Apartment rentals in Chicago

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Chicago apartments
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Apartments in Chicago

Best family-friendly Chicago holiday apartments

Among the 13595 accommodations in Chicago, here are the 4 best family friendly apartments

Newly Remodeled Gem | Heart Of Chicago - Chicago
9.4 6 reviews

Newly Remodeled Gem | Heart Of Chicago

apartment, Chicago
This two-bedroom Humboldt Park flat, located approximately 1.6km from the Walt Disney House and 2.1km from Humboldt Park, offers convenient access to the United Centre and Michigan Avenue (9.7km).
The 121 square metre self-catering property sleeps four, boasting a fully equipped kitchen, in-unit laundry, a terrace, garden access, parking, and excellent guest reviews; outdoor barbecue grills are available for guest use.
New Garden Studio Near Wrigley/depaul/dwtn - Chicago
9.7 65 reviews

New Garden Studio Near Wrigley/depaul/dwtn

apartment, Chicago
This Lincoln Park garden flat offers self-check-in and is conveniently located near Wrigley Field, DePaul University, and Chicago's city centre, providing easy access to O'Hare International Airport (distances unspecified).
The one-bedroom apartment, sleeping up to three guests, includes a fully equipped kitchen, high-speed internet, a washer/dryer, and free on-street parking, plus a dedicated workspace and access to multiple streaming platforms.
Boho House | Chic, 1903 Chicago Workers Cottage - Chicago
9.8 205 reviews

Boho House | Chic, 1903 Chicago Workers Cottage

apartment, Chicago
This three-bedroom Chicago cottage, sleeping eight, is situated in a neighbourhood near popular bars and restaurants, approximately 16km from O'Hare International Airport and 8km from Chicago's city centre.
The property boasts a redesigned kitchen with stainless steel appliances, a private fenced backyard with a fire pit and deck, high-speed WiFi (800+ Mbps), and secure parking for two cars; wellness services are also available nearby.
City View 3br Condo/garage Parking/rooftop Deck - Chicago
9.4 88 reviews

City View 3br Condo/garage Parking/rooftop Deck

apartment, Chicago
This Wicker Park apartment in Chicago offers easy access to downtown via public transport and is close to Wicker Park's restaurants and shops.
Sleeping up to 12 guests, this three-bedroom property features two bathrooms, a loft with a queen bed, two balconies, a shared patio with a gas fire pit, a fully equipped kitchen with granite island, flat-screen TVs, and an arcade machine; garage parking is included.

Best Chicago holiday apartments with a balcony

The Banksy-free Parking -4 Bedroom W King Bed- Firepit Rooftop Near United Center - Chicago
8.4 18 reviews

The Banksy-free Parking -4 Bedroom W King Bed- Firepit Rooftop Near United Center

apartment, Chicago
This spacious Chicago apartment, ideal for families or large groups, is located a 14-minute walk from the United Centre and 4.2km from Union Station, offering easy access to public transport and Chicago's attractions.
The 223 square metre property boasts four bedrooms, two bathrooms, a fully equipped kitchen, a private patio with barbecue, and accommodates up to 23 guests, making it perfect for events near the United Centre.
1 #31 - 4 Bedroom Condo - Mccormick Place, Wintrust Arena, Chinatown - Chicago
9.5 94 reviews

1 #31 - 4 Bedroom Condo - Mccormick Place, Wintrust Arena, Chinatown

apartment, Chicago
This newly renovated dual-suite apartment is located in Chicago's Chinatown, just a short walk from public transport and a 5-kilometre drive from downtown and other attractions like Millennium Park. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment has two separate living spaces, each with its own kitchen, dining room, and living room, making it ideal for larger groups. Each suite is fully equipped with modern appliances, including a fridge, freezer, microwave, dishwasher, and air conditioning, along with a terrace, garden, and spa.
Gold Coast Group Retreat + Breathtaking Views - Chicago
No reviews

Gold Coast Group Retreat + Breathtaking Views

apartment, Chicago
This four-bedroom flat in Chicago's Gold Coast, a historic and affluent district, is a 7-minute walk from Michigan Avenue and a 10-minute walk from the Lakefront Trail.
This family-friendly residence offers accommodation for up to 10 guests, featuring a fully-equipped kitchen, smart TVs, fast WiFi, and access to building amenities including an outdoor swimming pool and fitness centre.
Charming Garden Pad With Spacious Deck - Enchanting Urban Retreat - Chicago
No reviews

Charming Garden Pad With Spacious Deck - Enchanting Urban Retreat

apartment, Chicago
This recently renovated three-bedroom flat is situated in a prime Chicago location, just steps from a major stadium and offering unique proximity to player parking, ideal for sports enthusiasts.
This family-friendly apartment accommodates up to 10 guests with nine beds, featuring air conditioning, a kitchen with essential appliances, and a shared back deck, with street parking permits available upon advance notice.

Popular destinations

Best Chicago holiday apartments with parking

Stylish Northside Retreat - Chicago
9.8 74 reviews

Stylish Northside Retreat

apartment, Chicago
This two-bedroom Chicago apartment is situated on the North Side, offering convenient access to local shops and public transport.
The 4-guest flat features a fully equipped kitchen, high-speed Wi-Fi, and free street parking, ensuring a comfortable stay.
Breathtaking & Chic Oasis Loc In Desirable Old Twn - Chicago
9.8 164 reviews

Breathtaking & Chic Oasis Loc In Desirable Old Twn

apartment, Chicago
This Old Town Chicago flat is conveniently located within walking distance of numerous restaurants and bars, and a short drive (approximately 8km) from Chicago's city centre.
The stylish one-bedroom condo sleeps four guests, offering a queen bed, pull-out sofa, fully equipped kitchen with island, building gym, and ninth-floor terrace; free street parking is available.
Experience Chicago Living Near United Center - Chicago
9.0 37 reviews

Experience Chicago Living Near United Center

apartment, Chicago
This two-bedroom flat is situated in the Austin neighbourhood, about 10 miles west of downtown Chicago, offering a more residential atmosphere than the bustling city centre. It has received excellent user ratings, making it a popular choice for travellers.
The flat is suitable for up to five guests, with two bedrooms and a bathroom, plus a sunroom and a living room with three large sofas. The kitchen features modern appliances, including a fridge, microwave, and dishwasher, and there is also air conditioning, internet, and a swimming pool.
Lincoln Square Gem! - Chicago
9.9 498 reviews

Lincoln Square Gem!

apartment, Chicago
This two-bedroom flat is located in Lincoln Square, a lively neighbourhood in Chicago, just 800 metres from the Western stop on the Brown Line, providing easy access to the city centre. The property has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The flat is suitable for up to four guests and features a well-equipped kitchen, a comfortable living space, and a private garden. Guests can enjoy the convenience of in-unit laundry facilities, air conditioning, and free Wi-Fi, as well as parking.

Best Chicago holiday apartments with air conditioning

Welcome To Nancy's Pad! - Chicago
9.7 354 reviews

Welcome To Nancy's Pad!

apartment, Chicago
This Lakeview flat, near Wrigley Field and Southport's nightlife, offers easy access to downtown Chicago.
Sleeping up to six guests, this two-bedroom, one-bathroom apartment includes a garden, parking, free laundry facilities, and a private patio; amenities such as a fridge, microwave, and air conditioning are also provided.
Rockwell By The River - Chicago
10 121 reviews

Rockwell By The River

apartment, Chicago
This three-bedroom Logan Square flat, in Chicago, Illinois, offers convenient access to local restaurants and breweries, and is a short cycle from other Logan Square attractions.
Sleeping seven guests, this newly renovated property features a queen-size pull-out sofa, keyless entry, a shared workspace, and access to a garden with a barbecue and fire pit (on request).
Private Suite In Logan Square, Walk To Everything! - Chicago
9.8 12 reviews

Private Suite In Logan Square, Walk To Everything!

apartment, Chicago
This newly remodelled one-bedroom flat is located in Chicago's Logan Square district, offering private accommodation with its own entrance, just 7 kilometres from the city centre.
This suite provides comfort and convenience for up to three adults, featuring air conditioning, a kitchenette with a fridge, freezer, and microwave, and on-site support from the homeowners.
High-end 8br Apartments In West Loop - Chicago
9.7 352 reviews

High-end 8br Apartments In West Loop

apartment, Chicago
This Chicago apartment rental is ideally located near Fulton Market, offering easy access to hundreds of restaurants within a 1.6 km radius and a large Target supermarket directly opposite.
The property boasts a private balcony, top-brand kitchen appliances, a Sonos sound system, and access to building amenities including a fitness centre, sky lounge, and rooftop terrace; parking is also available.