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

Discover Central Short-Term Rentals in Chicago

Experience vibrant local dining and nightlife by reserving central short-term rentals placed inside the heart of Chicago.

Premier Penthouses And Apartment With Captivating Views Of Millennium Park - Chicago
9.2 9 reviews

Premier Penthouses And Apartment With Captivating Views Of Millennium Park

apartment, Chicago
This penthouse apartment in downtown Chicago offers breathtaking views of Millennium Park and the iconic Cloud Gate sculpture ("The Bean"), within walking distance of Ohio Street Beach, Millennium Station, and the CIBC Theatre.
The 2,662 square foot apartment features three bedrooms, three bathrooms, a fully equipped kitchen, and a private balcony, comfortably accommodating up to six guests and offering access to a hot tub, indoor pool, and bar.
52nd Floor Magmile Penthouse Views Fireplace Pool - Chicago
9.9 1376 reviews

52nd Floor Magmile Penthouse Views Fireplace Pool

apartment, Chicago
This penthouse apartment sits in downtown Chicago, just steps from the upscale shops and restaurants of North Michigan Avenue and the art galleries and trendy eateries of River North. It boasts excellent ratings for location, cleanliness, and user experience.
This luxury dwelling has floor-to-ceiling windows showcasing stunning views of Lake Michigan and the Chicago skyline. Enjoy a fireplace, a swimming pool, a fitness center, a sauna, a spa, a terrace, and a garden, all while taking advantage of the concierge service.
Livn West Loop Chicago King Studio Apartment - Chicago
9.9 34 reviews

Livn West Loop Chicago King Studio Apartment

apartment, Chicago
This newly renovated studio apartment is located in Chicago's West Loop, a 5-minute walk from Union Station and Willis Tower, offering excellent connectivity to transit and acclaimed dining like Girl & The Goat. This loft-style unit features a fully equipped kitchen with a refrigerator, dishwasher, and cooktop, accommodates two guests, and includes an in-unit washer and dryer for your convenience.
Theatre Terrace Tower (Indoor Pool/gym!) - Chicago
9.9 95 reviews

Theatre Terrace Tower (Indoor Pool/gym!)

apartment, Chicago
This downtown Chicago rental is a block from an 'L' train station and within walking distance of Millennium Park, Navy Pier, and the Magnificent Mile.
The two-bedroom, one-bathroom apartment sleeps eight guests and includes a king bed, full bed, pull-out couch, and air mattress, plus in-unit laundry, Roku, high-speed Wi-Fi, and access to a building pool, hot tub, and fitness center.

Find the Best Family-Friendly Lodgings in Chicago

Stay near Millennium Park or the Shedd Aquarium for easy access to world-class museums. These apartments offer extra bedrooms and full kitchens, making logistics simple near the Lakefront Trail and Navy Pier.

Luxury Penthouse Collection Ph3 - Fulton Market - Chicago
No reviews

Luxury Penthouse Collection Ph3 - Fulton Market

apartment, Chicago
This brand new penthouse apartment is located in Chicago's Fulton Market district, known for its dining and nightlife, offering direct cityscape views.
This 1-bedroom, 1-bathroom condo accommodates up to 5 guests and features a full kitchen, air conditioning, internet, a fitness center, and common rooftop grilling stations.
Red Robin Rentals - Wicker Park - Chicago
8.2 67 reviews

Red Robin Rentals - Wicker Park

apartment, Chicago
This Chicago apartment rental is located in the Wicker Park neighborhood, just 2.9 miles from the United Center and 3.5 miles from Lincoln Park Zoo.
This 1,000 square foot apartment features a private garden, terrace, and barbecue facilities, along with free parking and Wi-Fi.
Cozy 3 Bedroom Apt Andersonville Neighborhood - Chicago
10 281 reviews

Cozy 3 Bedroom Apt Andersonville Neighborhood

apartment, Chicago
This charming Chicago apartment is located in the Andersonville neighborhood, just a short walk from Clark Street and its lively restaurants, shops, and bars. It has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travelers looking for a comfortable and convenient stay.
The apartment features three bedrooms and one bathroom, spanning 990 square feet, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a private patio, a shared laundry, and parking, offering everything you need for a relaxing and enjoyable stay in Chicago.

Frequently Asked Questions about short term rentals in Chicago

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

    You definitely want to check out the iconic Willis Tower, formerly known as Sears Tower, for panoramic city views. The Art Institute of Chicago is a must-see for art lovers, and Millennium Park is home to the famous Cloud Gate sculpture, affectionately known as 'The Bean.'
  • What are the best short term rentals in Chicago?

  • What's the best district to book a short term rental in Chicago?

    For short-term rentals in Chicago, the best district would be the Loop. It's the downtown area and offers proximity to major business centers, theaters, and cultural institutions.
  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has four distinct seasons. Summers are hot and humid, with temperatures often reaching the 80s. Winters are cold and snowy, with temperatures often below freezing. Spring and fall are mild and pleasant, with temperatures in the 50s and 60s.
  • What are the best short term rentals with a pool in Chicago?

  • What are the most affordable attractions to visit in Chicago?

    The most affordable attractions to visit in Chicago include exploring Millennium Park, visiting the Art Institute of Chicago on free admission days, and enjoying the scenic views from Navy Pier.
  • What are the most popular festivals and events in Chicago, IL?

    Chicago is known for its vibrant festival scene. The Chicago Blues Festival is a major event, and the Taste of Chicago is a great way to sample the city's diverse culinary offerings. The Lollapalooza music festival is a huge draw for music fans.
  • What are the best short term rentals with a jacuzzi in Chicago?

  • How accessible are attractions and amenities for families with strollers or wheelchairs in Chicago?

    Most attractions and amenities in Chicago are accessible for families with strollers or wheelchairs.
  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a major sports city. Wrigley Field is home to the Chicago Cubs baseball team, and Guaranteed Rate Field is home to the Chicago White Sox. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team.
  • What are the best short term rentals for families and kids in Chicago?

    The best short term rentals for families and kids in Chicago are 2bd/2ba Mag Mile Masterpiece (+Rooftop), Kasa South Loop Chicago and Sonder South Wabash.

  • Are popular attractions more affordable in off-peak season in Chicago?

    Popular attractions in Chicago may be more affordable in the off-peak season, which is typically during the winter months.
  • What notable natural landmarks are near Chicago, IL?

    The Indiana Dunes National Park is a short drive from Chicago and offers beautiful beaches, hiking trails, and scenic views of Lake Michigan. The Morton Arboretum is a great place to explore different types of trees and plants.
  • What are the top nightlife spots and party destinations in Chicago?

    For the best party travel experience in Chicago, head to River North for its upscale nightclubs and trendy bars. Wicker Park and Logan Square are also fantastic for a more laid-back, hipster vibe with plenty of dive bars and live music venues.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighborhood is a popular choice for its trendy restaurants, bars, and art galleries. The Magnificent Mile is another great option, with its upscale shopping and dining. If you're looking for a more budget-friendly option, consider staying in the Wicker Park or Bucktown neighborhoods.
  • What are the most popular festivals and events in Chicago for party lovers?

    For party lovers, Lollapalooza is a must-attend music festival held every summer in Grant Park. Chicago Pride Parade and Northalsted Market Days in Boystown are also huge events that draw lively crowds and offer a fantastic party atmosphere.
  • Are there any outdoor sports activities that one can participate in while visiting Chicago?

    While visiting Chicago, you can enjoy outdoor sports activities like kayaking on the Chicago River, biking along Lake Michigan, or playing beach volleyball at North Avenue Beach.

Popular destinations

Best Chicago Short term rentals with a jacuzzi

Among the 13281 accommodations in Chicago, here are the 4 best rentals with a jacuzzi

K2 Sky High Apartments With Stunning Chicago Views In West Loop - Chicago
9.6 353 reviews

K2 Sky High Apartments With Stunning Chicago Views In West Loop

apartment, Chicago
This Chicago apartment is located in the West Loop, a trendy neighborhood with restaurants, bars, and art galleries, just a mile and a half from Union Station and Willis Tower. The apartment has excellent ratings for location, cleanliness, and overall experience.
The apartment offers a comfortable and convenient stay with modern amenities, including a kitchen with a fridge, freezer, microwave, and dishwasher, plus a swimming pool, jacuzzi, and fitness center. Enjoy the outdoor space with a terrace or balcony, and relax with free WiFi and parking.
Level Two Bedroom Suite | Fulton Market - Chicago
9.7 42 reviews

Level Two Bedroom Suite | Fulton Market

apartment, Chicago
This West Loop Chicago apartment rental is steps from Fulton Market's restaurants and shops, a short distance from the Chicago Riverwalk, Willis Tower, and Soho House Chicago.
The two-bedroom, two-bathroom unit sleeps four guests and boasts amenities including a swimming pool, jacuzzi, fitness center, parking, and on-site guest services; bi-weekly housekeeping is included for extended stays.
Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop - Chicago
8.5 98 reviews

Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop

apartment, Chicago
This apartment is in the heart of Chicago, just a short walk from popular attractions like the CIBC Theatre, Willis Tower, and DePaul University. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The rental features a modern kitchen with a dishwasher, a comfortable living area, and a private bathroom. It can accommodate up to 5 guests and offers amenities like a swimming pool, jacuzzi, terrace, and free Wi-Fi.
Your Relaxing Space Away From Home - Chicago
9.8 83 reviews

Your Relaxing Space Away From Home

apartment, Chicago
This Chicago apartment is located in the Pullman area, a short walk from the Historic Pullman district, Illinois' first National Monument. The apartment has excellent ratings for location, cleanliness, and user experience.
This two-bedroom, one-bathroom rental can accommodate up to five guests. The apartment is fully equipped with a kitchen, a jetted bathtub, and a bar, offering everything needed for a comfortable stay.

Neighborhoods and points of interest in Chicago

Our Favorite Luxury Short-Term Rentals in Chicago

Live in the heart of the Gold Coast or Streeterville in rentals featuring floor-to-ceiling windows and high-end finishes. These units place you steps from the Magnificent Mile and Michelin-starred dining in the West Loop.

The Neighborhood Hotel-little Italy - Chicago
9.6 288 reviews

The Neighborhood Hotel-little Italy

aparthotel, Chicago
This 3.5-star Chicago Near West Side apartment hotel is located less than a mile from Rush University Medical Center and within three miles of the United Center and Millennium Park, offering easy access to public transportation.
Each apartment features a kitchenette with a refrigerator, stovetop, microwave, and dishwasher, plus a smart TV with satellite channels, a sitting area, and coffee/tea maker; on-site laundry facilities are also available.
Kasa South Loop Chicago - Chicago
9.4 3246 reviews

Kasa South Loop Chicago

aparthotel, Chicago
Kasa South Loop Chicago is located in the South Loop neighborhood, just a short walk from DePaul University and a quick drive from attractions like Willis Tower and the Art Institute of Chicago. The aparthotel has excellent ratings for location, cleanliness, and overall user experience.
The apartments are spacious and well-equipped with kitchens, seating areas, and private bathrooms. Guests can enjoy amenities like a swimming pool, fitness center, and a sun terrace, along with free Wi-Fi and a business center.
Kasa Lake Shore Chicago - Chicago
9.4 3 reviews

Kasa Lake Shore Chicago

aparthotel, Chicago
This aparthotel is located in Downtown Chicago, offering proximity to Ohio Street Beach, Michigan Avenue, and Lake Michigan, all within a 0.19-mile walk, with Grant Park and Navy Pier also a short distance away.
This lodging provides fully equipped kitchens, in-unit washers/dryers, and a rooftop terrace, with convenient access to public transportation and on-site self-parking.
Kasa Magnificent Mile Chicago - Chicago
9.2 1420 reviews

Kasa Magnificent Mile Chicago

aparthotel, Chicago
Kasa Magnificent Mile Chicago is located on the Magnificent Mile, a bustling shopping and dining district, just a short walk from the Shops at Northbridge, CIBC Theatre, and Millennium Station. This aparthotel boasts excellent user ratings for its location, cleanliness, and overall experience.
The apartment features modern amenities like a flat-screen TV, air conditioning, and a private bathroom. Guests can enjoy a terrace or balcony, a garden, a fitness center, and a restaurant.

Guest-Favorite Dog-Friendly Lodgings in Chicago

Book a stay near the off-leash areas of Grant Park or the shaded paths of Lincoln Park. These rentals provide immediate access to the Lake Michigan shoreline and pet-friendly cafes in neighborhoods like Wicker Park.

Iconic Journey | Navy Pier. Free Breakfast* - Chicago
No reviews

Iconic Journey | Navy Pier. Free Breakfast*

B&B, Chicago
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