Chicago, IL Short term rentals

13281 available short term rental offers

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Chicago, IL short term rentals
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Best Short term and Weekly rentals in Chicago, IL

Top-Rated Short-Term Rentals in the Old Town of Chicago, IL

Stay footsteps from popular independent bistros and excellent transit connections at central short-term rentals in Chicago, IL.

Apt In The Heart Of Loop - Chicago, IL
9.3 48 reviews

Apt In The Heart Of Loop

apartment, Chicago
This two-bedroom, two-bathroom Chicago apartment enjoys a prime downtown location, within easy walking distance of Millennium Park and Cloud Gate ("The Bean"), and a short stroll from State Street and Lake Michigan's lakeshore.
The 8-guest dwelling boasts a modern, renovated interior, including a fully equipped kitchen with dishwasher, air conditioning, and access to a fitness centre; nearby parking is readily available, and a noise monitoring system ensures a peaceful stay.
Spacious 2br Apartment Steps From Uic Rush Stroger Hospital And Restaurant Row - Chicago, IL
10 1 review

Spacious 2br Apartment Steps From Uic Rush Stroger Hospital And Restaurant Row

apartment, Chicago
This flat offers immediate proximity to UIC Rush Stroger Hospital, located in the West Fillmore Street area, and is a short distance from Restaurant Row, the Chicago Theatre, and Grant Park.
This spacious two-bedroom, two-bathroom flat, spanning 102 square metres, accommodates up to seven guests and features a fully equipped kitchen, a kitchenette, an in-unit washing machine, and a private balcony.
Modern Minimalist Studio | Heart Of Gold Coast - Chicago, IL
9.4 31 reviews

Modern Minimalist Studio | Heart Of Gold Coast

apartment, Chicago
This studio flat is situated in Chicago's Gold Coast district, a mere 500 metres from Oak Street Beach and a 1.4 kilometre walk to the Magnificent Mile, with the Art Institute of Chicago approximately 1.2 kilometres away and Rush Street dining and bars just 500 metres distant.
This accommodation welcomes pets, offers air conditioning, a kitchen with a fridge and microwave, and provides a dedicated workspace with WiFi, accommodating up to two guests.
50th Floor Mag Mile Views, Balcony, Pool, Gym - Chicago, IL
10 43 reviews

50th Floor Mag Mile Views, Balcony, Pool, Gym

apartment, Chicago
This Downtown Chicago penthouse, situated between North Michigan Avenue and the River North district, offers easy access to Millennium Park and the Art Institute of Chicago.
The 68-square-metre (732 sq ft) apartment features one bedroom, one bathroom, and sleeps two guests, boasting a terrace, swimming pool, and on-site parking, alongside stunning 50th-floor city views.

Check Out Family-Friendly Holiday Lets in Chicago, IL

Getting the accommodation right makes all the difference for a family trip to Chicago, IL. City attractions within easy reach at these options.

Luxury House 4-bed 2.5-bath Near Chicago Downtown - Chicago, IL
9.9 171 reviews

Luxury House 4-bed 2.5-bath Near Chicago Downtown

apartment, Chicago
This spacious house is located in North Park, a safe and convenient neighbourhood with restaurants, supermarkets, and parks within walking distance, and is about 16km from O'Hare Airport. The property has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
This 3000 square metre home has 6 bedrooms, although only 4 are available for guests, and features an open kitchen, living room, and dining room. Guests can enjoy a private garden, modern amenities such as a laundry room and multiple bathrooms, and convenient access to public transport.
Fully Stocked Kitchen And Easy Parking - Charming Modern Suite - Chicago, IL
No reviews

Fully Stocked Kitchen And Easy Parking - Charming Modern Suite

apartment, Chicago
This Lincoln Park flat offers a prime Chicago location, situated directly opposite the well-known Birds Nest bar and restaurant, with easy access to city attractions.
This accommodation provides two bedrooms, sleeping up to eight guests, with a fully equipped kitchen, air conditioning, and complimentary Wi-Fi, all within 3.5 kilometres of central Chicago.
Cozy, Central Location, Studio, Parking For 4 - Chicago, IL
9.9 196 reviews

Cozy, Central Location, Studio, Parking For 4

apartment, Oak Park
This Oak Park garden apartment is situated 0.5km from the Green Line CTA station, offering easy access to Chicago and proximity to the Ernest Hemingway Birthplace Museum and Frank Lloyd Wright Home and Studio.
The 65-square-metre open-plan flat sleeps four guests, featuring three beds, a kitchenette, on-site parking, and kid-friendly amenities including a travel cot, high chair, and toys, plus access to a nearby urban farm.
4 Br  Theater Room  Gym  Walk To Lincoln Park! - Chicago, IL
9.7 63 reviews

4 Br Theater Room Gym Walk To Lincoln Park!

apartment, Chicago
This Old Town Chicago house, situated on a tree-lined street, is within a 3-5 minute drive (approximately 2.4-4 km) of Lincoln Park Zoo, the Immersive Van Gogh Exhibit, North Avenue Beach, and the Chicago History Museum.
This four-bedroom, two-bathroom dwelling sleeps up to twelve guests and boasts two living areas with Smart TVs, a full kitchen with high-end appliances, basement amenities including laundry facilities and games, plus free parking and family-friendly extras (pack 'n play, high chair, children's dinnerware available on request).

Frequently asked questions about short term rentals in Chicago, IL

  • Which top landmarks you shouldn't miss in Chicago, IL?

    You definitely want to see the iconic Willis Tower, formerly known as the Sears Tower, and the impressive Art Institute of Chicago. And don't forget to take a stroll along Navy Pier, especially at night when the lights come on.
  • 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 averaging around 25°C. Winters are cold and snowy, with temperatures often dropping below freezing. Spring and autumn are mild and pleasant, with temperatures ranging from 10°C to 20°C.
  • 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 known for its vibrant festivals and events. Some popular ones include the Chicago Blues Festival, the Lollapalooza music festival, and the Taste of Chicago food festival. There's also the Chicago Air and Water Show, which takes place every August.
  • 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! You've got Wrigley Field, home to the Chicago Cubs baseball team, and Guaranteed Rate Field, home to the Chicago White Sox. And for basketball fans, there's the United Center, home to both the Chicago Bulls and the Chicago Blackhawks.
  • What are the best short term rentals for families and kids in Chicago, IL?

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from Chicago, you can find Indiana Dunes National Park, which features sandy beaches, towering dunes, and a variety of wildlife. You can also visit the Morton Arboretum, a beautiful botanical garden with over 1,700 species of trees and plants.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighbourhood is popular with travellers, offering a mix of hotels, restaurants, and art galleries. If you're looking for something more budget-friendly, the Lincoln Park area has a good selection of hotels and hostels.

Popular destinations

Browse Holiday Lets with a Jacuzzi in Chicago, IL

These short-term lets in Chicago, IL come with a hot tub or jacuzzi, ideal for a relaxing hot tub soak at the end of a long day exploring.

Lakeview 2b1b Vacation Home With Kitchen & W/d - Chicago, IL
9.9 188 reviews

Lakeview 2b1b Vacation Home With Kitchen & W/d

apartment, Chicago
This West Lakeview, Chicago flat is a two-minute walk from Hamlin Park, offering easy access to local amenities and green space.
The 2-bedroom, 1-bathroom apartment sleeps 6, features a brand-new kitchen with marble countertops, a furnished patio, and amenities including Wi-Fi, Netflix, and a Jacuzzi, perfect for families exploring Chicago.
Luxe 1br: Unmatched Views & Location - Chicago, IL
10 1 review

Luxe 1br: Unmatched Views & Location

apartment, Chicago
This River West apartment, situated in the West Town district of Chicago, offers convenient access to the Chicago Academy for the Arts and Ogden International High School.
The 93 square metre one-bedroom flat sleeps four, boasting a fully equipped kitchen with high-end appliances (Cuisinart, Nespresso, KitchenAid, Henckels, Bodum, and OXO), a 75” TV and Sonos sound system, plus building amenities including a gym, yoga studio, pool, and hot tub.
Sky-high 3br Penthouse In West Loop - Chicago, IL
10 4 reviews

Sky-high 3br Penthouse In West Loop

apartment, Chicago
This four-bedroom, two-bathroom apartment in downtown Chicago is situated less than 1.6km from Milwaukee Avenue and the Merchandise Mart, and under 3.2km from the Chicago Riverwalk and Michigan Avenue, offering easy access to public transport.
The 8-guest dwelling boasts a fully equipped kitchen, balcony, garden access, on-site fitness centre, and is within 1.6km of the University of Illinois Chicago; laundry facilities and barbecue grills are also available.
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests - Chicago, IL
9.4 27 reviews

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests

apartment, Chicago
Mayor's Manor, a spacious apartment in Chicago's Bridgeport neighbourhood, offers convenient access to local amenities and is within a reasonable distance of attractions such as Michigan Avenue, Navy Pier, and the Field Museum.
This 186-square-metre (1999 square-foot) property boasts four bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, a game room with projector screens, an in-house bar, a large deck with a hot tub, and a private garden; nearby activities include boating, swimming and rock climbing.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL luxury short term rentals

Kasa Lake Shore Chicago - Chicago, IL
8.2 30 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 Magnificent Mile Chicago - Chicago, IL
9.2 1582 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.
Kasa South Loop Chicago - Chicago, IL
9.4 3284 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
9.6 327 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.

Best Short-Term Rentals with Parking in Chicago, IL

Parking is sorted from the start. Every short-term let in Chicago, IL includes free on-site spaces.

Near Downtown Nest - Chicago, IL
9.4 5 reviews

Near Downtown Nest

apartment, Chicago
The Oakley - Cozy Retreat In Prime Location - Chicago, IL
9.9 30 reviews

The Oakley - Cozy Retreat In Prime Location

apartment, Chicago
5 Star Epicurean Experience With Hip, Modern, Gazebo With Bbq Grill & Sleeps 16 - Chicago, IL
10 9 reviews

5 Star Epicurean Experience With Hip, Modern, Gazebo With Bbq Grill & Sleeps 16

apartment, Chicago
Walkable Logan! Spa Shower, Dining Destination - Chicago, IL
9.9 500 reviews

Walkable Logan! Spa Shower, Dining Destination

apartment, Chicago

Our Favourite Pet-Friendly Short-Term Rentals in Chicago, IL

Explore with your best friend by your side; book a pet-friendly short-term rental in Chicago, IL that feels like a home away from home for you both.

1 Br&1bath/lakeview/lincolnpark/close To Wrigley - Chicago, IL
9.4 16 reviews

1 Br&1bath/lakeview/lincolnpark/close To Wrigley

apartment, Chicago
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