This three-bedroom rental unit is housed in a building that dates back to 1886. The third-floor walk-up has been renovated, but the old-school charm remains in its hardwood floors, ample windows, and brick façade. This Airbnb has also been applauded for its popular amenities, like a washer and dryer, dishwasher, travel crib, bathtub, and patio. Don’t miss the opportunity to walk by one of the only homes to survive the Great Chicago Fire of 1871, located on the same block. From $685 per night.
Perks: Newly renovated, private access, smart Tv
Luxury meets ease in this 2,500-square-foot penthouse located in the heart of the vibrant West Loop neighborhood. With three bedrooms, 15-foot ceilings, and brick-lined walls, this rental is ideal for larger groups looking to relax with a sky-high view of all Chicago has to offer. Located on the top floor of a historic 1920s building right by Fulton Market, this prime Airbnb is great for entertaining. With a grand open living space and ample natural light—thanks to a corner unit location—you can’t go wrong opting into a stay at this luxe rental. From $492 per night.
Perks: Eco-friendly linens and tech, kid-friendly, shared backyard, fire pit, TV
Each room seamlessly transitions to the next in this airy one-bedroom rental. A separate study has been set up for those who need to take a break from vacation to check in on work, while a light-filled dining area gives you a bird’s-eye view over the rest of the neighborhood. Located in the popular Logan Square neighborhood, you’ve got easy access to theaters, parks, restaurants, bars, cafés, shopping, and more. No matter how you choose to fill your day, wind down with a cocktail and a vinyl session in your rental’s living area. From $133 per night.
Perks: Along bus and train transit routes, SMEG refrigerator, free parking spot, shared deck area
You’ll find this studio apartment right between South Old Irving and Kilbourn parks, right off North Milwaukee Avenue, which is known for its craft beer and cocktail scene. Equipped with all of the creature comforts of home (air-conditioning, free parking, Wi-Fi, and a full kitchen, to name a few), you’re less than a 20-minute drive from O’Hare International Airport and Logan Square, which has some of the city’s best nightlife options. The swinging chair adjacent to the queen bed is another great spot to relax and recharge. From $179 per night.
Perks: Large open-floor kitchen, free parking, stainless steel appliances, central heat, smart TV
