Chicago, Illinois, is perhaps one of the most famous cities in the United States. According to statistics, it is also the third most populous city in America. It’s no wonder why people are flocking to the “windy city”. It is a world-renowned hub for finance, culture, transport, and commerce. The city has a booming economy — do you know that the city alone has one of the highest gross domestic products (GDP) in the world? Besides a booming economy, Chicago is also home to a diverse cultural scene. Art buffs can talk for hours about the city’s numerous public installation, while music lovers have a wide genre to dive into. The city’s unforgettable attractions include the Willis Tower and the ever-famous Chicago River. Scroll down for the top 10 short term rentals in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and short-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on July 25, 2024.
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1. Modest top-floor apartment in a residential area (from USD 99)
Looking for a simple place to crash? This modest top-floor apartment is your best bet, especially if you’re tagging along with some friends or bringing the whole family along. This unit is located in a residential area, so you can enjoy your peace while in the city. All the amenities you can ask for are here. The living room has a plush sofa with a fold-out bed and cable TV. The bedroom seems cramped, but it is actually spacious for two, all thanks to the queen-size bed. The spacious, well-stocked kitchen is located at the entrance. This unit also comes with a backyard and a garden area. When it’s time to explore, make sure to check out the chic bars and award-winning restaurants within the neighborhood.
Weekly discount: 10% off
Superhost
2. Airy and minimalistic apartment with backyard (from USD 59)
Host Marissa invites you to stay at her Airbnb rental located in the basement of her family’s abode. The entire apartment is well-ventilated and has a simple design that gives off a spacious and minimalistic vibe. Only two can fit comfortably inside though. You and your companion will have a queen-size bed all to yourselves. You’re also welcome to enjoy a varied selection of award-winning movies and Netflix shows from the comfort of the living room. You can cook a meal or two in the kitchen; however, the oven is not really functional at the moment. Still, it’s better than nothing, and what you’re getting here is a bargain, especially when you consider the fact that it is minutes away from great hangout spots and downtown Chicago.
Weekly discount: 10% off
3. Contemporary unit with a rustic feel
If the sixth listing is already booked, then choose this instead — a modern, contemporary apartment with a rustic feel. It’s unmistakably rustic, thanks to the warm tones and dark hues prevalent in the furnishings and decor. Twin bedrooms offer respite to weary travelers, with a comfy mattress on the queen-size and double-size beds, thus providing a good night’s sleep. The sofa in the living room is large enough for a single person. Speaking of entertainment, you and your companion can bond over movies and shows as the property features internet-connected smart TV. Better yet, bond over with your friends or family as you cook the most delicious meals in the kitchen. The bonding doesn’t have to stop there since downtown Chicago is just a ride away.
Chicago, Illinois, United StatesAccommodates: 4
4. Newly renovated unit with minimalist decor (from USD 65)
This Airbnb unit was recently renovated to fit the sensibilities of modern times. Inside, the furnishings and the decor are kept to a bare minimum. You could very well say that it adheres to a minimalist design. The unit is designed for couples with its single queen-size bed, but it could fit one person more, thanks to the lofty sofa in the living room. Working on the go has never been easier, thanks to WiFi access and laptop-friendly workspaces. Meanwhile, preparing a meal is a breeze here as the unit has an organized and well-stocked kitchen. Transportation access is not a problem because the unit is close to the Jefferson Transit Center.
Weekly discount: 10% off
5. Romantic studio located near Gold Coast (from USD 109)
Couples scouring for a two-person studio have this place to call home away from home. It’s a simple studio located near the Gold Coast, but its proximity to Oak Beach and Magnificent Mile means that it is very near to some fantastic spots in the city. The studio has everything that you and your partner can ask for. It has a laptop-friendly desk, a cable TV plus WiFi access for catching up on important matters. The cushy mattress of the queen-size bed offers a well-deserved rest for the night. The kitchen is well-stocked, too. You don’t have to worry about forgetting your towels at home since linens are generously provided by the host.
Weekly discount: 10% off
6. Quiet studio within Jefferson Park (from USD 87)
This studio is located within the serene Jefferson Park. A few walks from here and you will be at the Blue Line that facilitates easy access to downtown Chicago. This studio is also close to great restaurants and bars, if hanging out is your kind of jam. Since the whole house is shared between tenants, the host will be providing you keys for the bedroom, kitchen, and large closet. It may not look much, but the whole space is comfy and spacious for two people. The studio also comes with free WiFi access, so you can watch Netflix on the TV before calling it a night. The kitchen is fully equipped with utensils and appliances for a delightful meal prep time. Meanwhile, the bathroom has a shower so you can rejuvenate after a tiring day in Chicago.
Weekly discount: 10% off
7. Well-lit apartment near Montrose Beach
The first in the list is this well-lit apartment East Lakeview with enough space for three people. The apartment unit has a luxurious vibe to it, thanks to the elegant decors. The living room, dining area, and kitchen are all incorporated into one huge space. The open space is cozy enough for an afternoon get-together, thanks to the plush sofa and large flat-screen TV upfront. The bedroom, meanwhile, invites you for an invigorating rest, thanks to a comfy mattress on the queen-size bed. There’s a balcony, as well, perfect if you want a breath of fresh air. On top of it all, this unit is within walking distance to Montrose Beach and Wrigley Field.
Chicago, Illinois, United StatesAccommodates: 3
8. Private and cozy apartment in a quiet neighborhood
Simple, clean, and modest are three words that can aptly describe this apartment. It is the perfect place to cap off a day’s worth of exploring Chicago since you’ll be staying in a quiet, residential neighborhood. The double-size bed in the bedroom and a twin-size bed in the living room provides respite for three guests. The open-space living room and the kitchen are spacious enough and kept to a bare minimum. Thanks to the WiFi access, TV, and coffee maker, you can catch up on the latest updates while enjoying your daily cup of joe. Towels and linens are provided for, and there’s a coin-operated laundry, if you rigorously wash your clothes. On top of it all, it’s close to fantastic bars and mouth-watering restaurants.
Chicago, Illinois, United States
9. Contemporary rental located in Old Town
There’s nothing old with this contemporary apartment located in the Old Town district. The decor and furnishings are well-thought-out. The design of the apartment will suit any sensibilities as it features cool, retro hues that blend well with warm tones of the wooden flooring. The open space concept means that you have all the space to relax anywhere you want. Two guests can comfortably sleep on the queen-size bed, with the large TV providing occasional entertainment. In the morning, have an energizing cup of coffee with the help of the K-cup coffee machine. The unit’s balcony provides a space where you can enjoy the view and reflect on life in general.
Chicago, Illinois, United States
10. Vibrant house with a vintage vibe
If you’re looking for a house with a space for a group of five, then look no further. This house is open for travelers looking to maximize their budget while traveling in Chicago. The furnishings and decor give off a vintage vibe to the whole house. On top of it all, it is very spacious for a house located in the city. Travelers who like to hit the road may park their car inside — it’s free and space is part of the house. The living room is well-lit and has large windows to let sunlight in. At night, you and your companions may stay in either one of the two bedrooms that have a queen-size bed, and double and single-size beds respectively. Nearby tourist spots include Frank Lloyd Wright’s home and studio as well as The Humboldt Park.
Accommodates: 5
Explore the Windy City
Chicago is truly a city that you must not miss because of its diverse culture, a booming economy, and top-notch attractions. So, why not come down to the windy city and enjoy what it has to offer to travelers? One only needs to choose from the varied selection of Airbnb rentals to get started.
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