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

15min To Loop | Free Street Parking | Full Kitchen - Chicago, IL
9.7 265 reviews

15min To Loop | Free Street Parking | Full Kitchen

apartment, Chicago
This three-bedroom, one-bathroom apartment is situated near the Eisenhower Expressway, offering easy access to Chicago's city centre (approximately 24km) and a 15-minute walk to the Western Blue and California Green Line stations.
The 3-bedroom flat features a private entrance, free street parking, a garden setting, and sleeps up to six guests, boasting a kitchen with a fridge and air conditioning.
Pretty Suite In Lincoln Park W/hvac +Free Parking - Chicago, IL
9.5 602 reviews

Pretty Suite In Lincoln Park W/hvac +Free Parking

apartment, Chicago
This Lincoln Park garden flat is situated three blocks (approximately 0.24 km) from the L train and near DePaul University, offering easy access to Chicago's public transport and local amenities.
The 800 sq ft (74.3 sq m) self-catering property features a large bedroom, walk-in closet, separate sitting room, private garden, and parking, comfortably sleeping three guests and providing complimentary breakfast items and snacks.
Quiet  Modern  Deck Sleeps 10 | Bridgeport Gem - Chicago, IL
9.9 41 reviews

Quiet Modern Deck Sleeps 10 | Bridgeport Gem

apartment, Chicago
This three-bedroom, two-bathroom apartment in Chicago's Bridgeport Arts District offers easy access to Chinatown (a short drive away) and major attractions such as McCormick Place and the Museum Campus (within 1.6-2.4 km).
Sleeping up to ten guests, the property features a fully equipped kitchen, in-unit laundry, and ample free on-street parking, ideal for families or groups visiting the city.
Clean & Best Location 2br+2ba | Mapletree Suites - Chicago, IL
9.9 150 reviews

Clean & Best Location 2br+2ba | Mapletree Suites

apartment, Chicago
This West Loop apartment, steps from Target, Skinner Park and the CTA, offers easy access to the United Centre, the Loop and the Medical District in Chicago.
The 100 sq m suite comprises two bedrooms, two bathrooms, and sleeps five guests, featuring keyless entry, in-unit laundry, a fully equipped kitchen, two private balconies, and on-site amenities including Cafe L'Appetito and luggage storage.

Best Chicago, IL holiday apartments with a balcony

Sky-high 2br W/ Gym & City Views - Chicago, IL
No reviews

Sky-high 2br W/ Gym & City Views

apartment, Chicago
This Downtown Chicago flat is conveniently located less than 1.6km from Union Park and the United Centre, and within 3.2km of the Chicago Riverwalk and Michigan Avenue.
The 125 square metre, two-bedroom, two-bathroom apartment sleeps five, boasting a fully equipped kitchen, in-unit laundry, private balcony, and access to a swimming pool, fitness centre, and concierge services.
Walk To Train & Bus: Updated Chicago Apartment - Chicago, IL
No reviews

Walk To Train & Bus: Updated Chicago Apartment

apartment, Chicago
This Chicago apartment, situated approximately 8-12 miles from attractions including Guaranteed Rate Field and the Museum of Science and Industry, offers easy access to Midway International Airport and excellent public transport links.
The 120 square metre property features a spacious two-bedroom layout sleeping up to seven guests, boasting a fully equipped kitchen, private balcony, parking, and air conditioning.
Flexhome Ukrainian Village  2br  Walkable + Private Balcony - Chicago, IL
10 1 review

Flexhome Ukrainian Village 2br Walkable + Private Balcony

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.
2 Bed Apt W/ Office, Free Parking, Near Wrigley - Chicago, IL
9.5 140 reviews

2 Bed Apt W/ Office, Free Parking, Near Wrigley

apartment, Chicago
This two-bedroom Chicago apartment is situated near Wrigleyville, a 15-minute walk from Wrigley Field, and within a 4.8-8 km radius of Lincoln Park Zoo, Water Tower Place, and the United Centre.
The 111 square metre flat offers a fully equipped kitchen, free parking, and amenities including a fireplace and patio, sleeping up to four guests comfortably.

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

Home In Forest Park Downstairs. - Chicago, IL
9.7 412 reviews

Home In Forest Park Downstairs.

apartment, Forest Park
This ground floor flat is located in Forest Park, just 12 kilometres from downtown Chicago and 24 kilometres from O'Hara International Airport, making it a convenient base for exploring the city and its surroundings. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat has two bedrooms and one bathroom, comfortably accommodating up to four guests. You'll enjoy a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, parking, and fast internet access.
Modern 3 Bedroom Close To Downtown Chicago - Chicago, IL
9.6 4 reviews

Modern 3 Bedroom Close To Downtown Chicago

apartment, Chicago
This Bronzeville flat offers convenient access to Chicago's attractions, being a 2-minute walk from the Green Line metro and a 5-kilometre drive to Lake Michigan and its beaches.
This family-friendly flat, covering 111 square metres, sleeps six with a king, queen, and two twin beds, and includes a kitchen with a fridge and microwave, air conditioning, and parking.
Inspiring Grotto Sleeps 10-20 Free Tv & Parking - Chicago, IL
9.0 2 reviews

Inspiring Grotto Sleeps 10-20 Free Tv & Parking

apartment, Chicago
This spacious Chicago apartment, located near Fullerton Beach (a 1.9km walk), Wrigley Field (1.9km), and Lincoln Park Zoo (2.7km), offers easy access to popular attractions.
The 186 square metre property boasts four bedrooms, two bathrooms, sleeps 10-20 guests, and includes a private garden, tennis court, free parking, and an electric vehicle charging point.
East Lincoln Park Gem Spacious 4 Br - Chicago, IL
10 2 reviews

East Lincoln Park Gem Spacious 4 Br

apartment, Chicago
This East Lincoln Park flat is situated near Fullerton Beach, a 3 km walk from Lincoln Park Zoo and 2.4 km from Wrigley Field.
This recently renovated four-bedroom property boasts 215 square metres of living space, including a living room, fully equipped kitchen, three bathrooms, a private terrace with garden views, and parking (at an extra cost), accommodating up to 21 guests.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

West Loop Loft|sleeps 4, Parking, Pool, & Rooftops - Chicago, IL
No reviews

West Loop Loft|sleeps 4, Parking, Pool, & Rooftops

apartment, Chicago
This stylish loft flat in Chicago's West Loop offers rare free onsite parking, a significant advantage for visitors to the city.
This studio apartment accommodates up to four guests and boasts a full kitchen, in-unit laundry, and extensive resort-style amenities including an indoor swimming pool, fitness centre, and skyline rooftop with grills.
Br - ️ Modern And Comfy 1br Apartment In Logan Square! - Chicago, IL
9.8 247 reviews

Br - ️ Modern And Comfy 1br Apartment In Logan Square!

apartment, Chicago
This comfortable one-bedroom flat is situated in a desirable neighbourhood in Chicago, just a short walk from excellent restaurants and local attractions. It has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The flat offers 75 square metres of living space, featuring a spacious living room, a comfortable bedroom with a queen-sized bed, and a fully equipped kitchen with modern appliances. Guests can enjoy the convenience of in-unit laundry, a dedicated work desk, and modern furnishings, along with full bathroom amenities and a quiet neighbourhood setting.
Comfortable And Trendy Design 1br | Lincoln Square - Chicago, IL
9.7 185 reviews

Comfortable And Trendy Design 1br | Lincoln Square

apartment, Chicago
This Lincoln Square flat is conveniently located near the Brown Line, offering easy access to Wrigleyville and Chicago's city centre.
The one-bedroom apartment, sleeping two, boasts a fully equipped kitchen, in-building laundry, a smart TV with Netflix, and is within walking distance of Cafe Selmarie.
Cozy/spacious Wfh Family Friendly W Permit Parking - Chicago, IL
9.9 168 reviews

Cozy/spacious Wfh Family Friendly W Permit Parking

apartment, Chicago
This Chicago apartment, ideal for families, is situated in a residential area, its precise location unspecified but implied to be near restaurants and requiring parking permits, suggesting proximity to a well-established neighbourhood.
The two-bedroom, two-bathroom flat offers 5 guests comfortable accommodation in a first-floor, open-plan layout with a fully equipped kitchen, private outdoor space, and family-friendly amenities including a highchair, travel cot, and baby monitor; additional features include two bathtubs, smart technology, and the unique character of an 1885 building.
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