Best apartment offers in Chicago, IL

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Chicago, IL apartments
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13595 Best apartments in Chicago, IL

Top Family-Friendly Holiday Apartments in Chicago, IL

Selecting the perfect family holiday apartment in Chicago, IL makes all the difference, especially when city attractions are within easy reach for a stress-free trip.

Beautiful/spacious 7bd - 4bth Home With Garage! - Chicago, IL
9.5 89 reviews

Beautiful/spacious 7bd - 4bth Home With Garage!

apartment, Chicago
This seven-bedroom house, near Portage Park in Chicago, is a 12-kilometre Uber ride from the city centre and an 11-kilometre drive from O'Hare International Airport.
The property offers two kitchens, sleeps fourteen guests across three floors, including a dedicated children's room, and boasts a private garage plus ample free on-street parking.
Comfortable 3br Getaway W/ Bonus Attic Lounge To Relax - Chicago, IL
9.2 11 reviews

Comfortable 3br Getaway W/ Bonus Attic Lounge To Relax

apartment, Calumet Park
This three-bedroom Chicago apartment, located in the Calumet Park neighbourhood in the city's south suburbs near the Indiana border, offers easy access to attractions such as the Museum of Science and Industry and is a short distance from downtown Chicago.
The property features a spacious layout including a loft area, sleeps six guests, and includes a kitchenette, free Wi-Fi, a smart TV, and on-site parking.
Cozy 3br City Living In South Loop Near Mccormick Place, Soldier Field & Lakefront - Chicago, IL
10 2 reviews

Cozy 3br City Living In South Loop Near Mccormick Place, Soldier Field & Lakefront

apartment, Chicago
This family-friendly apartment near Chicago's Museum Campus is 2.3km from the Field Museum and within 3.2km of Grant Park and the Art Institute of Chicago.
The 104 square metre dwelling boasts three bedrooms, two bathrooms, sleeps eight, and includes a fully equipped kitchen, fitness centre access, parking, and a patio with city views.
The Biddle House - Chicago, IL
9.5 173 reviews

The Biddle House

apartment, Chicago
This two-storey house is situated in the Old Town district, a short walk from Lincoln Park Zoo and the Second City comedy club.
The house features two fully furnished apartments, each with two bedrooms, accommodating up to nine guests and offering amenities such as high-speed internet, cable TV, and a washer and dryer.

Check Out Holiday Apartments with a Balcony in Chicago, IL

Watching the sunset over the city skyline from your own private balcony is a premium detail that elevates any trip to Chicago, IL.

Stay Chic In Chicago: River North Suites W/ Luxe Amenities & Prime Location! - Chicago, IL
8.0 1 review

Stay Chic In Chicago: River North Suites W/ Luxe Amenities & Prime Location!

apartment, Chicago
This Level River North apartment, situated in Chicago's River North district, is minutes from the Magnificent Mile and the Loop, offering easy access to the Chicago River and its cultural attractions.
The 48-square-metre studio flat features a sofa bed, sleeping space for four guests, a fully equipped kitchen (fridge, microwave, dishwasher), and access to a swimming pool, sauna, and parking; nearby water activities include motor boating.
Magic Factory Loft 3east 4 Bd/4 Ba Families Groups - Chicago, IL
10 156 reviews

Magic Factory Loft 3east 4 Bd/4 Ba Families Groups

apartment, Chicago
This spacious Chicago apartment, ideal for large groups, boasts four bedrooms, four bathrooms, and sleeps up to 14 comfortably; its precise location within the city is undisclosed, but its central position offers easy access to Chicago's many attractions without needing a car.
The 160 square metre property features a fully equipped chef's kitchen, a terrace, garden, parking (fee applies, reservation required), and provides access to board games and a smart TV; amenities include Wi-Fi, air conditioning, and a dishwasher.
Dual Penthouse Retreat: Perfect For Groups - Chicago, IL
No reviews

Dual Penthouse Retreat: Perfect For Groups

apartment, Chicago
This West Loop flat offers direct access to Union Park and Fulton Market, situated a mere 5-minute walk from both, with a private footbridge providing convenient 100-metre access to Jewel Osco for groceries.
This spacious accommodation accommodates up to 14 guests with six bedrooms and five bathrooms, featuring a chef's kitchen, two private balconies, access to a building cinema, an outdoor swimming pool, a fitness centre, a steam room, and a basketball court.
Edgewater Apt With Free Parking, Gym, City Living - Chicago, IL
9.8 15 reviews

Edgewater Apt With Free Parking, Gym, City Living

apartment, Chicago
This two-bedroom flat in Chicago's Edgewater district is situated within 500 meters of the Lake Michigan shoreline and offers convenient access to the CTA Red Line at Granville Station for travel into the city centre.
This family-friendly residence accommodates up to four guests, featuring a fully equipped kitchen, in-unit laundry, air conditioning, a balcony, and complimentary on-site parking, with a fitness centre also available.

Frequently asked questions about apartment rentals in Chicago, IL

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Top-Rated Holiday Apartments with Parking in Chicago, IL

Parking is sorted from the moment you arrive, as these holiday apartments in Chicago, IL include free on-site spaces for the duration of your stay.

Heart Of East Village 2-bed 2-bath Peaceful Oasis Condo - Chicago, IL
10 1 review

Heart Of East Village 2-bed 2-bath Peaceful Oasis Condo

apartment, Chicago
This two-bedroom flat is situated in Chicago's East Village district, offering 2.9 kilometres to the United Center and within 3.9 kilometres of Water Tower Chicago and Union Station.
This 102 square metre apartment accommodates up to seven guests, featuring on-site parking, complimentary WiFi, a fully equipped kitchen, and a washing machine.
Beautiful & Inspiring Three Bedroom Home In Roscoe Village - Chicago, IL
9.8 486 reviews

Beautiful & Inspiring Three Bedroom Home In Roscoe Village

apartment, Chicago
This three-bedroom Chicago apartment, ideal for families, is situated in Roscoe Village, a 1.4 km walk from the Paulina–Lincoln/Roscoe Brown Line station, 1.6 km from Wrigley Field, and 8 km from Chicago's city centre.
The 3-bathroom property sleeps five, boasts a full kitchen with dishwasher, high-speed internet, and a flexible office space convertible to a child's room; nearby attractions include Wrigley Field and easy access to downtown Chicago via public transport.
3br Spacious Home Away From Home. Coziest Neighborhood In Chicago. - Chicago, IL
9.9 155 reviews

3br Spacious Home Away From Home. Coziest Neighborhood In Chicago.

apartment, Chicago
This three-bedroom flat is situated in a neighbourhood close to the lakefront, offering easy access to the lake and nearby parks. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property spans 111 square metres and comfortably accommodates up to six guests. Amenities include a fully equipped kitchen, a private back porch, and a range of extras such as coffee, toiletries, and plenty of towels and crockery.
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.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

The Dakin Estate 4br Speakeasy Walk To Wrigley - Chicago, IL
10 1 review

The Dakin Estate 4br Speakeasy Walk To Wrigley

apartment, Chicago
This Wrigleyville flat offers a prime Chicago location, situated a 9-minute walk from Wrigley Field and 2.7 kilometres from Montrose Beach on Lake Michigan.
This spacious 204 square metre flat, accommodating up to 23 guests, features four bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher and oven, air conditioning, a fireplace, and complimentary private parking with high-speed WiFi.
Convenient 2br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field - Chicago, IL
9.6 188 reviews

Convenient 2br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field

apartment, Chicago
This two-bedroom apartment on Michigan Avenue is ideally located for exploring Chicago, with the Field Museum, Art Institute and Symphony Orchestra all within a short distance. The apartment has received excellent ratings for location, cleanliness and overall experience.
The apartment comfortably sleeps six guests and has a fully-equipped kitchen with a dishwasher, a fitness centre and air conditioning. Guests can enjoy views of the Chicago skyline, free Wi-Fi and optional parking.
Top Floor City Apartment - Free Street Parking! - Chicago, IL
9.7 149 reviews

Top Floor City Apartment - Free Street Parking!

apartment, Chicago
This Lincoln Park flat, situated approximately 0.8-1.6km from DePaul University and 1.4km from a Metra and 'L' train station, offers easy access to Bucktown, Wicker Park, and Lakeview neighbourhoods.
The three-bedroom, one-bathroom property sleeps seven guests comfortably, boasting a fully equipped kitchen, in-unit laundry, and free on-street parking – a rarity in Chicago – alongside a private garden.
Plymouth Collection: 4bd 3ba High Floor With Gym - Chicago, IL
9.6 10 reviews

Plymouth Collection: 4bd 3ba High Floor With Gym

apartment, Chicago
This newly renovated four-bedroom flat is situated in Chicago's historic Printers Row, a mere 400 meters from Millennium Park and the Loop, within an 1899 landmark building.
This property, accommodating up to eight guests, offers a fully equipped kitchen, in-unit laundry, and access to shared amenities including a fitness centre and a rooftop with grills and city views.
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