Best apartment offers in Chicago, IL

10028 available apartment offers

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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

Dramatic Wrigley Loft +Private Rooftop, Center Of Wrigley, Ranked Guest Favorite - Chicago, IL
9.9 299 reviews
Chicago, IL
27/07 – 30/07
₹83078/nighttotal: ₹249234 (3 )

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

4 3
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.
Lakeview/lincolnpark 2br/1ba  Updated Vintage Apartment In Walkable Neighborhood - Chicago, IL
10 169 reviews
Chicago, IL
12/10 – 14/10
₹41983/nighttotal: ₹83966 (2 )

Lakeview/lincolnpark 2br/1ba Updated Vintage Apartment In Walkable Neighborhood

2 4
apartment , Chicago
This Lakeview flat is situated less than 1.6km from Wrigley Field and Lake Michigan, offering easy access to Chicago's North Side attractions and public transport.
The 93 square metre property comprises two bedrooms, one bathroom, and accommodates up to six guests, boasting a private garden, spa access, and parking, alongside a fully equipped kitchen and family-friendly amenities.
Peaceful Living-2bdrm/2bath W/private Parking, Wifi-work Station-wicker Park! - Chicago, IL
10 5 reviews
Chicago, IL
14/07 – 18/07
₹41255/nighttotal: ₹165020 (4 )

Peaceful Living-2bdrm/2bath W/private Parking, Wifi-work Station-wicker Park!

2 5
apartment , Chicago
This Wicker Park duplex apartment in Chicago's West Town neighbourhood is conveniently located near the Western Blue Line station and The 606 trail.
The two-bedroom, two-bathroom property sleeps six guests and features a well-equipped kitchen, private parking, a garden, and amenities such as Netflix and a workstation, making it ideal for families or groups visiting Chicago.
Casanova Modern City Living - Chicago, IL
9.8 75 reviews
Chicago, IL
26/06 – 28/06
₹74648/nighttotal: ₹149296 (2 )

Casanova Modern City Living

4 7
apartment , Chicago
This spacious four-bedroom house, ideal for families, is located in Chicago's North Kenwood/Bronzeville neighbourhood, a short walk from Lake Michigan and a 6.4km drive from the Loop.
Offering a three-floor layout with a private garden, patio, parking, and all modern conveniences including a fully equipped kitchen and air conditioning, this Chicago residence comfortably sleeps eight guests and provides easy access to the city's attractions.

Best Chicago, IL holiday apartments with a balcony

Swanky Rooftop, Birthday, Anniversary Sleeps 16 - Chicago, IL
10 1 review
Chicago, IL
14/08 – 16/08
₹141285/nighttotal: ₹282570 (2 )

Swanky Rooftop, Birthday, Anniversary Sleeps 16

7 9
apartment , Forest Park
This seven-bedroom Forest Park dwelling is situated a short walk from Madison Avenue's shops and restaurants, and a 0.96km stroll from the Frank Lloyd Wright Historic District.
The spacious property, boasting an open-plan layout with hardwood floors, accommodates up to 16 guests and includes a rooftop terrace, private backyard, garage parking, and a fully equipped kitchen.
Lakeview 3br Walk To Wrigley, Lake, Dining & Train - Chicago, IL
8.8 26 reviews
Chicago, IL
13/09 – 16/09
₹40473/nighttotal: ₹121419 (3 )

Lakeview 3br Walk To Wrigley, Lake, Dining & Train

3 2
apartment , Chicago
This Lakeview apartment, a short walk from Wrigley Field and 2.7km from Fullerton Beach, offers easy access to Lincoln Park Zoo (3.2km) and Chicago's downtown area (6.4-7.4km).
The self-catering flat features a fully equipped kitchen, private patio, air conditioning, free Wi-Fi, and accommodates families with amenities including a baby safety gate, all within easy reach of local attractions.
A Quiet Stay While You Are Away - Chicago, IL
9.8 36 reviews
Chicago, IL
18/09 – 20/09
₹28936/nighttotal: ₹57872 (2 )

A Quiet Stay While You Are Away

2 2
apartment , Oak Park
This apartment is in the Frank Lloyd Wright historic district, a short walk from Unity Temple and the town centre. It has excellent user ratings and is popular with families.
The home has two bedrooms and can comfortably sleep four people. Guests can enjoy a garden, a terrace, a fully-equipped kitchen and parking.
Chic Luxe Spa Retreat Light Filled King Bed Garage - Chicago, IL
Chicago, IL
07/08 – 09/08
₹44137/nighttotal: ₹88274 (2 )

Chic Luxe Spa Retreat Light Filled King Bed Garage

1 2
apartment , Chicago
This Chicago flat offers a peaceful escape with private parking and Wi-Fi, located conveniently for exploring the city's attractions.
This 102 square metre, one-bedroom apartment accommodates up to three guests and features a fully equipped kitchen, air conditioning, and a balcony, with a garden for added relaxation.

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

Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar - Chicago, IL
10 11 reviews
Chicago, IL
24/07 – 26/07
₹310807/nighttotal: ₹621614 (2 )

Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar

6 13
apartment , Chicago
This six-bedroom home is situated in Jefferson Park, a quiet neighbourhood in Chicago, just 10 kilometres from Navy Pier and Michigan Avenue, and within easy reach of the airport and downtown. The property has received excellent reviews from previous guests.
The apartment offers 297 square metres of space, comfortably accommodating up to 16 guests. It features a fully equipped kitchen, a games room, a spa, a garden, a terrace, parking, and a Super Mario-themed bunk room for kids.
Skyline 2br On 20th Floor Near Grant Park With Paid Parking - Chicago, IL
Chicago, IL
28/07 – 06/08
₹75632/nighttotal: ₹680688 (9 )

Skyline 2br On 20th Floor Near Grant Park With Paid Parking

2 8
apartment , Chicago
This 2-bedroom flat is situated in downtown Chicago, a mere 1.9 kilometres from the city centre and a 10-minute walk from DePaul University, offering convenient access to Grant Park and the Art Institute of Chicago.
This 112 square metre residence accommodates up to 15 guests, boasting a private balcony with city views on the 20th floor, an equipped kitchen, two bathrooms, complimentary Wi-Fi, and on-site fitness and entertainment facilities.
2bd 2ba Home W Office Near Obama Library & Museums - Chicago, IL
Chicago, IL
10/07 – 31/08
₹19042/nighttotal: ₹990184 (52 )

2bd 2ba Home W Office Near Obama Library & Museums

2 1
apartment , Chicago
This Chicago apartment is located near the Obama Presidential Centre, offering easy access to Chicago's museums and approximately 8km from Midway International Airport.
The 186 square metre (1998 square foot) property boasts two bedrooms, two bathrooms, and can comfortably accommodate up to 11 guests, featuring a fully equipped kitchen, terrace, garden, free parking, and complimentary Wi-Fi.
3br · Steps From Mccormick · Balcony & Gym - Chicago, IL
9.4 3 reviews
Chicago, IL
06/07 – 10/07
₹28477/nighttotal: ₹113908 (4 )

3br · Steps From Mccormick · Balcony & Gym

3 2
apartment , Chicago
This spacious three-bedroom flat is ideally situated in downtown Chicago, offering convenient access to McCormick Place (10 minutes' walk) and the 'L' train at Cermak-McCormick Place station (11 minutes' walk), with Lake Michigan and Grant Park also within easy reach.
This 167 square metre apartment accommodates up to eight guests, featuring a fully equipped kitchen with a fridge, microwave and dishwasher, air conditioning, in-unit laundry, and a private terrace or balcony, complemented by access to a communal fitness centre.

Best Chicago, IL holiday apartments with air conditioning

Cabin 103 By 747 Lofts - Chicago, IL
9.4 169 reviews
Chicago, IL
15/07 – 20/07
₹23508/nighttotal: ₹117540 (5 )

Cabin 103 By 747 Lofts

1 1
apartment , Chicago
This studio apartment is ideally situated near the Blue Line L in Chicago, providing easy access to both the city centre and the trendy West Loop, home to Randolph Street's renowned restaurant scene. The studio has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably accommodates one guest and features a modern kitchen with a fridge and microwave. Amenities include air conditioning, parking, internet access, and a laundry facility, ensuring a comfortable and convenient stay.
Modern 2br Apt | Free Parking & Pet-friendly - Chicago, IL
10 4 reviews
Chicago, IL
23/06 – 25/07
₹11751/nighttotal: ₹376032 (32 )

Modern 2br Apt | Free Parking & Pet-friendly

1 1
apartment , Chicago
This stylish, newly built (2023) two-bedroom garden flat is located in the Woodlawn neighbourhood of Chicago, close to the University of Chicago and Jackson Park, offering easy access to Lake Michigan and public transport.
The fully furnished 2-bathroom dwelling, sleeping up to four guests in two queen-size beds, boasts a dedicated workspace, in-unit laundry, a private outdoor space, and smart technology including a Keurig coffee machine and fireplace; SimpliSafe security system is also provided.
Chic & Cozy Boho Vibe In Heart Of Logan Square - Chicago, IL
9.9 67 reviews
Chicago, IL
22/12 – 26/12
₹19135/nighttotal: ₹76540 (4 )

Chic & Cozy Boho Vibe In Heart Of Logan Square

1 3
apartment , Chicago
This Logan Square flat is ideally situated near the CTA Blue Line, providing easy access to Chicago's city centre, and within walking distance of Milwaukee Avenue's shops and restaurants.
The two-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen with dishwasher, air conditioning, parking, and excellent user reviews; enjoy its stylish design and abundant natural light.
Gamers Getaway 20 Minutes From Downtown - Chicago, IL
9.7 150 reviews
Chicago, IL
26/06 – 28/06
₹37754/nighttotal: ₹75508 (2 )

Gamers Getaway 20 Minutes From Downtown

1 6
apartment , Chicago
This apartment is located in the Loop, Chicago’s central business district, just a short walk from Millennium Park and the Art Institute of Chicago. The area is bustling with activity, offering a wealth of dining, shopping, and cultural experiences. This accommodation has received excellent ratings for location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It features a modern kitchen with a fridge, microwave, and dishwasher, along with high-speed internet, air conditioning, and parking.
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