Best apartment offers in Chicago, IL

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Chicago, IL apartments
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10028 Holiday apartments in Chicago, IL

Best family friendly Chicago, IL Holiday Apartments

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

The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile - Chicago, IL
9.1 68 reviews
Chicago, IL
17/07 – 19/07
A$3044/nighttotal: A$6088 (2 )

The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile

2 4
apartment , Chicago
This Chicago Magnificent Mile apartment rental is situated less than 1.6km from the city centre, offering easy access to the Water Tower Place, the Museum of Contemporary Art Chicago, and 360 Chicago Observation Deck, with Oak Street Beach an 11-minute walk away.
The fully furnished flat includes a kitchen with microwave and fridge, free Wi-Fi, air conditioning, a rooftop pool, garden, terrace, and private parking; nearby attractions include Ohio Street Beach (1.4km) and various high-end shops and restaurants.
Stylish 2br South Loop Family Unit Near Mccormick Place & Soldier Field - Chicago, IL
9.0 12 reviews
Chicago, IL
01/01 – 31/01
A$196/nighttotal: A$5880 (30 )

Stylish 2br South Loop Family Unit Near Mccormick Place & Soldier Field

2 6
apartment , Chicago
This family-friendly Chicago apartment is situated in the Near South Side, less than 1.6km from State Street and the Wintrust Arena, and under 2km from McCormick Place and Soldier Field.
The 88-square-metre property boasts three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, free Wi-Fi, a terrace, and access to a fitness centre and parking.
Clean & Sunny, 2bd, Private Deck, 15min To Wrigley! - Chicago, IL
10 15 reviews
Chicago, IL
09/09 – 12/09
A$461/nighttotal: A$1383 (3 )

Clean & Sunny, 2bd, Private Deck, 15min To Wrigley!

2 2
apartment , Chicago
This Irving Park, Chicago flat is a short walk from Addison and Irving Park buses, a 15-minute walk (approx. 1.2km) from the train, and a 15-minute bus ride or free shuttle to Wrigley Field.
The 84-square-metre (904 sq ft) two-bedroom apartment sleeps six, boasting a fully equipped kitchen, in-unit laundry, a private porch, access to a shared garden, and is close to Horner Park and numerous restaurants and bars.
Skyline Oasis: City & Lake Views - Chicago, IL
9.9 35 reviews
Chicago, IL
06/10 – 15/10
A$700/nighttotal: A$6300 (9 )

Skyline Oasis: City & Lake Views

1 2
apartment , Chicago
This luxurious Chicago penthouse apartment is located in the Fulton Market District of the West Loop, offering easy access to the city's attractions.
The one-bedroom, one-bathroom flat sleeps two guests and boasts a high-floor corner unit with stunning city, lake, and river views, a spacious balcony, full kitchen, and access to a swimming pool, jacuzzi, fitness centre, and sauna.

Best Chicago, IL holiday apartments with a balcony

Luxury House In The Heart Of Old Town With Parking - Chicago, IL
10 57 reviews
Chicago, IL
14/07 – 18/07
A$3439/nighttotal: A$13756 (4 )

Luxury House In The Heart Of Old Town With Parking

5 4
apartment , Chicago
This luxury home is situated in Chicago's Old Town neighbourhood, just 3.5 kilometres from the United Center and Wrigley Field, and within walking distance of North Avenue Beach, the Magnificent Mile, and Navy Pier. The property has received excellent guest reviews, with many praising its spaciousness, modern design, and exceptional amenities.
This five-bedroom, eight-bathroom property spans 576 square metres and comfortably accommodates up to 12 guests. The house offers a range of amenities, including a rooftop lounge with city views, a game hall, a sauna, a gym, and a fully equipped kitchen.
South Loop Rooftop With In & Out Parking 1 - Chicago, IL
9.0 2 reviews
Chicago, IL
10/07 – 15/07
A$1083/nighttotal: A$5415 (5 )

South Loop Rooftop With In & Out Parking 1

2 4
apartment , Chicago
This centrally located downtown Chicago flat offers a 2-bedroom, 2-bathroom layout spanning 82 square metres, situated within a 15-minute walk of Millennium Park, the Chicago Riverwalk, and the Art Institute of Chicago, with Willis Tower also nearby.
This modern accommodation provides parking, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, a terrace, and access to building amenities including a rooftop pool and gym, comfortably accommodating up to five guests.
4br Bright City Retreat-sleeps 12-garage Parking - Chicago, IL
10 1 review
Chicago, IL
08/07 – 13/07
A$1385/nighttotal: A$6925 (5 )

4br Bright City Retreat-sleeps 12-garage Parking

5 10
apartment , Chicago
This expansive flat is situated in Chicago's Belmont Cragin district, offering convenient access to cultural attractions and major event venues.
Boasting 186 square meters of living space, this family-friendly five-bedroom apartment accommodates up to 12 guests and features a fully equipped kitchen, three bathrooms, high-speed WiFi, on-site parking, and a terrace/balcony.
Luxury Meets Comfort: River North Rentals With Chic Style & Prime Chicago Access - Chicago, IL
8.0 1 review
Chicago, IL
15/08 – 16/08
A$1112/nightfor 1 night

Luxury Meets Comfort: River North Rentals With Chic Style & Prime Chicago Access

1 1
apartment , Chicago
This Level River North apartment, a 70 square metre (753 square foot) one-bedroom flat, is situated in the River North district, minutes from the Magnificent Mile and a short distance across the river from the Loop.
The self-catering property sleeps four guests and boasts a fully equipped kitchen, including a dishwasher, plus a terrace, swimming pool, sauna, and parking; nearby riverside parks offer green space.

Frequently asked questions about apartment rentals in Chicago, IL

Destinations nearby

Best Chicago, IL holiday apartments with parking

Cabin 102 By 747 Lofts - Chicago, IL
9.5 113 reviews
Chicago, IL
27/08 – 30/08
A$483/nighttotal: A$1449 (3 )

Cabin 102 By 747 Lofts

1 1
apartment , Chicago
This studio apartment is conveniently located in Chicago, close to the Blue Line L, providing easy access to both downtown and the West Loop's vibrant restaurant scene. The studio has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment is ideal for solo travellers and features a modern kitchen with a fridge and microwave, as well as a washer and dryer for added convenience. Amenities include air conditioning, parking, and internet access, along with spa baths for a touch of luxury.
Stylish Two Bedroom - A Block From Wrigley Field - Chicago, IL
9.9 109 reviews
Chicago, IL
01/10 – 05/10
A$467/nighttotal: A$1868 (4 )

Stylish Two Bedroom - A Block From Wrigley Field

1 3
apartment , Chicago
This Lakeview/Wrigleyville flat is situated a short walk from Wrigley Field and the Red Line, offering easy access to Lake Michigan and Chicago's attractions.
The 93 square metre (1000 square foot) property features two queen-sized bedrooms, a dining and living area, private porch, in-unit laundry, and parking for one large or two small vehicles, accommodating up to five guests.
Spacious 3br In Lakeview - Walk To Wrigley - Family Friendly, Newly Renovated! - Chicago, IL
10 2 reviews
Chicago, IL
06/07 – 12/07
A$655/nighttotal: A$3930 (6 )

Spacious 3br In Lakeview - Walk To Wrigley - Family Friendly, Newly Renovated!

3 5
apartment , Chicago
This Lakeview apartment, a 10-15 minute walk from Wrigley Field and 15-20 minutes from Lincoln Park and the lakefront, offers easy access to Chicago's attractions and public transport.
This three-bedroom property, boasting 118 square metres of floor space and sleeping eight, includes a fully equipped kitchen, garden, spa, parking and is within a short walk of the Belmont Theatre District.
Garage Parking - Vintage Charm - And A Fabulous Location! Easily Enjoy The Best Of Chicago! - Chicago, IL
9.6 306 reviews
Chicago, IL
20/09 – 25/09
A$409/nighttotal: A$2045 (5 )

Garage Parking - Vintage Charm - And A Fabulous Location! Easily Enjoy The Best Of Chicago!

2 2
apartment , Chicago
This two-bedroom Chicago apartment is situated in a neighbourhood a 1.6km walk from Chicago's best bars and restaurants.
The property offers a fully equipped kitchen, including a fridge, microwave, and dishwasher, accommodates four guests, and includes a private garage parking space, plus access to a shared garden.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Beautiful (No Chores  No Cleaning Fees) - Chicago, IL
9.9 132 reviews
Chicago, IL
27/06 – 27/07
A$377/nighttotal: A$11310 (30 )

Beautiful (No Chores No Cleaning Fees)

1 1
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.
River North Rooftop With In And Out Parking 3 - Chicago, IL
9.6 5 reviews
Chicago, IL
28/06 – 29/06
A$865/nightfor 1 night

River North Rooftop With In And Out Parking 3

2 1
apartment , Chicago
This River North flat, a three-minute walk from Chicago's Grand Red Line station and close to the Magnificent Mile, offers easy access to the city's key attractions.
The 102-square-metre, two-bedroom, two-bathroom apartment sleeps four, includes a fully equipped kitchen, in-unit streaming services, and access to a rooftop patio with barbecue facilities and a fitness centre.
Modern Oasis | 4 Beds | Sleeps 7 | Mins To Loop - Chicago, IL
9.1 32 reviews
Chicago, IL
12/09 – 18/09
A$298/nighttotal: A$1788 (6 )

Modern Oasis | 4 Beds | Sleeps 7 | Mins To Loop

1 7
apartment , Chicago
This two-bedroom flat in Chicago offers excellent proximity to major attractions, situated just a few minutes from the city centre and The Loop, with convenient access to Chinatown and McCormick Place, placing it within 2 kilometres of Museum Campus and Union Station.
This residence accommodates up to seven guests with two queen beds, a further queen bed, and a sofa bed, boasting a fully equipped kitchen, in-unit laundry, dedicated office space with Wi-Fi, and multiple Smart TVs, all within a property offering air conditioning and parking.
Bright Logan Square 1br | Walk To Blue Line - Chicago, IL
9.8 187 reviews
Chicago, IL
30/09 – 07/10
A$225/nighttotal: A$1575 (7 )

Bright Logan Square 1br | Walk To Blue Line

1 2
apartment , Chicago
This Logan Square flat is situated a short distance from Palmer Square Park and a five-minute walk (approximately 0.8 kilometres) from the California Blue Line CTA station, offering easy access to Chicago's other neighbourhoods.
The one-bedroom apartment, sleeping up to three guests with a pull-out sofa bed, includes a kitchen with fridge, freezer and microwave, high-speed internet, a smart TV, air conditioning, central heating, and on-street parking nearby on Lyndale Street or Palmer Square Street.
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