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

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.
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.

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

Penthouse Escape + Vibrant West Loop Access - Chicago, IL
10 4 reviews

Penthouse Escape + Vibrant West Loop Access

apartment, Chicago
This West Loop penthouse apartment, situated in Chicago's Fulton District near Union Park and Little Italy, offers easy access to Randolph Street Market (a 5-minute drive, or approximately 3.2 kilometres).
The recently renovated three-bedroom property sleeps seven guests, boasting a large layout, private balcony, access to a swimming pool and fitness centre, plus free parking (subject to availability) and a well-equipped kitchen.
Luxury Ph: Panoramic Views + Prime Location - Chicago, IL
10 1 review

Luxury Ph: Panoramic Views + Prime Location

apartment, Chicago
This four-bedroom penthouse apartment in the Chicago Loop is situated on the 23rd floor, offering west-facing city skyline and sunset views, and is a 5-minute walk (approximately 400 metres) from Millennium Park and a 10-minute walk (approximately 800 metres) from the Art Institute of Chicago.
This stylish flat accommodates up to nine guests and boasts premium furnishings, a fully equipped kitchen, air conditioning, and access to extensive building amenities including indoor and outdoor swimming pools, rooftop lounges with fire pits and barbecues, a fitness centre, and professional workspaces.
Prime Lincoln Park Views + Modern Amenities Await - Chicago, IL
10 2 reviews

Prime Lincoln Park Views + Modern Amenities Await

apartment, Chicago
This Near North Side Chicago flat is situated less than 0.8km from the Steppenwolf Theatre and within 4.8km of Michigan Avenue, Lake Michigan, the Riverwalk, and Millennium Park.
The two-bedroom, two-bathroom apartment sleeps four guests and offers a fully equipped kitchen, in-building fitness centre, balcony, and is within easy reach of public transport, including the North-Clybourn and Armitage stations.
Level Studio | Fulton Market - Chicago, IL
9.5 63 reviews

Level Studio | Fulton Market

apartment, Chicago
This Chicago apartment, registration number 2957081, boasts a central location, though precise proximity to landmarks such as Millennium Park or Navy Pier remains unspecified.
The self-catering flat offers a swimming pool, jacuzzi, fitness centre, parking and sleeps two guests, featuring a kitchen with fridge, air conditioning, and internet access; further details on the property's size and specific interior layout are unavailable.

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, for stunning views of the city. The Art Institute of Chicago is a must-see for art lovers, with works by Monet, Picasso, and Van Gogh. And no trip to Chicago is complete without a visit to Millennium Park, home to the famous Cloud Gate sculpture, affectionately nicknamed 'The Bean'.
  • What are the best short term rentals in Chicago, IL?

  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has a humid continental climate, so you'll experience all four seasons. Summers are hot and humid, with average temperatures around 25°C. Winters are cold and snowy, with average temperatures around -5°C. Spring and autumn are generally mild, but can be unpredictable.
  • 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! You'll find something for everyone, from the massive Lollapalooza music festival in the summer to the Taste of Chicago food festival in July. The Chicago Air and Water Show in August is always a crowd-pleaser, and the Chicago Marathon in October is a major sporting event.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

    The best short term rentals with a jacuzzi in Chicago, IL are Sentral Michigan Avenue, The Neighborhood Hotel Lincoln Park and Level Chicago – Old Town.

  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a sports town! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field is home to the Chicago Bears, and the United Center is home to both 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?

    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 the city, you can find Indiana Dunes National Park, with its beautiful beaches and towering sand dunes. The Morton Arboretum is a great place to escape the city and enjoy a peaceful walk among the trees. And if you're looking for some outdoor adventure, the Chain O'Lakes State Park offers boating, fishing, and hiking.
  • What part of Chicago, IL is ideal for finding lodging?

    It depends on what you're looking for! If you want to be in the heart of the action, the Magnificent Mile is a great option, with plenty of hotels and restaurants. For a more relaxed experience, consider staying in the Lincoln Park neighbourhood, with its beautiful park and museums. And if you're on a budget, the River North neighbourhood is a good choice.

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

Theater Room And Gym | 4br Near Lincoln Park - Chicago, IL
No reviews

Theater Room And Gym | 4br Near Lincoln Park

apartment, Chicago
This six-bedroom, two-bathroom flat is situated in Chicago's Lincoln Park district, a five-minute walk from Lincoln Park and the Second City comedy club, and an eight-minute walk from the Sedgwick subway station.
This accommodation offers space for 12 guests and features air conditioning, a television, Wi-Fi, and a fully equipped kitchen with a stove, oven, refrigerator, coffee maker, microwave, and cooking utensils, along with an in-unit washer and dryer.
Blissful Journey | Millennium Park. Gym* - Chicago, IL
No reviews

Blissful Journey | Millennium Park. Gym*

B&B, Chicago
Home2 Suites by Hilton Chicago River North Hotel offers serviced apartment accommodation in Chicago's River North district, situated 2 kilometres from the Magnificent Mile and within 3.2 kilometres of Millennium Park and Navy Pier.
This family-friendly establishment provides spacious one-bedroom suites for up to four guests, featuring a king bed, sofa bed, fully equipped kitchen, and complimentary daily breakfast, with an on-site fitness centre and 24/7 reception also available.
Luxury Lincoln Park Retreat 2 Bedroom 2 Living Room Dublex - Chicago, IL
No reviews

Luxury Lincoln Park Retreat 2 Bedroom 2 Living Room Dublex

apartment, Chicago
This two-bedroom flat is located in Chicago's Lincoln Park district, offering proximity to the Lincoln Park Zoo and Wrigley Field, with the Merchandise Mart approximately 4.8 kilometres away and the Cloud Gate sculpture around 6.4 kilometres distant.
This family-friendly apartment accommodates up to four guests and includes a kitchen with a fridge, microwave, and dishwasher, along with air conditioning, two bathrooms, a washing machine, and Wi-Fi for a comfortable stay.
Skyline Luxury 19th Floor Retreat Near Grant Park - Chicago, IL
No reviews

Skyline Luxury 19th Floor Retreat Near Grant Park

apartment, Chicago
This 112 square metre, two-bedroom flat is located in Chicago's central district, a 10-minute walk from DePaul University and 1.9 kilometres from the city centre, offering city views from the 19th floor and proximity to Grant Park and the Art Institute of Chicago.
This family-friendly accommodation boasts two bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a balcony, on-site parking, a fitness centre, and entertainment options including billiards and table tennis, with a guest capacity of 15.

Best Chicago, IL lodging with parking

4 Bedroom Sleeps 20 People - Chicago, IL
10 1 review

4 Bedroom Sleeps 20 People

apartment, Chicago
This Chicago flat is located between 3.2 and 5.6 kilometres from Union Station, Willis Tower, Guaranteed Rate Field and the United Centre.
This spacious dwelling offers 167 square metres of living space, with four bedrooms accommodating up to 20 guests and featuring a fully equipped kitchen, four bathrooms, on-site casino and free WiFi.
Elevated, Open-concept Loft With Industrial Feel - Chicago, IL
9.5 35 reviews

Elevated, Open-concept Loft With Industrial Feel

apartment, Chicago
This spacious loft is located in Chicago's Lincoln Park district, a 5-10 minute Uber journey from the Art Institute of Chicago and Millennium Park's Cloud Gate sculpture.
This 232 square metre apartment offers a unique open-plan layout with vaulted ceilings and can accommodate up to 8 guests, featuring a separate bedroom, a kitchen, a living area, an additional flexible bungalow room, and includes air conditioning, internet, and private parking.
Skyline 2br In South Loop Chicago Near Mccormick - Chicago, IL
9.6 152 reviews

Skyline 2br In South Loop Chicago Near Mccormick

apartment, Chicago
This Michigan Avenue apartment offers a prime location near McCormick Place, within walking distance of public transport and Grant Park.
The two-bedroom, two-bathroom flat sleeps six guests comfortably, boasting a fully equipped kitchen, in-building gym, and 4K smart HDTV; optional parking is available at £24 per day.
Private Logan Square Garden Apt - Chicago, IL
9.9 113 reviews

Private Logan Square Garden Apt

apartment, Chicago
This Chicago garden flat is located in the West Logan Square neighbourhood, three blocks (approximately 0.24 kilometres) from the western entrance to the 606 Trail.
The self-contained unit, sleeping two guests, features a queen-size bed, well-equipped kitchen with full-sized appliances, a private garden, parking, and fast Wi-Fi; nearby attractions include North and Pulaski avenues' restaurants and cafes.
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