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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.

Livn West Loop Chicago Queen Superior Studio - Chicago
9.2 117 reviews

Livn West Loop Chicago Queen Superior Studio

studio, Chicago
This studio apartment is located in Chicago's West Loop, a 2-minute walk from Union Station and 0.4 miles from Willis Tower.
This 380 square foot studio offers air conditioning, complimentary WiFi, a full kitchen with a dishwasher and microwave, and accommodates up to 3 guests with an on-site fitness center.
Downtown Chicago Stay With Free In & Out Parking-2 - Chicago
9.8 8 reviews

Downtown Chicago Stay With Free In & Out Parking-2

apartment, Chicago
This 1,400 sq. ft. downtown Chicago condo offers excellent access to city attractions and includes free parking.
This spacious dwelling accommodates up to 10 guests with 4 bedrooms, 2 bathrooms, a fully equipped kitchen, and entertainment options like Netflix and Hulu.
New Private Apartment - Pilsen Downtown - Chicago
9.6 36 reviews

New Private Apartment - Pilsen Downtown

apartment, Chicago
This East Pilsen apartment offers easy access to downtown Chicago, Soldier Field, Grant Park, and the United Center, with convenient public transportation including the Metra, 'L' train, and Greyhound buses nearby.
The newly remodeled one-bedroom unit features a queen bed, full-size futon, fully equipped kitchen, and self check-in; it comfortably sleeps four guests and includes parking.
Downtown Mich Ave #10 | Gym+rooftop - Chicago
9.4 14 reviews

Downtown Mich Ave #10 | Gym+rooftop

apartment, Chicago
This penthouse apartment is located in downtown Chicago on Michigan Avenue, directly overlooking Grant Park and Lake Michigan, just a short walk from popular attractions like The Bean, Soldier Field, and the Art Institute of Chicago. The apartment has received excellent user ratings and offers convenient access to public transportation with the Red "L" subway just three blocks away.
This one-bedroom, one-bathroom apartment features a modern design with a spacious 600 square feet layout that can accommodate up to four guests. Enjoy amenities like a fully equipped kitchen, a private terrace, a shared rooftop deck with city views, and an on-site gym, along with convenient features like a washer and dryer in the unit, contact-free check-in, and pet-friendly accommodations.

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.

A Cosy One Bedroom With Independent Entry & Exit - Chicago
9.5 294 reviews

A Cosy One Bedroom With Independent Entry & Exit

apartment, Willow Springs
This Willow Springs guesthouse is conveniently located near a forest preserve with walking trails, easily accessible within a five-minute walk.
The one-bedroom, one-bathroom rental offers a private master suite with patio access, sleeps four guests, and includes amenities such as a coffee maker, mini-fridge, microwave, TV, and free driveway parking; a vegan-friendly environment is maintained.
Lincoln Park 3 Br Penthouse - Chicago
9.1 147 reviews

Lincoln Park 3 Br Penthouse

apartment, Chicago
This three-bedroom Lincoln Park penthouse offers stunning city views and is conveniently located near Fullerton Beach (1.5 miles), North Avenue Beach (1.6 miles), and Wrigley Field (1.3 miles).
The 1780-square-foot residence boasts a spacious layout, accommodating up to 11 guests, with a fully equipped kitchen, private balcony, terrace, garden access, on-site parking, and a tennis court.
Duplex 3 Bed 2 Bat Apt Steps From Lincoln Square - Chicago
8.6 8 reviews

Duplex 3 Bed 2 Bat Apt Steps From Lincoln Square

apartment, Chicago
This three-bedroom Chicago duplex is located in Lincoln Square, 2.3 miles from Wrigley Field and 4.6 miles from Lincoln Park Zoo.
The 1300-square-foot rental boasts two living rooms, accommodates up to 10 guests, and includes a private balcony, free parking, and Wi-Fi.
The Blue Room - Chicago
9.7 586 reviews

The Blue Room

apartment, Chicago
This charming bed and breakfast is conveniently located near Midway Airport, within easy walking distance of parks, supermarkets, and convenience stores, making it a great base for exploring Chicago. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cozy guesthouse offers a comfortable bedroom with a walk-in closet and a fully equipped kitchen, perfect for couples or solo travelers. Enjoy the home theater system with a 42" LCD TV, Bluetooth connectivity, and speakers in every corner, ideal for relaxing evenings.

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

The Gathering House & Cinema - Chicago
9.7 6 reviews

The Gathering House & Cinema

apartment, Elmhurst
This 6-bedroom home is located in a residential neighborhood in Elmhurst, offering a private retreat just a short drive from Elmhurst's downtown area with its restaurants and shops.
This residence features a private pool and jacuzzi, a home theater, a billiard room, a chef-ready kitchen, and a spacious backyard with a paver patio and grill, accommodating up to 12 guests.
Designer 3br With Resort Amenities And Balcony - Chicago
9.8 13 reviews

Designer 3br With Resort Amenities And Balcony

apartment, Chicago
This downtown Chicago condo offers prime access, located a 5-minute walk from the Museum of Contemporary Art and a 10-minute walk to the Magnificent Mile.
This family-friendly residence features 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests with amenities including a private balcony, a full kitchen, air conditioning, a swimming pool, hot tub, fitness center, and on-site parking.
Top Floor Views + Central Comfort - Chicago
10 103 reviews

Top Floor Views + Central Comfort

apartment, Chicago
This top-floor Chicago condo provides spectacular skyline views, located a 4-minute walk from Union Station and an 8-minute walk from Willis Tower.
This modern 2-bedroom, 2-bathroom apartment sleeps up to 6 guests and features a designer kitchen, access to a fitness center and outdoor sky terrace, and is a 10-minute walk to the Chicago Riverwalk and a 15-minute walk to Millennium Park.
Chicagochinatowncenterb - Chicago
9.9 64 reviews

Chicagochinatowncenterb

apartment, Chicago
This Chinatown Chicago guesthouse is a one-minute walk from the bus station, two minutes from the Red Line, and a twenty-minute walk from McCormick Place.
The one-bedroom apartment, designed by a Stanford-trained artist, features a full kitchen with a range hood, ovens, microwave, and rice cooker, plus high-speed Wi-Fi (300-500 Mbps), air conditioning, a Jacuzzi, and free street parking (availability may vary).

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
8.4 25 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 1572 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
9.6 322 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 3281 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.

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.

Spacious 4br Condo | Pool Table | Near Mccormick - Chicago
9.1 26 reviews

Spacious 4br Condo | Pool Table | Near Mccormick

apartment, Chicago
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