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Chicago apartments
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10028 Apartments or condos in Chicago

Search Family-Friendly Vacation Apartments in Chicago

Getting the vacation apartment right makes all the difference for a family trip to Chicago, ensuring city attractions are within easy reach for everyone.

Cozy Garden Unit 1st Flr With Private Entrance And Turo Vehicle Available. - Chicago
9.6 8 reviews
Chicago
11/05 – 11/06
$204/nightfor 1 night

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

1 2
apartment , Hickory Hills
This Hickory Hills apartment rental is conveniently located near PGN Jump N' Fun Entertainment (1 mile) and Resurrection Cemetery & Mausoleums (2.7 miles), with easy access to Moraine Valley Community College and Chicago Ridge Mall (both within 6 miles).
This one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, in-unit laundry, a patio, a Smart TV, and access to a fitness center, spa, and parking; nearby attractions include PGN Jump N' Fun and the Chicago Ridge Mall.
Modern Suite W/fast Wi‑fi, 4k Tv & Washer - Chicago
9.3 24 reviews
Chicago
09/09 – 09/14
$302/nighttotal: $1510 (5 )

Modern Suite W/fast Wi‑fi, 4k Tv & Washer

1 3
apartment , Chicago
This three-bedroom, two-bathroom South Loop apartment on State Street offers easy access to McCormick Place (a 10-12 minute walk) and is a mile from the Museum Campus (Field Museum, Shedd Aquarium, Adler Planetarium).
Sleeping up to eight guests, this Chicago rental boasts a fully equipped kitchen with stainless steel appliances, in-unit laundry, and 24/7 building security.
Chicago Charm! Quiet And Inviting ! - Chicago
10 28 reviews
Chicago
09/16 – 09/23
$321/nighttotal: $2247 (7 )

Chicago Charm! Quiet And Inviting !

3 2
apartment , Chicago
This apartment is situated in West Ridge, a neighborhood in Chicago, just a 20-minute walk from the shores of Lake Michigan, offering easy access to the lakefront and its recreational activities.
This 1,350-square-foot apartment features three bedrooms, two bathrooms, and can accommodate up to six guests, making it an ideal choice for families or groups of friends exploring Chicago.
Spacious 3br · Bronzeville/south Loop · Sleeps 8 - Chicago
10 3 reviews
Chicago
06/28 – 07/05
$402/nighttotal: $2814 (7 )

Spacious 3br · Bronzeville/south Loop · Sleeps 8

1 5
apartment , Chicago
This 3-bedroom rental unit is located in Bronzeville, Chicago's historic Black Metropolis, offering immediate proximity to acclaimed soul food restaurants like Peach's and Honey 1 BBQ, live jazz venues such as Room 43, the Bronzeville Walk of Fame, and the Wabash Arts Corridor.
This family-friendly accommodation comfortably sleeps 8 guests and features two spacious suites with en-suite bathrooms, spectacular city views through large windows, a fully-equipped kitchen with stainless steel appliances, a washer & dryer, and access to a state-of-the-art fitness center and a shared rooftop deck.

Discover Apartments with Balconies in Chicago

A terrace with views of the city skyline is a fantastic reason to book a vacation apartment in Chicago.

Luxury Designer Penthouse 3801 | Pool | Gold Coast - Chicago
9.8 13 reviews
Chicago
08/30 – 09/02
$721/nighttotal: $2163 (3 )

Luxury Designer Penthouse 3801 | Pool | Gold Coast

3 6
apartment , Chicago
This penthouse apartment is located in Chicago's Gold Coast district, steps away from Michigan Avenue and within walking distance of Navy Pier and the Art Institute of Chicago. This highly rated apartment is perfect for families and groups looking for a luxurious stay in the heart of Chicago.
The apartment offers a spacious living area, 3 bedrooms, and 2 bathrooms, accommodating up to 10 guests. Enjoy a modern design, high-end appliances, a rooftop pool, a gym, and a terrace with panoramic city views.
1 Free Parking, Sleeps 10 - Chicago
Chicago
07/03 – 07/05
$841/nighttotal: $1682 (2 )

1 Free Parking, Sleeps 10

3 5
apartment , Chicago
This Chicago apartment in the West Town neighborhood offers convenient access, being a 5-minute walk to Milwaukee Avenue and a 4-minute drive to the United Center, with two CTA stations within a 14-minute walk.
This rental unit provides a fully equipped kitchen, air conditioning, on-site parking, and in-unit laundry, with easy access to Lake Michigan, Millennium Park, the Chicago Theatre, and the Art Institute of Chicago.
Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife - Chicago
10 2 reviews
Chicago
09/03 – 09/06
$794/nighttotal: $2382 (3 )

Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife

1 4
apartment , Chicago
This Level River North apartment rental is located in Chicago's River North neighborhood, minutes from the Magnificent Mile and across the river from the Loop.
The 600-square-foot one-bedroom unit sleeps four guests and features a fully equipped kitchen, in-suite laundry (in Deluxe suites), a balcony, and access to a swimming pool and sauna.
River North 3br/2ba: Huge, Parking, Center Chicago - Chicago
10 178 reviews
Chicago
09/21 – 09/24
$742/nighttotal: $2226 (3 )

River North 3br/2ba: Huge, Parking, Center Chicago

3 6
apartment , Chicago
This River North apartment is located in Chicago, just a short walk from Lake Michigan's beaches and a few blocks from the trendy River North neighborhood, known for its art galleries and restaurants. It has excellent user, location, and cleanliness ratings.
This 3-bedroom home comfortably sleeps 10 guests and offers a spacious 1800 square feet of living space. It features a fully equipped kitchen, a private balcony, free parking, and a variety of amenities like a spa, a garden, and cable TV.

Frequently Asked Questions about apartment rentals in Chicago

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    You can't miss the iconic Willis Tower, formerly known as the Sears Tower, for stunning city views. Navy Pier is a must for its Ferris wheel, shops, and restaurants. Millennium Park is a must-see for its Cloud Gate sculpture, known as 'The Bean', and Crown Fountain.
  • What are the best apartments in Chicago?

  • What's the best district to book an apartment in Chicago?

    Lincoln Park is a fantastic choice to book an apartment in Chicago. This area offers a perfect mix of greenery and city life with its parks, zoos, and great dining options. The Loop is another great district, especially because it is close to iconic attractions and have easy access to public transportation, making it convenient for exploring the city.
  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, trendy atmosphere, check out Wicker Park, Bucktown, or Logan Square. For a more quiet and classic feel, Lincoln Park, Lakeview, or Old Town are great options. If you're looking for something more affordable, consider Pilsen or Ukrainian Village.
  • What are the best apartments with a pool in Chicago?

  • What are the top family-friendly attractions in Chicago?

    The top family-friendly attractions in Chicago are the Shedd Aquarium and the Lincoln Park Zoo.
  • What are the top cultural and historical sites in Chicago, IL?

    The Art Institute of Chicago is a must-see for art lovers, showcasing masterpieces from Monet to Picasso. The Field Museum boasts a world-renowned dinosaur exhibit, while the Museum of Science and Industry offers interactive exhibits on everything from transportation to technology.
  • What are the best apartments with a jacuzzi in Chicago?

  • Are there any discounts or special offers available for budget travelers visiting Chicago's attractions?

    Budget travelers can often find discounts or special offers for attractions in Chicago by checking online travel platforms or inquiring directly with tour operators.
  • 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, hot dogs, and its vibrant theater scene, with world-class performances at the Lyric Opera and the Goodman Theatre.
  • What are the best apartments for families and kids in Chicago?

  • Are there opportunities to learn about traditional customs, or take workshops in local crafts or cooking in Chicago?

    There are opportunities to learn about traditional customs and take workshops in local crafts or cooking through organizations like the Chicago Cultural Alliance and local community centers.
  • Where can you find the best local markets and street food in Chicago, IL?

    The Maxwell Street Market is a must-visit for its eclectic mix of vendors, from fresh produce to vintage clothing. For a taste of Chicago's diverse culinary scene, head to the Wicker Park Farmers Market or the Logan Square Farmers Market, where you'll find local produce, baked goods, and artisanal crafts.
  • What are the best pet friendly apartments in Chicago?

  • What are the best cultural activities and events in Chicago that one should attend?

    The best cultural activities and events to attend in Chicago include the Chicago Jazz Festival, the Chicago Blues Festival, and the Taste of Chicago food festival.
  • How is the public transportation system in Chicago, IL?

    Chicago has a comprehensive public transportation system, with the 'L' train, buses, and the CTA, which connects you to most parts of the city. It's a great way to get around, especially during rush hour.
  • What are the best apartments with parking in Chicago?

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

    Chicago's summer is filled with festivals, from the Chicago Blues Festival to the Taste of Chicago. In the fall, the city comes alive with the Chicago Marathon and the Magnificent Mile Lights Festival. Winter brings the Christkindlmarket, a traditional German Christmas market, and the ice skating rink at Millennium Park.
  • What amenities are typically included in apartments in Chicago, IL?

    Most apartments in Chicago include central heating and air conditioning, as well as laundry facilities, either in-unit or on-site. Some apartments may also offer amenities like a fitness center, a swimming pool, or a rooftop deck.
  • What leisure activities are available for relaxation in Chicago, IL?

    Chicago offers plenty of opportunities for relaxation. You can stroll along the lakefront path, visit the Lincoln Park Zoo, or enjoy a picnic in Millennium Park. For a more active experience, you can bike the 18-mile Lakefront Trail or explore the city's many parks.

Destinations nearby

Guest-Favorite Apartments with Parking in Chicago

Having parking at your vacation apartment in Chicago ensures the city center is easy to navigate every day without extra hassle.

Spacious 3br Home W Parking. Perfect For Families & Longer Stays - Chicago
10 3 reviews
Chicago
06/27 – 06/30
$292/nighttotal: $876 (3 )

Spacious 3br Home W Parking. Perfect For Families & Longer Stays

3 1
apartment , Chicago
This 3-bedroom, 1-bathroom apartment in Chicago's Hermosa neighborhood is located 5 minutes on foot from major bus routes, offering transit access to Michigan Avenue and Navy Pier.
This rental sleeps 6 guests and features a kitchen with a fridge and microwave, air conditioning, a garden, and parking, with a backyard available for guest use.
2-bedroom Apartment In The Heart Of Oak Park - Chicago
9.9 143 reviews
Chicago
06/23 – 06/27
$223/nighttotal: $892 (4 )

2-bedroom Apartment In The Heart Of Oak Park

1 2
apartment , Oak Park
This Oak Park studio is located in the heart of the village, just steps from Frank Lloyd Wright's Home and Studio.
The two-bedroom apartment features a spacious living area, a fully equipped kitchen with a dishwasher, and a basement with a foosball table and a movie projector.
Daquietplacetorelax/5bdrm/15min Downtown/8mmidway. - Chicago
9.6 151 reviews
Chicago
09/11 – 09/13
$628/nighttotal: $1256 (2 )

Daquietplacetorelax/5bdrm/15min Downtown/8mmidway.

1 11
apartment , Chicago
This apartment is located in the quiet Brighton Park neighborhood, just minutes from downtown Chicago and major attractions like Chinatown, McCormick Place, and Soldier Field. It has excellent user and location ratings, and is very clean.
It is a spacious and comfortable apartment that can accommodate up to 16 people in five bedrooms. It has a fully equipped kitchen, a private back patio, and modern amenities like keyless locks, a safety box, Wi-Fi, and four smart TVs. It also has private garage parking available for a special rate.
Spacious&modern Condo, Near Dwtn, Secure Parking - Chicago
10 126 reviews
Chicago
06/17 – 06/21
$888/nighttotal: $3552 (4 )

Spacious&modern Condo, Near Dwtn, Secure Parking

1 8
apartment , Chicago
This 1800 sq ft apartment is in the heart of Chicago's West Loop neighborhood, steps from the United Center and a short walk from the Loop. It has excellent user, location, and cleanliness ratings.
The apartment has 10 ft high ceilings and zero stairs for easy access. It has 2 bedrooms, 2 bathrooms, and can accommodate up to 10 guests. It has a fully equipped kitchen, a 65" TV with streaming subscriptions, board games, high-speed Wi-Fi, and an in-unit washer and dryer.

Neighborhoods and points of interest in Chicago

Best Chicago apartment rentals with air conditioning

Bright And Cozy 1br Apartment In Logan Square! - Chicago
9.8 269 reviews
Chicago
07/08 – 07/13
$194/nighttotal: $970 (5 )

Bright And Cozy 1br Apartment In Logan Square!

1 2
apartment , Chicago
This one-bedroom apartment is located in Logan Square, a trendy neighborhood with easy access to the Chicago River and popular neighborhoods like Wicker Park and Bucktown. It has received excellent ratings for cleanliness, location, and user experience.
The apartment offers 650 square feet of space, comfortably accommodating up to two guests. Enjoy modern design, a fully equipped kitchen, a spacious living area, free Wi-Fi, and pet-friendly accommodations.
Wicker Park : Stylish Comfort Meets Urban Ease - Chicago
9.5 109 reviews
Chicago
07/02 – 07/06
$820/nighttotal: $3280 (4 )

Wicker Park : Stylish Comfort Meets Urban Ease

1 10
apartment , Chicago
This Chicago apartment rental is located in the Wicker Park/West Town neighborhood, a short walk from the L train and a 5-minute commute to The Loop.
The 4-bedroom, 2-bathroom condo features a fully equipped kitchen, private balcony, and a shared patio, accommodating up to 12 guests.
By Loop/millennium Park/bean Pl4 - Chicago
9.5 8 reviews
Chicago
06/18 – 06/21
$483/nighttotal: $1449 (3 )

By Loop/millennium Park/bean Pl4

1 7
apartment , Chicago
This downtown Chicago condo is located in the Loop, 0.2 miles from Millennium Park and 0.4 miles from Willis Tower.
This 2-bedroom, 1-bathroom condo accommodates up to 8 guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and internet.
Modern Chicago Getaway – Near Downtown - Chicago
10 4 reviews
Chicago
07/11 – 07/24
$262/nighttotal: $3406 (13 )

Modern Chicago Getaway – Near Downtown

2 2
apartment , Chicago
This newly remodeled condo is located between Logan Square and Avondale, offering convenient access to downtown Chicago, O'Hare International Airport, and the Blue Line CTA train within 0.5 miles, with local dining and shops within walking distance.
This 2-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, in-unit laundry, and a spa-like bathroom.
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