Best apartment offers in Chicago, IL

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Chicago, IL apartments
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10028 Best apartments in Chicago, IL

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

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

Modern 4br Pilsen Retreat Near Illinois Medical District & Chicago Downtown - Chicago, IL
10 2 reviews
Chicago, IL
15/07 – 17/07
₹65902/nighttotal: ₹131804 (2 )

Modern 4br Pilsen Retreat Near Illinois Medical District & Chicago Downtown

4 10
apartment , Chicago
This 4-bedroom flat in Pilsen is situated 3.9 kilometres from Union Station, providing straightforward access to the Illinois Medical District and downtown Chicago.
This family-friendly property offers 10 square metres of floor area, accommodates up to 19 guests, and includes a kitchen with a dishwasher, a fitness room, a garden, and parking.
Cozy Chicago House Near Obama Center And Beach! - Chicago, IL
9.9 82 reviews
Chicago, IL
14/08 – 16/08
₹74935/nighttotal: ₹149870 (2 )

Cozy Chicago House Near Obama Center And Beach!

1 9
apartment , Chicago
This spacious Chicago house, sleeping up to 12 guests, is conveniently located in an unspecified area of the city, though its registration number provides a general location within Chicago.
The four-bedroom, three-bathroom property boasts a well-equipped kitchen, multiple entertainment options including a projector and smart home features, and offers easy access to all levels, including a basement bedroom and bathroom; a garden and parking are also available.
Cozy Garden Unit 1st Flr With Private Entrance And Turo Vehicle Available. - Chicago, IL
9.6 8 reviews
Chicago, IL
18/09 – 19/09
₹18995/nightfor 1 night

Cozy Garden Unit 1st Flr With Private Entrance And Turo Vehicle Available.

1 2
apartment , Hickory Hills
This Hickory Hills apartment is situated approximately 1.6km from PGN Jump N' Fun Entertainment and 4.3km from Resurrection Cemetery & Mausoleums, with Moraine Valley Community College and Chicago Ridge Shopping Mall within a 9.7km radius.
The one-bedroom, one-bathroom flat sleeps two guests and offers a full kitchen, in-unit laundry, patio, Smart TV, and access to a fitness centre and spa; nearby attractions include the PGN Jump N' Fun Entertainment centre.
Brand New 3br Chicago Retreat Near Fulton Market And United Center - Chicago, IL
8.5 2 reviews
Chicago, IL
13/07 – 16/07
₹34431/nighttotal: ₹103293 (3 )

Brand New 3br Chicago Retreat Near Fulton Market And United Center

3 2
apartment , Chicago
This newly constructed three-bedroom flat in Chicago is situated near Fulton Market and the United Centre, offering a 2.9 kilometre walk to the United Centre and proximity to Union Station.
This family-friendly apartment provides complimentary high-speed WiFi, free private parking, and a fully equipped kitchen, with a check-out time of 11:00 AM.

Best Chicago, IL holiday apartments with a balcony

Elegant 3-bed, 3-bath Home In Chicago <25-minutes To Ohare & Downtown + Parking - Chicago, IL
9.8 8 reviews
Chicago, IL
21/07 – 23/07
₹63311/nighttotal: ₹126622 (2 )

Elegant 3-bed, 3-bath Home In Chicago <25-minutes To Ohare & Downtown + Parking

3 7
apartment , Chicago
This Irving Park family home, situated 4.7km from Wrigley Field and 5km from Portage Park, offers easy access to Chicago's Brown Line and Lake Michigan (approx. 9.7km).
The 279 square metre property sleeps up to 10 guests in three bedrooms and three bathrooms, boasting a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
Modern 2-bedroom Townhome In Chicago With Private Patio - Chicago, IL
10 3 reviews
Chicago, IL
12/09 – 18/09
₹68735/nighttotal: ₹412410 (6 )

Modern 2-bedroom Townhome In Chicago With Private Patio

2 7
apartment , Chicago
This Bucktown townhouse, situated on a quiet corner block within easy walking distance of the Six Corners intersection of North, Milwaukee, and Damen Avenues, offers a convenient base for exploring Chicago.
This 167 square metre (1798 square foot) property sleeps up to nine guests, boasting two living rooms, three bathrooms, a fully equipped kitchen with coffee station, a private patio with fire pit, a game room with shuffleboard and Connect 4, and free street parking.
Cozy Downtown Mich Ave #7 | Gym+rooftop - Chicago, IL
9.7 297 reviews
Chicago, IL
30/07 – 13/08
₹85422/nighttotal: ₹1195908 (14 )

Cozy Downtown Mich Ave #7 | Gym+rooftop

2 2
apartment , Chicago
This penthouse apartment is situated on Michigan Avenue, just a short walk from Grant Park and Lake Michigan, offering easy access to Chicago's vibrant attractions. The apartment boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The two-bedroom, two-bathroom apartment offers 84 square metres of living space, providing ample room for relaxation and comfort. The apartment comes equipped with a modern kitchen, a spacious living area, a terrace, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.
Spacious And Cozy Home Near Ohare Airport - Chicago, IL
Chicago, IL
11/09 – 13/09
₹118718/nighttotal: ₹237436 (2 )

Spacious And Cozy Home Near Ohare Airport

5 11
apartment , Bensenville
This Bensenville property offers a superior location for travellers, situated just a short drive from O'Hare International Airport and within easy reach of Woodfield Mall and the Fashion Outlets of Chicago.
This five-bedroom, four-bathroom flat accommodates up to fourteen guests and boasts a cinema room, on-site gym, and a garden, with nearby access to Spring Valley and Kent Fuller Air Station Prairie.

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 absolutely must visit the iconic Willis Tower, formerly known as the Sears Tower, for incredible views of the city. You'll also want to wander through Millennium Park and see the Cloud Gate sculpture, nicknamed 'The Bean'. And no visit to Chicago is complete without a stroll along the Magnificent Mile, a stretch of North Michigan Avenue known for its high-end shopping and dining.
  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a great mix of vibrancy and convenience, consider renting in the West Loop, River North, or Lincoln Park. These neighbourhoods offer easy access to public transport, fantastic restaurants, and a variety of shops and entertainment options.
  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is packed with cultural gems! You'll want to check out the Art Institute of Chicago, home to world-renowned art collections, and the Field Museum, where you can explore natural history exhibits. For a dose of history, visit the Chicago Cultural Center, a stunning building with beautiful stained glass windows and free cultural events.
  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, with iconic skyscrapers like the Willis Tower and the John Hancock Center. It's also famous for its deep-dish pizza, a culinary tradition unique to the city. And don't forget the Chicago River, which flows through the heart of the city and is a popular spot for boat tours and water taxis.
  • Where can you find the best local markets and street food in Chicago, IL?

    For a true taste of Chicago, head to Maxwell Street Market, a bustling open-air market with a wide variety of street food vendors. You can also find great local produce and artisanal goods at the Green City Market, held in various locations throughout the city during the warmer months.
  • How is the public transportation system in Chicago, IL?

    Chicago has a comprehensive public transport system, with the 'L' train, buses, and a network of commuter trains. It's a great way to get around the city, especially if you're staying in a central neighbourhood. Just be sure to get a Ventra card for easy payment.
  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago comes alive with festivals throughout the year! In the summer, you'll want to check out the Chicago Air and Water Show, a spectacular display of aviation and watercraft. And during the winter, the Christkindlmarket, a traditional German Christmas market, brings a festive atmosphere to the city.
  • What amenities are typically included in apartments in Chicago, IL?

    Most apartments in Chicago include basic amenities like central heating and air conditioning, a refrigerator, stove, and oven. Depending on the building and the price, you might also find in-building laundry facilities, a fitness centre, and a rooftop deck.
  • What leisure activities are available for relaxation in Chicago, IL?

    Chicago offers plenty of relaxation options! You can stroll through Lincoln Park, a sprawling green space with a zoo, a conservatory, and a lakefront. Or, for a more urban experience, head to the Chicago Riverwalk, a scenic path along the river where you can enjoy views of the city skyline.

Destinations nearby

Best Chicago, IL holiday apartments with parking

New! Large/beautiful Home With 6bds/4bth + Garage! - Chicago, IL
9.9 46 reviews
Chicago, IL
08/07 – 13/07
₹110311/nighttotal: ₹551555 (5 )

New! Large/beautiful Home With 6bds/4bth + Garage!

1 10
apartment , Chicago
This six-bedroom Chicago house, situated in a residential area 32-48 km from both Midway and O'Hare International Airports, offers convenient access to the city.
Sleeping up to 12 guests, this spacious property boasts four bathrooms, a fully equipped kitchen with dishwasher, a garden, parking, and amenities including a furnished deck with grill and ping pong table.
Your Home Away From Home -12 Mins From Downtown - Chicago, IL
9.4 3 reviews
Chicago, IL
12/09 – 18/09
₹28124/nighttotal: ₹168744 (6 )

Your Home Away From Home -12 Mins From Downtown

3 7
apartment , Chicago
This New City apartment, situated a short drive (approx. 1.6km) from the Dan Ryan Expressway and within easy reach of Chicago's White Sox Park, McCormick Place, and Soldier Field, offers convenient access to major attractions.
Sleeping eight guests comfortably, this three-bedroom, two-bathroom dwelling includes parking, air conditioning, Wi-Fi, and a kitchen equipped with a fridge and microwave; nearby amenities include a grocery store (less than 2km away).
Modern Condo • Safe Chicago Stay Near O’hare - Chicago, IL
10 5 reviews
Chicago, IL
01/08 – 31/08
₹14770/nighttotal: ₹443100 (30 )

Modern Condo • Safe Chicago Stay Near O’hare

1 1
apartment , Chicago
This one-bedroom flat is located in a secure district near Rosemont, Rivers Casino, and O'Hare Airport, with the Blue Line providing easy access to central Chicago, approximately 25 kilometres away.
This apartment offers a Smart TV, electric fireplace, a fully equipped kitchen with modern appliances, complimentary Wi-Fi, and private parking, accommodating up to four guests and their pets.
Luxe Loft Vibe With King Suite - 4br 3ba - Chicago, IL
9.7 7 reviews
Chicago, IL
01/09 – 02/09
₹46139/nightfor 1 night

Luxe Loft Vibe With King Suite - 4br 3ba

4 2
apartment , Chicago
This luxurious Chicago apartment, situated near 63rd Street Beach (1.9km) and the Museum of Science and Industry (2.7km), offers easy access to these attractions and is approximately 9.9km from Guaranteed Rate Field and the Field Museum.
The 232 square metre property boasts a spacious four-bedroom, three-bathroom layout sleeping up to 15 guests, complete with a fully equipped kitchen, private patio, hot tub, free Wi-Fi, and free private parking.

Best Chicago, IL holiday apartments with air conditioning

Heart Of Chicago 5 Bedroom Modern 12 Guest  Home - Chicago, IL
9.0 103 reviews
Chicago, IL
22/06 – 25/06
₹33060/nighttotal: ₹99180 (3 )

Heart Of Chicago 5 Bedroom Modern 12 Guest Home

1 7
apartment , Chicago
This five-bedroom house in Chicago's Bucktown neighbourhood offers easy access to public transport and is ideally located for exploring the city's attractions.
The 5-bedroom property sleeps up to 12 guests, boasts a fully equipped kitchen with dishwasher, high-speed Wi-Fi, a private garden, parking, and keyless entry; enjoy streaming TV and luxurious amenities.
Cozy Home In Suburbs Near Chicago - Chicago, IL
10 5 reviews
Chicago, IL
18/09 – 19/09
₹42765/nightfor 1 night

Cozy Home In Suburbs Near Chicago

1 2
apartment , Bridgeview
This Bridgeview flat is situated in Chicago's southwest suburbs, approximately 32 kilometres from downtown Chicago, offering a peaceful base in a quiet and safe neighbourhood.
This pet-friendly property accommodates up to six guests across three rooms, featuring two bedrooms with queen beds and a third room with a daybed and trundle, complete with a private fenced garden with a fire pit, air conditioning, parking, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher.
A Sunny, Well-kept & Comfy Studio In Gold Coast - Chicago, IL
8.3 7 reviews
Chicago, IL
27/06 – 04/07
₹16460/nighttotal: ₹115220 (7 )

A Sunny, Well-kept & Comfy Studio In Gold Coast

1 2
apartment , Chicago
This Gold Coast studio apartment is situated in a prime Chicago location, a short walk from Oak Street Beach, Michigan Avenue shopping, and the Art Institute.
This pet-friendly flat offers a capacity for two guests, with a fully equipped kitchen (excluding a dishwasher) and air conditioning, located a 5-minute walk from the Red Line Subway at Clark/Division Station.
Brand New 2br/2ba In Ravenswood - Chicago, IL
10 3 reviews
Chicago, IL
01/09 – 31/10
₹12984/nighttotal: ₹779040 (60 )

Brand New 2br/2ba In Ravenswood

1 2
apartment , Chicago
This Chicago apartment rental is conveniently located near Andersonville, Ravenswood, and Uptown, offering easy access to the Red, Brown, and Metra lines.
The two-bedroom, two-bathroom flat sleeps five guests, boasting a renovated interior with hardwood floors, stainless steel appliances, and a garden; parking is also available.
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