Explore the Windy City from a local perspective in spacious One-, Two-, and Three- Bedroom Suites complete with full size kitchens, relaxing living areas, separate bedrooms, and private balconies with gas grills.
Cozy up to the fireplace in the Clubroom with a book from our extensive Library or lounge away on the Roof Deck in summer while soaking up the view. This is no ordinary boutique hotel…this is home!
Located at the crossroads of Andersonville, Uptown, Lincoln Square, and Ravenswood, The Guesthouse Hotel is steps away from unique specialty shops, award-winning restaurants, local craft breweries, and great neighborhood entertainment. Chicago is a city of neighborhoods and we are in the sweet spot!
Whether traveling as a family, on business or as an intrepid solo explorer, we are here to curate an authentic Chicago experience from a local’s point of view.
Catch a Cubs game at Wrigley Field; hit the bike path along Lake Michigan; stock your kitchen from our neighborhood farmer’s market; enjoy a local craft beer on your balcony. This is local Chicago immersion at it’s best! Your travel memory is waiting. Let’s make it happen. Wander home to The Guesthouse Hotel.
Whether you need a short-term housing solution because your job demands it, you are the unfortunate victim of a residential fire or flood, or just need a safe place to temporarily call home, The Guesthouse Hotel is here to ensure that your extended stay with us is as close to home as you’ll get.
Suites
These two bedroom units feature gourmet kitchens, spa-like bathrooms, and outdoor spaces, perfect for family travelers. Choose from our standard two bedroom or our two bedroom deluxe for some extra pampering.
THE CLUB ROOM
Setting a perfect tone for an intimate gathering, The Club Room features a warm and welcoming fireplace, crystal lighting, along with a collection of repurposed vintage and leather seating. Art galleries throughout the room tell the story of Chicago’s past and present.
From wine tastings and private parties to cocktails receptions and dinners, The Club Room is an impressive venue for small groups up to 48 people.
The Library
Our Library is a blend of marble, reclaimed wood and iron, impressive book cases, old word billiards lighting and expansive 10′ foot custom table creating a warm backdrop for a variety of events.
This versatile space is the ideal venue for your next intimate dinner, business meeting, corporate workshop, or event. The Library accommodates up to 12 people, depending on your type of event.
Events
Create a memorable experience at The Guesthouse Hotel. Whether you’re planning an intimate wedding, unforgettable event, or a great business meeting or retreat, our exceptional spaces are designed to impress. You’ll find all the style of a unique boutique hotel, with friendly and exceptional service from the hotel staff.
One of the “13 most pet-friendly hotels in the country”- Time Out
No need to leave part of the family behind. Well-behaved dogs of all shapes and sizes are always welcome at The Guesthouse Hotel and there is never an extra charge!
From treats upon arrival to belly rubs during their stay, your pup will receive Very Important Pooch service from our team of dog-lovers! We offer complimentary beds, food & water bowls and baggies upon request.
Outdoors
There’s a lot of the great outdoors you can explore in The Windy City.
BY WATER
Chicago Architecture Foundation River Cruise
If there’s one “must-do” while in Chicago, it’s this tour… a 90-minute cruise down the Chicago River that uncovers the history of the city’s magnificent architecture.
Chicago River Canoe and Kayak
Want to do your own exploring down the Chicago River? Rent a canoe or kayak (or sign up for a guided tour).
Chicago Sailing Club
If you’re an experienced sailor looking to explore new waters, or want to take a fireworks cruise—the Chicago Sailing Club will help you sail along the shores of Lake Michigan.
BY LAND
Lakeshore Trail
Fishing, birdwatching, biking, running, beach volleyball, paddle boating, or skateboarding—you can find it all along Chicago’s Lakeshore Trail, which has easy access from The Guesthouse via Foster or Lawrence Avenue.
The 606
Chicago’s newest park system, The 606 is a former elevated train rail turned walking, running, and cycling path, that connects 2.7 miles of Chicago with four neighborhood parks from Wicker Park to Humboldt Park. Access the trail by hopping on the Damen bus (25 minute ride) and getting off at Churchill Park.
Chicago Park District
From yoga on the beach to movies in the park, there’s always a chance to enjoy fun in the sun or under the stars in Chicago—and for little to no cost!
RUNNING TRAILS
Lakeshore Trail
Take a run down Chicago’s Lakeshore Trail, which has easy access from the Guesthouse via Foster or Lawrence Avenue.
The 606
The 606 is a former elevated train rail turned walking, running, and cycling path, that connects 2.7 miles of Chicago from Wicker Park to Humboldt Park. Access the trail by hopping on the Damen bus (20 minute ride) and getting off at Churchill Park.
LINCOLN SQUARE
Lincoln Square is Chicago’s historic German neighborhood located just about a mile west of The Guesthouse Hotel. And while you won’t see many lederhosen anymore, you can travel the globe while strolling along Lincoln Avenue and enjoy cuisine from France, Greece, Mexico, Italy and many more!
Lincoln Square has so much to offer, including wonderful music performances at the Old Town School of Folk Music or hitting one of the great festivals held throughout the year including AppleFest, Kids in the Square and one of Chicago’s best music festivals—Square Roots.
ANDERSONVILLE
Chicago has been called a city of neighborhoods. With so much to do in the lively downtown area, it may seem difficult to venture out of The Loop. But, do it! Chicago is best experienced by exploring its neighborhoods, and we hope you enjoy your stay in ours.
Andersonville has its roots in Sweden, originating in the late 1800s when immigrants from the country settled in what was once a cherry orchard north of downtown.
While you’ll still find Swedish businesses on Clark Street, the neighborhood has grown into a diverse community, supporting cultures of all kinds with its eclectic restaurants and independently-owned small businesses.
UPTOWN
This constantly evolving neighborhood—one of Chicago’s most historic—features city landmarks as well as up-and-coming dining. From the Vietnamese restaurants in the “Little Saigon” area on Argyle Street to cozy neighborhood coffee bars, Uptown is a neighborhood worth getting to know.
ENTERTAINMENT
The Guesthouse Hotel is located at the crossroads of Chicago’s most popular destination neighborhoods—Andersonville, Lincoln Square and Uptown.
While each has its own distinct personality, they all offer some of the best options for entertainment in Chicago—and most venues are within walking distance of The Guesthouse Hotel!