Chicago, IL Short term rentals

13281 available short term rental offers

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

Best Short term and Weekly rentals in Chicago, IL

Best Chicago, IL luxury short term rentals

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 Magnificent Mile Chicago - Chicago, IL
9.2 1517 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.
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 South Loop Chicago - Chicago, IL
9.4 3238 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.

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

Luxe 3br, 2ba + Hot Tub - Chicago, IL
9.6 135 reviews

Luxe 3br, 2ba + Hot Tub

apartment, Hillside
This raised ranch is ideally located in Hillside, just a short drive from the I-294 and I-88 motorways, making it easy to reach Elmhurst Hospital and downtown Chicago, which is 32 kilometres away. This property has consistently received excellent ratings for its location, cleanliness and overall experience.
This spacious three-bedroom house can comfortably accommodate up to eight guests. The house includes a well-equipped kitchen, a relaxing family room, a large garden with upper and lower decks, a hot tub, and a garage.
Casa Brookfield - Hot Tub, Bbq, Sleeps 14 Near Chicago - Chicago, IL
9.6 7 reviews

Casa Brookfield - Hot Tub, Bbq, Sleeps 14 Near Chicago

apartment, Brookfield
This Brookfield residence is situated in the town centre, a short distance from Brookfield Zoo and 30 minutes from downtown Chicago, with convenient access to the Metra station.
This four-bedroom flat, spanning 186 square metres, accommodates up to 12 guests and features a fully equipped kitchen, a private outdoor space with a grill, and is located near walking trails and a golf course.
Streeterville Junior 1 Bed With Skyline Views - Chicago, IL
10 1 review

Streeterville Junior 1 Bed With Skyline Views

apartment, Chicago
This one-bedroom flat in Chicago's Streeterville district is situated just 100 metres from Michigan Avenue, offering immediate access to dining, shopping, and entertainment, with a Whole Foods market located within the building.
This fully furnished apartment accommodates two guests and boasts extensive resort-style building amenities, including indoor and outdoor swimming pools, multiple fitness centres, a spa, and rooftop terraces with grilling stations, alongside an in-unit washer and dryer for your convenience.
Luxury 2br On Michigan Ave With Private Balcony - Chicago, IL
9.8 17 reviews

Luxury 2br On Michigan Ave With Private Balcony

apartment, Chicago
This Magnificent Mile apartment in downtown Chicago is situated near Washington Square Park, Jane Byrne Plaza, and the Museum of Contemporary Art, offering easy access to the city's cultural attractions.
The 131-square-metre (1405 sq ft) dwelling boasts two bedrooms with queen-size beds, two bathrooms, and sleeps up to seven guests, featuring a high-end kitchen, a balcony with city views, and access to building amenities including a heated pool, fitness centre, and rooftop sky club.

Frequently asked questions about short term rentals in Chicago, IL

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

    You definitely want to see the iconic Willis Tower, formerly known as the Sears Tower, for incredible views of the city. The Art Institute of Chicago is a must-see for art lovers, with masterpieces from Monet to Van Gogh. And don't forget to walk along Navy Pier, a bustling entertainment complex with shops, restaurants, and a Ferris wheel.
  • What are the best short term rentals in Chicago, IL?

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

    Chicago has four distinct seasons, so be prepared for anything! Summers are hot and humid, with average temperatures around 25°C. Winters are cold and snowy, with average temperatures around -3°C. Spring and autumn are beautiful, with mild temperatures and changing colours.
  • 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! The Chicago Blues Festival is a must for music lovers, while the Taste of Chicago is a food lover's paradise. The Chicago Air and Water Show is a spectacular event for aviation enthusiasts.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

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

    Absolutely! Wrigley Field is home to the Chicago Cubs baseball team, while Soldier Field hosts the Chicago Bears football team. The United Center is home to 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?

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from the city, you'll find the stunning Indiana Dunes National Park. This beautiful area features towering sand dunes, beaches, and forests. It's a great place to escape the hustle and bustle of the city and enjoy some fresh air.
  • What part of Chicago, IL is ideal for finding lodging?

    The Magnificent Mile is a popular choice for tourists, with plenty of high-end hotels and shops. River North is another good option, with a lively nightlife scene and a wide range of restaurants. If you're on a budget, consider staying in the Lincoln Park neighbourhood, which offers a more residential feel.

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

Chicago Home (1st Floor) By Midway Near Downtown - Chicago, IL
9.9 107 reviews

Chicago Home (1st Floor) By Midway Near Downtown

apartment, Chicago
This three-bedroom, one-bathroom apartment is situated near Midway Airport (8km) and downtown Chicago (24km), offering easy access to buses 62 and 62H, plus local amenities.
The ground-floor flat sleeps six guests and boasts a newly remodelled kitchen, bathroom and living room, free parking, and access to a yard and patio; it is ideal for families or groups visiting Chicago.
Group Lux In Old Town 4bd/3ba (+Rooftop/parking) - Chicago, IL
9.6 359 reviews

Group Lux In Old Town 4bd/3ba (+Rooftop/parking)

apartment, Chicago
This Old Town Chicago flat, moments from Wells Street's restaurants and a 0.8 km walk from the Red Line, offers easy access to the city's attractions.
The two-bedroom, two-bathroom property boasts a private rooftop deck with a Weber grill, a state-of-the-art kitchen with a built-in bar, and in-unit laundry facilities; parking is available.
Remodeled, Spacious And Bright Apartment  Near Loyola, Beach & Subway - Chicago, IL
10 424 reviews

Remodeled, Spacious And Bright Apartment Near Loyola, Beach & Subway

apartment, Chicago
This apartment is located in the Rogers Park neighbourhood, just a short walk from Hartigan Beach and the Loyola Red Line "L" station, making it easy to explore Chicago's attractions. Guests have consistently rated it excellent for location, cleanliness, and overall experience.
The three-bedroom property offers ample space for up to six guests, spanning 139 square metres. It features modern amenities including a fully equipped kitchen, a private balcony, a heated back porch, and a Jacuzzi, ensuring a comfortable and enjoyable stay.
100 Yr. Old Chicago Brick Craftsman With Yard, Near Beach And Loyola! - Chicago, IL
10 169 reviews

100 Yr. Old Chicago Brick Craftsman With Yard, Near Beach And Loyola!

apartment, Chicago
This charming three-bedroom flat is situated in a historic Chicago neighbourhood, just 3 kilometres from Lake Michigan and a 2.4 kilometre walk to Wrigleyville. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 139 square metre apartment comfortably accommodates up to eight guests and features a spacious layout with a sunroom and a dining room that can seat up to 10 people. Guests can enjoy a fully equipped kitchen, a charming backyard, parking facilities, and family-friendly amenities such as a baby gate and toddler dishes.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Cabin 101 By 747 Lofts - Chicago, IL
9.6 173 reviews

Cabin 101 By 747 Lofts

apartment, Chicago
This studio apartment is conveniently located near the Blue Line L, offering easy access to downtown Chicago and the bustling West Loop neighbourhood. The property has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The studio is ideal for a group of up to three guests and features a modern kitchen, a bathroom with a spa bath, and in-unit laundry facilities. Guests can enjoy convenient access to local amenities, including restaurants, bars, and shops, all within walking distance.
Modern & Chic 3br | Fireplace+netflix - Chicago, IL
9.8 189 reviews

Modern & Chic 3br | Fireplace+netflix

apartment, Chicago
This three-bedroom Chicago apartment, ideal for families, is situated near Wrigley Field, a six-minute walk from the train station and a 2.4km taxi ride from Chicago's major attractions.
The 3-bathroom flat offers a spacious living/dining area, sleeps four guests comfortably, and includes a fully equipped kitchen, high-speed internet, and family-friendly amenities such as a travel cot and changing mat.
Suite - Queen Bed Non-smoking - Chicago, IL
9.3 49 reviews

Suite - Queen Bed Non-smoking

apartment, Chicago
This studio apartment is situated near the University of Chicago Hospitals Heliport, placing it 4.6 kilometres from the Museum of Science and Industry and 7.7 kilometres from Guaranteed Rate Field.
This 14 square metre studio offers accommodation for two guests, featuring air conditioning, a private bathroom, and on-site parking, with a refundable cash deposit of US$50 required upon arrival.
Lincoln Square Gem! - Chicago, IL
9.9 498 reviews

Lincoln Square Gem!

apartment, Chicago
This two-bedroom flat is located in Lincoln Square, a lively neighbourhood in Chicago, just 800 metres from the Western stop on the Brown Line, providing easy access to the city centre. The property has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The flat is suitable for up to four guests and features a well-equipped kitchen, a comfortable living space, and a private garden. Guests can enjoy the convenience of in-unit laundry facilities, air conditioning, and free Wi-Fi, as well as parking.
©2026 cozycozy.com