10 Chicago Airbnbs to Plan Your Trip Around

If you’re planning a trip to Chicago, we’ve got you covered. From where to eat and where to get inspired, and even where to #gram, it’s no secret that Chicago is one of our favorite destinations. With all of the unique things that the Windy City offers, why settle for a status-quo hotel stay.

From a refurbished church to a 1930’s mansion, there is an Airbnb for every type of getaway and group.

 

1. The Wicker Park Church

Sleeps: 2

Rate: $200/night

Neighborhood: Wicker Park

This one-bedroom apartment is located within a re-purposed church that was built over a century ago. Located across the street from Wicker Park, the Airbnb is a beautiful mix of new modernity and the original woodwork and stained glass windows. Although the listing recommends just two guests, the space is large and bright to host in.

 

2. An Artist’s Loft

Sleeps: 2

Rate: $150/night

Neighborhood: Wicker Park

This dreamy loft is also located in the Wicker Park neighborhood of Chicago. In addition to the industrial wrought iron touches and exposed brick walls, the apartment boasts a rooftop deck, a soaking tub and a private sauna for guests. What more could you ask for?

 

3. The Florsheim Mansion

Sleeps: 10

Rate: $1,275/night

Neighborhood: Gold Coast

The Florsheim Mansion is a famous property in Chicago’s Gold Coast neighborhood along Lake Michigan. Originally built in the 1930’s, the home has since been under the ownership of the heiress Lillian Florsheim, and the Director of the city’s contemporary art museum. Impress your friends and family with a stay fit for royalty in the mansion that was deemed one the “sexiest homes in Chicago” by Chicago Magazine.

 

4. A Cobbler Square Loft

Sleeps: 4

Rate: $150/night

Neighborhood: Old Town

The Cobbler Square Lofts offer residents unique units with open concept floor plans, exposed brick walls and plenty of sunlight; but the perks of this Airbnb rental don’t stop there. The Loft complex includes a gym, roof deck, hot tub and a resident’s lounge to foster a community for their residents. If you’re new to the city, it’s a great way to rub elbows with locals and learn more about Chicago.

 

5. Fulton Market Townhouse

Sleeps: 10

Rate: $450/night

Neighborhood: Fulton Market

This luxury townhouse located is just a short walk away from the West Loop and offers guests complete access to four floors of bedrooms, living spaces and a private balcony. Beds are covered in 800 thread count sheets, plasma televisions are on every floor and a private parking garage is below the building – and these are just the beginning of the premium touches throughout this rental.

 

6. A Colorful River West Loft

Sleeps: 6

Rate: $150/night

Neighborhood: River West

This corner unit is 1,100 square feet of open concept loft space for a group of 6 to call home. The design is especially whimsical with yellow walls in the dining room, a chalkboard backsplash in the kitchen and full size canoe lighting up both spaces.

 

7. Logan Square French Garden

Sleeps: 6

Rate: $175/night

Neighborhood: Logan Square

How dreamy is this two-bedroom apartment? Located on the bottom floor of a newly renovated Logan Square home, the garden level unit is bright and welcoming. Guests can stay warm in the winter next to an antique wood burning stove in the living room, or enjoy the sun outside on a private patio right outside the kitchen door.

 

8. The Roosevelt Suite

Sleeps: 4

Rate: $100/night

Neighborhood: Marshall Square

The Roosevelt Suite is perfect for travelers in search of a truly different type of stay. The garden level unit of a home next to Douglas Park has original exposed brick walls, beautiful crosshatch wood floors and one wall covered entirely with pages of a Roosevelt novel. The space is a perfect home away from home for a couple.

 

9. Bright Bucktown Apartment

Sleeps: 4

Rate: $150/night

Neighborhood: Bucktown

This apartment in Bucktown is a breath of fresh air with high ceilings and uncluttered white walls. With a small private deck, Crosley turn table and a record collection, it’s a perfect space to relax and unwind. The apartment building is just a few blocks away from Wicker Park, treating guests to free parking on a quiet street and an easy commute to downtown.

 

10. Wicker Park Coach House

Sleeps: 6

Rate: $150/night

Neighborhood: Wicker Park

Another property in Wicker Park to add to your Airbnb wish list – this coach house is a perfect getaway for a group of six. Two stories, and an open concept living room and kitchen, provide just the right amount of private and communal areas for a group getaway.

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