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 Magnificent Mile Chicago - Chicago, IL
9.2 1517 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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 288 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 Lake Shore Chicago - Chicago, IL
9.4 3 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.
Kasa South Loop Chicago - Chicago, IL
9.4 3240 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.

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.

New Modern 3br, Gym, Workspace, Quiet Location - Chicago, IL
9.3 3 reviews

New Modern 3br, Gym, Workspace, Quiet Location

house, Dunning
This modern three-bedroom house is located in Chicago, approximately 6 kilometres from O'Hare International Airport and within a 16-21 kilometre radius of attractions such as Wrigley Field, Lincoln Park Zoo, the United Center, and Loyola University.
The 929-square-metre property offers ample space for up to eight guests, boasting a fully equipped kitchen, a jacuzzi, a fitness centre, and free Wi-Fi; its proximity to major Chicago landmarks makes it ideal for exploring the city.
Level One Bedroom Suite | Fulton Market - Chicago, IL
9.3 33 reviews

Level One Bedroom Suite | Fulton Market

apartment, Chicago
This West Loop studio apartment is ideally situated in Chicago's Fulton Market district, offering easy access to the city's many attractions.
The self-catering apartment sleeps three guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a private bathroom, plus access to a swimming pool, Jacuzzi, fitness centre, and parking (additional nightly fees apply).
Ray's Bucktown Bed And Breakfast - Chicago, IL
9.7 702 reviews

Ray's Bucktown Bed And Breakfast

B&B, Chicago
Ray's Bucktown Bed and Breakfast is located in the Bucktown neighbourhood of Chicago, just a short distance from the Congress Theater, DePaul University, Wrigley Field, and Lincoln Park Zoo. The B&B has excellent user, location, and cleanliness ratings.
Each room in the guesthouse has hardwood floors and a flat-screen TV, while some rooms also have a spa bath. Guests can enjoy a delicious breakfast delivered to their room, relax in the communal areas, or unwind in the sauna after a day exploring the city.
Private Room & Shared Bathroom | Work Desk - Chicago, IL
9.8 33 reviews

Private Room & Shared Bathroom | Work Desk

apartment, Chicago
This Chicago guest house is situated in the Avondale/Logan Square neighbourhood, conveniently close to the Kimball Blue Line station offering easy access to downtown Chicago and O'Hare International Airport.
The self-contained unit features a double bed, private patio, and access to a shared kitchen with fridge, microwave, and dishwasher; it sleeps one guest and offers a shared bathroom.

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.

Arcade  Theater  Gym  Office  Sleeps 15 - Chicago, IL
8.8 3 reviews

Arcade Theater Gym Office Sleeps 15

apartment, Chicago
This spacious flat is located in Chicago's Portage Park district, offering access to Lake Michigan and Millennium Park, approximately 10 kilometres away, with Michigan Avenue and Navy Pier also within a moderate distance.
This 231 square metre residence accommodates up to 15 guests across seven bedrooms and three bathrooms, featuring a fully equipped kitchen, an arcade room, a private cinema, a home gym, and on-site laundry facilities, with pets welcome.
Welcoming 3-bedroom House In Vibrant Chicago - Chicago, IL
8.8 5 reviews

Welcoming 3-bedroom House In Vibrant Chicago

apartment, Chicago
This Ukrainian Village flat, situated in Chicago's West Town district, is a short 800-metre walk to the United Centre and offers convenient access to downtown attractions, Millennium Park, and Lake Michigan.
This three-bedroom, two-bathroom apartment accommodates up to eight guests, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and a patio, with free street parking available.
Grace Place In Wrigleyville - Chicago, IL
10 106 reviews

Grace Place In Wrigleyville

apartment, Chicago
This first-floor apartment in Chicago's Wrigleyville neighbourhood is situated one block from Wrigley Field, offering easy access to the ballpark and the Red Line.
The 1-bedroom, 1-bathroom flat sleeps six guests comfortably, boasting a chef's kitchen, a gas fireplace, and a soaking tub and walk-in steam shower; nearby attractions include the Clark Street strip and Southport Corridor.
2 Bed Apt W/ Office, Free Parking, Near Wrigley - Chicago, IL
9.4 137 reviews

2 Bed Apt W/ Office, Free Parking, Near Wrigley

apartment, Chicago
This two-bedroom Chicago apartment is situated near Wrigleyville, a 15-minute walk from Wrigley Field, and within a 4.8-8 km radius of Lincoln Park Zoo, Water Tower Place, and the United Centre.
The 111 square metre flat offers a fully equipped kitchen, free parking, and amenities including a fireplace and patio, sleeping up to four guests comfortably.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Cozy 2br/1ba Garden Apartment Near Lincoln Square - Chicago, IL
9.3 345 reviews

Cozy 2br/1ba Garden Apartment Near Lincoln Square

apartment, Chicago
This garden-level flat is situated near Lincoln Square, a lively neighbourhood in Chicago, with a 5-minute walk to the Brown Line and easy access to local attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom home comfortably accommodates up to five guests and features a spacious living/dining area, a sunroom, and a fully equipped kitchen. The flat offers a shared laundry, free street parking, and Apple TV access, ensuring a comfortable and convenient stay.
Andersonville Garden Living - Chicago, IL
9.7 149 reviews

Andersonville Garden Living

apartment, Chicago
This Chicago garden flat, conveniently located off Clark Street near Coffee Studio and Little Bad Wolf, offers easy access to shops and restaurants.
The one-bedroom apartment sleeps three, boasting a brand-new kitchen and bathroom, two full-size beds (one in a private bedroom, one in a living room nook), two Ashley Furniture reclining leather couches, a smart TV with Netflix, private laundry access, and free street parking.
23rd Pl 2d - Chicago, IL
9.7 57 reviews

23rd Pl 2d

apartment, Chicago
This Chicago guesthouse is conveniently located near the University of Illinois Chicago campus and downtown Chicago, offering easy access to public transport and grocery stores.
The self-catering studio sleeps two, features a fridge, freezer, microwave, air conditioning, parking, and excellent guest reviews, promoting environmentally conscious practices.
Charming & Cozy 4bd Retreat Steps To Wrigley Field - Chicago, IL
9.8 50 reviews

Charming & Cozy 4bd Retreat Steps To Wrigley Field

apartment, Chicago
This Wrigleyville apartment, a five-minute walk from Wrigley Field and close to the Southport Corridor and Addison and Irving Park Red Line stations, offers easy access to Chicago's attractions.
Sleeping nine guests comfortably, this four-bedroom, two-bathroom property features a fully equipped kitchen, in-unit laundry, a private backyard, keyless entry, and free street parking permits; nearby, Wrigley Field hosts year-round events.

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.

Studio Flat In The Heart Of Downtown Chicago - Chicago, IL
9.4 294 reviews

Studio Flat In The Heart Of Downtown Chicago

studio, Chicago
Mccormick Apt 3br Corner Oasis Near Soldier Field - Chicago, IL
9.7 87 reviews

Mccormick Apt 3br Corner Oasis Near Soldier Field

apartment, Chicago
Upscale High-rise Apt · Rooftop Pool + Views - Chicago, IL
9.8 41 reviews

Upscale High-rise Apt · Rooftop Pool + Views

apartment, Chicago
2nd Floor Flat In River North - 2n - Chicago, IL
9.6 75 reviews

2nd Floor Flat In River North - 2n

apartment, Chicago
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