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

13281 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
9.6 307 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 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.
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

Prime 2br Apartments: Perfect Group Comfort - Chicago, IL
No reviews

Prime 2br Apartments: Perfect Group Comfort

apartment, Chicago
This four-bedroom, four-bathroom flat is situated on the Magnificent Mile, a 500-metre walk from the Museum of Contemporary Art and 1 kilometre from the Mag Mile itself, offering prime access for tourists and business travellers.
This family-friendly residence accommodates up to 14 guests with a fully-equipped chef's kitchen, high-tech entertainment, and building amenities including a heated lap pool, hot tub, and 24/7 concierge service.
Premium Lake Views + Ideal For Group Getaways - Chicago, IL
No reviews

Premium Lake Views + Ideal For Group Getaways

apartment, Chicago
This luxury flat is situated in Chicago's South Loop, a mere 200 metres from Grant Park and 300 metres from the Art Institute of Chicago, placing it on the Cultural Mile with effortless access to the Museum Campus.
Boasting 9 bedrooms and 8 bathrooms to accommodate up to 22 guests, this residence offers a king suite, 8 queen beds, and rollaway beds, alongside access to over 7,432 square metres of amenities including observation decks, pools, a fitness centre, game room and golf simulator, with fully-equipped chef's kitchens and complimentary Nespresso.
Chicagochinatowncenterb - Chicago, IL
9.9 58 reviews

Chicagochinatowncenterb

apartment, Chicago
This Chicago Chinatown guesthouse is a minute's walk from the bus station, two minutes from the Red Line, and a 20-minute walk (1.6 km) from McCormick Place, offering easy access to Chicago's attractions.
The stylish three-bedroom apartment, designed by a Stanford-trained artist, sleeps one guest and features a well-equipped kitchen, high-speed Wi-Fi (300-500 Mbps), a shared bathroom, and free street parking (availability may be limited).
Luxury Condo W/ Hot Tub And Stunning Roof Top Deck - Chicago, IL
9.9 60 reviews

Luxury Condo W/ Hot Tub And Stunning Roof Top Deck

apartment, Chicago
This three-bedroom Chicago apartment is superbly located in Wicker Park, a short walk (0.8 km) from the Division El Stop offering a 10-minute ride to the city centre.
The 3-bathroom dwelling sleeps eight, boasting a king-size and queen-size bedroom, a bunk room with two queen-size bunks, and features including a fully equipped kitchen, in-unit parking, and access to building outdoor spaces.

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

Roscoe Village- Only Steps To Cute Shops & Dining! Sleeps 4-6 - Chicago, IL
10 103 reviews

Roscoe Village- Only Steps To Cute Shops & Dining! Sleeps 4-6

apartment, Chicago
This Roscoe Village flat is situated in Chicago's North Center district, offering convenient access to the Chicago Theatre, Art Institute of Chicago, Michigan Avenue, State Street, Wrigley Field, and the United Center, all within a few kilometres.
This 111 square metre dwelling accommodates up to six guests across two bedrooms, a den, and a pull-out sofa, and features a well-equipped kitchen, air conditioning, parking, and is close to opportunities for motor boating, sailing, fishing, and cycling.
The Drake - Chic 2br Private Unit - Chicago, IL
9.7 154 reviews

The Drake - Chic 2br Private Unit

B&B, Chicago
This Irving Park garden flat offers convenient access to Chicago's public transport network, placing Wrigley Field approximately 2 kilometres away and Tony's Fresh Market nearby.
Sleeping four guests, this two-bedroom, one-bathroom property includes two queen-size beds, a convertible futon, a well-equipped kitchen, Roku and Smart TVs, and free on-street parking for one car; guests also benefit from a spacious garden and access to amenities such as board games and a dehumidifier.
Beautiful 5-bedroom Pilsen Home W/ Parking! - Chicago, IL
9.3 59 reviews

Beautiful 5-bedroom Pilsen Home W/ Parking!

apartment, Chicago
This five-bedroom flat is located in Chicago's Art District, offering proximity to the city's renowned dining establishments.
This spacious accommodation sleeps 10-12 guests across three floors and features two living areas, four bathrooms, a private garden, and a 1-car garage, with a fully stocked kitchen and bathrooms provided.
Old Irving Park 2 Bd/1 Ba, 20 Mins To Downtown - Chicago, IL
9.5 92 reviews

Old Irving Park 2 Bd/1 Ba, 20 Mins To Downtown

apartment, Chicago
This comfortable flat is located in Old Irving Park, a neighbourhood just 8 kilometres from downtown Chicago and 15 kilometres from O'Hare Airport, offering easy access to both via public transport. It consistently receives excellent reviews for its location, cleanliness and overall experience.
The apartment has two bedrooms and one bathroom, comfortably sleeping up to six guests. It comes equipped with a fully equipped kitchen, in-unit laundry, air conditioning, parking and free internet access, making it ideal for families or groups of friends.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL lodging with parking

Super 8 Chicago - Chicago, IL
No reviews

Super 8 Chicago

B&B, Chicago
This B&B is situated 16 kilometres from Chicago's city centre, offering convenient access to Marion Mahoney Griffin Beach, Loyola Beach, and the Emil Bach House.
Guests can enjoy complimentary Wi-Fi, on-site parking, and elevator access, with rooms featuring a shower and television.
Beautiful Condo In Chicago Near Loyola Med Center - Chicago, IL
9.6 38 reviews

Beautiful Condo In Chicago Near Loyola Med Center

apartment, Forest Park
This Forest Park apartment, near Loyola Medical Centre and a 24km drive from central Chicago, offers convenient access to both medical facilities and the city centre.
The one-bedroom flat sleeps three, features a queen-sized bed, fold-out futon, in-building washer/dryer, Amazon TV, Xfinity internet, free parking, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
$N-privateroom+safe North Area+free Street Parking - Chicago, IL
9.4 93 reviews

$N-privateroom+safe North Area+free Street Parking

house, Chicago
This charming bed and breakfast is located in a peaceful residential area just 15 kilometres from downtown Chicago, making it ideal for exploring the city while enjoying a quiet retreat. With excellent ratings for location, cleanliness, and user experience, you can be sure of a comfortable and enjoyable stay.
The apartment offers a choice of a single private bedroom or the entire space, accommodating up to three guests. Amenities include a fully equipped kitchen, free parking, and Wi-Fi, along with a shared living area perfect for socialising with fellow guests.
Bronzevilles Finest Apartment - Chicago, IL
9.4 14 reviews

Bronzevilles Finest Apartment

apartment, Chicago
This Chicago apartment, conveniently located near the Red Line, offers easy access to Guaranteed Rate Field (a 5-minute drive), Lake Shore Drive and beaches (under 5 minutes), and the proposed Obama Presidential Centre (minutes away), placing you within easy reach of downtown Chicago (under 15 minutes).
The two-bedroom, one-bathroom flat sleeps four guests and boasts a kitchen with fridge, freezer, and microwave, air conditioning, a Jacuzzi, parking, and internet access; enjoy stylish interiors and proximity to excellent restaurants within a 20-minute drive.
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