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

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 South Loop Chicago - Chicago, IL
9.4 3214 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 Magnificent Mile Chicago - Chicago, IL
9.2 1382 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.
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.

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

West Loop Studio~pool/gym! - Chicago, IL
10 2 reviews

West Loop Studio~pool/gym!

apartment, Chicago
This flat is situated in Chicago's West Loop district at 727 Madison, offering proximity to boutique shops and restaurants.
The property accommodates two guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning, a swimming pool, jacuzzi, fitness centre, and parking, with floor-to-ceiling windows providing city views.
Spacious 1 Bd Sleeps 4 Quiet And Near Michigan Ave. Free Gift - Chicago, IL
No reviews

Spacious 1 Bd Sleeps 4 Quiet And Near Michigan Ave. Free Gift

apartment, Chicago
This Chicago city apartment is ideally situated near State Street, a short walk (approximately 2km) from the Willis Tower and within easy reach of two train stations, offering convenient access to downtown attractions such as Millennium Park and the Art Institute of Chicago.
This one-bedroom flat sleeps up to five guests and boasts a fully equipped kitchen, in-unit laundry, a private balcony, and access to a swimming pool, hot tub, and parking; all within easy walking distance of the Magnificent Mile and Lake Michigan.
Soaring Dramatic Wrigley Loft W/ Private Rooftop - Chicago, IL
9.9 307 reviews

Soaring Dramatic Wrigley Loft W/ Private Rooftop

apartment, Chicago
This spacious apartment is situated in Wrigleyville, a lively neighbourhood just a short walk from Wrigley Field, home to the Chicago Cubs, and within easy reach of bars and restaurants. It has excellent user, location and cleanliness ratings.
The apartment has four bedrooms and three bathrooms, spread over 214 square metres, offering ample space for large groups or families. Amenities include a private rooftop with skyline views, a fully equipped kitchen, a game room with a foosball table and arcade, a Jacuzzi, a spa, a fitness centre, and parking.
Beautiful Downtown 3br With Free Parking - Chicago, IL
9.8 31 reviews

Beautiful Downtown 3br With Free Parking

apartment, Chicago
This three-bedroom, two-bathroom Chicago apartment is located in the Fulton Market district, offering easy access to public transport and proximity to Millennium Park and Grant Park (distances unspecified).
Sleeping up to ten guests, this recently renovated dwelling boasts a jacuzzi, terrace, parking, and modern amenities including a dishwasher and microwave, all within walking distance of Chicago's best restaurants.

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

The Woodlawn Grey  - Large 3bd/3ba Apt By Uchicago - Chicago, IL
9.6 128 reviews

The Woodlawn Grey - Large 3bd/3ba Apt By Uchicago

apartment, Chicago
This Hyde Park flat is situated near the University of Chicago campus, less than 1.6km from the Museum of Science and Industry and the lakefront path, offering convenient access to public transport.
The three-bedroom, three-bathroom dwelling sleeps six comfortably, boasting a well-equipped kitchen, in-unit laundry, high-speed Wi-Fi, and ample street parking in a quiet, two-unit building; nearby attractions include the University of Chicago and the Museum of Science and Industry.
Peaceful River West, Free Parking - Chicago, IL
9.9 451 reviews

Peaceful River West, Free Parking

apartment, Chicago
This River West apartment, bordering River North, offers easy access to downtown Chicago's attractions, being conveniently located near the city centre.
The two-bedroom, one-bathroom flat sleeps four guests comfortably, featuring a fully equipped kitchen, private washer/dryer, gated parking (including an EV charging point), and access to shared garden space.
Walk To Uc, No Stairs, Free Parking - Chicago, IL
10 179 reviews

Walk To Uc, No Stairs, Free Parking

apartment, Chicago
This spacious Chicago apartment, ideal for families or large groups, enjoys a central location offering easy access to both the United Centre and McCormick Place.
The 168 sq m property boasts two bedrooms, two bathrooms, two sofa beds, and a chef's kitchen, comfortably accommodating up to nine guests and featuring amenities such as a 65" 4K Roku TV and free parking (restrictions apply).
Luxury House 4-bed 2.5-bath Near Chicago Downtown - Chicago, IL
9.9 166 reviews

Luxury House 4-bed 2.5-bath Near Chicago Downtown

apartment, Chicago
This spacious house is located in North Park, a safe and convenient neighbourhood with restaurants, supermarkets, and parks within walking distance, and is about 16km from O'Hare Airport. The property has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
This 3000 square metre home has 6 bedrooms, although only 4 are available for guests, and features an open kitchen, living room, and dining room. Guests can enjoy a private garden, modern amenities such as a laundry room and multiple bathrooms, and convenient access to public transport.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL lodging with parking

Tranquil Stay - 10 Mins To Ohare, Free Parking! - Chicago, IL
8.7 3 reviews

Tranquil Stay - 10 Mins To Ohare, Free Parking!

apartment, Franklin Park
This Franklin Park flat is situated a 16km drive from O'Hare International Airport, offering convenient access to Rosemont Theatre (24km) and Allstate Arena (32km).
The one-bedroom apartment sleeps four, features a fully equipped kitchen including a dishwasher, free on-site parking, and complimentary Wi-Fi, ensuring a comfortable stay near Franklin Park's local amenities.
Spacious Centrally Located West Loop Loft - Chicago, IL
9.8 317 reviews

Spacious Centrally Located West Loop Loft

apartment, Chicago
This spacious Chicago apartment, a 120-square-metre loft, is centrally located, offering easy access to popular neighbourhoods and restaurants within a 1-1.5 kilometre radius and close proximity to Chicago's public transport links.
The two-bedroom, two-bathroom dwelling boasts high ceilings, an open-plan layout, sleeps up to six guests, and includes amenities such as parking (subject to limitations), a garden, and secure internet access.
En Suite Private Queen Bedroom/bathroom - Chicago, IL
9.7 264 reviews

En Suite Private Queen Bedroom/bathroom

apartment, Chicago
This charming flat is situated in the Lakeview neighbourhood on Chicago's North Side, just a short walk from Wrigley Field and the bustling Southport Corridor. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The self-catering property features a private garden level with a fully equipped kitchen, a bathroom, a spacious living area and a cosy fireplace. Guests can enjoy the outdoor oasis with a patio, pergola, fire pit and hammock, as well as access to a fitness centre, parking and laundry facilities.
Alewyfe Farm Urban Garden Oasis- Free Parking! - Chicago, IL
9.5 216 reviews

Alewyfe Farm Urban Garden Oasis- Free Parking!

B&B, Chicago
This Bohemian Garden Apartment is located in a bohemian neighbourhood in Chicago, two blocks from the Pink Line CTA, Lagunitas Brewery, and Cinespace Film Studios, offering a view of Douglas Park and just 5.6 kilometres from the Loop.
The apartment, situated on the first floor of an 1880s brick cottage, features a private bathroom, private entrances, multiple fans, a small window AC for hot days, and a stocked pantry and coffee/tea bar, with a permaculture garden with chickens, a fire pit, and a BBQ available for guests to enjoy.
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