look at how comfortable that woman looks in the photo above! Who wouldn’t want that?
The Freehand
Photo Credit: The Freehand Instagram
Located in Chicago’s River North neighborhood, The Freehand is a total celebration of everything midwestern. The buildings early 20th century origins and Art-Deco style are a nice departure from the stuffy style of traditional chain hotels and will make any Chicago staycation-er feel eons away from their regular life. The Freehand offers both shared rooms and private rooms, as well as communal living spaces intended to encourage socialization between guests. With the added bonus of an amazing cocktail bar and cafe in the lobby, The Freehand Chicago is your one-stop-shop for an amazing vacay in the city.
Hotel Lincoln
Photo Credit: Hotel Lincoln Instagram
A Joie de Vivre production, Hotel Lincoln is one of Chicago’s premier boutique hotels. In the center of the city’s beautiful Lincoln Park neighborhood, this playful guesthouse offers its guests unmatched comfort with a twist. An eclectic design and friendly design truly separate the Lincoln from its contemporary – and an amazing rooftop bar certainly doesn’t hurt! Moreover, their resident cafe – Elaine’s Coffee Call – has been dubbed one of the best in the area and if all that doesn’t convince you to book a room then I don’t know what will.
The Guesthouse Hotel
Photo Credit: The Guesthouse Hotel Instagram
For starters, The Guesthouse Hotel is Fido-friendly, which, for any dog parent, is an automatic go. But more importantly, this Andersonville reside prides itself on being every guest’s home-away-from-home, renting out full, apartment style rooms instead of the standard double. With luxury furnishes and a bevy of amazing amenities, activities and dining options, The Guesthouse is more like a miniature neighborhood than any hotel I’ve ever seen. Hell, book a room at this stylish spot and you might just find yourself wanting to move in.
theWit
Photo Credit: theWit
TheWit is one of the hottest hotels in the entire Chicagoland area. With an uber-modern look and sweeping skyline views, staying in one of these suites is sure to be a treat. In the center of the city’s arts and theater district, theWit is dedicated to all things dramatic. From the furnishings to the food, guests should arrive expecting a show. Be sure to check out this hotel’s exclusive movie theater for a private screen experience you’ll have to see to believe.
Airbnbs
The Sunny Loft
Photo Credit: Cory via Airbnb
Hotels aren’t your only option for an amazing Chicago staycation. This enormous space allows you to get away from your life by stepping into someone else’s. Listed as a “Huge, Sunny, Open Loft” this 1500 sq.ft space can accommodate up to 8 people, ensuring that no one in the family is left out of your staycay fun.
The Artist’s Loft
Photo Credit: Nathan via Airbnb
This hip Northside loft has everything you could ever wan’t in a staycation. I’m talking a sauna, a fireplace, a massive kitchen and a beautiful rooftop deck with stunning views of the Chicago skyline. Not only will this place put your apartment to shame, it will be the perfect respite from all things ordinary.
The Historic Florsheim Mansion
Photo Credit: Russ via Instagram
Why stay at home when you can stay in a literal mansion? Yup, that’s right: this historic Gold Coast mansion is available for rent to weekend warriors like yourself on Airbnb. This giant modern masterpiece will comfortably sleep eight and comes replete with a Grand Piano. Your vacation could never.
The Wrigleyville Rooftop
Photo Credit: David vis Airbnb
Three words: rooftop hot tub.
Get a taste of the good life at this Lakeview apartment. With stellar views of Wrigley itself and a huge communal living space to boot, this apartment is any baseball junkie’s dream getaway.
The Loop High Rise
Photo Credit: Kari via Airbnb
Stay high in the sky at this swanky Airbnb in the Chicago loop. With clean lines and a modern design, this lodge will have any guest living in the lap of luxury. Oh, and did I forget to mention the full-sized pool? Because this fancy place also comes with a pool.
Bed and Breakfasts
Villa D’Citta
Photo Credit: Villa D’Citta Facebook
Sometimes all you’re looking for in a hotel is a little comfort. Enter: Villa D’Citta, a cozy little B&B housed in one of Lincoln Park’s iconic greystones. With a beautiful courtyard, winding staircases and grand master bedrooms, this home away from home will leave you feeling relaxed, recharged and ready to get back to the daily grind.
The Sono Chicago
Photo Credit: The Sono Chicago
Head to Old Town to get a taste of The Sono Chicago on your next vacation. This unique bed and breakfast offers a large community social space and kitchen in addition to cute and romantic suites. Take a stroll down the neighborhood’s tree-filled streets or check out any number of Old Town’s amazing restaurants. Nothing says staycation like an amazing meal!
The Publishing House
Photo Credit: The Publishing House
The Publishing House Chicago boasts 11 suites housed in a newly renovated pre-war building. True to its name, The Publishing House was once home to Free Methodist Publishing and still retains much of the company’s eccentric charm and style. With rooms full of exposed brick and Mid-Century Modern furnishings, this B&B will leave you feeling like Instagram irl. If you book a room, make sure you take a peek at the expansive living and dining areas.
