Best apartment offers in Chicago, IL

10028 available apartment offers

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Chicago, IL apartments
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10028 Holiday apartments in Chicago, IL

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

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

Lincoln Park Hideaway - 5 Min Walk To The Park! - Chicago, IL
9.7 192 reviews
Chicago, IL
25/11 – 29/11
NZ$377/nighttotal: NZ$1508 (4 )

Lincoln Park Hideaway - 5 Min Walk To The Park!

1 4
apartment , Chicago
This Lincoln Park flat is conveniently located within walking distance of Lincoln Park Zoo and numerous restaurants and shops.
The 74 square metre (800 square feet) self-catering property sleeps four, featuring a king-size bed, a convertible daybed, a queen air mattress, a fully equipped kitchen, and a terrace.
20th Floor Skyline 2br Grant Park Unit | Parking - Chicago, IL
10 3 reviews
Chicago, IL
28/07 – 03/08
NZ$1475/nighttotal: NZ$8850 (6 )

20th Floor Skyline 2br Grant Park Unit | Parking

1 5
apartment , Chicago
This two-bedroom, two-bathroom flat is located in downtown Chicago, offering convenient access to Grant Park (640 metres away), Millennium Park (960 metres away), and the Lakefront, with museums, dining, shopping, and nightlife all within walking distance.
This family-friendly residence accommodates up to eight guests and boasts a private balcony with city views, a fully equipped kitchen, high-speed WiFi, and access to building amenities including a fitness centre, game room, and theatre.
Lux 5br Near Downtown | Rooftop +Garage + Spa Bath - Chicago, IL
9.9 107 reviews
Chicago, IL
01/07 – 06/07
NZ$1431/nighttotal: NZ$7155 (5 )

Lux 5br Near Downtown | Rooftop +Garage + Spa Bath

1 11
apartment , Chicago
This luxurious four-storey house is located in Humboldt Park, Chicago, approximately 8 kilometres from the city centre.
The 370 sqm property boasts five ensuite bedrooms, sleeping up to 16 guests, and features a chef's kitchen, rooftop deck with Chicago skyline views, a games room, and ample outdoor space.
In The Heart Of Andersonville-steps From Clark St. - Chicago, IL
10 123 reviews
Chicago, IL
10/07 – 14/07
NZ$1004/nighttotal: NZ$4016 (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.

Best Chicago, IL holiday apartments with a balcony

Bright & Modern Apt | Steps To Lake, Train, Food - Chicago, IL
10 13 reviews
Chicago, IL
11/07 – 13/07
NZ$1106/nighttotal: NZ$2212 (2 )

Bright & Modern Apt | Steps To Lake, Train, Food

2 2
apartment , Chicago
This two-bedroom apartment in Chicago's Edgewater neighbourhood is situated a short walk from the Red Line, Foster Beach, and Lake Shore Drive, offering easy access to Uptown, Andersonville, and Wrigley Field (approximately 3 Red Line stops away).
The 2-bedroom flat sleeps six, includes reserved parking, air conditioning, internet access, and is conveniently located near grocery stores, the Riviera Theatre, and Aragon Ballroom.
5 Mi To Midway Walkable Chicago Apartment - Chicago, IL
Chicago, IL
01/09 – 31/10
NZ$292/nighttotal: NZ$17520 (60 )

5 Mi To Midway Walkable Chicago Apartment

2 2
apartment , Chicago
This two-bedroom Chicago apartment is situated 8 kilometres from Midway International Airport, offering convenient access to the airport and other city attractions.
The 130-square-metre dwelling boasts a spacious layout sleeping up to seven guests, complete with a fully equipped kitchen, free Wi-Fi, air conditioning, parking, and a private balcony.
Kasa South Loop Chicago - Chicago, IL
9.4 3083 reviews
Chicago, IL
10/07 – 14/07
NZ$870/nighttotal: NZ$3480 (4 )

Kasa South Loop Chicago

1 4
aparthotel , Chicago
Kasa South Loop Chicago is situated in the South Loop, a short walk from DePaul University and within a mile of the CIBC Theatre, offering easy access to the city's vibrant attractions. This aparthotel has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation features modern, comfortable apartments with fully equipped kitchens, including a dishwasher, and a separate living area with a flat-screen TV. Guests can enjoy a range of amenities, such as a swimming pool, a fitness centre, a garden, and a terrace, as well as a business centre and a restaurant.
Flexhome Ukrainian Village  2br  Walkable + Private Balcony - Chicago, IL
Chicago, IL
31/07 – 17/08
NZ$946/nighttotal: NZ$16082 (17 )

Flexhome Ukrainian Village 2br Walkable + Private Balcony

2 1
apartment , Chicago
This West Town flat is situated on Damen Avenue, placing guests a short walk from popular BYOB restaurants featured on The Bear, grocery shops, breweries, and bars, and a brief distance from notable city attractions.
This 55 square metre flat offers two bedrooms, a bathroom, and accommodates up to 4 guests, featuring in-unit laundry, a dedicated workspace in the second bedroom, a Smart TV with Airplay, high-speed WiFi, and a Nest thermostat, with self-check-in available until 9 pm.

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 can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. Then, explore Millennium Park, home to Cloud Gate, nicknamed 'The Bean', and the Crown Fountain with its interactive water displays. Finally, stroll along Navy Pier for its Ferris wheel, shops, and restaurants.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, walkable neighbourhood, consider Lincoln Park with its green spaces and Lake Michigan access. If you prefer a more historic feel, try the Gold Coast, known for its elegant architecture. For a more affordable option with great restaurants and nightlife, check out Wicker Park.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is brimming with cultural and historical gems. The Art Institute of Chicago houses masterpieces by Monet and Van Gogh, while the Field Museum boasts dinosaur skeletons and ancient Egyptian artefacts. For a taste of history, visit the Chicago Cultural Center, a stunning building with free concerts and exhibitions, or the Museum of Science and Industry.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of the Gold Coast. It's also a culinary powerhouse, with world-class restaurants and a renowned deep-dish pizza scene. And don't forget the vibrant arts and culture scene, with world-class museums, theatres, and music venues.
  • What are the best apartments for families and kids in Chicago, IL?

  • Where can you find the best local markets and street food in Chicago, IL?

    For a taste of Chicago's diverse food scene, head to Maxwell Street Market on Sundays for a mix of local produce, crafts, and street food. The Wicker Park Farmers Market on Saturdays offers fresh, seasonal produce, while the Green City Market in Lincoln Park has a wide selection of local vendors.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a reliable and extensive public transportation system, the 'L', which is a combination of elevated trains and underground subway lines. It's a great way to get around the city, especially during rush hour. You can also use the CTA buses for more local travel.
  • What are the best apartments with parking in Chicago, IL?

  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago is a city that comes alive with seasonal events. In the spring, enjoy the Chicago Blues Festival, while summer brings the Taste of Chicago food festival. Autumn is perfect for the Chicago Marathon, and winter offers festive holiday markets and ice skating at Millennium Park.
  • What amenities are typically included in apartments in Chicago, IL?

    Apartments in Chicago typically include central heating and air conditioning, in-building laundry facilities, and sometimes a gym or a rooftop terrace. Some newer buildings may also offer amenities like a swimming pool, a dog park, or a resident lounge.
  • What leisure activities are available for relaxation in Chicago, IL?

    For relaxation, Chicago offers a variety of options. You can stroll along the Lakefront Trail for stunning views of Lake Michigan, visit the Lincoln Park Zoo for a free day out, or take a boat tour on the Chicago River. For a quieter experience, explore the Garfield Park Conservatory, a beautiful greenhouse with exotic plants.

Destinations nearby

Best Chicago, IL holiday apartments with parking

Location! Location! 2bd 1bth Spacious Apartment! - Chicago, IL
8.4 14 reviews
Chicago, IL
29/06 – 04/07
NZ$499/nighttotal: NZ$2495 (5 )

Location! Location! 2bd 1bth Spacious Apartment!

2 4
apartment , Chicago
This Chicago flat offers convenient access to landmarks such as Guaranteed Rate Field (2.2 kilometres), the Field Museum of Natural History (4.3 kilometres), and Union Station (4.7 kilometres), situated in a well-connected district.
This 48-square-metre apartment accommodates up to 7 guests across 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen with a fridge and microwave, complimentary on-site parking, and free high-speed WiFi.
Norwood Park/edison Park! Workstation & In-unit Laundry! 2nd Floor Apt - Chicago, IL
Chicago, IL
26/06 – 30/06
NZ$843/nighttotal: NZ$3372 (4 )

Norwood Park/edison Park! Workstation & In-unit Laundry! 2nd Floor Apt

2 4
apartment , Chicago
This two-bedroom flat is situated in the Norwood Park/Edison Park neighbourhood of Chicago, a quiet area located 12 kilometres from Loyola University Chicago and 15 kilometres from Wrigley Field.
The 85 square metre property can accommodate up to four guests and features a fully equipped kitchen, a patio, a garden, and outdoor play equipment, ideal for families with children.
Belmont House, Classy & Chic/walk To Wrigley Field - Chicago, IL
9.7 301 reviews
Chicago, IL
28/10 – 05/11
NZ$268/nighttotal: NZ$2144 (8 )

Belmont House, Classy & Chic/walk To Wrigley Field

1 5
apartment , Chicago
This two-bedroom apartment is ideally located in the Southport Corridor, a lively neighbourhood just a short walk from Wrigley Field and the Brown and Red line trains. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably sleeps six guests with its three beds and a spacious deck. Guests can enjoy a fully equipped kitchen, a large TV with streaming services, a washer/dryer, and a private garage with an EV charger for an additional fee.
Wicker Park Loft W/ Free Parking; Easy Dwtn Access - Chicago, IL
9.8 231 reviews
Chicago, IL
30/07 – 02/08
NZ$2009/nighttotal: NZ$6027 (3 )

Wicker Park Loft W/ Free Parking; Easy Dwtn Access

1 4
apartment , Chicago
This modern loft is situated in Wicker Park, a trendy Chicago neighbourhood, within walking distance of North Avenue, Milwaukee Avenue, and Division Street, offering easy access to shopping, dining, and nightlife. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The apartment has a spacious open-plan living space, ideal for larger groups, with a modern design and exposed brickwork adding character, and can accommodate up to 8 guests. The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, parking, and high-speed internet access, ensuring a comfortable and convenient stay.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Luxury 3 Bd, 2 Bath Condo - 15 Min From Downtown - Chicago, IL
8.9 30 reviews
Chicago, IL
25/06 – 29/06
NZ$467/nighttotal: NZ$1868 (4 )

Luxury 3 Bd, 2 Bath Condo - 15 Min From Downtown

3 3
apartment , Chicago
This Chicago luxury condo, sleeping six adults, is situated a 0.6km walk from a train station, providing easy access to Chicago's public transport network and various neighbourhoods.
The three-bedroom, two-bathroom apartment boasts a fully equipped kitchen, private patio deck, and on-site parking, offering comfortable accommodation for families or groups visiting the city.
Spacious 4 Br Northside Retreat Sleeps 12/ Parking - Chicago, IL
9.6 250 reviews
Chicago, IL
01/07 – 06/07
NZ$1034/nighttotal: NZ$5170 (5 )

Spacious 4 Br Northside Retreat Sleeps 12/ Parking

4 11
apartment , Chicago
This four-bedroom, two-bathroom apartment is located in Chicago's Lincoln Square neighbourhood, 0.5 kilometres from Lincoln Avenue's restaurants and bars.
The two-storey property offers a spacious open-plan living area, sleeps twelve guests, includes a fully equipped kitchen with dishwasher, and boasts a private patio (7 am–9 pm), plus designated parking and pet-friendly options (one pet, £100 fee).
Entire House 1 City Block From Wrigley Field. - Chicago, IL
9.9 162 reviews
Chicago, IL
16/09 – 23/09
NZ$2868/nighttotal: NZ$20076 (7 )

Entire House 1 City Block From Wrigley Field.

5 14
apartment , Chicago
This five-bedroom apartment is located in Wrigleyville, a lively neighbourhood just a short walk from Wrigley Field, restaurants and nightlife. It has been rated excellent for location, cleanliness and user experience.
The apartment is spread over two floors and a basement, comfortably accommodating up to 16 guests. It offers a fully equipped kitchen with a fridge, microwave oven and dishwasher, as well as air conditioning, parking and internet access.
Hip East Lakeview/lincoln Park Designer Flat - Chicago, IL
9.2 17 reviews
Chicago, IL
20/08 – 23/08
NZ$556/nighttotal: NZ$1668 (3 )

Hip East Lakeview/lincoln Park Designer Flat

1 2
apartment , Chicago
This Lakeview flat is situated on Orchard Street, offering tranquil surroundings yet convenient access to Lake Michigan and Chicago attractions such as Michigan Avenue and Navy Pier.
The 37 square metre (approx. 400 square feet) one-bedroom apartment sleeps two, boasting a fully equipped kitchen, in-unit laundry, and a private garden, plus access to a spa and parking.
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