Best apartment offers in Chicago, IL

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Chicago, IL apartments
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13595 Holiday apartments in Chicago, IL

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

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

Designer 3bd | Marble Shower | Parking Included - Chicago, IL
10 3 reviews

Designer 3bd | Marble Shower | Parking Included

apartment, Chicago
This Woodlawn flat is situated a stone's throw from the Obama Presidential Center and within minutes of Hyde Park and the University of Chicago.
This family-friendly flat accommodates six guests and offers three bedrooms, two bathrooms, in-unit laundry, two off-street parking spaces, and a private rear patio, with amenities including a fridge, freezer, microwave, and dishwasher.
Bright 2br Apt With Gym And Optional Parking Near Soldier Field, Museum Campus, Mccormick Place - Chicago, IL
9.3 12 reviews

Bright 2br Apt With Gym And Optional Parking Near Soldier Field, Museum Campus, Mccormick Place

apartment, Chicago
This Chicago apartment is conveniently located near the Museum Campus, approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of both the Art Institute of Chicago and the Chicago Symphony Orchestra.
This two-bedroom, two-bathroom flat offers 88 square metres of space, sleeping up to eleven guests, and boasts amenities including a fully equipped kitchen, fitness centre, terrace, garden, parking, and complimentary Wi-Fi; an outdoor fireplace is available for guest use.
The Roscoe Village Guesthouse - Chicago, IL
9.6 8 reviews

The Roscoe Village Guesthouse

apartment, Chicago
This Roscoe Village flat is situated 2.3km from Wrigley Field and within an 8km radius of Loyola University Chicago, Water Tower Place, 360 Chicago, and the Museum of Contemporary Art Chicago.
The one-bedroom, one-bathroom apartment sleeps eleven guests, features a fully equipped kitchen, free Wi-Fi, air conditioning, and a flat-screen TV; local shops and restaurants are nearby.
Designer Chicago Escape | Walkable | Free Parking - Chicago, IL
9.0 4 reviews

Designer Chicago Escape | Walkable | Free Parking

apartment, Chicago
This flat is located in Chicago's Pilsen district, offering a 10-minute drive to the city centre, 5 minutes to the University of Illinois Chicago (UIC) and Chinatown, and 10 minutes to McCormick Place and the United Center.
Accommodating up to 10 guests, this 3-bedroom, 3-bathroom property features an open-plan living area, a fully equipped kitchen, free WiFi, air conditioning, and on-site parking, with self-check-in available.

Best Chicago, IL holiday apartments with a balcony

Walk To Train L Near Attractions And Ord L Free Parking L Patio - Chicago, IL
No reviews

Walk To Train L Near Attractions And Ord L Free Parking L Patio

apartment, Chicago
Holiday rental listing. Your accommodation will be located in Chicago.
Services and facilities include a terrace, free parking and air conditioning. This apartment in Chicago is ideal for families.
Peaceful Cozy Beach View| 13 Mins Dt | 4 Mins Lake - Chicago, IL
8.8 19 reviews

Peaceful Cozy Beach View| 13 Mins Dt | 4 Mins Lake

apartment, Chicago
This Uptown Chicago flat is conveniently located near Montrose Beach, with the Argyle Red Line station a 1.4 kilometre walk away and several car parks within a short distance.
The one-bedroom, one-bathroom apartment sleeps two guests and features a fully equipped kitchen, in-unit laundry, a rooftop terrace with city views, and proximity to Montrose Beach, the Aragon Ballroom, and the Riviera Theatre; a fitness centre is also available on-site.
Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.7 152 reviews

Jeffjack Heated Pool Penthouse In Chicago's West Loop

apartment, Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.
3 Stylish 2brs Steps From Magnificent Mile - Chicago, IL
No reviews

3 Stylish 2brs Steps From Magnificent Mile

apartment, Chicago
This six-bedroom, six-bathroom residence offers generous accommodation for up to 15 guests in Chicago's Gold Coast district, a mere 300 metres from the Magnificent Mile and 600 metres from the Lakefront Trail.
Guests can enjoy panoramic city views from private balconies, a fully equipped chef's kitchen, and access to a 241 square metre health club, alongside extensive building amenities including an outdoor pool deck, a gaming centre, and a rooftop terrace.

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.

Popular destinations

Best Chicago, IL holiday apartments with parking

6br Humboldt Park Home | Speakeasy + Hot Tub - Chicago, IL
10 1 review

6br Humboldt Park Home | Speakeasy + Hot Tub

apartment, Chicago
Casa Sacramento is a historic Humboldt Park residence in Chicago, offering a unique Puerto Rican hospitality experience with convenient access to Paseo Boricua, Logan Square, and Wicker Park.
This luxury Chicago flat boasts six bedrooms, four bathrooms, and accommodates fourteen guests, featuring a private speakeasy, a six-person hot tub, an outdoor kitchen, and fire pits for entertainment.
Logan Sq 4br  Free Parking  Near Nightlife & Dt - Chicago, IL
9.7 167 reviews

Logan Sq 4br Free Parking Near Nightlife & Dt

apartment, Chicago
This four-bedroom apartment is ideally located in Chicago's trendy Humboldt Park/Wicker Park/Logan Square neighbourhood, offering easy access to numerous attractions and public transport.
Sleeping eight guests, this fully renovated flat boasts a fully equipped kitchen with marble countertops, in-unit laundry, private parking for up to four cars, high-speed internet, and family-friendly amenities such as board games.
Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus - Chicago, IL
9.2 8 reviews

Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus

apartment, Chicago
This Chicago apartment, near the city's Museum Campus, is 2.4 kilometres from the Field Museum and under 3.2 kilometres from both the Art Institute of Chicago and the Chicago Symphony Orchestra.
The 84-square-metre, two-bedroom flat sleeps up to six guests and boasts a fully equipped kitchen, balcony, private parking (optional), and on-site fitness centre; it's allergy-free and non-smoking.
-Extended Stay- 4 Bed/2 Bath, 2 Kings, 2 Queens - Chicago, IL
10 21 reviews

-Extended Stay- 4 Bed/2 Bath, 2 Kings, 2 Queens

apartment, Oak Lawn
This Oak Lawn flat is situated within walking distance of the Oak Lawn Library and the Oak Lawn Park District, offering easy access to local amenities and green spaces.
The family-friendly apartment features a stylish design, comfortable seating, a fully equipped kitchen, and parking, accommodating up to seven guests.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

4br Downtown Retreat Free Street Parking - Chicago, IL
No reviews

4br Downtown Retreat Free Street Parking

apartment, Chicago
This four-bedroom flat in downtown Chicago offers free street parking and Wi-Fi, located just 1.3 kilometres from Guaranteed Rate Field.
This residence provides accommodation for up to 23 guests, featuring air conditioning, a fridge, microwave oven, and complimentary towels and bed linen.
Guest Favorite | Private Entrance | Free Parking - Chicago, IL
9.8 113 reviews

Guest Favorite | Private Entrance | Free Parking

apartment, Chicago
This Chicago apartment, registration number R23000115687, is ideally located for exploring the city, although its precise neighbourhood and proximity to landmarks such as Millennium Park, Navy Pier, or Wrigley Field requires further clarification.
The two-bedroom, one-bathroom flat sleeps four, offering a fridge, freezer, microwave, and dishwasher; further details on the property's size, style, and nearby activities are needed to complete the description.
Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location - Chicago, IL
9.0 5 reviews

Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location

apartment, Chicago
This two-bedroom flat in Chicago's Ukrainian Village offers a walkable base with easy access to local attractions and dining.
This 55 square metre flat accommodates up to five guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and microwave, and a balcony with outdoor seating, with free WiFi provided.
Little Italy/uic 3 Bdrm, 2.5 Bath Condo - Chicago, IL
9.9 222 reviews

Little Italy/uic 3 Bdrm, 2.5 Bath Condo

apartment, Chicago
This spacious Chicago duplex, near the Medical District and within 5km of the Magnificent Mile, Grant Park, and McCormick Place, offers easy access to Pilsen, Greektown, and the West Loop.
The 232 sqm property boasts three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, two living areas with 49" smart TVs, a private washer/dryer, and free street parking (permit provided for one car).
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