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

In The Heart Of Andersonville-steps From Clark St. - Chicago, IL
10 123 reviews
Chicago, IL
10/07 – 14/07
A$772/nighttotal: A$3088 (4 )

In The Heart Of Andersonville-steps From Clark St.

1 4
apartment , Chicago
This three-bedroom Chicago apartment, ideal for families, is situated in Andersonville, a short distance from Clark Street, offering easy access to shops and restaurants.
The first-floor flat sleeps six guests, boasts a private garden, free on-street parking, a dedicated office space with an iMac, and a sunroom, plus modern amenities including a 55" TV and a well-equipped kitchen.
Luxurious Four-level Home With Personal Touches Everywhere - Chicago, IL
10 111 reviews
Chicago, IL
08/07 – 12/07
A$3721/nighttotal: A$14884 (4 )

Luxurious Four-level Home With Personal Touches Everywhere

6 2
apartment , Chicago
This six-bedroom mansion, situated in a quiet neighbourhood near Wrigley Field, offers easy access to Lake Michigan, Lincoln Park Zoo, and the 606 trail.
The 465-square-metre property boasts a chef's kitchen, private courtyard, balconies with skyline views, a jacuzzi, sauna, and fitness centre; sleeping up to 16 guests and close to Southport Corridor's restaurants and bars.
Freshly Minted 2br - Elegance & Comfort In Central - Chicago, IL
9.8 72 reviews
Chicago, IL
28/07 – 03/08
A$952/nighttotal: A$5712 (6 )

Freshly Minted 2br - Elegance & Comfort In Central

1 5
apartment , Chicago
This luxurious two-bedroom Chicago apartment boasts an excellent location in the downtown area, offering easy access to public transport and proximity to Chicago's top restaurants and attractions.
The 2-bathroom flat, sleeping up to six guests, features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, a smart TV, and access to a building swimming pool, fitness centre, and rooftop deck with city views; making it ideal for exploring Chicago.
Family Friendly Spacious 3br Suite Sleeps Up To 10 Guests With Optional Parking And Gym Access Near Mccormick Place And Soldier Field - Chicago, IL
8.5 2 reviews
Chicago, IL
21/08 – 23/08
A$1027/nighttotal: A$2054 (2 )

Family Friendly Spacious 3br Suite Sleeps Up To 10 Guests With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

3 8
apartment , Chicago
This three-bedroom Chicago apartment, near McCormick Place, is conveniently located approximately 2.4 kilometres from the Field Museum and 2.9 kilometres from the Art Institute of Chicago.
The 111 square metre property sleeps up to 10 guests and boasts a fully equipped kitchen, free Wi-Fi, a fitness centre, and on-site parking; it also benefits from a garden and is allergy-free.

Best Chicago, IL holiday apartments with a balcony

The Penthouse, Lux Stay Near Downtown, Uofc & Lake - Chicago, IL
9.2 38 reviews
Chicago, IL
29/06 – 02/07
A$445/nighttotal: A$1335 (3 )

The Penthouse, Lux Stay Near Downtown, Uofc & Lake

2 2
apartment , Chicago
This Chicago penthouse apartment, near the University of Chicago campus and approximately 8km from Downtown Chicago, offers easy access to Lake Michigan and Oakwood Beach (a 17-minute walk away).
The 135-square-metre (1453 sq ft) property boasts two bedrooms, two bathrooms, a fully equipped kitchen, and a terrace, accommodating up to seven guests and providing free Wi-Fi and toiletries.
Private Balcony, 1 Garage Parking, Sleeps 8! - Chicago, IL
10 2 reviews
Chicago, IL
24/07 – 27/07
A$1123/nighttotal: A$3369 (3 )

Private Balcony, 1 Garage Parking, Sleeps 8!

2 3
apartment , Chicago
This West Loop apartment, a three-minute drive from Fulton Market and under 13km from both Millennium Park and Navy Pier, offers convenient access to Chicago's key attractions.
The 107 square metre property boasts a two-bedroom layout sleeping up to eight guests, featuring a king-size bed, double bed, bunk bed, a fully equipped kitchen with Keurig coffee maker, in-unit laundry, private balcony, and a heated garage parking space.
5 Mi To Midway: Walkable Chicago Apartment - Chicago, IL
Chicago, IL
01/09 – 31/10
A$196/nighttotal: A$11760 (60 )

5 Mi To Midway: Walkable Chicago Apartment

2 2
apartment , Chicago
This Ashburn apartment in Chicago is conveniently located 5 blocks from Pete's Fresh Market, within 16km of the Illinois Medical District and 14km from Jackson Park on Lake Michigan.
This two-bedroom, one-bathroom flat offers 120 square metres of living space, including a covered balcony, full kitchen with modern appliances, and free on-street parking; it comfortably sleeps four guests.
Mccormick Place 2b/2b Family Unit With Optional Parking For Up To 8 Guests - Chicago, IL
8.0 2 reviews
Chicago, IL
23/07 – 27/07
A$961/nighttotal: A$3844 (4 )

Mccormick Place 2b/2b Family Unit With Optional Parking For Up To 8 Guests

2 4
apartment , Chicago
This Near South Side Chicago flat is situated a 7-9 minute walk from McCormick Place, and within a short taxi ride of Soldier Field, the Museum Campus, and the city centre.
The 74-square-metre (800 sq ft) property offers two bedrooms, two bathrooms, sleeps eight comfortably, and includes a fully equipped kitchen, terrace, garden, parking (optional, £24 per day), and fast internet.

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Destinations nearby

Best Chicago, IL holiday apartments with parking

Stylish Two Bedroom - A Block From Wrigley Field - Chicago, IL
9.9 107 reviews
Chicago, IL
24/07 – 27/07
A$812/nighttotal: A$2436 (3 )

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.
Wrigley 2br, 1ba With Free Parking - Chicago, IL
8.6 9 reviews
Chicago, IL
22/06 – 24/06
A$552/nighttotal: A$1104 (2 )

Wrigley 2br, 1ba With Free Parking

2 2
apartment , Chicago
This two-bedroom Chicago apartment is situated near Wrigleyville, a 13-minute walk from Wrigley Field, 5.3km from Lincoln Park Zoo, and within 8km of Loyola University and 360 Chicago Observation Deck.
The 116 square metre property offers a spacious layout sleeping up to 11 guests, boasting a fully equipped kitchen, private entrance, garden, parking, and an outdoor fireplace; all within easy reach of local attractions.
Steps To Shops & Eats: Apt In Portage Park! - Chicago, IL
Chicago, IL
01/09 – 31/10
A$168/nighttotal: A$10080 (60 )

Steps To Shops & Eats: Apt In Portage Park!

2 2
apartment , Chicago
This two-bedroom Chicago apartment is situated near Portage Park in the Northwest Side, conveniently located approximately 9.6km from Wrigley Field and 11.2km from the Garfield Park Conservatory.
The 88 square metre flat offers in-unit laundry, a well-equipped kitchen including a dishwasher and espresso machine, and sleeps up to five guests, making it ideal for families or small groups visiting the city.
Stylish 2br Apartment With Patio And Gym Near Mccormick Place & Lakefront Trail - Chicago, IL
8.0 4 reviews
Chicago, IL
21/07 – 01/08
A$603/nighttotal: A$6633 (11 )

Stylish 2br Apartment With Patio And Gym Near Mccormick Place & Lakefront Trail

2 2
apartment , Chicago
This Near South Side Chicago flat is conveniently located a short walk from State Street and Wintrust Arena, and within 1.6km of McCormick Place and Soldier Field.
The 79 square metre, two-bedroom, two-bathroom apartment sleeps six, features a fully equipped kitchen, in-unit laundry, free Wi-Fi, a terrace, garden access, and a fitness centre; parking is also available.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

The Roscoe Village Guesthouse - Chicago, IL
9.4 16 reviews
Chicago, IL
21/06 – 23/06
A$363/nighttotal: A$726 (2 )

The Roscoe Village Guesthouse

3 2
apartment , Chicago
This Roscoe Village guesthouse in Chicago is situated 2.4 kilometres from Wrigley Field and within 8 kilometres of Lincoln Park Zoo and other key attractions including 360 Chicago and the United Centre.
This three-bedroom apartment offers 111 square metres of space, sleeping up to six guests, and features a fully equipped kitchen with a dishwasher, air conditioning, and a private entrance; towels and bed linen are provided.
Pine Beam Sloth Apartment Next To Blue Line - Chicago, IL
10 6 reviews
Chicago, IL
18/06 – 19/06
A$648/nightfor 1 night

Pine Beam Sloth Apartment Next To Blue Line

1 1
apartment , Chicago
This Irving Park flat is ideally situated near Milwaukee Avenue, a 2-minute walk from the Irving Park Blue Line station offering swift access to Chicago's city centre, and close to Portage Park and the Copernicus Center.
The one-bedroom, one-bathroom apartment sleeps two, boasts a fully equipped kitchen including a dishwasher, in-unit laundry, free Wi-Fi, a smart TV, and is within easy reach of the Walt Disney House.
Chicago Riverhouse With Private Fenced In Oasis - Chicago, IL
9.9 260 reviews
Chicago, IL
03/09 – 06/09
A$690/nighttotal: A$2070 (3 )

Chicago Riverhouse With Private Fenced In Oasis

2 4
apartment , Chicago
This apartment is situated between the Chicago River and Forest Preserves, offering a peaceful retreat just 3.5 miles from the beach and close to Lake Shore Drive and the 90/94 expressway. It has been highly rated for its location, cleanliness and overall experience by previous guests.
The 167 square metre property features an open-plan living and kitchen area, perfect for families or groups. Enjoy the private patio and fenced-in yard, relax in the jacuzzi, or stay fit in the on-site gym, all while benefiting from free parking and a fully equipped kitchen.
Stylish Friendly 3br Suite Near Mccormick - Chicago, IL
Chicago, IL
27/06 – 28/06
A$1100/nightfor 1 night

Stylish Friendly 3br Suite Near Mccormick

3 4
apartment , Chicago
This South Loop flat offers a prime Chicago location, just a short walk to McCormick Place and Grant Park, and a quick Uber to Museum Campus and Soldier Field.
This spacious 86-square-metre residence features three bedrooms and two bathrooms, accommodating up to six guests with amenities including in-unit laundry, fast Wi-Fi, and 4K Roku Smart TVs.
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