Find short term rentals in Chicago, IL at the best prices

13281 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
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 Magnificent Mile Chicago - Chicago, IL
9.2 1546 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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 307 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 South Loop Chicago - Chicago, IL
9.4 3254 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

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests - Chicago, IL
9.4 27 reviews

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests

apartment, Chicago
Mayor's Manor, a spacious apartment in Chicago's Bridgeport neighbourhood, offers convenient access to local amenities and is within a reasonable distance of attractions such as Michigan Avenue, Navy Pier, and the Field Museum.
This 186-square-metre (1999 square-foot) property boasts four bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, a game room with projector screens, an in-house bar, a large deck with a hot tub, and a private garden; nearby activities include boating, swimming and rock climbing.
Top-floor Oasis: 2br In Heart Of Fulton Market - Chicago, IL
No reviews

Top-floor Oasis: 2br In Heart Of Fulton Market

apartment, Chicago
This two-bedroom flat is situated in Chicago's Fulton Market district, a short walk to Union Park and Google HQ, and a brief drive to Willis Tower and Millennium Park.
This family-friendly apartment offers a fully-equipped kitchen, air conditioning, and access to extensive amenities including a swimming pool, jacuzzi, fitness centre, and co-working spaces, accommodating up to five guests with a 11:00 AM check-out.
Luxe Loft Vibe 4br/3ba Apt King Suite-11 Minutes From Downtown-families-groups - Chicago, IL
10 6 reviews

Luxe Loft Vibe 4br/3ba Apt King Suite-11 Minutes From Downtown-families-groups

apartment, Chicago
This spacious Chicago apartment, located in the Woodlawn neighbourhood, offers easy access to the lakefront, the University of Chicago, the Museum of Science and Industry, and the Obama Presidential Centre.
The 218 square metre property boasts a four-bedroom, three-bathroom layout, sleeping up to eight guests, and includes a fully equipped kitchen, in-unit laundry, and a terrace.
Front Row To The Lake & Skyline: Epic 60th Flr 3br - Chicago, IL
10 3 reviews

Front Row To The Lake & Skyline: Epic 60th Flr 3br

apartment, Chicago
This lakeside Chicago apartment, situated in the downtown area near Soldier Field and the Field Museum, offers easy access to State Street and Michigan Avenue shopping.
The 187-square-metre property boasts three bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, and access to a swimming pool, jacuzzi, and fitness centre.

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. It's the tallest building in Chicago, and the views from the top are incredible. You should also visit Millennium Park, where you can see the famous Cloud Gate sculpture, nicknamed 'The Bean', and the Crown Fountain. And no trip to Chicago is complete without a stroll along the Magnificent Mile, a stretch of North Michigan Avenue known for its high-end shopping and dining.
  • 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. Summers are warm and humid, with temperatures averaging around 25 degrees Celsius. Winters are cold and snowy, with temperatures often dropping below freezing. Spring and autumn are mild, with pleasant temperatures and beautiful foliage in the fall. You'll want to pack layers for all seasons, as the weather can change quickly.
  • 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 has a vibrant festival scene. The Chicago Blues Festival is a must-see for music lovers, and the Taste of Chicago is a great way to sample the city's diverse culinary offerings. If you're visiting in the summer, you can catch the Chicago Air and Water Show, a spectacular display of aviation and watercraft. And for the holidays, the Christkindlmarket in Daley Plaza is a festive tradition.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

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

    Chicago is a city of sports fans. Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark and a must-visit for any baseball enthusiast. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team. And Soldier Field is the home of the Chicago Bears football 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 Chicago, you can find the Indiana Dunes National Park. It's a beautiful area with rolling sand dunes, beaches, and forests. It's a great place to hike, bike, or simply relax and enjoy the scenery.
  • What part of Chicago, IL is ideal for finding lodging?

    The best area for lodging really depends on your preferences and budget. For easy access to the city's main attractions, the Magnificent Mile is a good choice. For a more affordable option, consider staying in the River North or West Loop neighborhoods. If you're looking for a quieter experience, the Lincoln Park or Lakeview neighborhoods are good options.

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

South Loop 2br Corner Unit With Natural Light, Optional Parking And Guest Access Near Downtown Chicago And Mccormick Place - Chicago, IL
9.0 4 reviews

South Loop 2br Corner Unit With Natural Light, Optional Parking And Guest Access Near Downtown Chicago And Mccormick Place

apartment, Chicago
This McCormick family-friendly apartment is situated near Chicago's Museum Campus, approximately 2.3 kilometres from the Field Museum, 2.7 kilometres from Grant Park, and 2.9 kilometres from the Art Institute of Chicago.
This 74 square metre, two-bedroom, two-bathroom flat sleeps up to six guests and offers amenities including a fully equipped kitchen, complimentary Wi-Fi, a private patio with city views, on-site parking, and access to a fitness centre.
3br Near O'hare • Office • Coffee Bar • Sleeps 9 - Chicago, IL
No reviews

3br Near O'hare • Office • Coffee Bar • Sleeps 9

apartment, Chicago
Reserve Chicago 358 is a three-bedroom, two-bathroom flat located in Chicago, offering convenient access to the city's attractions without being in the immediate city centre.
This family-friendly residence accommodates up to nine guests and features air conditioning, internet, a kitchen equipped with a fridge, freezer, microwave, and dishwasher, alongside on-site parking.
2nd Floor Of 1908 Brick Two-flat In Logan Square - Chicago, IL
9.9 610 reviews

2nd Floor Of 1908 Brick Two-flat In Logan Square

apartment, Chicago
This two-bedroom Chicago apartment, perfect for families, is situated in a diverse neighbourhood; precise location within the city is unspecified, but the description suggests it's on a moderately busy residential street.
The 2-bathroom flat offers sleeping for up to six guests across two bedrooms with queen beds and a living room futon, features a fully equipped kitchen (excluding a full oven), in-unit laundry, a private deck, and parking; a friendly host lives downstairs.
Blueground | River N, Gym & Roof, Nr Riverwalk - Chicago, IL
10 5 reviews

Blueground | River N, Gym & Roof, Nr Riverwalk

apartment, Chicago
This one-bedroom flat is ideally located in River North, just a short walk from the Chicago River and a quick drive to Millennium Park and Navy Pier. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment features a modern design with a fully equipped kitchen and a spacious living room offering city views. Residents have access to a range of amenities, including a gym, swimming pool, lounge, parking, and a BBQ area, ensuring a comfortable and enjoyable stay.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL lodging with parking

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.
1 Free Parking, Sleeps 10 - Chicago, IL
9.6 20 reviews

1 Free Parking, Sleeps 10

apartment, Chicago
This 1500 sqft garden flat is situated in Chicago's Wicker Park district, offering a 2.4 kilometre commute to downtown Chicago's attractions, including Millennium Park and Navy Pier.
This residence accommodates up to 10 guests with three bedrooms, featuring hotel-grade bedding, a fully-equipped kitchen with a Keurig, a pool table that converts to a dining table, a 65-inch Smart TV, in-unit laundry, and secure gated parking.
Cozy Cottage Room - Chicago, IL
9.8 406 reviews

Cozy Cottage Room

house, Chicago
This Chicago guesthouse, offering a private gated entrance and fenced yard, is situated in an unspecified neighbourhood; further details regarding proximity to specific Chicago landmarks are unavailable.
The self-catering unit comprises one double bedroom, three bathrooms, and can accommodate two guests; features include air conditioning, Wi-Fi, a summer garden, and parking.
Modern And Bright 2br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park - Chicago, IL
9.5 2 reviews

Modern And Bright 2br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park

apartment, Chicago
This family-friendly Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers convenient access to major cultural attractions.
The 84-square-metre property features a spacious two-bedroom, two-bathroom layout sleeping up to eight guests, complete with a fully equipped kitchen, complimentary Wi-Fi, private parking, and a patio offering city views; a fitness centre is optionally available.
©2026 cozycozy.com