Chicago, IL Holiday Apartments and Self Contained

9.7 179 reviews

Chicago, IL

04/07 – 31/07

NZ$335/nighttotal: NZ$9045 (27 )

Comfortable And Trendy Design 1br | Lincoln Square

1 1

apartment, Chicago

This Lincoln Square flat is conveniently located near the Brown Line, offering easy access to Wrigleyville and Chicago's city centre.
The one-bedroom apartment, sleeping two, boasts a fully equipped kitchen, in-building laundry, a smart TV with Netflix, and is within walking distance of Cafe Selmarie.

Chicago, IL

28/06 – 31/07

NZ$489/nighttotal: NZ$16137 (33 )

Corporate Apartment With 2 Bedrooms And Fantastic View Of Lake And Skyline

2 1

apartment, Chicago

This corporate flat is located in Chicago's Lincoln Park district, offering proximity to the Chicago History Museum and Michigan Avenue, approximately 3 kilometres away.
This two-bedroom flat accommodates two guests and includes a microwave, dishwasher, and air conditioning, with Wrigley Field and the United Center within easy reach for entertainment.

9.5 81 reviews

Chicago, IL

27/08 – 29/08

NZ$559/nighttotal: NZ$1118 (2 )

1br Captivating Apartment

1 3

apartment, Chicago

This West Loop flat offers easy walking access to Chicago's city centre, Little Italy, and the Medical District.
The one-bedroom apartment sleeps two, includes Wi-Fi, air conditioning, a microwave, and is within easy reach of West Loop's numerous restaurants and bars.

9.9 58 reviews

Chicago, IL

06/09 – 18/09

NZ$370/nighttotal: NZ$4440 (12 )

University Of Chicago Condo-upgraded And Spacious

1 2

apartment, Chicago

This Chicago condo is situated in the University of Chicago neighbourhood, a short distance from Hyde Park and within easy walking distance (approximately 1.6 km) of Lake Michigan, Jackson Park Golf Course, and the Obama Presidential Center.
The spacious one-bedroom apartment, sleeping up to three guests, boasts two bathrooms, a fully equipped kitchen including a dishwasher, in-unit laundry, private parking, and a patio; nearby activities include the Regal Mile Film Studios.

9.3 141 reviews

Chicago, IL

26/08 – 30/08

NZ$617/nighttotal: NZ$2468 (4 )

Cabin 106 By 747 Lofts

1 2

apartment, Chicago

This studio apartment is situated in a prime location in Chicago, just a short stroll from the West Loop and Randolph Street's renowned restaurant scene, offering easy access to downtown via the Blue Line L. The apartment consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The self-catering studio comfortably accommodates two guests and features a modern kitchen with a fridge and microwave, as well as a laundry facility. Amenities include air conditioning, parking, and 24/7 customer support, ensuring a comfortable and convenient stay.

9.4 22 reviews

Chicago, IL

25/07 – 31/07

NZ$519/nighttotal: NZ$3114 (6 )

Welcome To Our Charming 2bd 2ba Pilsen Apartment

1 4

apartment, Chicago

This two-bedroom, two-bathroom flat is located in Chicago's Pilsen district, offering a local experience with convenient access to the city centre, situated approximately 5 kilometres from Millennium Park.
The accommodation features a fully equipped kitchen with stainless steel appliances, air conditioning, in-unit laundry, and high-speed Wi-Fi, accommodating up to four guests.

10 36 reviews

Chicago, IL

25/09 – 27/09

NZ$400/nighttotal: NZ$800 (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.

9.8 11 reviews

Chicago, IL

05/08 – 06/08

NZ$639/nightfor 1 night

Ideal 1-bedroom Stay

1 2

apartment, Chicago

This Lakeview flat in Chicago offers a convenient location, close to cultural attractions such as the Art Institute of Chicago and the Chicago Theatre, though precise distances aren't specified.
The one-bedroom apartment sleeps two guests and includes a fully equipped kitchen with a fridge and microwave, air conditioning, and Wi-Fi; nearby activities and venues like McCormick Place and Wintrust Arena are easily accessible.

8.9 27 reviews

Chicago, IL

08/10 – 13/10

NZ$460/nighttotal: NZ$2300 (5 )

2br Airy & Tidy Apt With Free Covered Parking - Central Modern

2 2

apartment, Chicago

This Chicago apartment is located just a short distance from Lincoln Park Zoo, Loyola University Chicago, and the United Center, offering easy access to popular attractions and amenities. The apartment has consistently received excellent ratings for its cleanliness, location, and overall value.
The flat offers a comfortable and convenient stay with a fully equipped kitchen, a washing machine, and free Wi-Fi. Guests can enjoy entertainment with a flat-screen TV and streaming services, and covered garage parking is included for added convenience.

Chicago, IL

28/07 – 30/12

NZ$263/nighttotal: NZ$40765 (155 )

Chicago Gem Near Subway ~ 5 Mi To Downtown

3 4

apartment, Chicago

This three-bedroom apartment in Chicago's East Garfield Park neighbourhood is situated approximately 8 kilometres from the city centre, close to Garfield Park Conservatory and well-served by public transport links to the United Centre and downtown attractions including Millennium Park and the Magnificent Mile.
The 141-square-metre flat offers comfortable accommodation for up to five guests, boasting a well-equipped kitchen, free Wi-Fi, free street parking, and step-free access; modern conveniences include Smart TVs and air conditioning.

9.0 27 reviews

Chicago, IL

20/07 – 11/08

NZ$272/nighttotal: NZ$5984 (22 )

You Can’t Be Closer To Loyola Uni And Lake! Gym

1 1

apartment, Chicago

This Rogers Park studio flat is ideally located near Loyola University Chicago and approximately 1.6 kilometres from Lake Michigan's shoreline.
The modern, self-contained unit sleeps two, features a well-equipped kitchenette, a queen-size bed, and includes parking, internet access, and is pet-friendly; nearby, guests can enjoy local shops and restaurants.

9.0 9 reviews

Chicago, IL

01/07 – 31/07

NZ$474/nighttotal: NZ$14220 (30 )

Comfortable And Trendy Design 1br In Lincoln Square

1 1

apartment, Chicago

This one-bedroom flat is located in Albany Park, a neighbourhood just a short walk from Lincoln Square, with easy access to the Brown Line for quick trips to Wrigleyville or downtown Chicago. The flat has an excellent user rating, with guests consistently praising its comfortable design and convenient location.
The flat is perfect for couples or solo travellers looking for a comfortable and well-equipped base in Chicago. It includes a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, parking, and internet access.

Best family friendly Chicago, IL Holiday Apartments and Self Contained Accommodations

Among the 10028 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments

9.9 322 reviews

Chicago, IL

02/10 – 05/10

NZ$622/nighttotal: NZ$1866 (3 )

Lincoln Park Light Filled Loft

1 4

apartment, Chicago

This studio apartment is located in Lincoln Park, a lively neighbourhood in Chicago, just a short distance from the lakefront and the Lincoln Park Zoo. The apartment is highly rated for its cleanliness, location, and overall experience.
The studio is a converted storefront, offering a spacious and open plan living space with floor-to-ceiling windows, covering 74 square metres and comfortably accommodating four guests. The studio comes with a fully equipped kitchen, a private garden, and parking facilities, as well as a comfortable sofa bed.

Chicago, IL

01/08 – 03/08

NZ$2445/nighttotal: NZ$4890 (2 )

29th Floor 2br Grant Park Suite With Balcony, Gym

2 2

apartment, Chicago

This 29th-floor flat is located in Chicago's Grant Park district, a 10-minute walk from DePaul University and approximately 1.9 kilometres from the city centre, offering proximity to the Art Institute of Chicago and Field Museum of Natural History.
This 2-bedroom, 2-bathroom apartment spans 1200 square meters, accommodates up to 15 guests, and features a balcony with city views, a fitness centre, billiards, table tennis, an outdoor fireplace, complimentary WiFi, and private parking.

10 2 reviews

Chicago, IL

31/07 – 02/08

NZ$3116/nighttotal: NZ$6232 (2 )

Gorgeous 5 Bedroom Gem Sleeps 18 With Pool, Ping Pong, Pac Man, Tons Of Games!

5 5

apartment, Chicago

This five-bedroom, two-bathroom Gresham apartment in Chicago is situated approximately 16 kilometres from the city centre, O'Hare International Airport, Lake Michigan, and the United Centre, and around 24 kilometres from Wrigley Field and Lincoln Park Zoo.
Sleeping up to 18 guests, this spacious property boasts two living rooms, a dining room, a game room with air hockey, pool, and ping pong, nine large-screen TVs (including an 85" Samsung QLED), a garden, tennis court, and outdoor dining area with charcoal grill; pet-friendly (with prior approval and fees).

9.8 183 reviews

Chicago, IL

01/07 – 06/07

NZ$584/nighttotal: NZ$2920 (5 )

Stylish 2br Stunner W/ Unbeatable Location

1 3

apartment, Chicago

This Chicago apartment is ideally located on the border of Ukrainian Village and Wicker Park, close to the Division and Damen intersection.
The two-bedroom flat sleeps six, offering a modern kitchen, in-unit laundry, a shared patio with a fire pit, and free on-site parking – a valuable amenity in Chicago.

Best Chicago, IL holiday apartments with a balcony

Chicago, IL

31/07 – 02/08

NZ$2342/nighttotal: NZ$4684 (2 )

Welcome To Our Charming 2bd 2ba Pilsen Apartment

2 1

apartment, Chicago

This two-bedroom flat is situated in downtown Chicago, a 640-metre drive from the United Center and an 800-metre drive from the State Street district, with the Western and Damen metro stations a 720-metre walk away for convenient city exploration.
This 83 square metre apartment accommodates up to four guests and features a fully equipped kitchen, Wi-Fi, air conditioning, laundry facilities, and a balcony, making it an ideal base for exploring attractions like Millennium Park and Lake Michigan, as well as for cycling and fishing.

Chicago, IL

21/10 – 20/01

NZ$299/nighttotal: NZ$27209 (91 )

New Midterm Furnished Rental - 32+days! - North Center Chicago

2 2

apartment, Chicago

This North Center flat is located 5 minutes' walk from the Brown Line and 2.4 kilometres from Wrigley Field.
This furnished two-bedroom flat accommodates four guests and features a private patio, in-unit laundry, and a dedicated workspace, with all utilities and starter supplies included.

9.9 302 reviews

Chicago, IL

25/06 – 27/06

NZ$2866/nighttotal: NZ$5732 (2 )

Dramatic Wrigley Loft +Private Rooftop, Center Of Wrigley, Ranked Guest Favorite

4 5

apartment, Chicago

This spacious apartment is situated in Wrigleyville, a lively neighbourhood just a short walk from Wrigley Field, home to the Chicago Cubs, and within easy reach of bars and restaurants. It has excellent user, location and cleanliness ratings.
The apartment has four bedrooms and three bathrooms, spread over 214 square metres, offering ample space for large groups or families. Amenities include a private rooftop with skyline views, a fully equipped kitchen, a game room with a foosball table and arcade, a Jacuzzi, a spa, a fitness centre, and parking.

Chicago, IL

21/10 – 20/01

NZ$354/nighttotal: NZ$32214 (91 )

New! Charming Andersonville Coach House | 3br/2.5ba

3 2

apartment, Chicago

This spacious two-storey coach house is situated in Chicago's Edgewater district, less than 500 metres from North Clark's amenities and within proximity to Lake Michigan and Millennium Park.
This 134 square metre dwelling offers three bedrooms, 2.5 bathrooms, accommodates up to five guests, and permits one pet for an additional fee, with a kitchen equipped with a fridge, microwave, and dishwasher.

Frequently asked questions about apartment rentals in Chicago, IL

What are the must-see attractions for a 2 days stay in Chicago, IL?
For a two-day trip, you can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. Then, explore Millennium Park, home to Cloud Gate, nicknamed 'The Bean', and the Crown Fountain with its interactive water displays. Finally, stroll along Navy Pier for its Ferris wheel, shops, and restaurants.
What are the best apartments in Chicago, IL?
Among the apartments in Chicago, IL, Mag Mile Mega Entire Floor 4bd\/4ba+parking&rooftop, Kasa | Walk To Lincoln Park Zoo | Chicago and Charming Chicago-style - Vintage - Tv Nfl Pass are the most popular ones.
Which neighborhoods in Chicago, IL are best for renting an apartment?
For a vibrant, walkable neighbourhood, consider Lincoln Park with its green spaces and Lake Michigan access. If you prefer a more historic feel, try the Gold Coast, known for its elegant architecture. For a more affordable option with great restaurants and nightlife, check out Wicker Park.
What are the best apartments with a pool in Chicago, IL?
Beautiful Corner 2 Bedroom In The Loop | Roof Deck, Amazing Location | Luxury Apt | Rooftop Pool and Whole Flat In Private Club - Walk To L - Dining & Shows are the best apartments with a pool in Chicago, IL.
What are the top cultural and historical sites in Chicago, IL?
Chicago is brimming with cultural and historical gems. The Art Institute of Chicago houses masterpieces by Monet and Van Gogh, while the Field Museum boasts dinosaur skeletons and ancient Egyptian artefacts. For a taste of history, visit the Chicago Cultural Center, a stunning building with free concerts and exhibitions, or the Museum of Science and Industry.
What are the best apartments with a jacuzzi in Chicago, IL?
The best apartments with a jacuzzi in Chicago, IL are The Neighborhood Hotel Lincoln Park, Wrigleyville Home Away From Home 5 Mins From Downtown Steps From Lake Cozy and Sun Filled Tranquil 2 Br Great Part Of Logan Sq.
What makes Chicago, IL unique or famous?
Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of the Gold Coast. It's also a culinary powerhouse, with world-class restaurants and a renowned deep-dish pizza scene. And don't forget the vibrant arts and culture scene, with world-class museums, theatres, and music venues.
What are the best apartments for families and kids in Chicago, IL?
The best apartments for families and kids in Chicago, IL are Mag Mile Mega Entire Floor 4bd\/4ba+parking&rooftop, Group Lofts Downtown Sleep 28 Vintage Penthouses +3 Patios and Urban Chicago Loft - 1 Blk To Train W/ 2 Pkg Spots.
Where can you find the best local markets and street food in Chicago, IL?
For a taste of Chicago's diverse food scene, head to Maxwell Street Market on Sundays for a mix of local produce, crafts, and street food. The Wicker Park Farmers Market on Saturdays offers fresh, seasonal produce, while the Green City Market in Lincoln Park has a wide selection of local vendors.
What are the best pet friendly apartments in Chicago, IL?
The best pet friendly apartments in Chicago, IL are Kasa | Walk To Lincoln Park Zoo | Chicago, Beautiful Luxury Loft In Fulton Market - Sleeps 12 | Featured In Architectural Di and Beautiful Corner 2 Bedroom In The Loop | Roof Deck.
How is the public transportation system in Chicago, IL?
Chicago has a reliable and extensive public transportation system, the 'L', which is a combination of elevated trains and underground subway lines. It's a great way to get around the city, especially during rush hour. You can also use the CTA buses for more local travel.
What are the best apartments with parking in Chicago, IL?
Mag Mile Mega Entire Floor 4bd\/4ba+parking&rooftop, Kasa | Walk To Lincoln Park Zoo | Chicago and Charming Chicago-style - Vintage - Tv Nfl Pass are the best apartments with parking in Chicago, IL.
Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?
Chicago is a city that comes alive with seasonal events. In the spring, enjoy the Chicago Blues Festival, while summer brings the Taste of Chicago food festival. Autumn is perfect for the Chicago Marathon, and winter offers festive holiday markets and ice skating at Millennium Park.
What amenities are typically included in apartments in Chicago, IL?
Apartments in Chicago typically include central heating and air conditioning, in-building laundry facilities, and sometimes a gym or a rooftop terrace. Some newer buildings may also offer amenities like a swimming pool, a dog park, or a resident lounge.
What leisure activities are available for relaxation in Chicago, IL?
For relaxation, Chicago offers a variety of options. You can stroll along the Lakefront Trail for stunning views of Lake Michigan, visit the Lincoln Park Zoo for a free day out, or take a boat tour on the Chicago River. For a quieter experience, explore the Garfield Park Conservatory, a beautiful greenhouse with exotic plants.

Destinations nearby

Best Chicago, IL holiday apartments with parking

Chicago, IL

21/10 – 20/01

NZ$215/nighttotal: NZ$19565 (91 )

Welcome To Our Modern Chicago Living! Free Parking, In The Heart Of The City.

2 2

apartment, Chicago

This two-bedroom Chicago apartment, near the University of Illinois Chicago campus, is a 1.6km walk from the Blue Line subway station, offering easy access to Michigan Avenue and Navy Pier.
The self-catering flat sleeps six, includes free on-site parking, a full kitchen with dishwasher, in-unit laundry, and a spa, making it ideal for exploring Chicago's cultural attractions such as the Art Institute of Chicago and sporting events at the United Centre.

9.7 116 reviews

Chicago, IL

09/09 – 12/09

NZ$529/nighttotal: NZ$1587 (3 )

Pulaski Point Properties

1 2

studio, Chicago

This Chicago studio apartment is located in Pulaski Point, approximately 6.4 km from Wrigley Field, 9.2 km from Lincoln Park Zoo, and within 11.3 km of Loyola University and the United Centre.
The self-catering apartment, sleeping up to three guests, boasts a fully equipped kitchen, free private parking, Wi-Fi, and a private bathroom; nearby attractions include O'Hare International Airport (16km).

Chicago, IL

12/07 – 20/07

NZ$711/nighttotal: NZ$5688 (8 )

Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking

2 3

apartment, Chicago

This flat is situated in Chicago's Edgewater district, offering convenient access to the Granville Red Line, Loyola University, lakefront attractions, and parks, with Lake Michigan and its beaches approximately 0.5 kilometres away.
This 93 square metre residence accommodates up to four guests in two bedrooms and features a fully equipped kitchen, in-unit laundry, air conditioning, and a complimentary garage parking spot, with the CTA Red Line just a short walk away for easy travel.

9.8 154 reviews

Chicago, IL

08/10 – 15/10

NZ$718/nighttotal: NZ$5026 (7 )

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 Mi From Wrigley!

2 4

apartment, Chicago

This charming bed and breakfast is situated in Roscoe Village, a lively neighbourhood just 1.6 kilometres west of Wrigley Field. It has received excellent guest reviews, highlighting its comfortable and convenient location.
The 102 square metre suite comfortably accommodates up to six guests and features two bedrooms, a fully equipped kitchen, and a spacious living area. It offers a range of amenities, including a terrace, garden, and access to bike rentals, making it an ideal base for exploring the city.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

9.4 34 reviews

Chicago, IL

20/08 – 23/08

NZ$285/nighttotal: NZ$855 (3 )

Modern 1br In Prime Location!

1 2

apartment, Chicago

This Chicago garden flat is located near the Kedzie Brown Line station, offering easy access to the city centre, approximately 0.64 kilometres from the station.
The one-bedroom, one-bathroom apartment sleeps three, features a king-size bed, fully equipped kitchen, and access to a small outdoor area; nearby amenities include numerous restaurants and cafes.

9.6 12 reviews

Chicago, IL

30/07 – 02/08

NZ$1587/nighttotal: NZ$4761 (3 )

Fulton Market / Noble Square Free Parking, Laundry, 2.5 Miles To Mag Mile!

2 4

apartment, Chicago

This West Town apartment is ideally located less than 1.6km from Wicker Park and 4.8km from the Magnificent Mile, offering easy access to the Blue Line 'L' train.
This 84 square metre flat sleeps six guests, features two bedrooms, one bathroom, in-unit laundry, free street parking, and a fully equipped kitchen; nearby attractions include numerous restaurants and shops.

10 32 reviews

Chicago, IL

01/07 – 31/07

NZ$445/nighttotal: NZ$13350 (30 )

Two Bedroom - Tranquil Retreat

1 4

apartment, Chicago

This Logan Square flat, in Chicago, offers convenient access to the city's attractions and is ideally situated near the trendy shops and restaurants of the neighbourhood.
The two-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen, shared laundry facilities with laundry pods, and designated parking; a combined shower/bathtub is in the modern bathroom.

10 32 reviews

Chicago, IL

17/07 – 19/07

NZ$647/nighttotal: NZ$1294 (2 )

Blake’s Place

1 4

apartment, Chicago

This Chicago garden flat enjoys a prime location near Lake Michigan, approximately 1.4-1.6 km from McCormick Place, the Wind Trust Arena, Grant Park, and Millennium Park.
The two-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen, smart TVs, and access to a private garden, offering comfortable accommodation near Chicago's lakefront attractions.

Best apartment offers in Chicago, IL

10028 Holiday apartments in Chicago, IL

Comfortable And Trendy Design 1br | Lincoln Square

Corporate Apartment With 2 Bedrooms And Fantastic View Of Lake And Skyline

1br Captivating Apartment

University Of Chicago Condo-upgraded And Spacious

Cabin 106 By 747 Lofts

Welcome To Our Charming 2bd 2ba Pilsen Apartment

Cozy Library

Ideal 1-bedroom Stay

2br Airy & Tidy Apt With Free Covered Parking - Central Modern

Chicago Gem Near Subway ~ 5 Mi To Downtown

You Can’t Be Closer To Loyola Uni And Lake! Gym

Comfortable And Trendy Design 1br In Lincoln Square

Best family friendly Chicago, IL Holiday Apartments and Self Contained Accommodations

Lincoln Park Light Filled Loft

29th Floor 2br Grant Park Suite With Balcony, Gym

Gorgeous 5 Bedroom Gem Sleeps 18 With Pool, Ping Pong, Pac Man, Tons Of Games!

Stylish 2br Stunner W/ Unbeatable Location

Best Chicago, IL holiday apartments with a balcony

Welcome To Our Charming 2bd 2ba Pilsen Apartment

New Midterm Furnished Rental - 32+days! - North Center Chicago

Dramatic Wrigley Loft +Private Rooftop, Center Of Wrigley, Ranked Guest Favorite

New! Charming Andersonville Coach House | 3br/2.5ba

Frequently asked questions about apartment rentals in Chicago, IL

Destinations nearby

Best Chicago, IL holiday apartments with parking

Welcome To Our Modern Chicago Living! Free Parking, In The Heart Of The City.

Pulaski Point Properties

Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 Mi From Wrigley!

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Modern 1br In Prime Location!

Fulton Market / Noble Square Free Parking, Laundry, 2.5 Miles To Mag Mile!

Two Bedroom - Tranquil Retreat

Blake’s Place