This five-bedroom, two-bathroom Chicago apartment enjoys a central location near Downtown Chicago, Hyde Park, and the Red Line, providing easy access to various neighbourhoods. Sleeping up to ten guests, this spacious property boasts a fully equipped kitchen (fridge, freezer, microwave), air conditioning, parking, and excellent guest reviews; further details on interior design and specific amenities are unavailable.
9.5 146 reviews
Chicago, IL
13/07 – 15/07
898 €/nighttotal: 1796 € (2 )
East Village 4-level-house With 5 Baths & Covered Attached Garage
4 6
apartment , Chicago
This four-storey townhouse is located in Chicago's East Village, a short walk from the Milwaukee 'L' station and a 12-minute subway ride from the Loop, Michigan Avenue, and the Lakefront. It has consistently received excellent user ratings for location, cleanliness, and overall experience. The property offers 223 square metres of living space, comprising four bedrooms and five bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, private terraces, a spa-like bathroom, a fireplace, games, and a Sonos sound system.
10 15 reviews
Chicago, IL
26/08 – 30/08
1370 €/nighttotal: 5480 € (4 )
6bd/6bth House, Sleeps 15, Rooftop Deck & Garage
1 13
apartment , Chicago
This six-bedroom, five-bathroom Chicago apartment is situated in a residential area, 4.8 kilometres from Wrigley Field and three blocks from the Belmont Blue Line station, offering easy access to the city centre. The 418-square-metre property boasts two kitchens, a private rooftop deck, a two-car garage, and family-friendly features including a playroom and children's equipment, accommodating up to fifteen guests.
9.9 67 reviews
Chicago, IL
24/07 – 26/07
321 €/nighttotal: 642 € (2 )
Spacius Unit In Historic Gem
1 5
apartment , Chicago
This family-friendly Chicago house, built in 1895, enjoys a convenient location within 2km of downtown Chicago, the University of Chicago, and sporting venues such as Soldier Field and Guaranteed Rate Field, offering easy access to public transport. Sleeping six guests, this ground-floor property (note: some steps to enter, not wheelchair accessible) features two bedrooms, one bathroom, a kitchen with modern appliances, a garden with a fire pit and swing set, and retro arcade games for family entertainment.
9.8 141 reviews
Chicago, IL
05/07 – 10/07
222 €/nighttotal: 1110 € (5 )
Wrigleyville Condo 2 Blks From Lake & Train
1 5
apartment , Chicago
This spacious East Lakeview apartment, a short 0.3km walk from the Sheridan Red Line and Lake Michigan, is ideally located near Wrigley Field and the nightlife of Wrigleyville and Boystown. The 93-square-metre one-bedroom, one-and-a-half-bathroom condo sleeps six, boasting a full kitchen, in-unit laundry, air conditioning, and proximity to amenities including Starbucks, a playground, and Montrose Beach (1.6km).
10 34 reviews
Chicago, IL
21/08 – 23/08
207 €/nighttotal: 414 € (2 )
Cozy Library
1 2
apartment , Chicago
This Chicago apartment rental is situated in the city's Medical District, close to the University of Illinois Chicago (UIC) and Rush University, offering convenient access to public transport and major roads. The one-bedroom flat, sleeping up to three guests, features a fully equipped kitchen, free laundry facilities, a built-in library, a gaming table, and a charming front garden, perfect for a relaxing Chicago stay.
9.9 48 reviews
Chicago, IL
14/08 – 16/08
969 €/nighttotal: 1938 € (2 )
Spacious 6 Br Sleeps 16 Birthday Anniversary
1 10
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.
9.6 1001 reviews
Chicago, IL
14/11 – 05/12
192 €/nighttotal: 4032 € (21 )
Kasa | Views From Your Private Balcony | Chicago
1 2
apartment , Chicago
This Chicago apartment is ideally situated in the downtown area, a stone's throw from Oak Street Beach and a short walk (approximately 0.8 km) from Michigan Avenue and Millennium Park. The self-catering flat offers a full kitchen, in-unit laundry facilities, high-speed Wi-Fi, and sleeps two guests, with on-site parking and a fitness centre available.
9.8 75 reviews
Chicago, IL
11/07 – 15/07
157 €/nighttotal: 628 € (4 )
Luxurious Cozy Boho 10 Min To Downtown Sleeps 5
1 3
apartment , Chicago
This Chicago apartment rental is located in Little Village, a 10-minute drive (approx. 4.8km) from the city centre, 4.8km from Little Italy and Chinatown, and a 15-minute drive (approx. 11.2km) from Millennium Park and Soldier Field. The one-bedroom flat sleeps five guests comfortably, offering a full kitchen, washer/dryer, in-unit entertainment (two smart TVs, Pac-Man arcade game, board games), a mini-patio with grill, and enhanced security features including keyless entry.
9.9 81 reviews
Chicago, IL
23/07 – 27/07
152 €/nighttotal: 608 € (4 )
Modern Farmhouse In Andersonville- No Cleaning Fee
1 2
apartment , Chicago
This one-bedroom flat in Chicago's Andersonville district is located 3.2 kilometres from Wrigley Field and 1.6 kilometres from the Lake Front, offering convenient access to Clark Street's shops and eateries. This newly remodelled residence accommodates two guests and features air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and keyless entry, with free street parking and excellent public transport links nearby.
9.7 36 reviews
Chicago, IL
26/06 – 28/06
485 €/nighttotal: 970 € (2 )
Comfy Chinatown Townhome And 2 Garage Spots!
1 8
apartment , Chicago
This 3-bedroom, 2.5-bathroom townhome is located in Chicago's Chinatown district, providing convenient access to major motorways and the city centre, just 5 kilometres away. This spacious 204 square metre residence accommodates up to 8 guests, featuring a fully equipped kitchen, a dedicated games room with foosball and darts, and private 2-car garage parking, with pets welcome for a £160 fee.
8.6 14 reviews
Chicago, IL
04/09 – 05/09
288 €/nightfor 1 night
Prime River North Location! Rooftop Deck
1 4
B&B , Chicago
This Chicago bed and breakfast is located in the River North district, offering walking access to the Magnificent Mile, approximately 500 meters away, and is also near Navy Pier, Willis Tower, and Wrigley Field. The accommodation provides 355 sq. ft. rooms with air conditioning and Wi-Fi, a fitness centre, an indoor heated shared swimming pool, and paid on-site parking, with daily cleaning services included and no pets permitted.
Best Chicago, IL luxury short term rentals
9.4 3084 reviews
Chicago, IL
24/08 – 26/08
344 €/nighttotal: 688 € (2 )
Kasa South Loop Chicago
1 3
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.
9.2 1379 reviews
Chicago, IL
23/07 – 26/07
1619 €/nighttotal: 4857 € (3 )
Kasa Magnificent Mile Chicago
3 8
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.
9.6 265 reviews
Chicago, IL
25/06 – 28/06
342 €/nighttotal: 1026 € (3 )
The Neighborhood Hotel-little Italy
1 2
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.
9.4 351 reviews
Chicago, IL
01/01 – 31/01
350 €/nighttotal: 10500 € (30 )
Kasa River North Chicago
3 6
aparthotel , Chicago
Kasa River North Chicago is situated in the River North district, a short walk from Oak Street Beach and the Shops at Northbridge, offering easy access to Chicago's attractions and vibrant nightlife. The property has received excellent ratings for its location, cleanliness, and overall user experience. The hotel offers a range of modern apartments with amenities such as air conditioning, a fridge, a dishwasher, and a coffee machine. Guests can enjoy the seasonal outdoor swimming pool, terrace, and fitness centre, or simply relax in the garden and take advantage of the concierge service.
Best Chicago, IL Short term rentals with a jacuzzi
Among the 9542 accommodations in Chicago, IL, here are the 4 best rentals with a jacuzzi
10 2 reviews
Chicago, IL
17/09 – 17/12
160 €/nighttotal: 14560 € (91 )
The Céline® Highrise - Stunning City Views, Gym
1 1
apartment , Chicago
This one-bedroom flat in a prime Chicago district offers excellent access to the city's attractions and business centres. Guests can enjoy exclusive access to building amenities including a clubhouse with city views, a pool/jacuzzi, a private conference room, and a 24/7 fitness centre, with a fully stocked kitchen and high-speed WiFi catering to both leisure and business travellers.
9.8 90 reviews
Chicago, IL
01/07 – 06/07
1035 €/nighttotal: 5175 € (5 )
United Center Compound W/rooftop, Hot Tub, Sauna
1 11
apartment , Chicago
This spacious four-bedroom Chicago home, near the United Centre in the West Loop, offers easy access to local attractions. Sleeping nine in total across four bedrooms and three bathrooms, this mid-century modern property boasts a chef's kitchen, multiple entertainment areas including a rooftop deck and a large heated private garage (111.5 m²).
9.6 133 reviews
Chicago, IL
22/07 – 23/07
511 €/nightfor 1 night
Luxe 3br, 2ba + Hot Tub
1 8
apartment , Hillside
This raised ranch is ideally located in Hillside, just a short drive from the I-294 and I-88 motorways, making it easy to reach Elmhurst Hospital and downtown Chicago, which is 32 kilometres away. This property has consistently received excellent ratings for its location, cleanliness and overall experience. This spacious three-bedroom house can comfortably accommodate up to eight guests. The house includes a well-equipped kitchen, a relaxing family room, a large garden with upper and lower decks, a hot tub, and a garage.
10 15 reviews
Chicago, IL
31/07 – 03/08
2100 €/nighttotal: 6300 € (3 )
The Jackpot | Hot Tub · Cinema · Bar · Sleeps 14
6 11
apartment , Chicago
This Chicago flat offers convenient access, being a 9-minute walk to the Blue Line, 24 kilometres from O'Hare Airport and 25 kilometres from downtown, with Wrigley Field and Millennium Park within a 32 kilometre drive. This spacious 6-bedroom, 3-bathroom property sleeps 14 guests and boasts a private 2-car garage, an all-season backyard with a hot tub, a game room, a 4K home theatre, and a sunroom.
Frequently asked questions about short term rentals in Chicago, IL
Which top landmarks you shouldn't miss in Chicago, IL?
You've got to see the iconic Willis Tower (formerly Sears Tower) for amazing views of the city. The Art Institute of Chicago is a must-visit for art lovers, and Millennium Park is perfect for a stroll with its famous Cloud Gate sculpture, nicknamed 'The Bean'.
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°C. Winters are cold and snowy, with average temperatures around -5°C. Spring and autumn are beautiful, with mild temperatures and vibrant 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's got a festival for everyone! The Lollapalooza music festival is a big draw in the summer, and the Chicago Air & Water Show is a spectacular event in August. The Chicago Blues Festival in June is a fantastic celebration of music.
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 sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field is home to the Chicago Bears, and the United Center is where you'll find 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 Indiana Dunes National Park. It has beautiful beaches, sand dunes, and forests, perfect for hiking, biking, and exploring nature.
What part of Chicago, IL is ideal for finding lodging?
The Magnificent Mile, along Michigan Avenue, is a popular area with plenty of hotels. River North is another great option, with trendy restaurants and nightlife. For a quieter stay, consider the Gold Coast or Lincoln Park.
Destinations nearby
Best family friendly Chicago, IL Short term rentals
Among the 9542 accommodations in Chicago, IL, here are the 4 best family friendly rentals
9.4 3 reviews
Chicago, IL
13/10 – 20/12
107 €/nighttotal: 7276 € (68 )
Hamaline Luxury - Guest House
3 2
apartment , Chicago
This Chicago guesthouse is located in the Douglas Park neighbourhood, offering convenient access to attractions such as the city centre, McCormick Place, and the lakefront. The 93-square-metre, three-floor townhome sleeps five guests, boasting three bedrooms, one bathroom, a fully equipped kitchen with an air fryer and Keurig coffee maker, plus two massage chairs and automated check-in.
9.9 131 reviews
Chicago, IL
27/06 – 30/06
612 €/nighttotal: 1836 € (3 )
Private Lincoln Park Condo With 2 Parking Spots
1 5
apartment , Chicago
This Lincoln Park flat, in a historically significant 1895 building, offers convenient access to Lincoln Park's attractions, within easy walking distance of many landmarks. The two-bedroom, one-bathroom apartment sleeps six, boasting a fully-remodelled kitchen, a private balcony, two off-street parking spaces, a 75" 4K Smart TV, and high-speed fibre internet; a friendly black lab, Buck, may even greet you.
8.5 14 reviews
Chicago, IL
09/12 – 26/12
106 €/nighttotal: 1802 € (17 )
Fully Furnished Extended Stay Work Or Insurance In Chicago
2 2
apartment , Chicago
This flat is located in a Chicago neighbourhood, approximately 9.2 kilometres from the United Centre and 12.6 kilometres from Willis Tower. This 28 square metre flat offers two bedrooms, a living room, and a kitchen equipped with a fridge and microwave, accommodating up to seven guests with free on-site parking and complimentary WiFi.
9.6 11 reviews
Chicago, IL
23/06 – 25/07
100 €/nighttotal: 3200 € (32 )
The Hyde Park Hide-a-way
1 1
apartment , Chicago
This Hyde Park flat is situated near the University of Chicago, Jackson Park, and the lakefront, offering easy access to Hyde Park's restaurants and attractions. The three-bedroom, two-bathroom apartment sleeps six guests and includes a fully equipped kitchen, in-unit laundry, and free street parking; external security cameras provide added peace of mind.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL short term rentals with parking
Chicago, IL
31/07 – 02/08
1395 €/nighttotal: 2790 € (2 )
Flexhome West Town - Spacious 2br Duplex
2 6
apartment , Chicago
This West Town flat is located in Chicago's West Town district, 3.2 kilometres from Union Station and 3.0 kilometres from Water Tower Chicago. This 60 square metre residence accommodates up to 11 guests, featuring two bedrooms, two bathrooms, air conditioning, a fully equipped kitchen with a dishwasher, and complimentary WiFi.
9.2 42 reviews
Chicago, IL
25/06 – 26/06
370 €/nightfor 1 night
1br Apartment - Walk To Shops - Downtown Oak Park
2 2
apartment , Oak Park
This one-bedroom flat in Oak Park offers a prime location in a district celebrated for its Frank Lloyd Wright architecture, placing guests within easy reach of local shops and restaurants, and just a 4-minute drive from the train station for access to Chicago. This accommodation provides dedicated WiFi, two Smart TVs, and a fully equipped kitchen and bathroom, with a Pack 'n Play available for families, and is conveniently located a 2-minute drive from grocery stores and shopping centres, and a 20-minute drive to Downtown Chicago.
Chicago, IL
14/08 – 16/08
1176 €/nighttotal: 2352 € (2 )
Spacious 5br Luxury Suite Perfect For Group Sleeps 12 Near Mccormick Place, Grant Park And Soldier Field
5 10
apartment , Chicago
This luxury Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers easy access to the city's cultural attractions. The 214-square-metre property boasts a spacious five-bedroom, four-bathroom layout sleeping up to 12 guests, complete with a fully equipped kitchen, fitness centre access, free Wi-Fi, and a patio offering city views.
10 2 reviews
Chicago, IL
05/07 – 11/07
275 €/nighttotal: 1650 € (6 )
Spacious 2br South Loop Suite With Skyline View, Optional Parking And Gym Access Close To Mccormick Place, Grant Park, Museum Campus & Cta Lines
2 5
apartment , Chicago
This family-friendly apartment near Chicago's Museum Campus is conveniently located approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra. The 74-square-metre dwelling boasts a spacious two-bedroom, two-bathroom layout sleeping up to eight guests, offering a private patio with skyline views, a fully equipped kitchen, free Wi-Fi, and access to an on-site fitness centre and parking.