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

Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1381 reviews
Chicago, IL
14/07 – 18/07
NZ$1302/nighttotal: NZ$5208 (4 )

Kasa Magnificent Mile Chicago

2 5
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 3083 reviews
Chicago, IL
02/10 – 05/10
NZ$744/nighttotal: NZ$2232 (3 )

Kasa South Loop Chicago

1 4
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.
Kasa River North Chicago - Chicago, IL
9.5 439 reviews
Chicago, IL
06/07 – 28/07
NZ$1640/nighttotal: NZ$36080 (22 )

Kasa River North Chicago

2 3
aparthotel , Chicago
Kasa River North Chicago is situated in the River North district, a short walk from Oak Street Beach and the Shops at Northbridge, offering easy access to Chicago's attractions and vibrant nightlife. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The hotel offers a range of modern apartments with amenities such as air conditioning, a fridge, a dishwasher, and a coffee machine. Guests can enjoy the seasonal outdoor swimming pool, terrace, and fitness centre, or simply relax in the garden and take advantage of the concierge service.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 265 reviews
Chicago, IL
04/08 – 10/08
NZ$1334/nighttotal: NZ$8004 (6 )

The Neighborhood Hotel-little Italy

2 3
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.

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

The Playwright's Palace - Chicago, IL
10 50 reviews
Chicago, IL
10/08 – 10/10
NZ$335/nighttotal: NZ$20435 (61 )

The Playwright's Palace

1 2
apartment , Chicago
This Chicago apartment is ideally located near Michigan Avenue, within walking distance of Millennium Park and Navy Pier, and a short distance from an 'L' train station offering easy access to the city's transport network.
The two-bedroom suite sleeps six, boasting a king and full bed, pull-out couch, and air mattress, alongside a fully equipped kitchen, private washer/dryer, and high-speed Wi-Fi; a swimming pool, Jacuzzi, gym, and sauna are also available.
Luxe Stay + Balcony | Top Food, Music, Bars, Shops - Chicago, IL
10 30 reviews
Chicago, IL
05/08 – 19/08
NZ$799/nighttotal: NZ$11186 (14 )

Luxe Stay + Balcony | Top Food, Music, Bars, Shops

1 4
apartment , Chicago
This three-bedroom Chicago apartment, situated in Andersonville, offers easy access to Lake Michigan and is within a 5-10 minute transit ride of popular attractions including Wrigleyville, the Loop, and Chinatown.
The 1908 Prairie School-style property boasts a fully equipped kitchen with high-end appliances, a private balcony, hotel-quality linens, and amenities such as beach gear and a Bluetooth sound system, comfortably sleeping six guests.
Vintage Chicago Gem: The Rockwell Retreat - Chicago, IL
Chicago, IL
10/07 – 31/08
NZ$5710/nighttotal: NZ$296920 (52 )

Vintage Chicago Gem: The Rockwell Retreat

3 1
apartment , Chicago
This Chicago apartment is located in the West Ridge neighbourhood, just 3 kilometres from Lake Michigan and 4 kilometres from Lincoln Park, offering a peaceful residential setting close to the city's attractions. The apartment is ideal for a solo traveller, featuring three bedrooms and two bathrooms. The apartment offers a fully equipped kitchen, a jacuzzi, internet access, and a washing machine and dryer, perfect for a comfortable and convenient stay.
Spacious 1-bedroom + Den In The Heart Of Chicago - Chicago, IL
10 4 reviews
Chicago, IL
13/08 – 15/08
NZ$672/nighttotal: NZ$1344 (2 )

Spacious 1-bedroom + Den In The Heart Of Chicago

1 3
apartment , Chicago
This two-bedroom flat is located in Chicago, between the districts of Lincoln Park and Old Town, offering excellent access to local eateries, shops, and entertainment venues, as well as being just a short walk to the Lakefront and downtown attractions.
This property accommodates up to four guests and features a fully equipped kitchen, air conditioning, a private balcony with city views, and access to a communal swimming pool, Jacuzzi, and fitness centre, with pets being welcome.

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.

Destinations nearby

Best family friendly Chicago, IL Short term rentals

Among the 9542 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Spacious&modern Condo, Near Dwtn, Secure Parking - Chicago, IL
10 126 reviews
Chicago, IL
24/06 – 24/12
NZ$889/nighttotal: NZ$162687 (183 )

Spacious&modern Condo, Near Dwtn, Secure Parking

1 2
apartment , Chicago
This spacious Chicago apartment, ideal for families or groups, enjoys convenient access to public transport, situated near a bus stop with easy connections to the city centre, United Centre, and McCormick Place.
The 167 sq m (1800 sq ft) property boasts two bedrooms, two bathrooms, sleeps eight to ten guests comfortably, and includes a chef's kitchen, in-unit laundry, free high-speed Wi-Fi, and a parking space with EV charging.
Easy And Comfy - Chicago, IL
9.7 55 reviews
Chicago, IL
10/08 – 13/08
NZ$286/nighttotal: NZ$858 (3 )

Easy And Comfy

2 3
apartment , Chicago
This Chicago guesthouse is situated in a TimeOut-rated top-two coolest neighbourhood globally, offering easy access to public transport within 800 metres.
The self-catering apartment sleeps six, comprising two double beds and a queen-size air mattress, plus a full kitchen, living room, and dining area, and features free on-street parking nearby.
Mccormick 3br/2ba Retreat | Chicago Group Getaway - Chicago, IL
9.7 51 reviews
Chicago, IL
10/07 – 13/07
NZ$854/nighttotal: NZ$2562 (3 )

Mccormick 3br/2ba Retreat | Chicago Group Getaway

3 5
apartment , Chicago
This three-bedroom Chicago apartment, situated in the South Loop district, is a short walk (approx. 1.4km) from McCormick Place and a short Uber ride from the Museum Campus and Soldier Field.
Sleeping eight guests, this self-catering property boasts a fully equipped kitchen, a fitness centre, and optional parking, all within a modern, spacious layout featuring three queen-size beds and Smart TVs.
The Lyons' Den - Chicago, IL
9.6 14 reviews
Chicago, IL
01/09 – 03/09
NZ$334/nighttotal: NZ$668 (2 )

The Lyons' Den

1 2
B&B , Chicago
The Lyons' Den, a bed and breakfast in Chicago, is situated 2.25 kilometres from Wrigley Field, 5.95 kilometres from Lincoln Park Zoo, and 6.76 kilometres from Loyola University Chicago.
This 15 square metre guesthouse offers accommodation for up to three guests in one bedroom and one bathroom, featuring air conditioning, a terrace, a fully equipped kitchen with a dishwasher and oven, and complimentary WiFi.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Experience Chicago Living Near United Center - Chicago, IL
8.8 34 reviews
Chicago, IL
01/07 – 03/07
NZ$444/nighttotal: NZ$888 (2 )

Experience Chicago Living Near United Center

3 2
apartment , Chicago
This Austin, Chicago condo, situated 11 kilometres from the city centre and 8 kilometres from the United Centre, offers easy access to public transport and major attractions including Michigan Avenue and Navy Pier.
This three-bedroom apartment, boasting 93 square metres of space and sleeping up to six guests, includes a fully equipped kitchen, free on-street parking, and air conditioning; it's perfect for families or groups visiting the city.
Luxury Penthouse Combo 07/02 Terrace | River North - Chicago, IL
10 1 review
Chicago, IL
26/08 – 30/08
NZ$2811/nighttotal: NZ$11244 (4 )

Luxury Penthouse Combo 07/02 Terrace | River North

5 13
apartment , Chicago
This spacious five-bedroom, five-bathroom flat is situated in Chicago's River North district, just 0.3 kilometres from Michigan Avenue and within walking distance to Lake Michigan and Oak Street Beach.
Offering over 278 square metres of living space, this property accommodates up to 18 guests with three living areas and chef's kitchens, plus secure parking is available nearby.
Vibrant 3br Pilsen Stayfree Parkingnear Downtown - Chicago, IL
10 35 reviews
Chicago, IL
01/08 – 31/08
NZ$632/nighttotal: NZ$18960 (30 )

Vibrant 3br Pilsen Stayfree Parkingnear Downtown

3 2
apartment , Chicago
This flat is in Chicago's Lower West Side, a short walk from 18th Street and approximately 5 kilometres from Downtown Chicago's Grant Park and Millennium Park.
This 79 square metre residence offers three bedrooms accommodating up to five guests, featuring a full kitchen, air conditioning, complimentary garage parking for one vehicle, and is equipped with 24/7 security cameras.
Entire Apt In Heart Of Chicago - Chicago, IL
9.8 8 reviews
Chicago, IL
26/07 – 27/07
NZ$917/nightfor 1 night

Entire Apt In Heart Of Chicago

2 2
apartment , Chicago
This Chicago apartment, situated in Wrigleyville, is an 8-minute walk from Wrigley Field and within 3.5km of Lincoln Park Zoo and Fullerton Beach.
The one-bedroom, one-bathroom flat sleeps six guests and features a fully equipped kitchen, free Wi-Fi, a balcony, and a flat-screen TV; nearby attractions include Wrigley Field and Lincoln Park Zoo.
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