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 Lake Shore Chicago - Chicago, IL
8.4 25 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 3281 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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 322 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 Magnificent Mile Chicago - Chicago, IL
9.2 1572 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.

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.

Front Row To The Lake & Skyline: Epic 60th Flr 3br - Chicago, IL
10 46 reviews

Front Row To The Lake & Skyline: Epic 60th Flr 3br

apartment, Chicago
This luxurious three-bedroom apartment, sleeping up to seven guests, is situated in Chicago's downtown cultural district, offering spectacular Lake Michigan and Grant Park views, close to South Michigan Avenue.
The 60th-floor flat boasts a private balcony with NASCAR race views, a fully equipped kitchen including a dishwasher, access to a swimming pool, Jacuzzi, fitness centre, and parking, plus complimentary Nespresso coffee and tea.
Scenic 3br Ph For Tourism + Prime Location - Chicago, IL
10 2 reviews

Scenic 3br Ph For Tourism + Prime Location

apartment, Chicago
This River West penthouse apartment, located in West Town, Chicago, offers easy access to Logan Square and Fulton Market, and is near the Chicago Academy for the Arts and Ogden International High School.
This 178 square metre three-bedroom, three-bathroom dwelling boasts two balconies with city views, a 75-inch TV, Sonos sound system, and access to a 24-hour gym, yoga studio, outdoor pool, and hot tub within the building, sleeping up to seven guests.
Relaxing 2br Apartment In Lively West Rogers Park - Chicago, IL
9.4 3 reviews

Relaxing 2br Apartment In Lively West Rogers Park

apartment, Chicago
This two-bedroom flat is situated in West Rogers Park, a quiet neighbourhood on Chicago's north side, just 30 minutes from downtown and a short distance from Lake Michigan. The area offers a diverse range of restaurants, shops, and parks within walking distance.
The flat is spacious and comfortable, with two large bedrooms, a bathroom, and a well-equipped kitchen, suitable for up to four guests. It comes with modern amenities such as a 55-inch smart TV, fast Wi-Fi, air conditioning, and a Jacuzzi, ensuring a relaxing and enjoyable stay.
Spacious Apt/comfy Bed/free Parking/22mins To Ord&mdw - Chicago, IL
9.6 20 reviews

Spacious Apt/comfy Bed/free Parking/22mins To Ord&mdw

apartment, Berwyn
This one-bedroom flat is conveniently situated in Berwyn, just a short drive from Oak Park, Little Village, and the Chicago Zoo, offering easy access to a range of attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The flat features a fully equipped kitchen with a microwave, fridge, coffee maker, and tea, allowing guests to prepare their own meals. Guests can enjoy the convenience of on-site laundry facilities, free parking, and a comfortable living space with a 50-inch TV, offering access to streaming services such as YouTube TV, Netflix, and Hulu.

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.

Modern Chicago Getaway  Sleeps 6  Near Downtown - Chicago, IL
9.2 149 reviews

Modern Chicago Getaway Sleeps 6 Near Downtown

apartment, Chicago
This Bronzeville apartment rental is situated in Chicago's South Side, a 3.4km drive from Guaranteed Rate Field and within 6km of the Museum of Science and Industry.
The three-bedroom, family-friendly flat boasts a fully equipped kitchen, private parking, a Jacuzzi, and a garden, sleeping up to six guests and offering easy access to Chicago's cultural attractions.
Prime Avondale - Chicago, IL
9.9 7 reviews

Prime Avondale

B&B, Chicago
Prime Avondale, a guesthouse in Chicago's Avondale neighbourhood, is situated under 5km from Wrigley Field, Lincoln Park Zoo, and the United Centre.
This Chicago B&B offers one bedroom, one bathroom, sleeps seven guests, and includes free Wi-Fi, parking, and air conditioning.
Stylish, Inviting 2-br Near Logan Square And Wrigley Field - Chicago, IL
10 87 reviews

Stylish, Inviting 2-br Near Logan Square And Wrigley Field

apartment, Chicago
This Avondale apartment, near three Blue Line stations and the I-90/94 expressway, offers easy access to Chicago's attractions and is within walking distance of Logan Square.
The two-bedroom, one-bathroom flat sleeps four, features a recently upgraded kitchen with dishwasher and microwave, a garden, on-site parking and is situated in a classic Chicago Greystone building with original wooden floors.
North Center - Modern, Safe, Family-friendly, Solar-powered Apartment - Chicago, IL
9.9 326 reviews

North Center - Modern, Safe, Family-friendly, Solar-powered Apartment

apartment, Chicago
This two-bedroom flat is situated in a quiet neighbourhood just a short distance from Wrigleyville, a lively area with restaurants, bars, and Wrigley Field. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 93 square metre flat comfortably accommodates up to six guests and features a modern kitchen, a bathroom, and a terrace. Amenities include a fridge, freezer, microwave oven, dishwasher, air conditioning, internet access, and a garden.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

North Side Pied-à-terre - Chicago, IL
9.5 303 reviews

North Side Pied-à-terre

apartment, Chicago
This top-floor Chicago flat is situated in a classic neighbourhood near Wrigley Field and the Paulina Brown Line 'L' station, offering easy access to Chicago's attractions.
The two-bedroom, one-bathroom apartment sleeps four, features a king-size bed, a vinyl record collection, and basic Wi-Fi, alongside a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
Eddy Street Upstairs Apartment - Chicago, IL
9.9 176 reviews

Eddy Street Upstairs Apartment

B&B, Chicago
This one-bedroom Chicago apartment is situated in the Portage Park neighbourhood, less than 16km from O'Hare International Airport and roughly 20km from the city centre.
The self-contained flat, sleeping up to three guests, offers a queen bed, a queen air mattress, free on-street parking, shared laundry facilities, and is conveniently located near Portage Park with its dog park and multiple bus routes; it’s also 420-friendly (outdoor smoking only).
Charming Andersonville Garden 1 Bdrm W/parking. - Chicago, IL
9.8 298 reviews

Charming Andersonville Garden 1 Bdrm W/parking.

apartment, Chicago
This one-bedroom Chicago apartment is located in the Edgewater/Andersonville neighbourhood, offering easy access to Lake Michigan and its attractions.
The 65-square-metre flat features a fully equipped kitchen, a comfortable living area with a smart TV, and accommodates up to three guests, with on-site laundry facilities and assigned parking.
Mccormick Place Huge 2br Cozy Loft Suite With Optional Parking Sleeps 8 Near Soldier Field And Grant Park - Chicago, IL
9.2 15 reviews

Mccormick Place Huge 2br Cozy Loft Suite With Optional Parking Sleeps 8 Near Soldier Field And Grant Park

apartment, Chicago
This Chicago McCormick Place loft is situated near the Museum Campus, approximately 2.4 kilometres from the Field Museum and 2.9 kilometres from the Art Institute of Chicago.
This spacious two-bedroom, two-bathroom apartment, offering 102 square metres of floor area, sleeps up to eight guests and boasts amenities including free Wi-Fi, on-site parking, and a fully equipped kitchen; nearby attractions include DePaul University and the Chicago Symphony Orchestra.

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.

Luxury Oasis | 1 Br | Near City | Free Parking - Chicago, IL
9.0 60 reviews

Luxury Oasis | 1 Br | Near City | Free Parking

apartment, Chicago
Kasa | Spectacular City Views | Chicago - Chicago, IL
9.5 1391 reviews

Kasa | Spectacular City Views | Chicago

apartment, Chicago
Studio Flat In The Heart Of Downtown Chicago - Chicago, IL
9.4 298 reviews

Studio Flat In The Heart Of Downtown Chicago

studio, Chicago
2 Pet-friendly Units! Near Chicago Riverwalk - Chicago, IL
9.5 16 reviews

2 Pet-friendly Units! Near Chicago Riverwalk

B&B, Chicago
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