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

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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
9.6 307 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.
Kasa Lake Shore Chicago - Chicago, IL
7.8 13 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 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.

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

Chic Private Room In Girlie Condo| G3 | Wifi & Tv! - Chicago, IL
10 4 reviews

Chic Private Room In Girlie Condo| G3 | Wifi & Tv!

apartment, Chicago
This Albany Park guest house is conveniently located near the Brown Line, providing easy access to Chicago's city centre, Wrigleyville, and O'Hare International Airport.
The self-contained apartment, sleeping two guests, boasts a fully equipped kitchen, two bathrooms, a private deck with grill, and in-unit laundry facilities, plus free on-street parking with permits provided.
Spanish Villa - Chicago, IL
9.7 6 reviews

Spanish Villa

apartment, Berwyn
This Berwyn flat is located in a quiet district, offering a secure and peaceful base with convenient access to local shops and restaurants, approximately 500 meters from the nearest public transport links.
This 2-bedroom flat accommodates up to 6 guests and features air conditioning, a kitchen, a jacuzzi, and private parking, making it ideal for those seeking a comfortable stay with amenities for relaxation and exploration of Berwyn.
Sky-high 2br W/ Gym & City Views - Chicago, IL
No reviews

Sky-high 2br W/ Gym & City Views

apartment, Chicago
This Downtown Chicago flat is conveniently located less than 1.6km from Union Park and the United Centre, and within 3.2km of the Chicago Riverwalk and Michigan Avenue.
The 125 square metre, two-bedroom, two-bathroom apartment sleeps five, boasting a fully equipped kitchen, in-unit laundry, private balcony, and access to a swimming pool, fitness centre, and concierge services.
H&h 1896 - Spacious, Fully Stocked, & Free Parking - Chicago, IL
9.9 118 reviews

H&h 1896 - Spacious, Fully Stocked, & Free Parking

apartment, Chicago
This Hermosa, Chicago property, a beautifully restored 1896 home, is situated a 5–10 minute drive (8–16 km) from Logan Square and Wicker Park, and 15–20 minutes (24–32 km) from Chicago's city centre.
Sleeping up to 16 guests in 6 bedrooms and 4 bathrooms, this large house boasts a private compound with a backyard, pergola, fire pit, basketball court, children's play area, home theatre, exercise room, and kids’ jungle gym, plus ample off-street parking for up to 6 cars.

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

The Lyons' Den - Chicago, IL
9.8 24 reviews

The Lyons' Den

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.
Native Garden At Chicago's Edge With Free Parking - Chicago, IL
10 5 reviews

Native Garden At Chicago's Edge With Free Parking

B&B, Chicago
Native Garden, a guesthouse in Harwood Heights, is situated 14.8 kilometres from Loyola University Chicago, 16.1 kilometres from Wrigley Field, and 17.7 kilometres from Lincoln Park Zoo, with Chicago O'Hare International Airport a mere 5.9 kilometres away.
This family-friendly establishment offers one bedroom and one bathroom accommodating up to three guests, with complimentary WiFi, air conditioning, a garden, and parking available, alongside a tranquil sun terrace and a non-smoking environment.
Serene Suburban Stay: Family-friendly W/ez Parking - Chicago, IL
9.6 81 reviews

Serene Suburban Stay: Family-friendly W/ez Parking

apartment, Berwyn
This Berwyn apartment, ideally situated near local restaurants and gambling establishments, offers easy access to Oak Park and Little Village within a 16km drive and Chicago's Midway and O'Hare airports.
The one-bedroom flat sleeps four, features a queen-size bed, 50" smart TV with YouTube TV, fully equipped kitchen, free Wi-Fi, and on-site coin-operated laundry facilities; free street parking is a bonus.
City Villa Sleeps 10-20 Free Tv & Parking - Chicago, IL
9.5 16 reviews

City Villa Sleeps 10-20 Free Tv & Parking

apartment, Chicago
This spacious Chicago apartment, ideal for large groups, is situated in Lakeview, a 19-minute walk from Fullerton Beach and 2.6 km from North Avenue Beach, close to Wrigley Field.
The 232-square-metre property boasts four bedrooms, two bathrooms, a fully equipped kitchen, terrace, and free parking, comfortably sleeping 10-20 guests with access to complimentary Wi-Fi.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL lodging with parking

3car Parking Bungalow/sleeps 8 W/2.5 Bath - Chicago, IL
10 2 reviews

3car Parking Bungalow/sleeps 8 W/2.5 Bath

apartment, Berwyn
This apartment in Berwyn offers a unique space for group stays, conveniently situated for access to local landmarks.
With one bedroom and one bathroom, this flat accommodates up to 12 guests and includes essential amenities like internet, a kitchen, and air conditioning, with the host available for local recommendations.
Bootlegger House Sleeps 10-20 Free Tv & Parking - Chicago, IL
10 3 reviews

Bootlegger House Sleeps 10-20 Free Tv & Parking

apartment, Chicago
This Chicago apartment, ideal for large groups, is situated in a peaceful neighbourhood near Lincoln Park, 2.7km from Lincoln Park Zoo and 5.5km from the 360 Chicago Observation Deck, offering easy access to Fullerton Beach and Wrigley Field.
The 325 square metre property boasts six bedrooms, two bathrooms, sleeps 10-20 guests, and includes a garden, tennis court, parking, and a balcony; nearby activities include fishing.
Historic Oasis In The Middle Of Everything. - Chicago, IL
9.9 321 reviews

Historic Oasis In The Middle Of Everything.

apartment, Chicago
This Sheridan Park flat is ideally located near the intersection of Uptown, Andersonville, Wrigleyville, Lincoln Square, and Ravenswood, an 8-minute walk (approximately 0.64 km) from the Wilson CTA station.
The three-bedroom property, sleeping six, boasts a private deck, in-unit laundry, three smart TVs, private parking, and access to shared gardens, offering a comfortable stay near diverse Chicago neighbourhoods.
Top Floor City Apartment - Free Street Parking! - Chicago, IL
9.7 144 reviews

Top Floor City Apartment - Free Street Parking!

apartment, Chicago
This Lincoln Park flat, situated approximately 0.8-1.6km from DePaul University and 1.4km from a Metra and 'L' train station, offers easy access to Bucktown, Wicker Park, and Lakeview neighbourhoods.
The three-bedroom, one-bathroom property sleeps seven guests comfortably, boasting a fully equipped kitchen, in-unit laundry, and free on-street parking – a rarity in Chicago – alongside a private garden.
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