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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.

Luxury Penthouse Collection Ph4 - Fulton Market - Chicago
10 5 reviews

Luxury Penthouse Collection Ph4 - Fulton Market

apartment, Chicago
This new penthouse is located in Chicago's Fulton Market district, placing you in a prime area for dining and nightlife with immediate access to the city's entertainment and business centers.
This 3-bedroom, 2-bathroom residence accommodates up to 10 guests and includes a private penthouse, private parking, and access to a building gym and common rooftop with city views.
Relaxation Retreat! 3 Modern Units, Near The Cove - Chicago
10 1 review

Relaxation Retreat! 3 Modern Units, Near The Cove

B&B, Chicago
This Chicago bed and breakfast boasts a prime downtown location near the Chicago River, within walking distance of numerous bars and restaurants and a short drive from Soldier Field, Wrigley Field, and the United Center.
Offering three spacious rooms, each with two queen beds and accommodating up to 12 guests, this inn features modern amenities including free Wi-Fi, a fitness center, a business center, and on-site dining at Hoyt's American Tavern.
Skyline 2br In South Loop Near Museums & Mccormick - Chicago
9.7 170 reviews

Skyline 2br In South Loop Near Museums & Mccormick

apartment, Chicago
This apartment is located in Chicago's South Loop, just a short walk from McCormick Place and a quick Uber ride to popular attractions like Soldier Field and the Museum Campus. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom suite offers 950 square feet of space, comfortably accommodating up to six guests. The apartment features a fully equipped kitchen, a fitness center, a terrace, a garden, and parking, providing everything you need for a relaxing and convenient stay in the Windy City.
Great Location Studio In The Gold Coast!! - Chicago
9.8 531 reviews

Great Location Studio In The Gold Coast!!

apartment, Chicago
This Gold Coast studio is a prime option for travelers seeking a central and well-rated accommodation in Chicago. Located in the heart of this upscale neighborhood, it offers easy access to Oak Beach, the Magnificent Mile, and the John Hancock Tower, all within a 5-minute walk.
The studio features a compact and cozy layout, ideal for solo travelers or couples. It includes a refrigerator, microwave, and coffee maker, as well as access to on-site laundry facilities. With excellent user, location, and cleanliness ratings, this studio provides a comfortable and convenient base for exploring Chicago's attractions and amenities.

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.

Regal Stylish Loft Rooftop|13 Mins Dt |4 Mins Lake - Chicago
9.4 111 reviews

Regal Stylish Loft Rooftop|13 Mins Dt |4 Mins Lake

apartment, Chicago
This one-bedroom, one-bathroom condo is located in Chicago's Uptown neighborhood, a 4-minute walk from the Lawrence Red Line station and close to Montrose Beach, Aragon Ballroom, and Riviera Theatre.
This pet-friendly apartment accommodates two guests and features a fully stocked modern kitchen, a dedicated workstation, Smart TV, in-unit washer/dryer, and access to a fitness center and rooftop with city views.
Welcome To Our 2-bed Apartment In West Town For 7! - Chicago
10 2 reviews

Welcome To Our 2-bed Apartment In West Town For 7!

apartment, Chicago
This 2-bedroom, 2-bathroom apartment in Chicago's West Town neighborhood is located less than 1 mile from the Medical District and West Loop, and approximately 3 miles from downtown Chicago.
This family-friendly unit accommodates up to 7 guests and features a fully equipped kitchen, in-unit laundry, central air conditioning, and complimentary high-speed Wi-Fi, with cafes, restaurants, and boutiques nearby.
Modern 2br W/ City View * Fast Wi-fi + Gym - Chicago
8.8 14 reviews

Modern 2br W/ City View * Fast Wi-fi + Gym

apartment, Chicago
This 2-bedroom, 1-bathroom condo is located just outside downtown Chicago, offering a 5-minute drive to McCormick Place and a 10-15 minute drive to The Loop, ideal for convention attendees and business travelers.
This family-friendly apartment accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, reliable Wi-Fi, a two-level fitness center, and one complimentary parking space.
Patio- 4 Br Northside Retreat Sleeps 12/ Parking - Chicago
9.6 263 reviews

Patio- 4 Br Northside Retreat Sleeps 12/ Parking

apartment, Chicago
This four-bedroom apartment is located in Lincoln Square, a lively neighborhood on Chicago's North Side, just a short walk from Lincoln Avenue with its shops and restaurants. The apartment has received excellent ratings for user experience, location, and cleanliness.
This spacious rental is perfect for families or groups of up to 12 guests. It offers a fully equipped kitchen, a private garden, parking, and access to all building amenities.

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

Spacious 7-br House For 13 Guests, Prime Location - Chicago
9.8 11 reviews

Spacious 7-br House For 13 Guests, Prime Location

apartment, Chicago
This centrally located 7-bedroom, 3-bathroom apartment in Chicago's prime district offers effortless access to key attractions like Millennium Park and the Art Institute of Chicago, situated within a short walk.
This spacious residence accommodates up to 13 guests and features air conditioning, a fully equipped kitchen with a dishwasher and microwave, a private jacuzzi, and on-site parking, making it an ideal base for exploring the city.
Stylish 2br With Skyline Views Near Riverwalk - Chicago
10 1 review

Stylish 2br With Skyline Views Near Riverwalk

apartment, Chicago
This downtown Chicago rental is a short walk from the Merchandise Mart and State Street, within 10 minutes of the Chicago Theatre and Willis Tower, offering easy access to public transportation via the Clark-Lake and Washington-Wells stations.
The two-bedroom, two-bathroom apartment sleeps four and includes a fully equipped kitchen with a dishwasher, in-unit laundry, a private balcony, and access to a building fitness center and indoor pool.
Modern Comfort In Roscoe Village - Chicago
9.8 32 reviews

Modern Comfort In Roscoe Village

apartment, Chicago
This 2-bedroom dwelling is located in Chicago's Roscoe Village, offering convenient public transit access to Wrigleyville and downtown Chicago.
This ground-floor apartment accommodates up to 4 guests and features air conditioning, internet, a kitchen, and free street parking, with nearby cafes and brunch spots.
Lux Apts With Lake Views And Top Amenities - Chicago
9.8 51 reviews

Lux Apts With Lake Views And Top Amenities

apartment, Chicago
This Chicago apartment rental boasts a central location near Grant Park, the Field Museum, and DePaul University, offering easy access to major attractions and Midway International Airport (10 miles away).
The two-bathroom unit features a private terrace, fully equipped kitchen (including a dishwasher and coffee maker), in-unit hot tub, free Wi-Fi, air conditioning, and access to a building swimming pool, jacuzzi, fitness center, bar, and parking, including an EV charging station.

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.

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.

Cute And Cozy Garden Apartment - Chicago
9.9 34 reviews

Cute And Cozy Garden Apartment

apartment, Chicago
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