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Chicago, IL Short term rentals

13281 available short term rental offers

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Best Short term and Weekly rentals in Chicago, IL

Kng+qn Bedrooms+office/by Dt/walk To Restaurants - Chicago, IL
9.6 68 reviews
Chicago, IL
4 3
NZ$462/nighttotal: NZ$924 (2 )

Kng+qn Bedrooms+office/by Dt/walk To Restaurants

apartment - Chicago
This Logan Square flat is conveniently located near restaurants, the Bloomingdale Trail (the 606), and a grocery store, all within a 0.6km walk.
The newly renovated two-bedroom apartment, sleeping five, boasts espresso hardwood floors, a private patio, free parking, and a shared laundry room serving only four units, with easy access to public transport for downtown Chicago and O'Hare International Airport.
Spacious 3br/2ba 15 Mins To Obama Library - Chicago, IL
9.2 34 reviews
Chicago, IL
5 3
NZ$507/nighttotal: NZ$14703 (29 )

Spacious 3br/2ba 15 Mins To Obama Library

apartment - Chicago
This Georgian-style house, sleeping up to 12 guests, enjoys a convenient location near Chicago's highway network, with shopping centres and restaurants readily accessible.
The three-bedroom, two-bathroom property features an open-plan kitchen, dining, and living area, a backyard deck, driveway parking for up to five vehicles (additional fee applies), and four Smart/Roku TVs, making it ideal for family groups or large parties.
Garden Apartment In Historic Pilsen Arts Area - Chicago, IL
9.8 74 reviews
Chicago, IL
2 1
NZ$246/nighttotal: NZ$738 (3 )

Garden Apartment In Historic Pilsen Arts Area

apartment - Chicago
This Pilsen flat, in Chicago's Mexican heritage neighbourhood, offers convenient access to local taquerias and cultural attractions.
The self-catering apartment features a newly remodelled bathroom, a pull-out sofa accommodating four guests, high-speed Wi-Fi, and a private garden.
A Hand-some Place  Vintage 1br Near Wrigley - Chicago, IL
9.8 152 reviews
Chicago, IL
2 1
NZ$696/nighttotal: NZ$2088 (3 )

A Hand-some Place Vintage 1br Near Wrigley

apartment - Chicago
This Chicago flat is situated in a peaceful area, a 1.6km walk from the Montrose Brown Line station and 3.2km from Wrigley Field.
The ground-floor one-bedroom apartment sleeps two, features a large kitchen (by Chicago standards), high-quality bedding, and includes free membership to The Metropolitan co-working space in the Willis Tower.
The Exclusive- 7 Bed, 6 Bath Retreat - Chicago, IL
9.8 104 reviews
Chicago, IL
14 7
NZ$1512/nighttotal: NZ$4536 (3 )

The Exclusive- 7 Bed, 6 Bath Retreat

apartment - Chicago
This seven-bedroom, six-bathroom apartment in Chicago's Wicker Park neighbourhood is a two-minute walk from the Blue Line 'L' train station and under 0.12km from a pay-and-display car park, offering easy access to the city centre.
Sleeping up to fourteen guests, this spacious property comprises two kitchens, two living areas, and nine beds across two combined units, plus free drinks at the adjacent Wave Sushi restaurant for groups of six or more, and dedicated parking for two cars.
Midcentury, Comfy 2bed/2bath - Chicago, IL
10 52 reviews
Chicago, IL
3 2
NZ$451/nighttotal: NZ$3157 (7 )

Midcentury, Comfy 2bed/2bath

apartment - Chicago
This spacious Logan Square flat is situated in a peaceful yet convenient neighbourhood, close to numerous restaurants and bars, offering easy access to other areas of Chicago.
The 167 sq m two-storey dwelling boasts two bedrooms with high-quality beds (Saatva king, Brooklyn Bedding queen), two bathrooms, a chef's kitchen, a private balcony, a mini-gym, a multi-cade arcade machine, and parking, accommodating up to six guests.
Spaulding Oasis On 4 Lots In Humboldt Park! - Chicago, IL
9.7 133 reviews
Chicago, IL
3 2
NZ$374/nighttotal: NZ$2618 (7 )

Spaulding Oasis On 4 Lots In Humboldt Park!

apartment - Chicago
This two-bedroom apartment is situated in a peaceful part of Chicago, just a short distance from a church and with no immediate neighbours, offering a tranquil setting. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The property provides ample space for up to five guests and features a fully equipped kitchen with a dishwasher, as well as a spacious garden with a fire pit and a large vegetable patch. Guests can enjoy a variety of amenities, including central heating and air conditioning, a smart TV, and a private outdoor area perfect for relaxing or hosting small events.
Stylish And Comfy Retreat 10 Minutes From Wrigley - Chicago, IL
9.5 313 reviews
Chicago, IL
4 2
NZ$280/nighttotal: NZ$1960 (7 )

Stylish And Comfy Retreat 10 Minutes From Wrigley

apartment - Chicago
This two-bedroom flat is located in Lincoln Square, a lively neighbourhood just a few kilometres from the Davis Theatre and a range of restaurants and shops. The property has excellent user, location and cleanliness ratings.
This self-catering apartment can accommodate up to four guests and is fully equipped with a kitchen, a garden and parking. It also has a comfortable living area with a smart TV and Netflix, and guests can enjoy free Wi-Fi and air conditioning.
Spacious 6 Br Sleeps 16 Birthday Anniversary - Chicago, IL
9.8 53 reviews
Chicago, IL
14 6
NZ$2064/nighttotal: NZ$6192 (3 )

Spacious 6 Br Sleeps 16 Birthday Anniversary

apartment - Dunning
This six-bedroom house in Dunning, Chicago, offers ample space for large groups, conveniently located near local attractions within the Dunning neighbourhood.
Sleeping up to 16 guests, the property boasts a gourmet kitchen, three bathrooms, a private garden, a two-car garage, and a unique basement acoustic room ideal for events of up to 20 people.
Wicker Park By Downtown And The Salt Shed Last Minute Deal 149.00 August 9-14 - Chicago, IL
9.8 64 reviews
Chicago, IL
4 2
NZ$617/nighttotal: NZ$3085 (5 )

Wicker Park By Downtown And The Salt Shed Last Minute Deal 149.00 August 9-14

apartment - Chicago
This West Town flat is situated approximately 1.6km from downtown Chicago, the Salt Shed music venue, and Lincoln Park, offering easy access to the Division Street Blue Line.
The two-bedroom, one-bathroom apartment sleeps four guests and features a 1950s-themed kitchen, a graffiti-art decorated living room, Roku TV, and permit parking; nearby attractions include art galleries on Chicago Avenue and restaurants on Division Street.
The Richmond Ii F | Sun-drenched Flat Next To 606 - Chicago, IL
10 1 review
Chicago, IL
2 2
NZ$306/nighttotal: NZ$18666 (61 )

The Richmond Ii F | Sun-drenched Flat Next To 606

apartment - Chicago
This two-bedroom flat in Chicago offers a family-friendly base with easy access to the city's attractions, located in a district providing ample space for enjoyment.
This pet-friendly apartment sleeps up to five guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning and a garden.
Private Studio Near Wrigley - Chicago, IL
9.9 146 reviews
Chicago, IL
1 1
NZ$250/nighttotal: NZ$750 (3 )

Private Studio Near Wrigley

apartment - Chicago
This Chicago studio apartment is situated in a peaceful neighbourhood, approximately 1.6 kilometres from Wrigley Field and within easy reach of public transport links.
The self-contained unit sleeps two guests and boasts a kitchen with fridge, freezer, microwave, and dishwasher, plus a private backyard with gas grill and fire pit.

Best Chicago, IL luxury short term rentals

Kasa Lake Shore Chicago - Chicago, IL
7.8 13 reviews
Chicago, IL
3 2
NZ$709/nighttotal: NZ$2127 (3 )

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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 307 reviews
Chicago, IL
2 1
NZ$576/nighttotal: NZ$1728 (3 )

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 South Loop Chicago - Chicago, IL
9.4 3254 reviews
Chicago, IL
8 2
NZ$1010/nighttotal: NZ$2020 (2 )

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.
Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1546 reviews
Chicago, IL
4 2
NZ$2370/nighttotal: NZ$7110 (3 )

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.

Best Chicago, IL Short term rentals with a jacuzzi

Among the 13281 accommodations in Chicago, IL, here are the 4 best rentals with a jacuzzi

High-end 3br Retreat + Steps To Millennium Park - Chicago, IL
10 5 reviews
Chicago, IL
2 3
NZ$1578/nighttotal: NZ$4734 (3 )

High-end 3br Retreat + Steps To Millennium Park

apartment - Chicago
This downtown waterfront flat in Chicago offers prime access, just a short walk from the Merchandise Mart and 333 West Wacker Drive, with Clark-Lake and Washington-Wells L train stations only 500 meters away.
This 136 square meter residence, accommodating up to six guests, features three bedrooms, two bathrooms, Wi-Fi, air conditioning, a fully equipped kitchen, on-site parking, and access to a shared swimming pool and hot tub.
Family 7bd Home With Game Rm, Hot Tub, And Sauna - Chicago, IL
9.7 136 reviews
Chicago, IL
11 7
NZ$3790/nighttotal: NZ$7580 (2 )

Family 7bd Home With Game Rm, Hot Tub, And Sauna

apartment - Chicago
This Chicago single-family home, location unspecified but implying proximity to Chicago's attractions, offers a spacious seven-bedroom, four-and-a-half-bathroom dwelling perfect for large groups.
The property boasts a fully equipped kitchen, basement recreation area with pool table, private garden with patio furniture and grill, accommodating up to 16 guests and providing ample space for relaxation and entertainment.
Dog-friendly Apt: Chef's Kitchen, Lake Walk - Chicago, IL
10 22 reviews
Chicago, IL
3 2
NZ$530/nighttotal: NZ$3710 (7 )

Dog-friendly Apt: Chef's Kitchen, Lake Walk

apartment - Chicago
This dog-friendly garden flat in Chicago's Edgewater district is a 15-minute walk to the public beach and a 20-minute train journey to the city centre.
This two-bedroom flat accommodates up to four guests and offers a chef's kitchen, a sunroom with garden views, a private washer/dryer, and access to a shared fitness centre, with Whole Foods and the Red Line public transport just 5 minutes away.
Front Row To The Lake & Skyline: Epic 60th Flr 3br - Chicago, IL
10 3 reviews
Chicago, IL
6 3
NZ$6998/nighttotal: NZ$20994 (3 )

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

apartment - Chicago
This lakeside Chicago apartment, situated in the downtown area near Soldier Field and the Field Museum, offers easy access to State Street and Michigan Avenue shopping.
The 187-square-metre property boasts three bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, and access to a swimming pool, jacuzzi, and fitness centre.

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, for incredible views of the city. The Art Institute of Chicago is a must-see for art lovers, with masterpieces from Monet to Van Gogh. And don't forget to walk along Navy Pier, a bustling entertainment complex with shops, restaurants, and a Ferris wheel.
  • 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, so be prepared for anything! Summers are hot and humid, with average temperatures around 25°C. Winters are cold and snowy, with average temperatures around -3°C. Spring and autumn are beautiful, with mild temperatures and changing colours.
  • 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 a good festival! The Chicago Blues Festival is a must for music lovers, while the Taste of Chicago is a food lover's paradise. The Chicago Air and Water Show is a spectacular event for aviation enthusiasts.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Absolutely! Wrigley Field is home to the Chicago Cubs baseball team, while Soldier Field hosts the Chicago Bears football team. 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, IL?

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from the city, you'll find the stunning Indiana Dunes National Park. This beautiful area features towering sand dunes, beaches, and forests. It's a great place to escape the hustle and bustle of the city and enjoy some fresh air.
  • What part of Chicago, IL is ideal for finding lodging?

    The Magnificent Mile is a popular choice for tourists, with plenty of high-end hotels and shops. River North is another good option, with a lively nightlife scene and a wide range of restaurants. If you're on a budget, consider staying in the Lincoln Park neighbourhood, which offers a more residential feel.

Popular destinations

Best family friendly Chicago, IL Short term rentals

Among the 13281 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Spacious 3 Br Game And Arcade Apt In Wrigleyville - Chicago, IL
9.9 38 reviews
Chicago, IL
5 3
NZ$935/nighttotal: NZ$2805 (3 )

Spacious 3 Br Game And Arcade Apt In Wrigleyville

apartment - Chicago
This 93 square metre flat in Lakeview East/Wrigley is located approximately 1.6 kilometres from Wrigley Field and Montrose Beach.
This family-friendly residence offers accommodation for up to 12 guests across three bedrooms, with amenities including a microwave, dishwasher, air conditioning, and 4K Wi-Fi, plus three arcade machines for entertainment.
Lyons' Suite - Chicago, IL
8.3 3 reviews
Chicago, IL
2 1
NZ$738/nightfor 1 night

Lyons' Suite

B&B - Chicago
This Chicago guesthouse is situated approximately 21 kilometres from Chicago O'Hare International Airport, in a quiet suburban location.
The 46-square-metre property features one bedroom, one bathroom, and can accommodate up to three guests, offering air conditioning, a private terrace, and parking.
Charming Garden Pad With Spacious Deck - Enchanting Urban Retreat - Chicago, IL
Chicago, IL
8 3
NZ$3661/nighttotal: NZ$7322 (2 )

Charming Garden Pad With Spacious Deck - Enchanting Urban Retreat

apartment - Chicago
This recently renovated three-bedroom flat is situated in a prime Chicago location, just steps from a major stadium and offering unique proximity to player parking, ideal for sports enthusiasts.
This family-friendly apartment accommodates up to 10 guests with nine beds, featuring air conditioning, a kitchen with essential appliances, and a shared back deck, with street parking permits available upon advance notice.
The Lyons' Den - Chicago, IL
9.8 24 reviews
Chicago, IL
2 1
NZ$375/nighttotal: NZ$1500 (4 )

The Lyons' Den

B&B - Chicago
The Lyons' Den, a bed and breakfast in Chicago, is situated 2.25 kilometres from Wrigley Field, 5.95 kilometres from Lincoln Park Zoo, and 6.76 kilometres from Loyola University Chicago.
This 15 square metre guesthouse offers accommodation for up to three guests in one bedroom and one bathroom, featuring air conditioning, a terrace, a fully equipped kitchen with a dishwasher and oven, and complimentary WiFi.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Ph W/ Bean & Lake Views, An Elite Stay - Chicago, IL
10 2 reviews
Chicago, IL
2 3
NZ$3545/nighttotal: NZ$46085 (13 )

Ph W/ Bean & Lake Views, An Elite Stay

apartment - Chicago
This luxurious Chicago Loop penthouse apartment boasts stunning views of Cloud Gate, and is within walking distance of Millennium Park and Lake Michigan.
The 2662 sq ft (approximately 0.25 km²) property offers four bedrooms, four bathrooms, sleeps seven guests, and includes a fully equipped kitchen, swimming pool, and terrace; nearby attractions include Soldier Field and McCormick Place.
Lairbnb - Garden Apartment - Chicago, IL
9.9 51 reviews
Chicago, IL
1 1
NZ$480/nighttotal: NZ$1440 (3 )

Lairbnb - Garden Apartment

apartment - Chicago
LairBnB, a self-contained apartment in Chicago's Portage Park neighbourhood, offers convenient access to public transport, including the Grayland Metra station (an 8-minute walk) and the Irving Park Blue Line (a 20-minute walk).
This one-bedroom, one-bathroom guesthouse sleeps two, features a private garden, and includes a fridge and microwave; free on-street parking is available nearby, or paid parking costs £4.50 per day.
Spacious 3600 Sq Ft. Home Next To Park & Transit - Chicago, IL
9.9 159 reviews
Chicago, IL
10 6
NZ$1208/nighttotal: NZ$3624 (3 )

Spacious 3600 Sq Ft. Home Next To Park & Transit

apartment - Chicago
This spacious Chicago apartment, situated in the Irving Park neighbourhood, offers easy access to downtown Chicago (approx. 21km), O'Hare International Airport (approx. 19km), and Wrigley Field (approx. 21km) via the nearby CTA Blue Line.
The 340 sq m property boasts six bedrooms, three bathrooms, sleeping up to 14 guests, and includes amenities such as a garden, parking, high-speed internet, and family-friendly extras like a travel cot and high chair; nearby attractions include a park with playground, gym, and pool.
Enjoy Chicagos Nightlife From Studio Apartment - Chicago, IL
9.6 683 reviews
Chicago, IL
2 1
NZ$295/nighttotal: NZ$1475 (5 )

Enjoy Chicagos Nightlife From Studio Apartment

apartment - Chicago
This Chicago Uptown studio flat is situated near Lake Michigan, 2.4 kilometres from Wrigley Field, and under 1.6 kilometres from Argyle Street's diverse eateries.
The self-contained apartment, sleeping two guests, offers free Wi-Fi, Netflix, a workspace, and a well-equipped kitchen including a stovetop, oven, and Keurig coffee maker; professional cleaning ensures a spotless stay.
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