Chicago, IL Short term rentals

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

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.
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.

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

Modern 2bdrm Westchester/chicago Home.with Hot Tub - Chicago, IL
9.8 125 reviews

Modern 2bdrm Westchester/chicago Home.with Hot Tub

apartment, Westchester
This apartment in Westchester, Illinois is located just 12 kilometres from downtown Chicago, 6 kilometres from Oak Brook Mall, and 12 kilometres from Rosemont shopping centre, making it a convenient base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and user experience.
This two-bedroom flat can comfortably accommodate up to five guests. It features a fully equipped kitchen, a private garden, a Jacuzzi, and a bonus room with games and TVs, ensuring a relaxing and enjoyable stay for the whole family.
Luxury Ph: Panoramic Views + Prime Location - Chicago, IL
9.4 7 reviews

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.
Casa Brookfield - Hot Tub, Bbq, Sleeps 14 Near Chicago - Chicago, IL
9.6 9 reviews

Casa Brookfield - Hot Tub, Bbq, Sleeps 14 Near Chicago

apartment, Brookfield
This Brookfield residence is situated in the town centre, a short distance from Brookfield Zoo and 30 minutes from downtown Chicago, with convenient access to the Metra station.
This four-bedroom flat, spanning 186 square metres, accommodates up to 12 guests and features a fully equipped kitchen, a private outdoor space with a grill, and is located near walking trails and a golf course.
Sky-high 3br Penthouse In West Loop - Chicago, IL
10 4 reviews

Sky-high 3br Penthouse In West Loop

apartment, Chicago
This four-bedroom, two-bathroom apartment in downtown Chicago is situated less than 1.6km from Milwaukee Avenue and the Merchandise Mart, and under 3.2km from the Chicago Riverwalk and Michigan Avenue, offering easy access to public transport.
The 8-guest dwelling boasts a fully equipped kitchen, balcony, garden access, on-site fitness centre, and is within 1.6km of the University of Illinois Chicago; laundry facilities and barbecue grills are also available.

Frequently asked questions about short term rentals in Chicago, IL

  • Which top landmarks you shouldn't miss in Chicago, IL?

    You can't visit Chicago without seeing the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in the city and offers breathtaking views. The Magnificent Mile, a stretch of North Michigan Avenue, is also a must-see, filled with shops, restaurants, and art galleries. And of course, no trip to Chicago is complete without a visit to Millennium Park, home to the Cloud Gate sculpture, affectionately nicknamed 'The Bean', and Crown Fountain, an interactive fountain that displays faces of Chicagoans.
  • 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 pack accordingly! Summers are hot and humid, with temperatures reaching around 27°C. Winters are cold and snowy, with average temperatures around -3°C. Spring and autumn can be unpredictable, with temperatures fluctuating between cool and warm. It's always a good idea to check the forecast before you go.
  • 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 known for its vibrant festival scene. The Chicago Blues Festival, held in June, is a must-see for music lovers. For something a bit different, the Taste of Chicago, held in July, showcases the city's diverse culinary scene. And if you're a film buff, the Chicago International Film Festival in October is a great way to experience some of the best independent and foreign films.
  • 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 huge sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field, home to the Chicago Bears, is also a popular destination for football fans. And United Center is where you can catch 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 Chicago, you'll find Indiana Dunes National Park, a stunning stretch of sand dunes along the shores of Lake Michigan. The park offers hiking trails, beaches, and scenic overlooks. If you're looking for something a little closer to the city, the Morton Arboretum, a sprawling botanical garden, is a great option.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighbourhood is a great option for travellers, with its trendy restaurants, art galleries, and proximity to the Magnificent Mile. If you're looking for something more budget-friendly, the Wicker Park and Bucktown neighbourhoods offer a vibrant atmosphere with plenty of bars, cafes, and shops.

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

Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown - Chicago, IL
9.6 4 reviews

Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown

apartment, Chicago
This spacious 223 square metre five-bedroom, three-bathroom residence in Chicago's Irving Park district offers a classic early-1900s Craftsman Foursquare design and is a 3.2 to 4 kilometre Uber journey from landmarks including Wrigley Field, the city centre, and Soldier Field.
This family-friendly apartment accommodates up to 14 guests and features a fully-equipped chef's kitchen, a dedicated games room with a pool table and 75" smart TV, high-speed Wi-Fi, air conditioning, and parking, with a check-out time of 10:00 AM.
Hip East Lakeview/lincoln Park Designer Flat - Chicago, IL
9.2 18 reviews

Hip East Lakeview/lincoln Park Designer Flat

apartment, Chicago
This Lakeview flat is situated on Orchard Street, offering tranquil surroundings yet convenient access to Lake Michigan and Chicago attractions such as Michigan Avenue and Navy Pier.
The 37 square metre (approx. 400 square feet) one-bedroom apartment sleeps two, boasting a fully equipped kitchen, in-unit laundry, and a private garden, plus access to a spa and parking.
Designer Loft 2w | Heart Of Gold Coast/river North - Chicago, IL
10 19 reviews

Designer Loft 2w | Heart Of Gold Coast/river North

apartment, Chicago
This Chicago apartment rental, situated in the prime River North/Gold Coast district, is a block from Michigan Avenue, four blocks from Lake Michigan, and within easy walking distance of Oak Street Beach and Navy Pier.
The 167 square metre (1800 square foot) property boasts three bedrooms, two bathrooms, sleeping up to ten guests, and features a chef's kitchen, 65-inch smart TV, secure parking, and is thoroughly cleaned before each arrival.
Chicago Luxurious 3br Near Mccormick Place - Chicago, IL
No reviews

Chicago Luxurious 3br Near Mccormick Place

apartment, Chicago
This three-bedroom flat in Chicago is situated just moments from major attractions such as McCormick Place, Soldier Field, and the Museum Campus.
This modern, artfully designed accommodation offers space for up to seven guests, featuring a fully equipped kitchen, air conditioning, parking, and is designated as '420 Friendly' with smoking permitted inside, though guests should note the hot water system requires 1-2 hours to reheat after heavy use.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Large One Bedroom In Heart Of Old Town/gold Coast - Chicago, IL
10 18 reviews

Large One Bedroom In Heart Of Old Town/gold Coast

apartment, Chicago
This Chicago apartment rental is ideally located on the border of Old Town and the Gold Coast, within walking distance of Downtown, Lincoln Park, and approximately 1.6km from Lake Michigan.
The one-bedroom, one-bathroom flat sleeps three guests and offers a kitchen with fridge and dishwasher, air conditioning, parking, and excellent guest reviews; note a reduced price reflects a non-functional bedroom window.
Large Super Cozy 2 Bed 1 Bath Apartment. - Chicago, IL
10 4 reviews

Large Super Cozy 2 Bed 1 Bath Apartment.

apartment, Chicago
This 2-bedroom flat is located in a prime Chicago district, offering convenient access to iconic landmarks such as Millennium Park, which is 1.5 kilometres away, and Navy Pier, situated 2.1 kilometres from the property.
This accommodation sleeps up to four guests and features a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, a jacuzzi, a garden, and parking, making it ideal for exploring Chicago.
Near Wrigley  Sleeps 6  Firepit & Free Parking - Chicago, IL
9.4 21 reviews

Near Wrigley Sleeps 6 Firepit & Free Parking

apartment, Chicago
This two-bedroom Chicago apartment is situated near Wrigley Field, offering easy access to public transport and attractions such as Millennium Park and Navy Pier.
The 2-bathroom flat sleeps six, features a fully equipped kitchen, two dedicated workspaces, a private backyard with a gas firepit, and free street parking with a permit; enjoy Cubs games and explore the city.
Lyons' Suite - Chicago, IL
8.3 3 reviews

Lyons' Suite

B&B, Chicago
This Chicago guesthouse is situated approximately 21 kilometres from Chicago O'Hare International Airport, in a quiet suburban location.
The 46-square-metre property features one bedroom, one bathroom, and can accommodate up to three guests, offering air conditioning, a private terrace, and parking.
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