Chicago, IL Short term rentals

9542 available short term rental offers

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Chicago, IL short term rentals
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Best Short term and Weekly rentals in Chicago, IL

Best Chicago, IL luxury short term rentals

The Neighborhood Hotel-little Italy - Chicago, IL
9.6 276 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 1419 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 South Loop Chicago - Chicago, IL
9.4 3242 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 9542 accommodations in Chicago, IL, here are the 4 best rentals with a jacuzzi

High-end 3br Retreat + Steps To Millennium Park - Chicago, IL
10 5 reviews

High-end 3br Retreat + Steps To Millennium Park

apartment, Chicago
This downtown waterfront flat in Chicago offers prime access, just a short walk from the Merchandise Mart and 333 West Wacker Drive, with Clark-Lake and Washington-Wells L train stations only 500 meters away.
This 136 square meter residence, accommodating up to six guests, features three bedrooms, two bathrooms, Wi-Fi, air conditioning, a fully equipped kitchen, on-site parking, and access to a shared swimming pool and hot tub.
Chicago Home With Sauna & Hot Tub - Chicago, IL
10 1 review

Chicago Home With Sauna & Hot Tub

apartment, Elmwood Park
This Dunning flat is situated a short distance from O'Hare International Airport, approximately 48 kilometres from downtown Chicago.
This spacious 3-bedroom residence offers accommodation for up to 7 guests, featuring a high-end kitchen, a steam shower, a dry barrel sauna, a 4-person hot tub, and a large garden with a firepit.
Stylish 2br Retreat In Fulton Market For Getaways - Chicago, IL
10 2 reviews

Stylish 2br Retreat In Fulton Market For Getaways

apartment, Chicago
This stylish two-bedroom apartment, situated in Chicago's Fulton Market district, is a 7-minute walk from Union Park and a 10-minute walk from Google's headquarters.
The 107-square-metre (1150 sq ft) property boasts a chef's kitchen, private balcony, and access to a 2800 sq m amenity space with a pool, spa, and fitness centre; it sleeps five guests and offers a rollaway bed and crib.
Spacious 3br 2ba Haven City Views Steps To Magmile - Chicago, IL
No reviews

Spacious 3br 2ba Haven City Views Steps To Magmile

apartment, Chicago
This 3-bedroom flat is located in Chicago's Loop district, a 15-minute walk from Millennium Park and a 20-minute walk from Navy Pier.
This 136 square metre residence accommodates up to 7 guests and features a fully equipped chef's kitchen, air conditioning, a swimming pool, and stunning city views.

Frequently asked questions about short term rentals in Chicago, IL

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

    You've got to see the iconic Willis Tower (formerly Sears Tower) for amazing views of the city. The Art Institute of Chicago is a must-visit for art lovers, and Millennium Park is perfect for a stroll with its famous Cloud Gate sculpture, 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 four distinct seasons. Summers are hot and humid, with temperatures often reaching over 30°C. Winters are cold and snowy, with average temperatures around -5°C. Spring and autumn are beautiful, with mild temperatures and vibrant 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's got a festival for everyone! The Lollapalooza music festival is a big draw in the summer, and the Chicago Air & Water Show is a spectacular event in August. The Chicago Blues Festival in June is a fantastic celebration of music.
  • 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 sports city! 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 where you'll find 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 Indiana Dunes National Park. It has beautiful beaches, sand dunes, and forests, perfect for hiking, biking, and exploring nature.
  • What part of Chicago, IL is ideal for finding lodging?

    The Magnificent Mile, along Michigan Avenue, is a popular area with plenty of hotels. River North is another great option, with trendy restaurants and nightlife. For a quieter stay, consider the Gold Coast or Lincoln Park.

Popular destinations

Best family friendly Chicago, IL Short term rentals

Among the 9542 accommodations in Chicago, IL, here are the 3 best family friendly rentals

Wicker Park 1-br · Walk To Train & Grocery - Chicago, IL
10 15 reviews

Wicker Park 1-br · Walk To Train & Grocery

apartment, Chicago
This Wicker Park flat offers a prime Chicago location, just a 7-minute walk to the Division Blue Line station for a 15-minute train journey to the city centre, with a grocery store a mere 5-minute walk away.
This one-bedroom flat accommodates two guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, private entrance, and shared laundry facilities.
Private Roofdeck! Location! Parking! Amazing Home! - Chicago, IL
9.7 111 reviews

Private Roofdeck! Location! Parking! Amazing Home!

apartment, Chicago
This Bucktown apartment, a short distance from the 606 trail and one block from the Blue Line, offers easy access to Chicago's attractions.
Sleeping eight guests, this three-bedroom property includes a fully equipped kitchen, custom bathroom with laundry facilities, and parking – a valuable asset in Chicago, plus a newly renovated roof deck boasting city views.
North Center Chicago - Walkable - Transit Accessible - King & Queen Beds - Chicago, IL
10 30 reviews

North Center Chicago - Walkable - Transit Accessible - King & Queen Beds

apartment, Chicago
This apartment is located in the Northcenter/St. Ben's area of Chicago, just 0.8 kilometres from the Irving Park Brown Line Station, providing easy access to various parts of the city. It has received excellent user ratings.
The apartment is a 74 square metre, two-bedroom property with one bathroom that can comfortably accommodate four guests. It comes equipped with a kitchen, a terrace, and a garden, as well as a Jacuzzi, parking, and air conditioning.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Perfect Spot & Spacious 2br+2ba | Mapletree Suites - Chicago, IL
9.9 375 reviews

Perfect Spot & Spacious 2br+2ba | Mapletree Suites

apartment, Chicago
This West Loop condo is ideally situated just steps from Skinner Park and the CTA, offering easy access to the United Centre, the Loop, and the Medical District.
The 1000 sq ft (93 sq m) apartment boasts two bedrooms, two bathrooms, two private balconies with city views, in-unit laundry, a fully equipped kitchen including a dishwasher, and keyless entry; nearby attractions include Café L’Appetito and Target.
Northside Famlynest - Lincoln Sq - 4br/1.5ba/2p - Rare Find - Chicago, IL
10 56 reviews

Northside Famlynest - Lincoln Sq - 4br/1.5ba/2p - Rare Find

apartment, Chicago
This three-storey townhouse is situated in Chicago's Lincoln Square neighbourhood, a family-friendly area with easy access to restaurants, shops, and bars. The property has received excellent ratings for cleanliness, location, and user experience.
The house offers 149 square metres of space and can accommodate up to nine guests in its four bedrooms. It features a fully equipped kitchen, a private backyard with a BBQ grill and fire pit, a basement entertainment area, and free high-speed Wi-Fi throughout.
Modern 2brd Apartment| 5min To Mccormick Place - Chicago, IL
9.8 195 reviews

Modern 2brd Apartment| 5min To Mccormick Place

apartment, Chicago
This recently refurbished two-bedroom flat is located in Chicago's South Loop, a short distance (approximately 1.6km) from the Illinois Institute of Technology, with easy access to the Green and Red lines, Guaranteed Rate Field (White Sox Stadium), and 31st Street Beach.
The spacious property sleeps four guests, offering a fully equipped kitchen, two private bedrooms with smart TVs, a dedicated workspace, fast Wi-Fi, and free on-street parking; nearby attractions include the Museum of Science and Industry and the Field Museum.
Hyde Park! 2 Min Uofc,6mi Dtwn, 4 Mi Soldier Field - Chicago, IL
9.5 34 reviews

Hyde Park! 2 Min Uofc,6mi Dtwn, 4 Mi Soldier Field

apartment, Chicago
This Hyde Park flat, a renovated condo in a former girls' boarding school, is situated a few blocks from the University of Chicago and Lake Michigan, approximately 10 kilometres from Chicago's city centre.
Sleeping up to eight guests in a two-bedroom, one-bathroom property, this Chicago apartment boasts a spacious kitchen, private patio, shared garden, parking, and excellent access to public transport, including express buses to Midway and O'Hare airports.
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