Best apartment offers in Chicago, IL

13595 available apartment offers

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Chicago, IL apartments
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13595 Holiday apartments Chicago, IL

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

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

Modern 2br In Roscoevillage-wrigley Free St Parkng - Chicago, IL
9.7 7 reviews

Modern 2br In Roscoevillage-wrigley Free St Parkng

apartment, Chicago
This Roscoe Village apartment is a 5-minute walk from the Paulina Brown Line station, offering easy access to downtown Chicago, Wrigley Field (3.2km), and Lake Michigan beaches (4.8km).
The two-bedroom, one-bathroom property sleeps four, features a fully equipped kitchen with dishwasher, private patio with Weber grill, fast Wi-Fi, and family-friendly amenities including high chairs; free street parking and optional garage parking are available.
Top Rated Condo • 65” Tv • Family-friendly 2br - Chicago, IL
No reviews

Top Rated Condo • 65” Tv • Family-friendly 2br

apartment, Elmwood Park
This Elmwood Park flat offers convenient access to dining, shopping, and public transport, with a short drive to downtown Chicago.
This family-friendly apartment sleeps up to six guests and features two bedrooms, one bathroom, air conditioning, on-site parking, and a full kitchen equipped with a fridge, freezer, microwave oven, air fryer, and rice cooker.
Secret Gallery On The Park - 2bd/1ba - Chicago, IL
8.0 1 review

Secret Gallery On The Park - 2bd/1ba

apartment, Chicago
This two-bedroom flat is located 1.4 kilometres from the city centre, offering a 18-minute walk to Oak Street Beach and convenient access to attractions such as Water Tower Chicago and the Chicago Museum of Contemporary Art.
This apartment, covering 80 square metres and accommodating up to six guests, features a fully equipped kitchen with a fridge and microwave, air conditioning, a private balcony, and complimentary WiFi, with a washing machine also provided for guest use.
Walkable Chicago Retreat : Cozy 2br W/ Porch : Near Transit, Dining & Stadiums - Chicago, IL
9.4 264 reviews

Walkable Chicago Retreat : Cozy 2br W/ Porch : Near Transit, Dining & Stadiums

apartment, Chicago
This Chicago apartment boasts an exceptional location, steps from CTA buses and trains, and within easy walking distance (less than 0.8 km) of Marianos grocery store and numerous restaurants.
The two-bedroom, one-bathroom flat sleeps seven guests and features on-site laundry, a private patio, a shared deck, and strong Wi-Fi; nearby attractions include various dining and entertainment options.

Best Chicago, IL holiday apartments with a balcony

Little Italy 4br Retreat With Optional Parking - Chicago, IL
No reviews

Little Italy 4br Retreat With Optional Parking

apartment, Chicago
This four-bedroom flat is located in Chicago's Little Italy district, 13.97 kilometres from Midway International Airport.
This spacious accommodation offers a fully equipped kitchen, air conditioning, free WiFi, a private balcony and terrace, and on-site paid parking, comfortably accommodating up to 23 guests.
55th Floor Penthouse With Award-winning Views - Chicago, IL
9.9 1404 reviews

55th Floor Penthouse With Award-winning Views

apartment, Chicago
This penthouse apartment is situated in Downtown Chicago, just a short walk from Millennium Park, the Art Institute, and Navy Pier. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment comfortably accommodates up to four guests and features a fireplace, floor-to-ceiling windows, and high-end finishes. Guests can enjoy access to a range of amenities, including a fitness centre, swimming pool, concierge service, and a terrace with stunning views of Lake Michigan and the city skyline.
Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking - Chicago, IL
No reviews

Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking

apartment, Chicago
This flat is situated in Chicago's Edgewater district, offering convenient access to the Granville Red Line, Loyola University, lakefront attractions, and parks, with Lake Michigan and its beaches approximately 0.5 kilometres away.
This 93 square metre residence accommodates up to four guests in two bedrooms and features a fully equipped kitchen, in-unit laundry, air conditioning, and a complimentary garage parking spot, with the CTA Red Line just a short walk away for easy travel.
1br Near O'hare • Balcony • Workspace - Chicago, IL
No reviews

1br Near O'hare • Balcony • Workspace

apartment, Chicago
River Chicago 506 by LuxuryLodgingSTR is a one-bedroom flat located in Chicago's River North district, providing convenient access to the Chicago River and within 1 kilometre of Magnificent Mile shopping and notable architecture.
This family-friendly apartment accommodates up to three guests, offering air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and a balcony, with parking available for added convenience.

Frequently asked questions about apartment rentals in Chicago, IL

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

    You can't miss the iconic Willis Tower for its views of the city. A visit to Millennium Park is a must, with the Cloud Gate sculpture (aka 'The Bean') and Crown Fountain. And no trip to Chicago is complete without a walk along Navy Pier, especially at night when the Ferris wheel lights up.
  • What are the best apartments in Chicago, IL?

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

    For a vibrant, trendy atmosphere, check out Wicker Park or Bucktown. If you prefer a more relaxed vibe with easy access to nature, consider Lincoln Park or Lakeview. And for a more budget-friendly option, Logan Square or Pilsen are popular choices.
  • What are the best apartments with a pool in Chicago, IL?

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

    The Art Institute of Chicago is a must-see for art lovers, with works from Monet, Picasso, and Van Gogh. For history buffs, the Field Museum houses dinosaur skeletons and ancient artifacts. And the Museum of Science and Industry offers interactive exhibits on everything from transportation to space exploration.
  • 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 Lincoln Park. The city also boasts a world-class food scene, with deep-dish pizza, hot dogs, and Italian beef sandwiches being local favourites. And don't forget the vibrant music scene, with blues, jazz, and rock all having strong roots in the city.
  • 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?

    The Maxwell Street Market is a great place to find a mix of local crafts, produce, and street food vendors. For a more upscale experience, head to the Green City Market in Lincoln Park, which features local and organic produce, artisanal goods, and prepared foods. And for a taste of Mexican cuisine, check out the Pilsen Food Truck Festival.
  • What are the best pet friendly apartments in Chicago, IL?

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

    Chicago has a well-developed public transportation system, with the 'L' (elevated train) and buses covering most of the city. The 'L' is particularly convenient for getting around downtown and the surrounding neighbourhoods. You can purchase a Ventra card for easy fare payments.
  • What are the best apartments with parking in Chicago, IL?

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

    In the summer, the Chicago Blues Festival is a must-see, while the Taste of Chicago food festival is a great way to sample local cuisine. In the autumn, the Chicago Marathon draws crowds of runners and spectators. And in the winter, the Christkindlmarket brings a touch of European charm to the city with its festive decorations and traditional treats.
  • What amenities are typically included in apartments in Chicago, IL?

    Most apartments in Chicago come with basic amenities like central heating and air conditioning, in-building laundry facilities, and sometimes a fitness centre. Some high-end buildings may offer additional amenities like swimming pools, rooftop decks, and concierge services.

Popular destinations

Best Chicago, IL holiday apartments with parking

Luxury King Bed • Remodeled Safe Chicago Condo - Chicago, IL
10 1 review

Luxury King Bed • Remodeled Safe Chicago Condo

apartment, Chicago
This Chicago flat is located 5.96 kilometres from Chicago O'Hare International Airport, offering convenient access to entertainment venues such as the Rosemont Theatre and Rivers Casino, with Wrigley Field and the United Centre also within reach.
This 38 square metre self-catering apartment accommodates up to five guests, featuring air conditioning, free Wi-Fi, a kitchen with a fridge and microwave, a private bathroom, and a terrace, with free on-site parking available.
Charming Home 5 Minutes From Ohare Airport - Chicago, IL
9.3 6 reviews

Charming Home 5 Minutes From Ohare Airport

apartment, Chicago
This five-bedroom, three-bathroom flat is conveniently situated near O'Hare International Airport, offering a mere 5-minute commute and excellent access to Chicago's major highways and public transport network, making it an ideal base for exploring the city or travelling further afield.
This spacious accommodation comfortably hosts up to 14 guests, featuring air conditioning, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, and a private 2-car garage, all within easy reach of shopping centres and restaurants.
Addison Garden Apartment - Chicago, IL
9.9 70 reviews

Addison Garden Apartment

apartment, Chicago
This Roscoe Village garden flat is situated two blocks from the area's centre, a short walk from the Brown Line and close to Wrigley Field and the Southport Corridor in Chicago.
The newly renovated one-bedroom apartment sleeps two, boasts a fully equipped kitchen with high-end appliances, a private garden, and includes family-friendly amenities such as a travel cot and high chair (on request), plus shared laundry facilities and a smart TV.
3br Heart Of Wrigley, 5min Walk To Train & Wrigley - Chicago, IL
9.9 151 reviews

3br Heart Of Wrigley, 5min Walk To Train & Wrigley

apartment, Chicago
This Wrigleyville apartment, a three-minute walk from Wrigley Field and a four-minute walk from the Red Line, offers easy access to Chicago's North Side attractions.
The 150-square-metre property features three bedrooms sleeping seven, two bathrooms, a fully equipped kitchen, in-unit laundry, and free street parking passes (availability permitting), plus board games and books.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2s - Chicago, IL
9.3 39 reviews

Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2s

apartment, Chicago
This River North flat, 2.4km from Ohio Street Beach and 2.7km from North Avenue Beach, offers easy access to attractions such as 360 Chicago and the Shops at Northbridge.
The 74 square metre, two-bedroom, two-bathroom apartment sleeps 19 guests and features a fully equipped kitchen, in-unit laundry, private rooftop access, and free Wi-Fi.
Modern Zen Retreat Mins From Downtown - Chicago, IL
10 2 reviews

Modern Zen Retreat Mins From Downtown

apartment, Chicago
This two-bedroom flat in Chicago's West Town district is situated approximately 3.2 kilometres from the Merchandise Mart and 4.8 kilometres from Cloud Gate, with Michigan Avenue and Navy Pier also within easy reach.
This residence accommodates up to five guests with two queen beds, a sofa bed, and an optional rollaway, featuring a well-equipped kitchen, a bathroom with a soaking tub, and an onsite washer and dryer, plus one private parking space.
Pristine Gold Coast 3bd|2ba | Free Parking| Beach. - Chicago, IL
9.7 53 reviews

Pristine Gold Coast 3bd|2ba | Free Parking| Beach.

apartment, Chicago
This Gold Coast flat is located in Chicago's Gold Coast district, a short walk from Oak Beach, high-end boutiques, and renowned dining, with Gucci and Dior just steps away.
This modern apartment sleeps six guests and offers a game room with shuffleboard and mini-bowling, complimentary Netflix, Hulu, and Apple Music on a 65-inch smart TV, and free garage parking for one car.
Relax In A Bright And Spacious Apt In Logan Square - Chicago, IL
10 170 reviews

Relax In A Bright And Spacious Apt In Logan Square

apartment, Chicago
This Logan Square flat, a 10-minute walk (1.6km) from Belmont or Logan Square Blue Line stations, offers easy access to the Logan Theatre and a farmers' market.
The ground-floor property features two bedrooms, one bathroom, a full dining room, living room, enclosed sunporch, and free in-building laundry, accommodating four guests and including a garden, parking, and a deep soaking tub.
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