Chicago, IL Short term rentals

13281 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chicago, IL short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Chicago, IL

Best Chicago, IL luxury short term rentals

Kasa South Loop Chicago - Chicago, IL
9.4 3246 reviews

Kasa South Loop Chicago

aparthotel, Chicago
Kasa South Loop Chicago is situated in the South Loop, a short walk from DePaul University and within a mile of the CIBC Theatre, offering easy access to the city's vibrant attractions. This aparthotel has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation features modern, comfortable apartments with fully equipped kitchens, including a dishwasher, and a separate living area with a flat-screen TV. Guests can enjoy a range of amenities, such as a swimming pool, a fitness centre, a garden, and a terrace, as well as a business centre and a restaurant.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 288 reviews

The Neighborhood Hotel-little Italy

aparthotel, Chicago
This Near West Side serviced apartment is situated less than 1.6km from Rush University Medical Centre and within 4.8km of both the United Centre and Millennium Park.
The self-catering apartments feature kitchenettes with fridges, microwaves, and dishwashers, smart TVs with satellite channels, and free Wi-Fi in public areas; guests also benefit from proximity to public transport links, including Polk and Racine train stations.
Kasa Lake Shore Chicago - Chicago, IL
9.4 3 reviews

Kasa Lake Shore Chicago

aparthotel, Chicago
This 4-star aparthotel in Downtown Chicago offers a prime location, situated a short walk from Ohio Street Beach, Michigan Avenue, and Lake Michigan, with Grant Park and Navy Pier within 1.5 kilometres.
Each apartment provides a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside an in-room washer/dryer, and the property features a rooftop terrace with city views.
Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1420 reviews

Kasa Magnificent Mile Chicago

aparthotel, Chicago
Kasa Magnificent Mile Chicago is situated on the Magnificent Mile, a short walk from the Shops at Northbridge and just over a mile from North Avenue Beach, making it ideal for exploring Chicago's attractions and enjoying the lakefront. This aparthotel consistently receives excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious rooms with desks, comfortable furnishings, and private bathrooms. Amenities include a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a terrace or balcony, a garden, a concierge, a restaurant, a fitness centre, and parking.

Best Chicago, IL Short term rentals with a jacuzzi

Among the 13281 accommodations in Chicago, IL, here are the 4 best rentals with a jacuzzi

Chicago Oasis | Spa Bath, Patio & Fireplace - Chicago, IL
10 19 reviews

Chicago Oasis | Spa Bath, Patio & Fireplace

apartment, Chicago
This apartment is located in downtown Chicago, just a short walk from Navy Pier and Michigan Avenue, making it easy to explore the city’s attractions and vibrant nightlife. It has received excellent reviews from previous guests.
The one-bedroom apartment spans 88 square metres and comfortably accommodates up to four guests. It boasts a fully equipped kitchen, a spa bathroom with a jetted tub and a rain shower, and a terrace where you can relax and enjoy the city views.
The Green Oasis In The Heart Of Gold Coast - Chicago, IL
No reviews

The Green Oasis In The Heart Of Gold Coast

apartment, Chicago
This Gold Coast flat offers 5 bedrooms and 4 bathrooms, situated within walking distance of the Magnificent Mile, Lincoln Park Zoo, and North Avenue Beach.
This spacious residence boasts a chef's kitchen with Thermador appliances, an outdoor patio with a hot tub, and a convertible game table, accommodating up to 12 guests.
Level Two Bedroom Suite | Fulton Market - Chicago, IL
9.7 42 reviews

Level Two Bedroom Suite | Fulton Market

apartment, Chicago
This two-bedroom, two-bathroom apartment in Chicago's West Loop neighbourhood is conveniently located within walking distance of the Chicago Riverwalk, Willis Tower, and Soho House Chicago.
Offering resort-style amenities including a swimming pool, jacuzzi, and fitness centre, this luxury flat sleeps four guests and boasts bi-weekly housekeeping.
Ph W/ Bean & Lake Views, An Elite Stay - Chicago, IL
10 2 reviews

Ph W/ Bean & Lake Views, An Elite Stay

apartment, Chicago
This luxurious Chicago Loop penthouse apartment boasts stunning views of Cloud Gate, and is within walking distance of Millennium Park and Lake Michigan.
The 2662 sq ft (approximately 0.25 km²) property offers four bedrooms, four bathrooms, sleeps seven guests, and includes a fully equipped kitchen, swimming pool, and terrace; nearby attractions include Soldier Field and McCormick Place.

Frequently Asked Questions about short term rentals in Chicago, IL

  • Which top landmarks you shouldn't miss in Chicago, IL?

    You definitely want to check out the iconic Willis Tower, formerly known as the Sears Tower, for stunning views of the city. The Art Institute of Chicago is a must-see for art lovers, with works by Monet, Picasso, and Van Gogh. And no trip to Chicago is complete without a visit to Millennium Park, home to the famous Cloud Gate sculpture, affectionately nicknamed 'The Bean'.
  • What are the best short term rentals in Chicago, IL?

  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has a humid continental climate, so you'll experience all four seasons. Summers are hot and humid, with average temperatures around 25°C. Winters are cold and snowy, with average temperatures around -5°C. Spring and autumn are generally mild, but can be unpredictable.
  • What are the best short term rentals with a pool in Chicago, IL?

  • What are the most popular festivals and events in Chicago, IL?

    Chicago is a city that loves a good festival! You'll find something for everyone, from the massive Lollapalooza music festival in the summer to the Taste of Chicago food festival in July. The Chicago Air and Water Show in August is always a crowd-pleaser, and the Chicago Marathon in October is a major sporting event.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

    The best short term rentals with a jacuzzi in Chicago, IL are Sentral Michigan Avenue, The Neighborhood Hotel Lincoln Park and Level Chicago – Old Town.

  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a sports town! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field is home to the Chicago Bears, and the United Center is home to both the Chicago Bulls basketball team and the Chicago Blackhawks hockey team.
  • What are the best short term rentals for families and kids in Chicago, IL?

    The best short term rentals for families and kids in Chicago, IL are 2bd/2ba Mag Mile Masterpiece (+Rooftop), Kasa South Loop Chicago and Sonder South Wabash.

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from the city, you can find Indiana Dunes National Park, with its beautiful beaches and towering sand dunes. The Morton Arboretum is a great place to escape the city and enjoy a peaceful walk among the trees. And if you're looking for some outdoor adventure, the Chain O'Lakes State Park offers boating, fishing, and hiking.
  • What part of Chicago, IL is ideal for finding lodging?

    It depends on what you're looking for! If you want to be in the heart of the action, the Magnificent Mile is a great option, with plenty of hotels and restaurants. For a more relaxed experience, consider staying in the Lincoln Park neighbourhood, with its beautiful park and museums. And if you're on a budget, the River North neighbourhood is a good choice.

Popular destinations

Best family friendly Chicago, IL Short term rentals

Among the 13281 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Skylit Boho Retreat In Wicker Park - Chicago, IL
9.4 241 reviews

Skylit Boho Retreat In Wicker Park

apartment, Chicago
This two-bedroom flat in Chicago's Wicker Park Bucktown district places guests within easy reach of the city's main attractions, offering a convenient base for exploration.
The accommodation sleeps up to five guests and includes a full kitchen, air conditioning, a shared patio, and is located approximately 5.6 kilometres from Millennium Park, with a 420-friendly environment and a pack and play available on request.
Chic 4-bedroom With Skyline Views, Firepit And Gym - Chicago, IL
9.5 8 reviews

Chic 4-bedroom With Skyline Views, Firepit And Gym

apartment, Chicago
This new luxury four-bedroom flat is located in central Chicago, offering immediate access to amenities and public transport, with spectacular city views from large windows.
This spacious accommodation sleeps up to ten guests and features two master en-suite bedrooms, a fully equipped kitchen with stainless steel appliances, in-unit laundry, high-speed internet, and individually controlled heating and air conditioning, with a fitness centre and garden also available.
The G Estate - Chicago, IL
10 75 reviews

The G Estate

apartment, Chicago
This three-bedroom, two-bathroom apartment is situated in the East Lakeview district of Chicago, a short 2.4km walk from Wrigley Field and close to Belmont Harbour.
The 156 sqm property sleeps six guests and offers a fully equipped kitchen, in-unit laundry facilities, and is conveniently located near public transport links, including the Belmont Red Line.
Lovely 2 Bedrooms Apartment 10min From O'hare Chicago - Chicago, IL
8.0 22 reviews

Lovely 2 Bedrooms Apartment 10min From O'hare Chicago

apartment, Rosemont
This family-friendly apartment is situated in Rosemont, close to the Rivers Casino and Donald E. Stephens Convention Center, offering a convenient location for exploring the area's attractions. It has received very good user ratings, making it a popular choice for travellers.
The apartment offers 84 square metres of living space, accommodating up to 8 guests comfortably within its two bedrooms. Amenities include a fully equipped kitchen, a jacuzzi, a terrace, a garden, a tennis court, and free internet access, ensuring a relaxing and enjoyable stay.

Best Chicago, IL lodging with parking

Stylish 2-bedroom Wicker Park Apartment - Chicago, IL
9.9 118 reviews

Stylish 2-bedroom Wicker Park Apartment

apartment, Chicago
This Wicker Park flat is conveniently located near the 606 trail and a short walk from the Blue Line, offering easy access to Chicago's city centre and O'Hare International Airport.
The two-bedroom, two-bathroom apartment sleeps four, features a chef's kitchen with modern appliances including a dishwasher, and offers in-unit laundry, a smart TV, and keyless entry; nearby attractions include Wicker Park's numerous bars, restaurants, and boutiques.
Hatties House - Chicago, IL
9.9 193 reviews

Hatties House

apartment, Chicago
This Chicago guesthouse is ideally situated near a neighbourhood hub, offering easy access to three bus routes and numerous amenities including a grocery store, French restaurant, and bakery, all within 0.16 km.
The self-catering apartment features a fridge, freezer, microwave, air conditioning, a private back porch, and accommodates one guest, with access to a shared living room and bathroom; registration number R19000044485.
Large Stylish Bedroom In Oak Park Bungalow - Chicago, IL
9.3 38 reviews

Large Stylish Bedroom In Oak Park Bungalow

apartment, Oak Park
This charming bed and breakfast is situated in a 1910s bungalow in Oak Park, just a short distance from the Frank Lloyd Wright Home and Studio, and within walking distance of the Oak Park Public Library and the Oak Park Avenue business district. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The accommodation offers guests the entire lower level of the bungalow, providing privacy and independence. It can comfortably accommodate up to four guests and features a unique 70s Tiki bathroom, a large backyard with a fire pit, a fitness area with a Peloton bike, weights, yoga mats, and resistance bands, and friendly hosts who are happy to offer local recommendations.
Newly Remodeled 2br Free Parking/private Backyard - Chicago, IL
9.9 32 reviews

Newly Remodeled 2br Free Parking/private Backyard

apartment, Chicago
This newly refurbished flat is situated in Chicago's 60618 district, offering convenient access to public transport, with the Belmont Blue Line just a 12-minute walk away and the Milwaukee Avenue bus stop nearby.
This 2-bedroom flat accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, free parking, and a 55-inch smart TV, with a shared backyard offering a vegetable garden for guests.
©2026 cozycozy.com