Best apartment offers in Chicago, IL

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Chicago, IL apartments
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13595 Best apartments in 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

Bright 2br Luxury Corner Suite With Optional Parking Sleeps 6 Guests Near Mccormick Place And Soldier Field - Chicago, IL
9.0 225 reviews

Bright 2br Luxury Corner Suite With Optional Parking Sleeps 6 Guests Near Mccormick Place And Soldier Field

apartment, Chicago
This modern apartment is located in Chicago's McCormick Place district, just a short distance from the Field Museum of Natural History and the Art Institute of Chicago. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, a fitness centre, a terrace, and on-site parking, making it perfect for families or groups of friends exploring the city.
Experience Chicago Living Near United Center - Chicago, IL
8.6 40 reviews

Experience Chicago Living Near United Center

apartment, Chicago
This Austin, Chicago condo, situated 11 kilometres from the city centre and 8 kilometres from the United Centre, offers easy access to public transport and major attractions including Michigan Avenue and Navy Pier.
This three-bedroom apartment, boasting 93 square metres of space and sleeping up to six guests, includes a fully equipped kitchen, free on-street parking, and air conditioning; it's perfect for families or groups visiting the city.
New Garden Studio Near Wrigley/depaul/dwtn - Chicago, IL
9.7 66 reviews

New Garden Studio Near Wrigley/depaul/dwtn

apartment, Chicago
This Lincoln Park garden flat offers self-check-in and is conveniently located near Wrigley Field, DePaul University, and Chicago's city centre, providing easy access to O'Hare International Airport (distances unspecified).
The one-bedroom apartment, sleeping up to three guests, includes a fully equipped kitchen, high-speed internet, a washer/dryer, and free on-street parking, plus a dedicated workspace and access to multiple streaming platforms.
Stunning Home, Awesome Game Room, A+ Location - Chicago, IL
9.9 132 reviews

Stunning Home, Awesome Game Room, A+ Location

apartment, Chicago
This six-bedroom Lincoln Park house, sleeping fourteen, is ideally located within easy walking distance of the Red and Brown Line 'L' train stations and Lincoln Park Zoo.
The property boasts a chef's kitchen with Sub-Zero and Wolf appliances, a games room with pool table, foosball, arcade games and Xbox, and a small outdoor seating area; ample space is provided across three floors with hardwood flooring throughout.

Best Chicago, IL holiday apartments with a balcony

Your Logan Square Oasis With Lush Outdoor Haven! - Chicago, IL
10 10 reviews

Your Logan Square Oasis With Lush Outdoor Haven!

apartment, Chicago
This two-bedroom flat is located in Chicago's Logan Square district, offering easy access to the city centre and cultural attractions such as the Chicago Theatre and the Art Institute of Chicago, with the Field Museum of Natural History also within reach.
This 139 square metre apartment accommodates up to four guests and features a kitchen with a microwave oven and dishwasher, air conditioning, a terrace/balcony, garden access, and off-street parking, providing a comfortable base for exploring Chicago, including potential visits to Wrigley Field.
Chicago Boutique Hideaway Private Deck Fire Pit - Chicago, IL
10 4 reviews

Chicago Boutique Hideaway Private Deck Fire Pit

apartment, Chicago
This two-bedroom flat is situated in Chicago's West Town district, offering immediate access to local boutiques and eateries, with Wicker Park, West Loop, and downtown Chicago reachable within 12 minutes by car or via the Blue Line.
The 51 square meter property accommodates up to five guests with a modern, fully equipped kitchen, a private outdoor patio, and keyless entry, while a dedicated local team provides assistance and recommendations for nearby attractions such as Beatnik and Forbidden Root Brewery.
The Bernadin- Designer 3br City Center With Balcony - Chicago, IL
8.0 1 review

The Bernadin- Designer 3br City Center With Balcony

apartment, Chicago
This casino-equipped flat offers a central Chicago location, a 17-minute stroll to Oak Street Beach, and is situated near Water Tower Chicago and 360 Chicago.
Spanning 149 square metres, this three-bedroom residence accommodates up to nine guests and boasts a patio with lake views, a hot tub, a fitness centre, and complimentary WiFi, with cycling opportunities nearby.
Brilliant Downtown Chicago 3-bedroom Condominium - Chicago, IL
9.8 261 reviews

Brilliant Downtown Chicago 3-bedroom Condominium

apartment, Chicago
This stylish apartment is situated in downtown Chicago, just a stone's throw from the Magnificent Mile and the Riverwalk, offering easy access to the city's best attractions. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment is spacious, with three bedrooms, two bathrooms, and a floor area of 149 square metres, comfortably accommodating up to eight guests. It comes fully equipped with modern amenities, including a kitchen with a fridge, freezer, microwave, and dishwasher, as well as a washing machine and dryer, smart home features, and memory foam mattresses for a restful night's sleep.

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 absolutely must visit the iconic Willis Tower, formerly known as the Sears Tower, for incredible views of the city. You'll also want to wander through Millennium Park and see the Cloud Gate sculpture, nicknamed 'The Bean'. And no visit to Chicago is complete without a stroll along the Magnificent Mile, a stretch of North Michigan Avenue known for its high-end shopping and dining.
  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a great mix of vibrancy and convenience, consider renting in the West Loop, River North, or Lincoln Park. These neighbourhoods offer easy access to public transport, fantastic restaurants, and a variety of shops and entertainment options.
  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is packed with cultural gems! You'll want to check out the Art Institute of Chicago, home to world-renowned art collections, and the Field Museum, where you can explore natural history exhibits. For a dose of history, visit the Chicago Cultural Center, a stunning building with beautiful stained glass windows and free cultural events.
  • 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, a culinary tradition unique to the city. And don't forget the Chicago River, which flows through the heart of the city and is a popular spot for boat tours and water taxis.
  • Where can you find the best local markets and street food in Chicago, IL?

    For a true taste of Chicago, head to Maxwell Street Market, a bustling open-air market with a wide variety of street food vendors. You can also find great local produce and artisanal goods at the Green City Market, held in various locations throughout the city during the warmer months.
  • How is the public transportation system in Chicago, IL?

    Chicago has a comprehensive public transport system, with the 'L' train, buses, and a network of commuter trains. It's a great way to get around the city, especially if you're staying in a central neighbourhood. Just be sure to get a Ventra card for easy payment.
  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago comes alive with festivals throughout the year! In the summer, you'll want to check out the Chicago Air and Water Show, a spectacular display of aviation and watercraft. And during the winter, the Christkindlmarket, a traditional German Christmas market, brings a festive atmosphere to the city.
  • What amenities are typically included in apartments in Chicago, IL?

    Most apartments in Chicago include basic amenities like central heating and air conditioning, a refrigerator, stove, and oven. Depending on the building and the price, you might also find in-building laundry facilities, a fitness centre, and a rooftop deck.
  • What leisure activities are available for relaxation in Chicago, IL?

    Chicago offers plenty of relaxation options! You can stroll through Lincoln Park, a sprawling green space with a zoo, a conservatory, and a lakefront. Or, for a more urban experience, head to the Chicago Riverwalk, a scenic path along the river where you can enjoy views of the city skyline.

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Best Chicago, IL holiday apartments with parking

Lux Apt In Bronzeville, Min From Downtown-rsv Now! - Chicago, IL
9.1 170 reviews

Lux Apt In Bronzeville, Min From Downtown-rsv Now!

apartment, Chicago
This Bronzeville apartment rental is situated in Chicago's South Side, a 3.4km drive from Guaranteed Rate Field and within 6km of the Museum of Science and Industry.
The three-bedroom, family-friendly flat boasts a fully equipped kitchen, private parking, a Jacuzzi, and a garden, sleeping up to six guests and offering easy access to Chicago's cultural attractions.
Modern 2br Oak Lawn Home - Easy Commute To Chicago, Perfect For Longer Stays - Chicago, IL
10 1 review

Modern 2br Oak Lawn Home - Easy Commute To Chicago, Perfect For Longer Stays

apartment, Oak Lawn
This Oak Lawn holiday home is conveniently situated near the Chicago Ridge Shopping Mall (1.3 km), Advocate Christ Medical Center (9.7 km), and SeatGeek Stadium (9.7 km).
This 104 square metre property offers two bedrooms, one bathroom, sleeps five guests, and boasts a private garden, swimming pool, spa, and free Wi-Fi; nearby attractions include an on-site water park.
Up-scale Wicker Park 4bd/3.5ba Home (+Garage) - Chicago, IL
9.9 144 reviews

Up-scale Wicker Park 4bd/3.5ba Home (+Garage)

apartment, Chicago
This Wicker Park flat, a short distance (less than 1.6km) from the Division Street restaurants and a 10-minute walk from the Blue Line CTA station, offers easy access to Chicago's attractions.
The four-level property sleeps twelve guests, boasting three bathrooms, a fully equipped kitchen, in-unit laundry, fast Wi-Fi, smart TVs, and a private garage; nearby activities include exploring Division Street's culinary scene.
4 Br/3ba, Great For Large Groups, Garage Parking. Spacious And Updated! - Chicago, IL
9.8 17 reviews

4 Br/3ba, Great For Large Groups, Garage Parking. Spacious And Updated!

apartment, Chicago
This spacious Chicago apartment, located in the Humboldt Park neighbourhood of West Town, offers easy access to attractions such as the Art Institute of Chicago, Michigan Avenue, and Lincoln Park Zoo, all within a reasonable driving or public transport distance.
The four-bedroom, three-bathroom dwelling boasts a duplex layout sleeping up to ten guests, featuring a fully equipped kitchen, a dedicated recreation area with a 75-inch TV and games, and a private balcony; free garage parking is also provided.

Best Chicago, IL holiday apartments with air conditioning

Bottle Top -  2b/1ba Band Apt Above Empty Bottle - Chicago, IL
9.6 109 reviews

Bottle Top - 2b/1ba Band Apt Above Empty Bottle

apartment, Chicago
This Chicago apartment, situated above The Empty Bottle music venue in the West Loop neighbourhood, offers an immersive music experience with included concert tickets (subject to availability).
The two-bedroom flat, sleeping up to five guests, features a full kitchen, Roku with Netflix, and a private second-floor entrance; audible music from the venue is a constant feature.
4br Modern Urban Escape, Walk To Zoo, Lakefront & Red Line - Chicago, IL
9.6 15 reviews

4br Modern Urban Escape, Walk To Zoo, Lakefront & Red Line

apartment, Chicago
This four-bedroom corporate apartment in Chicago's Near North Side offers prime access to Old Town, Lincoln Park, and the Clybourn Corridor, situated just 500 meters from New City shopping plaza and a short walk from the Second City Theater, with the North Branch Trail leading to the lakefront and multiple public transport options including the Red Line train for direct routes downtown.
The 112 square meter dwelling accommodates up to ten guests with four bedrooms, including two en-suite suites, a fully equipped kitchen featuring stainless steel appliances, and in-unit laundry, all complemented by spectacular city views and high-speed internet.
The Perla® - Luxury Highrise W/ City Views, Gym - Chicago, IL
10 6 reviews

The Perla® - Luxury Highrise W/ City Views, Gym

apartment, Chicago
This downtown Chicago flat is ideally situated within a 1-2.4 kilometre radius of Michigan Avenue, Navy Pier, Millennium Park, and the Museum of Contemporary Art.
The one-bedroom, one-bathroom apartment sleeps three guests and boasts a fully equipped kitchen, in-unit laundry, two Smart Roku TVs, and access to a swimming pool, jacuzzi, fitness centre, and parking.
Welcoming 2br In Chicago's Best Neighborhood! - Chicago, IL
9.7 359 reviews

Welcoming 2br In Chicago's Best Neighborhood!

apartment, Chicago
This Ukrainian Village flat, near excellent restaurants and shops, is a short distance (approximately 1.6km) from the United Centre and Wrigley Field.
The two-bedroom, one-bathroom property sleeps four, offering a full kitchen with dishwasher, laundry facilities, Wi-Fi, a private patio, and family-friendly amenities including a highchair and travel cot.
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