Chicago, IL Short term rentals

9542 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

Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1379 reviews
Chicago, IL
18/07 – 15/08
NZ$550/nighttotal: NZ$15400 (28 )

Kasa Magnificent Mile Chicago

1 1
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
9.6 265 reviews
Chicago, IL
21/09 – 25/09
NZ$565/nighttotal: NZ$2260 (4 )

The Neighborhood Hotel-little Italy

1 2
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 River North Chicago - Chicago, IL
9.4 351 reviews
Chicago, IL
01/01 – 31/01
NZ$695/nighttotal: NZ$20850 (30 )

Kasa River North Chicago

3 6
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.
Kasa South Loop Chicago - Chicago, IL
9.4 3084 reviews
Chicago, IL
20/08 – 23/08
NZ$651/nighttotal: NZ$1953 (3 )

Kasa South Loop Chicago

1 2
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

Gym, Steam Room, Sauna Jacuzzi & Pickleball Court - Chicago, IL
10 5 reviews
Chicago, IL
08/07 – 13/07
NZ$5330/nighttotal: NZ$26650 (5 )

Gym, Steam Room, Sauna Jacuzzi & Pickleball Court

7 10
apartment , Oak Brook
This seven-bedroom, eight-bathroom Oak Brook residence, situated on the corner of York Road and Canterbury Lane, offers convenient access to Oak Brook's shopping and dining.
The property boasts a heated circular driveway, private outdoor amenities including a pool and spa, a separate guest house, extensive lower-level recreation areas, and a luxurious master suite, comfortably accommodating up to ten guests.
Modern 2br Avondale With Free Parking Near Cta - Chicago, IL
Chicago, IL
01/09 – 05/09
NZ$284/nighttotal: NZ$1136 (4 )

Modern 2br Avondale With Free Parking Near Cta

2 2
apartment , Chicago
This 2-bedroom flat in Chicago's Avondale district is located 6.76 kilometres from Wrigley Field and 8.99 kilometres from Lincoln Park Zoo.
This 100 square metre apartment offers a garden, hot tub, on-site parking, and complimentary Wi-Fi, accommodating up to 7 guests with a kitchen featuring a fridge, microwave oven, and dishwasher.
Best Spot In Chicago - Chicago, IL
Chicago, IL
22/06 – 22/08
NZ$294/nighttotal: NZ$17934 (61 )

Best Spot In Chicago

1 1
apartment , Chicago
This Chicago apartment rental offers a peaceful one-bedroom flat sleeping three, ideally located for families seeking a relaxing city break, although its precise neighbourhood and proximity to specific landmarks remains unspecified.
The self-catering property features a kitchen, air conditioning, swimming pool, jacuzzi, and fitness centre; further details regarding its size, layout, and specific amenities are unavailable.
Belmont Pleasures - Hot Tub / Arcade Gaming Room - Chicago, IL
9.8 173 reviews
Chicago, IL
25/06 – 27/06
NZ$1270/nighttotal: NZ$2540 (2 )

Belmont Pleasures - Hot Tub / Arcade Gaming Room

1 10
apartment , Chicago
This Belmont-Cragin, Chicago apartment is situated 0.8km from Brickyard Mall, 3.5km from Hip Mall, and within 13-14km of Chicago's city centre, O'Hare International Airport, and Rivers Casino.
This three-bedroom property sleeps up to 12 guests, boasting a games room with pool table and foosball, a private Xbox room, a hot tub, a dedicated cinema room with an 85-inch Smart 4K TV, an outdoor patio with barbecue and fire pit, free garage parking, and super-fast Wi-Fi.

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

Level One Bedroom Suite | Fulton Market - Chicago, IL
9.3 31 reviews
Chicago, IL
24/12 – 26/12
NZ$525/nighttotal: NZ$1050 (2 )

Level One Bedroom Suite | Fulton Market

1 2
apartment , Chicago
This West Loop studio apartment is ideally situated in Chicago's Fulton Market district, offering easy access to the city's many attractions.
The self-catering apartment sleeps three guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a private bathroom, plus access to a swimming pool, Jacuzzi, fitness centre, and parking (additional nightly fees apply).
Cozy Comfy Clean 420 Compliant Free Parking Quiet Neighborhood A Guest Favorite! - Chicago, IL
10 125 reviews
Chicago, IL
02/10 – 05/10
NZ$408/nighttotal: NZ$1224 (3 )

Cozy Comfy Clean 420 Compliant Free Parking Quiet Neighborhood A Guest Favorite!

3 4
apartment , Chicago
This renovated flat is located in a peaceful, family-friendly neighbourhood in northwest Chicago, just a short distance from downtown attractions like Navy Pier and Michigan Avenue. The property enjoys excellent user ratings and is a popular choice for travellers seeking a comfortable and convenient base for exploring the city.
The three-bedroom apartment spans 93 square metres and can comfortably accommodate up to 10 guests. A range of amenities are provided, including free Wi-Fi, a well-equipped kitchen, a Jacuzzi, a garden, and a spa, ensuring a relaxing and enjoyable stay.
4br Old Town Chicago Loft | Walk To Wells St - Chicago, IL
10 121 reviews
Chicago, IL
02/07 – 06/07
NZ$1851/nighttotal: NZ$7404 (4 )

4br Old Town Chicago Loft | Walk To Wells St

4 10
apartment , Chicago
This four-bedroom apartment is situated in Chicago's SONO neighbourhood, just two blocks south of Chicago's "little Michigan Avenue" and within walking distance of the Magnificent Mile, Millennium Park, Navy Pier, and the city's finest museums.
This family-friendly apartment, with its 160 square metre floor area, offers a spacious open plan living area, a well-equipped kitchen, and a terrace, making it ideal for groups of up to 14 guests.
Private Lincoln Park Condo With 2 Parking Spots - Chicago, IL
9.9 131 reviews
Chicago, IL
27/06 – 30/06
NZ$1217/nighttotal: NZ$3651 (3 )

Private Lincoln Park Condo With 2 Parking Spots

1 5
apartment , Chicago
This Lincoln Park flat, in a historically significant 1895 building, offers convenient access to Lincoln Park's attractions, within easy walking distance of many landmarks.
The two-bedroom, one-bathroom apartment sleeps six, boasting a fully-remodelled kitchen, a private balcony, two off-street parking spaces, a 75" 4K Smart TV, and high-speed fibre internet; a friendly black lab, Buck, may even greet you.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Mccormick Place 2b/2b Family Unit With Optional Parking For Up To 8 Guests - Chicago, IL
10 1 review
Chicago, IL
31/07 – 03/08
NZ$1621/nighttotal: NZ$4863 (3 )

Mccormick Place 2b/2b Family Unit With Optional Parking For Up To 8 Guests

2 8
apartment , Chicago
This Near South Side Chicago flat is conveniently located a short walk from State Street and Wintrust Arena, and within 1.6km of McCormick Place and Soldier Field.
The 88 square metre property boasts three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, private patio, free Wi-Fi, and access to a fitness centre and parking.
Steps From Wrigley Field And Lake Michigan - Chicago, IL
10 2 reviews
Chicago, IL
01/08 – 03/08
NZ$3646/nighttotal: NZ$7292 (2 )

Steps From Wrigley Field And Lake Michigan

1 2
apartment , Chicago
This Wrigleyville flat is located in Chicago, a short walk from Wrigley Field and 2.7 kilometres from Montrose Beach, offering air-conditioned accommodation with a patio and free WiFi.
This 167 square metre apartment accommodates up to 10 guests across 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a dishwasher and oven, plus an on-site casino and cycling opportunities nearby.
Modern 3br Stay Near Dt Chi - Chicago, IL
Chicago, IL
10/07 – 12/07
NZ$1107/nighttotal: NZ$2214 (2 )

Modern 3br Stay Near Dt Chi

3 5
apartment , Chicago
This three-bedroom flat in Chicago is situated conveniently close to Guaranteed Rate Field (1.8 kilometres), Oakwood Beach (2.4 kilometres), Grant Park (6.1 kilometres), and the Art Institute of Chicago (6.3 kilometres).
This 140 square metre property, accommodating up to six guests, offers air conditioning, a fully equipped kitchen with a dishwasher and microwave, complimentary WiFi, and on-site private parking.
Spacious 1br Close To Sinai Hosp - Chicago, IL
Chicago, IL
30/06 – 01/10
NZ$189/nighttotal: NZ$17577 (93 )

Spacious 1br Close To Sinai Hosp

1 1
apartment , Chicago
This one-bedroom flat is conveniently located in Chicago, just 100 metres from Sinai Hospital and 1.6 kilometres from the Medical District, making it ideal for medical professionals.
This first-floor accommodation offers a private balcony, in-unit laundry, and high-speed internet, comfortably accommodating two guests with a dedicated dining space.
©2026 cozycozy.com