This Chicago apartment, near the 606 trail, offers easy access to various neighbourhoods and is minutes from the Blue Line. The two-bedroom, one-bathroom flat sleeps six, features a fully equipped kitchen including a dishwasher, and boasts a garden and parking; its excellent location provides proximity to parks, farmers' markets, and the city's nightlife.
9.9 89 reviews
Chicago, IL
10/07 – 13/07
£347/nighttotal: £1041 (3 )
Renovated Loft On Milwaukee Ave
1 5
apartment , Chicago
This three-bedroom, two-bathroom apartment in Chicago's Logan Square is situated 0.64km from the Logan Square Blue Line station, offering easy access to O'Hare International Airport and the city centre. The modern loft-style flat, sleeping up to seven guests, features a fully equipped kitchen, private entrance, garden, parking, and is located above Mother's Ruin bar, with thick floors for sound insulation.
10 1 review
Chicago, IL
17/06 – 21/06
£561/nighttotal: £2244 (4 )
Luxe 4br Brick & Stone By Douglass Park + Med Dist
1 8
apartment , Chicago
This recently renovated four-bedroom, two-bathroom flat offers a peaceful urban retreat on a quiet, tree-lined street, providing convenient access to Chicago's Medical District, hospitals, and the city centre, approximately 5 kilometres away. This fully furnished apartment accommodates up to eight guests, featuring in-unit laundry, hardwood floors, wall-mounted televisions, and modern amenities ideal for mid-term stays, with an open kitchen complete with quartz-style counters.
Chicago, IL
24/06 – 31/07
£91/nighttotal: £3367 (37 )
Serene Chic In Ravenswood Manor! 20 Mins To Grant Park Or Wrigley Field!
1 2
apartment , Chicago
This Chicago apartment rental in Albany Park offers convenient access to the Brown Line (Kedzie and Kimball stations) and is within 5km of the Riviera Theatre, Aragon Ballroom, and Copernicus Centre. The one-bedroom, one-bathroom flat sleeps six guests and includes in-unit laundry, a fitness centre, and essential amenities such as a hairdryer and iron; Milwaukee Avenue, with its shops and restaurants, is also nearby.
Chicago, IL
01/08 – 30/09
£86/nighttotal: £5160 (60 )
Vintage Firehouse Quiet Two Bedroom Apt
2 2
apartment , Chicago
This West Town apartment, situated 1.1 km from Union Park and within 4.8 km of the United Centre, offers easy access to Chicago's major attractions. The three-bedroom, one-bathroom flat sleeps four guests and includes a fully equipped kitchen, private balcony, free Wi-Fi, and on-site parking.
10 7 reviews
Chicago, IL
09/09 – 22/12
£110/nighttotal: £11440 (104 )
Spectacular Lincoln Park Duplex Apartment
1 2
apartment , Chicago
This Lincoln Park duplex flat is situated on a quiet residential street, a short distance (approximately 0.8 km) from Lincoln Park Zoo and DePaul University, offering easy access to Lake Michigan's shoreline. The self-catering apartment, sleeping two guests, features a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and one bathroom; nearby attractions include the zoo and university, providing numerous activities.
9.7 128 reviews
Chicago, IL
13/08 – 15/08
£159/nighttotal: £318 (2 )
Logan Square Cozy Corner
1 3
apartment , Chicago
This Logan Square flat is conveniently located within walking distance of local amenities and less than 5 km from downtown Chicago, museums, and beaches via public transport. The one-bedroom apartment sleeps four, features keyless entry, WiFi, a fully equipped kitchen (including fridge, freezer, and microwave), and a garden, and is on the second floor (please note: no lift).
9.0 29 reviews
Chicago, IL
26/06 – 30/06
£202/nighttotal: £808 (4 )
Luxury 3 Bd, 2 Bath Condo - 15 Min From Downtown
3 4
apartment , Chicago
This Chicago luxury condo, sleeping six adults, is situated a 0.6km walk from a train station, providing easy access to Chicago's public transport network and various neighbourhoods. The three-bedroom, two-bathroom apartment boasts a fully equipped kitchen, private patio deck, and on-site parking, offering comfortable accommodation for families or groups visiting the city.
9.6 144 reviews
Chicago, IL
22/06 – 26/06
£615/nighttotal: £2460 (4 )
Jeffjack Heated Pool Penthouse In Chicago's West Loop
2 4
apartment , Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers. The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.
9.9 132 reviews
Chicago, IL
25/06 – 26/07
£207/nighttotal: £6417 (31 )
Beautiful (No Chores No Cleaning Fees)
1 3
apartment , Chicago
This stylish two-bedroom Chicago apartment, near Humboldt Park, offers easy access to the park's amenities. The 50-inch TV, Netflix, Prime Video, in-unit laundry, and private patio with grill, accommodate four guests comfortably in this well-equipped flat.
10 3 reviews
Chicago, IL
26/06 – 28/06
£330/nighttotal: £660 (2 )
New! O'hare Cozy Home /Patio/ Free Prk/king Bed
1 4
apartment , Chicago
This family-friendly flat in Chicago is situated in a comfortable neighbourhood, offering a 16-minute drive to O'Hare Airport and the Rosemont Entertainment District, with easy access to downtown Chicago via the Edison Park Metra station or Harlem Blue Line, a 8-minute drive away. This three-bedroom, one-bathroom dwelling accommodates up to six guests and features a private patio, a fully stocked kitchen with multiple coffee makers, and high-speed Wi-Fi, ideal for families with young children and remote workers.
9.0 2 reviews
Chicago, IL
04/09 – 10/09
£156/nighttotal: £936 (6 )
Well-equipped Studio Apartment - Dorchester 511
1 2
studio , Chicago
This Chicago studio apartment, located in the Dorchester neighbourhood, is 1.8km from the Museum of Science and Industry and 1.9km from 57th Street Beach. The 31-square-metre self-contained apartment sleeps three, features a fully equipped kitchen with fridge and microwave, free Wi-Fi, air conditioning, and a separate bedroom.
Best Chicago, IL luxury short term rentals
9.2 1379 reviews
Chicago, IL
04/09 – 07/09
£516/nighttotal: £1548 (3 )
Kasa Magnificent Mile Chicago
1 3
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
11/07 – 18/07
£565/nighttotal: £3955 (7 )
The Neighborhood Hotel-little Italy
2 4
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
08/07 – 12/07
£281/nighttotal: £1124 (4 )
Kasa River North Chicago
1 2
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.
9.4 3084 reviews
Chicago, IL
03/07 – 06/07
£635/nighttotal: £1905 (3 )
Kasa South Loop Chicago
2 8
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.
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.
10 26 reviews
Chicago, IL
19/06 – 21/06
£1340/nighttotal: £2680 (2 )
Luxe 67th Flr 2br: Endless Lake Views, Top Skydeck
2 2
apartment , Chicago
This luxurious two-bedroom apartment, situated on Chicago's Cultural Mile, offers unparalleled lake and NASCAR race views from its 67th-floor location and proximity to Chicago's many cultural attractions. The 2-bathroom property sleeps five, boasting a state-of-the-art kitchen, a Sonos sound system, access to a swimming pool, jacuzzi, fitness centre and parking, plus a private observation deck on the 73rd floor.
9.6 34 reviews
Chicago, IL
11/09 – 17/09
£353/nighttotal: £2118 (6 )
Cozy 3-bedroom House In Family-oriented Melrose Park.
3 1
apartment , Franklin Park
This Franklin Park holiday home is located minutes from Chicago O'Hare International Airport, offering easy access to Woodfield Mall and Fashion Outlets of Chicago. The three-bedroom property sleeps six guests, boasting a fully equipped kitchen, Jacuzzi, WiFi, and a fenced backyard, plus it is pet-friendly (additional charges apply).
10 6 reviews
Chicago, IL
10/08 – 10/10
£91/nighttotal: £5551 (61 )
All New 2br In Pilsen, Laundry Incl
2 2
apartment , Chicago
This Pilsen flat, situated on Oakley Avenue, Chicago, is 0.8 km from public transport and 4.8 km from the city centre, within a historically significant building formerly used as a funeral home. The 74-square-metre, two-bedroom, one-bathroom apartment sleeps four, boasting a modern kitchen with quartz countertops, in-unit laundry, a jacuzzi, parking, high-speed internet, and proximity to three Italian restaurants.
10 311 reviews
Chicago, IL
03/08 – 11/08
£150/nighttotal: £1200 (8 )
Urban Luxury 1br/2ba Logan Square Condo W/garage
1 2
apartment , Chicago
This one-bedroom flat is situated in the Logan Square district, a 1.6 km walk from the Logan Square Monument and a short distance from the Logan Square Blue Line Station, providing easy access to Chicago's city centre. The property boasts a large garden with a patio and fire pit, perfect for relaxing, and comes with a fully equipped kitchen, a Jacuzzi, free on-site parking, and high-speed Wi-Fi.
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.
Destinations nearby
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.
9.3 87 reviews
Chicago, IL
18/07 – 23/07
£285/nighttotal: £1425 (5 )
Mccormick Place 2br Spacious Corner Unit With Optional Parking Sleeps 6 Guests Near Soldier Field And Grant Park
2 4
apartment , Chicago
This stylish apartment is situated in Chicago's McCormick Place area, just 2.4 kilometres from the Field Museum of Natural History and 2.9 kilometres from the Art Institute of Chicago, making it a great base for exploring the city's cultural attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall user experience. The apartment is a spacious 84 square metre two-bedroom property, with two bathrooms, offering comfortable accommodation for up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a fitness centre, and parking, as well as complimentary Wi-Fi and air conditioning.
9.5 170 reviews
Chicago, IL
13/08 – 18/08
£400/nighttotal: £2000 (5 )
Garage Parking! Stay In, Walk To Great Local Spots, Grab The Cta, Or Hop On I-290 - The Perfect Location For All Your Adventures By Allset Turnover
1 8
apartment , Chicago
This four-bedroom apartment is located in the Tri-Taylor neighbourhood of Chicago, just a short walk from the Medical District and Interstate 290, offering easy access to the city's attractions and amenities. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment is ideal for families or groups of up to eight people, with plenty of space for everyone to relax and enjoy their stay. It comes with a fully equipped kitchen, air conditioning, parking, and Wi-Fi, ensuring a comfortable and convenient experience.
9.8 26 reviews
Chicago, IL
11/09 – 13/09
£1634/nighttotal: £3268 (2 )
Prime 4 Br Sleeps 13, Chef Kitchen, 8 Blks To Wrigley, 15min Train To Mag Mile
4 11
apartment , Chicago
This North Center family-friendly home, a 232 square metre property, is situated within 3.2 kilometres of Wrigley Field, Lincoln Park, and Lake Michigan, offering convenient access to Addison and Paulina stations. The four-bedroom, three-bathroom dwelling sleeps thirteen guests and boasts amenities including free Wi-Fi, a fireplace, a fully equipped kitchen with dishwasher, and on-site parking, plus a playground and books for guests' enjoyment.
10 1 review
Chicago, IL
19/08 – 18/12
£134/nighttotal: £16214 (121 )
The Lantern: Charming 2 Bed Ground Floor Apartment
2 2
apartment , Forest Park
This Forest Park flat is conveniently located a 2.2km walk from the Frank Lloyd Wright Historic District and an 18km drive from the United Centre, offering easy access to public transport. The two-bedroom, one-bathroom apartment sleeps six guests and includes a fully equipped kitchen, in-unit laundry, Wi-Fi, and on-site parking.
Neighborhoods and points of interest in Chicago, IL
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.
10 3 reviews
Chicago, IL
24/07 – 26/07
£1130/nighttotal: £2260 (2 )
Beach Side In The City - Chicago [Near Nwu] [Near Red Line]
6 11
apartment , Chicago
This five-bedroom flat in Chicago's Rogers Park district provides excellent access to attractions such as the Chicago Theatre, the Art Institute of Chicago, Michigan Avenue shopping, and Wrigley Field entertainment, with the latter being approximately 10 kilometres away. This residence accommodates up to eleven guests and features a microwave oven, air conditioning, heating, and parking, with a 11:00 AM check-out time.
9.0 2 reviews
Chicago, IL
25/06 – 26/06
£750/nightfor 1 night
Chic River North Retreat: Luxe Suites, Stunning Views, Steps From Chicago Life!
2 5
apartment , Chicago
This Level River North apartment is situated in the River North district, a short distance from the Magnificent Mile and the Loop, offering easy access to Chicago's riverside parks. The 81-square-metre (870 sq ft) two-bedroom, two-bathroom flat sleeps six guests and boasts a fully equipped kitchen, in-suite laundry, and a balcony; nearby recreational activities include motor boating.
9.8 19 reviews
Chicago, IL
28/06 – 30/06
£128/nighttotal: £256 (2 )
1-bedroom Condo Next To Chicago Midway International Airport
1 3
apartment , Chicago
This one-bedroom Chicago apartment, situated in the quiet Garfield Ridge neighbourhood, is conveniently located within 14.5 kilometres of attractions such as SeatGeek Stadium, the United Centre, and McCormick Place. The 70-square-metre flat offers guests a comfortable stay with a fully equipped kitchen, in-unit laundry, free Wi-Fi, on-site parking, and sleeps up to three people.
10 8 reviews
Chicago, IL
13/08 – 15/08
£149/nighttotal: £298 (2 )
King Comfort Apartment, Quiet, Clean, Ac & Wifi
1 3
apartment , Chicago
This Austin, Chicago dwelling is situated near the Frank Lloyd Wright Historic District, within 4.8km of the Walt Disney House and Humboldt Park, offering convenient access to public transport (a 7-minute walk to the Chicago Grand-Cicero Station). This one-bedroom, one-bathroom property sleeps three guests and features a fully equipped kitchen with oven, hob, and microwave, plus a Smart TV and other modern conveniences; nearby attractions include the United Center and Portage Park, both within 9.6km.