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

Premium Urban 4br - Perfect Mix Of Comfort & Locat - Chicago, IL
9.9 31 reviews

Premium Urban 4br - Perfect Mix Of Comfort & Locat

apartment, Chicago
This luxurious B&B is situated in central downtown Chicago, offering immediate access to renowned dining establishments, shopping districts, and major attractions such as Millennium Park, which is approximately 800 metres away.
This family-friendly establishment provides four bedrooms and three bathrooms accommodating up to ten guests, boasting a fully equipped kitchen with essential appliances, air conditioning, a garden, and a fitness centre, alongside complimentary Wi-Fi and convenient self check-in for a seamless stay.
Lux 3-level Chicago Home +Garage & Patio - Chicago, IL
10 1 review

Lux 3-level Chicago Home +Garage & Patio

apartment, Chicago
This Wicker Park apartment in Chicago is situated a 0.5km walk from the Blue Line CTA station, offering easy access to the city's attractions and Division Street's restaurants.
This three-level, 301 square metre dwelling boasts a four-bedroom, four-bathroom layout sleeping up to 14 guests, complete with a two-car garage, private patio, games room, and family-friendly amenities.
4 King Beds + Parking | 20 Min Train To Chicago - Chicago, IL
10 17 reviews

4 King Beds + Parking | 20 Min Train To Chicago

apartment, Berwyn
The Metra Suite is a flat located in Berwyn's Depot District, offering direct access to the Metra BNSF Line for a 20-minute journey to Downtown Chicago.
This accommodation sleeps eight guests across four king beds, features a fully equipped kitchen with a fridge and microwave, air conditioning, and complimentary off-street parking for one vehicle, with fast WiFi available.
Stylish Bright Apt Private Parking Available - Chicago, IL
9.8 202 reviews

Stylish Bright Apt Private Parking Available

apartment, Chicago
This three-bedroom Pilsen flat, sleeping seven, is ideally located near the Pink Line CTA station, within a short walk of Chinatown and the West/South Loops.
The 7-room property offers a fully equipped kitchen, in-unit laundry, a private backyard with a BBQ, and is close to attractions such as Thalia Hall and Honky Tonk BBQ.

Best Chicago, IL holiday apartments with a balcony

Modern 2br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail - Chicago, IL
8.8 42 reviews

Modern 2br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

apartment, Chicago
This Chicago apartment, near McCormick Place and the Museum Campus, is conveniently located approximately 2.4-3.2km from the Field Museum, Art Institute of Chicago, and the Chicago Symphony Orchestra.
The 88 square metre property features a two-bedroom, two-bathroom layout sleeping up to six guests, offering a private patio, fitness centre access, and free Wi-Fi; parking is available.
Stylish 2br With Skyline Views Near Riverwalk - Chicago, IL
10 1 review

Stylish 2br With Skyline Views Near Riverwalk

apartment, Chicago
This two-bedroom, two-bathroom Chicago apartment enjoys a prime downtown location, less than 1km from the Merchandise Mart, State Street, the Chicago Theatre, and the Willis Tower, with easy access to Clark-Lake and Washington-Wells public transport stations.
The self-catering flat offers a fully equipped kitchen, in-unit laundry facilities, a private balcony, an indoor swimming pool, a fitness centre, and sleeps up to four guests, perfect for exploring Chicago's attractions.
Bucktown Condo Just Two Blocks From The L By Allset Turnover - Chicago, IL
10 14 reviews

Bucktown Condo Just Two Blocks From The L By Allset Turnover

apartment, Chicago
This West Town flat is conveniently located near Damen Station, less than 3.2km from Humboldt Park and within 5km of both The Salt Shed and the United Centre.
The two-bedroom, one-bathroom apartment sleeps four guests and boasts a balcony, in-unit laundry, parking, and a fully equipped kitchen including a dishwasher; enjoy nearby Steppenwolf Theatre.
Downtown 3bd Penthouse Lake Mich Views Plus Gym #13 - Chicago, IL
9.5 2 reviews

Downtown 3bd Penthouse Lake Mich Views Plus Gym #13

apartment, Chicago
This downtown Chicago penthouse offers direct Lake Michigan views and is located 1.1 kilometres from DePaul University and 1.1 kilometres from the Art Institute of Chicago, a 10-minute walk from Grant Park.
This spacious 3-bedroom flat, accommodating up to 9 guests, features a balcony with lake vistas, a fully equipped kitchen, air conditioning, free WiFi, and access to an on-site fitness centre.

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

Chic 1b In Wicker Park W/parking King Size Bed - Chicago, IL
9.3 60 reviews

Chic 1b In Wicker Park W/parking King Size Bed

apartment, Chicago
This Chicago apartment, a 10-minute walk (1.6km) from Milwaukee Avenue's nightlife, offers convenient access to the city's entertainment.
The self-contained flat features a queen-size bed, two futons, in-unit laundry, a fully equipped kitchen, and designated parking, comfortably accommodating four guests.
An Elegant Chicago Northside Getaway - Chicago, IL
10 377 reviews

An Elegant Chicago Northside Getaway

apartment, Chicago
This three-bedroom Chicago apartment, The Catfish Flat, is situated in Ravenswood, above a tavern and coffee house, offering convenient access to local businesses such as Bad Johnny's and AJ's Bakery & Diner.
The largest unit in the Bluebird Inn, it sleeps six guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and unique designer wallpaper; local artwork and Chicago-themed books and vinyl records add to its character.
Live Like A Local - Lincoln Park Basement Walkout - Chicago, IL
9.8 49 reviews

Live Like A Local - Lincoln Park Basement Walkout

apartment, Chicago
This Lincoln Park, Chicago flat is conveniently located near Lincoln Park itself, offering easy access to public transport and a plethora of shops and restaurants.
The two-bedroom, one-bathroom apartment sleeps six guests, boasts a fully equipped kitchen including a dishwasher, and features a private garden and parking; the modern, recently renovated property is ideal for families or groups exploring the city.
Modern Studio At Uptown By Red Line (02) - Chicago, IL
9.3 875 reviews

Modern Studio At Uptown By Red Line (02)

apartment, Chicago
This Chicago studio flat boasts a superb location, steps from the Red Line 'L' train and within easy reach of Lake Michigan's beaches.
The self-contained apartment, sleeping two guests, includes a fully equipped kitchenette, in-unit laundry, Roku Smart TV, and complimentary toiletries; a fitness centre and parking are also available.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

The Reset Space  A Minimalist 1br Oasis - Chicago, IL
9.8 13 reviews

The Reset Space A Minimalist 1br Oasis

apartment, Chicago
This Chicago flat is located in the Park Manor district, offering authentic neighbourhood character and convenient access to Hyde Park and the University of Chicago, approximately 1.6 kilometres away, with The Loop reachable by car in 16 to 32 kilometres.
This modern apartment, accommodating up to two guests, features a fully equipped kitchen with a fridge, freezer, and microwave, high-speed Wi-Fi for remote work, air conditioning, and a garden, situated near culinary attractions and offering excellent transport links to I-90/94 and the CTA Red Line.
Mccormick Place 2br Spacious Corner Unit With Optional Parking Sleeps 6 Guests Near Soldier Field And Grant Park - Chicago, IL
9.3 89 reviews

Mccormick Place 2br Spacious Corner Unit With Optional Parking Sleeps 6 Guests Near Soldier Field And Grant Park

apartment, Chicago
This stylish apartment is situated in Chicago's McCormick Place area, just 2.4 kilometres from the Field Museum of Natural History and 2.9 kilometres from the Art Institute of Chicago, making it a great base for exploring the city's cultural attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment is a spacious 84 square metre two-bedroom property, with two bathrooms, offering comfortable accommodation for up to six guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a fitness centre, and parking, as well as complimentary Wi-Fi and air conditioning.
North Center Apartment, Walker's Paradise - Chicago, IL
9.7 65 reviews

North Center Apartment, Walker's Paradise

apartment, Chicago
This North Center flat is situated above The Globe Pub, within walking distance (approximately 0.8 km) of the Brown Line and Metra, offering easy access to Southport Corridor, Wrigleyville, and Lakeview.
The two-bedroom, one-bathroom apartment sleeps four guests and boasts a fully equipped kitchen with Nespresso machine and French press, high-speed internet (500 Mbps), in-unit laundry, and extensive entertainment options including Roku TV, Direct TV, Netflix, Disney+, HBO Max, and Apple TV+.
Huge Projector And Designated Workspace, Near Wrigley - Chicago, IL
No reviews

Huge Projector And Designated Workspace, Near Wrigley

house, Chicago
This Chicago house rental is situated near Wrigleyville, approximately 18 kilometres from Chicago O'Hare International Airport and a short distance from Wrigley Field.
The 92-square-metre property offers two bedrooms, one bathroom, sleeps thirteen guests, and includes a fully equipped kitchen, in-unit laundry, a projector, and free Wi-Fi.
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