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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.

Garden Apartment In The Historic Heart Of The City - Chicago
9.8 283 reviews

Garden Apartment In The Historic Heart Of The City

apartment, Chicago
This apartment is located in a quiet block near the lively Madison/Randolph Street nightlife, Little Italy, Greek Town, and the United Center, making it easy to explore the city's diverse neighborhoods. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The rental unit features a spacious living area that extends into the kitchen, comfortably accommodating up to four guests. Amenities include a private backyard with a rock garden and fountain, a stone-covered bathroom with a tub, and ample closet space.
Kasa | Spectacular City Views | Chicago - Chicago
9.5 1391 reviews

Kasa | Spectacular City Views | Chicago

apartment, Chicago
This one-bedroom Chicago apartment boasts a prime downtown location, steps from Oak Street Beach and a short walk from Michigan Avenue's Magnificent Mile and Millennium Park.
The 1-bathroom unit sleeps 3 guests and features a full kitchen with dishwasher, in-unit laundry, and self check-in, plus access to a fitness center, garden, and parking.
Livn West Loop Chicago Classic Studio Apartment - Chicago
9.7 103 reviews

Livn West Loop Chicago Classic Studio Apartment

apartment, Chicago
This urban loft retreat is located in Chicago's West Loop, a short walk from Union Station and Willis Tower, offering easy access to dining and transit.
This newly renovated studio apartment accommodates up to 2 guests and features a fully equipped kitchen, in-unit washer and dryer, and air conditioning, with ADA rooms available by request.
Apt In The Heart Of Loop - Chicago
9.3 48 reviews

Apt In The Heart Of Loop

apartment, Chicago
This downtown Chicago apartment offers prime access to Millennium Park, Cloud Gate ("The Bean"), and State Street, all within walking distance of the Lake Michigan lakefront.
The two-bedroom, two-bathroom unit sleeps eight guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, and a fitness center, plus 24/7 building access and nearby parking options.

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.

The Logan Greystone - Chicago
10 77 reviews

The Logan Greystone

apartment, Chicago
This Logan Square, Chicago apartment is a 7-minute walk from the Logan Square Blue Line station, offering easy access to O'Hare Airport and downtown.
The three-bedroom, one-bathroom unit sleeps six, features a fully equipped kitchen with a Keurig coffee station, in-unit laundry, and a private patio deck, plus family-friendly amenities like a pack 'n play and high chair.
Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown - Chicago
9.4 6 reviews

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

apartment, Chicago
This 2400 sq ft Irving Park residence offers a spacious 5-bedroom, 3-bathroom layout, accommodating up to 14 guests with a chef's kitchen, game room, and multiple smart TVs, located a 15-25 minute Uber ride from Chicago landmarks like Wrigley Field, Millennium Park, and the United Center. This family-friendly house features high-speed Wi-Fi, air conditioning, and parking, with a fully-equipped kitchen including a fridge, microwave, and dishwasher, ensuring a comfortable stay.
Newly Remodeled Gem | Heart Of Chicago - Chicago
9.9 32 reviews

Newly Remodeled Gem | Heart Of Chicago

apartment, Chicago
This Humboldt Park apartment rental offers easy access to the 606 Trail and CTA buses, with a 20-minute drive to downtown Chicago and convenient proximity to O'Hare and Midway airports.
The two-bedroom, one-bathroom unit sleeps four guests and includes a fully equipped kitchen, free street parking with permit, and a garden; enjoy nearby shops, restaurants, and parks.
Go Grand In This Massive Old Town Mansion - Sleeps 22! Apts - Chicago
9.6 226 reviews

Go Grand In This Massive Old Town Mansion - Sleeps 22! Apts

apartment, Chicago
This 8-bedroom condo is located in Old Town, just steps from Wells Street and the beach. The apartment is highly rated for its cleanliness, location, and overall experience.
The apartment is perfect for large groups or families, accommodating up to 16 guests. Amenities include free internet, a kitchen with a fridge and microwave, parking, and a pet-friendly policy.

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

Wrigleyville Condo, Sleeps 10, 1/2 Block From Wrigley Field - Chicago
10 132 reviews

Wrigleyville Condo, Sleeps 10, 1/2 Block From Wrigley Field

apartment, Chicago
This Wrigleyville apartment is located just half a block from Wrigley Field and Clark Street, within walking distance of the Southport corridor and the Brown Line, and a ¾ mile walk from Lake Michigan. It's close to the action but also offers a peaceful retreat in a lively neighborhood. Guests consistently rate this apartment excellent.
This 3-bedroom, 3-bathroom apartment offers 1100 square feet of space and comfortably accommodates up to 6 guests. Enjoy a fully equipped kitchen, a jacuzzi tub, a steam shower, a lower-level living area, four TVs with streaming capabilities, free Wi-Fi, and parking passes.
West Loop Ph: Unmatched Views & Private Deck - Chicago
10 4 reviews

West Loop Ph: Unmatched Views & Private Deck

apartment, Chicago
This West Loop penthouse is located in Chicago's Fulton Market District, a 10-15 minute walk from Ogilvie Transportation Center, Union Station, and the Chicago Riverwalk.
This 2,010-square-foot luxury condo offers three bedrooms, three bathrooms, sleeps eight guests, and boasts a private deck with skyline views, plus building amenities including a pool, fitness center, and movie theater.
The Velvet Manor | Luxe 3br  Jacuzzi  Garage - Chicago
10 5 reviews

The Velvet Manor | Luxe 3br Jacuzzi Garage

apartment, Chicago
This 3-bedroom, 1-bathroom rental unit is located in Chicago's Andersonville neighborhood, offering moody, boutique-hotel interiors and convenient street parking.
This spacious accommodation sleeps up to 8 guests, with a king primary bedroom, two queen bedrooms, and two twin rollaway beds available upon request, featuring a full kitchen with a fridge, microwave, and dishwasher, plus air conditioning and a private garage parking space.
Irving Park/avondale Updated Vintage Top Unit - Chicago
9.9 105 reviews

Irving Park/avondale Updated Vintage Top Unit

apartment, Chicago
This Chicago apartment rental is conveniently located near Wrigley Field, a 10-minute drive from the stadium, with easy access to I-90/94 and the Blue Line.
The two-bedroom unit, sleeping up to six guests, boasts a private balcony, shared backyard (under renovation to include a fire pit and pizza oven), a full kitchen with dishwasher, and central air conditioning; plus free street parking.

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.

Kasa Lake Shore Chicago - Chicago
8.2 30 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 South Loop Chicago - Chicago
9.4 3284 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 Magnificent Mile Chicago - Chicago
9.2 1582 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.
The Neighborhood Hotel-little Italy - Chicago
9.6 327 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.

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.

Amazing River North Jr 1br W/ Game Room, Nr Beach & L, By Blueground - Chicago
No reviews

Amazing River North Jr 1br W/ Game Room, Nr Beach & L, By Blueground

apartment, Chicago
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