Chicago, IL Short term rentals

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Chicago, IL short term rentals
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Best Short term and Weekly rentals in Chicago, IL

See Top-Rated Luxury Lodgings in Chicago, IL, United States

Check into a high-end city pad with premium concierge services and elite finishes at luxury lodgings in Chicago, IL, United States.

Kasa Lake Shore Chicago - Chicago, IL
8.2 30 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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 327 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 3284 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 1582 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.

Top-Rated Lodgings with a Hot Tub in Chicago, IL, United States

Sip champagne above the city lights in a private hot tub at city lodgings in Chicago, IL, United States.

43rd-floor Luxury Escape + Lake Views - Chicago, IL
10 2 reviews

43rd-floor Luxury Escape + Lake Views

apartment, Chicago
This Chicago apartment is situated in the Downtown Chicago neighbourhood, a 0.6km walk from State Street and 1.9km from Lake Michigan, offering easy access to the Willis Tower, Merchandise Mart, Field Museum of Natural History, and Museum of Science and Industry.
The 123 square metre dwelling comprises three bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry facilities, and access to a shared swimming pool, hot tub, and fitness centre; it sleeps up to six guests comfortably.
Luxury Ph: Panoramic Views + Prime Location - Chicago, IL
No reviews

Luxury Ph: Panoramic Views + Prime Location

apartment, Chicago
This spacious four-bedroom flat is situated in downtown Chicago's waterfront district, a short walk from Michigan Avenue and Millennium Park, and within 500 metres of the Randolph-Wabash and Lake L train stations.
The 246 square metre residence offers a garden, balcony, air conditioning, Wi-Fi, and on-site parking, with a communal swimming pool and hot tub available for guests.
Logan Square Cozy 2br Basement Apartment - Chicago, IL
10 147 reviews

Logan Square Cozy 2br Basement Apartment

apartment, Chicago
This Logan Square basement flat offers convenient access to Chicago's Blue Line, providing quick commutes to both the city centre and O'Hare International Airport.
The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen, a private garden, and a dedicated HVAC system, plus free on-street parking nearby.
Premium Lake Views + Ideal For Group Getaways - Chicago, IL
10 1 review

Premium Lake Views + Ideal For Group Getaways

apartment, Chicago
This luxurious Chicago apartment complex is situated on the city's Cultural Mile, offering easy access to Chicago's many cultural attractions.
Four units within this prestigious tower boast nine bedrooms, eight bathrooms, accommodate sixteen guests, include a swimming pool, Jacuzzi, fitness centre and stunning lake views, plus offer access to over 7,432 square metres of amenities and the unique opportunity to watch NASCAR races from the living room.

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-visit for art lovers, with masterpieces like Grant Wood's 'American Gothic'. And no trip to Chicago is complete without a stroll along Navy Pier, with its Ferris wheel, shops, and restaurants.
  • 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 hot and humid, with temperatures often reaching over 30 degrees Celsius. Winters are cold and snowy, with average temperatures around -5 degrees Celsius. Spring and autumn are mild and pleasant, with temperatures ranging from 10 to 20 degrees Celsius.
  • 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 its festivals! The Chicago Blues Festival in June is a huge celebration of blues music, while the Taste of Chicago in July offers a chance to sample food from all over the city. The Chicago Air and Water Show in August is a spectacular display of aerial acrobatics.
  • 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 big sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a must-see for any baseball fan. Soldier Field, home of the Chicago Bears football team, is another popular destination. And if you're a hockey fan, you can catch a game at the United Center, home to both the Chicago Blackhawks and Chicago Bulls.
  • 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 Mag Mile Mega Entire Floor 4bd\/4ba+parking&rooftop, Kasa South Loop Chicago and Sonder South Wabash.

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from Chicago, you'll find the Indiana Dunes National Park, with its beautiful beaches and towering sand dunes. For a different kind of natural beauty, head to the Morton Arboretum, a sprawling arboretum with over 17,000 trees and plants.
  • What part of Chicago, IL is ideal for finding lodging?

    The Magnificent Mile, along Michigan Avenue, is a popular spot for luxury hotels and high-end shops. For something more budget-friendly, consider staying in the River North or Wicker Park neighbourhoods. If you're looking for a more authentic Chicago experience, try the Lincoln Park or Lakeview neighbourhoods.

Popular destinations

Elite Family Lodgings in Chicago, IL, United States

Keep everyone comfortable and stress-free with spacious living areas and child-friendly features at family-friendly lodgings in Chicago, IL, United States.

The Roscoe Village Guesthouse - Chicago, IL
9.4 20 reviews

The Roscoe Village Guesthouse

apartment, Chicago
This Roscoe Village guesthouse in Chicago is situated 2.4 kilometres from Wrigley Field and within 8 kilometres of Lincoln Park Zoo and other key attractions including 360 Chicago and the United Centre.
This three-bedroom apartment offers 111 square metres of space, sleeping up to six guests, and features a fully equipped kitchen with a dishwasher, air conditioning, and a private entrance; towels and bed linen are provided.
Space&style New Rehab, First Flr + Bsmt Of Duplex, Driveway Prkng, Walk To Train - Chicago, IL
10 17 reviews

Space&style New Rehab, First Flr + Bsmt Of Duplex, Driveway Prkng, Walk To Train

apartment, Oak Park
This Oak Park apartment is situated a 15-minute walk from the Frank Lloyd Wright Historic District and Concordia University Chicago, and within 9.6km of both the Walt Disney House and Loyola University Medical Centre.
The three-bedroom, three-bathroom property sleeps seven guests and boasts a private patio, fully equipped kitchen, free Wi-Fi, on-site parking, a spa, and a shared garden with an arcade/games room.
Luxury 1br In The Loop, Resort-style Amenities! - Chicago, IL
10 1 review

Luxury 1br In The Loop, Resort-style Amenities!

apartment, Chicago
This modern one-bedroom flat is located in Chicago's downtown district, offering skyline views and immediate access to dining, shopping, and nightlife within 500 meters.
This family-friendly apartment provides a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a garden, a sauna, and a fitness centre for up to three guests.
Designer Loft In Fulton Market With Parking - Chicago, IL
10 11 reviews

Designer Loft In Fulton Market With Parking

apartment, Chicago
This three-bedroom, two-bathroom Chicago apartment, situated on Restaurant Row, is a two-minute drive from the city centre and within easy reach of attractions such as the Chicago Theatre and the Art Institute of Chicago.
The luxury dwelling boasts a renovated kitchen and bathrooms, a large terrace, a patio with a fire pit, and accommodates up to eight guests, with one parking space included.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Lincoln Park Single Family Home (4bdrm 3.5 Bth)-2 Car Garage 4200sqft Sleeps 24 - Chicago, IL
9.8 315 reviews

Lincoln Park Single Family Home (4bdrm 3.5 Bth)-2 Car Garage 4200sqft Sleeps 24

apartment, Chicago
This spacious house in Lincoln Park is ideally located just 15 blocks from Wrigley Field, 5 blocks from the Kennedy Expressway, and 6 blocks from the EL, making it easy to explore the city. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
This four-bedroom home spans 390 square metres and comfortably accommodates up to 24 guests. The house offers a range of amenities, including a private garage, a fully equipped kitchen, a jacuzzi, a terrace, a garden, and a spa, ensuring a relaxing and enjoyable stay.
Lakeview Loft-vintage Chicago, Modern Amenities - Chicago, IL
9.9 602 reviews

Lakeview Loft-vintage Chicago, Modern Amenities

apartment, Chicago
This Lakeview flat is ideally situated in Chicago's Lakeview neighbourhood, less than 0.8km from the Brown and Red Line 'L' trains, under 1.6km from Wrigley Field, and 2.4km from the lakefront.
The freshly remodelled one-bedroom loft, sleeping four guests, boasts a king-size bed, 65" TV, private patio, fully equipped kitchen (fridge, microwave), and self check-in; nearby activities include exploring Wrigleyville and enjoying Chicago's lakefront.
Modern 2br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail - Chicago, IL
8.8 42 reviews

Modern 2br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

apartment, Chicago
This Chicago apartment, near McCormick Place and the Museum Campus, is conveniently located approximately 2.4-3.2km from the Field Museum, Art Institute of Chicago, and the Chicago Symphony Orchestra.
The 88 square metre property features a two-bedroom, two-bathroom layout sleeping up to six guests, offering a private patio, fitness centre access, and free Wi-Fi; parking is available.
50th Floor Mag Mile Views, Balcony, Pool, Gym - Chicago, IL
10 43 reviews

50th Floor Mag Mile Views, Balcony, Pool, Gym

apartment, Chicago
This Downtown Chicago penthouse, situated between North Michigan Avenue and the River North district, offers easy access to Millennium Park and the Art Institute of Chicago.
The 68-square-metre (732 sq ft) apartment features one bedroom, one bathroom, and sleeps two guests, boasting a terrace, swimming pool, and on-site parking, alongside stunning 50th-floor city views.

Top-Rated Short-Term Rentals in the CBD of Chicago, IL, United States

Walk to the best local museums, shopping strips, and transit links from centrally located lodgings in Chicago, IL, United States.

Comfy River West, Free Parking - Chicago, IL
9.9 268 reviews

Comfy River West, Free Parking

apartment, Chicago
Perfect Destination! Onsite Bar And Restaurant! - Chicago, IL
9.6 5 reviews

Perfect Destination! Onsite Bar And Restaurant!

B&B, Chicago
1f Chicago's Little Italy Graystone Neardowntown - Chicago, IL
10 200 reviews

1f Chicago's Little Italy Graystone Neardowntown

apartment, Chicago
Modern Single-family Home W/outdoor Space + Garage - Chicago, IL
9.5 51 reviews

Modern Single-family Home W/outdoor Space + Garage

apartment, Chicago
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