I spent many years living in Chicago and getting to know the diverse neighborhoods throughout the city. When I had friends or family visit, most of them stayed with me, other people they knew, or in hotels. Vacation rental homes can be challenging to come by in Chicago, especially if you have a tight budget or want more than just a room in someone else’s house to rent.
However, there are some highly rated Airbnbs to consider in downtown Chicago so that you can be in the middle of all the action, including the following options.
Kasa Premium One-Bedroom
Up to three people can stay at this Airbnb rental that is within walking distance of Michigan Avenue, the Gold Coast, and Oak Street Beach. It has a king-size bed in the bedroom, a sofa bed in the common space, and one bathroom. The apartment rental has an open layout and comes with Nespresso coffee and Malin+Goetz bath products. When you stay here, you’ll have a full kitchen with a dishwasher, in-unit laundry machines, and a private balcony. You can bring one dog or cat to stay with you here for an extra fee. Onsite parking is available for $50 per night.
Kasa Unit, Walk to Lincoln Park Zoo
Five people can stay in this downtown Chicago Airbnb and have their own two bedrooms and two bathrooms. It is a walkable area near the Gold Coast and Michigan Avenue. The Lincoln Park Zoo, children’s museum, and Millennium Park are close by too. The sleeping arrangements are a king-size bed in one bedroom, two twin-size beds in the second bedroom, and a sleeper sofa in the living room. In the living space, you’ll find a full kitchen, laundry machines, smart TV, and Wi-Fi. Onsite parking and pet-friendly accommodation are available for extra fees.
Two-Bedroom Masterpiece
This Airbnb rental is located on a quiet street and has floor-to-ceiling windows that look out to views of Lake Michigan. Up to six people can be comfortable staying here. It offers guests a custom chef kitchen, comfy beds, and access to a common rooftop space. Inside the rental unit, you’ll have a full dining room, a large sectional sofa, stainless steel appliances, and granite countertops. There is a small elevator in the building, so you won’t have to haul your luggage up flights of stairs.
Hypebeast's Haven, Downtown Chicago Loft
Located just seven minutes from the Riverwalk, this loft rental is a comfortable space with a queen-size bed and twin roller bed upon request for a third guest. It has large windows to let in the natural light and trendy décor throughout the space. You’ll have access to the entire unit and be in a downtown building above Rocbar. The bar stays open until 4 am or 5 am, so expect loud music, especially on weekends. This Airbnb is best for travelers who want to experience the local nightlife scene rather than those looking for a quieter stay.
Downtown Two-Bedroom Near McCormick
For your trip to downtown Chicago, you can also rent this two-bedroom, two-bathroom unit for your group of up to four people. One bedroom has a king-size bed, the other bedroom has a queen-size bed, and there is an air mattress in the living room. From here, it is a four-minute drive to McCormick Place, and a CTA bus stop is around the corner. Your rental includes complimentary coffee and tea and has smart TVs in the living room and bedrooms. The common space offers laundry machines, board and card games, an iron and ironing board, and Wi-Fi. You will need to climb two flights of stairs to access the unit.
Magnificent Mile Gold Coast Gem
Groups of up to six people can book this Chicago Airbnb that has two bedrooms and two bathrooms. The bedrooms have a queen-size bed and king-size bed, while the living room has a sofa bed and air mattress. The rental is close to the lake and the Magnificent Mile while also being just steps from the Drake Hotel and Oak Street Beach. You’ll enjoy the rooftop that overlooks the lake and have your own complimentary parking spot onsite with in/out access. The freshly renovated condo comes with hotel-size toiletries, a hair dryer, and other essentials. The hosts own both units on this floor of the building, so they may be able to accommodate a larger group of up to 12 guests between the two spaces.
The Executive’s Escape
This downtown rental is a two-bedroom, two-bathroom unit in a location where you can walk to Millennium Park, Navy Pier, and other attractions. It is in a building with a fitness center, basketball court, yoga studio, outdoor pool, BBQ grills, cabanas, and other fun perks. You’ll have the whole suite to yourselves and also have your own laundry machines, TV streaming services, and high-speed Wi-Fi. There are king and queen beds in the unit, plus a pull-out couch and air mattress for sleeping.
Guest Suite in Single-Family Home
With this Airbnb rental, one or two guests can be comfortable with a queen-size bed in a guest suite and a private, attached bathroom. The rental room is in a historic, single-family home in the Gold Coast area of downtown Chicago. From here, you can walk to restaurants, stores, and nightlife on Rush and Oak. The rental room has large windows, privacy curtains, a flat-screen TV with cable, Wi-Fi, and a queen-size bed. Guests have access to the shared kitchen to make coffee or tea and do light meal prep. The Airbnb hosts live here too and are available by phone and text, but they work long hours and are rarely home.
Chicago Speakeasy-Style Loft Space
Located in a two-floor loft space that is shared with other guests, this Airbnb host offers multiple private rooms for two travelers each. This Airbnb listing is a speakeasy-style loft space built in the early 1900s in the River North/downtown Chicago area. It offers 12-foot ceilings, unique artwork, and eclectic antiques inside. The room is on the street side of the building and in a busy nightlife area, so it is best for travelers who want to go out and party rather than light sleepers who want to stay in. The Airbnb host has quieter rooms available in the same building if this is an issue. The private bathroom is located down the hall from your private room and comes with robes, towels, and toiletries. The common areas include the kitchen, living room, and foyer.
