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.

Cozy Chicago Garden Apartment - Chicago, IL
10 87 reviews

Cozy Chicago Garden Apartment

apartment, Chicago
This Chicago ground-floor flat is conveniently located in a neighbourhood near Lincoln Square and Albany Park, offering easy access to the city centre via the CTA Blue Line.
The self-catering apartment sleeps four, featuring a queen-size bed, sofa bed, fully equipped kitchen with appliances including a stove, oven, microwave and coffee maker, plus high-speed Wi-Fi and a flat-screen TV; a nearby laundromat provides added convenience.
Vibrant 3br Pilsen Stayfree Parkingnear Downtown - Chicago, IL
9.8 56 reviews

Vibrant 3br Pilsen Stayfree Parkingnear Downtown

apartment, Chicago
This three-bedroom Pilsen apartment is a short walk from 18th Street and a short drive (approximately 3-4 km) from Grant Park and Millennium Park in Chicago, Illinois.
The fully renovated flat sleeps five, features a fully equipped kitchen with dishwasher, includes smart TVs in each bedroom, and offers beach equipment on request; making it ideal for families exploring Chicago's attractions.
Roscoe Village Inn -Guesthouse - Walk To Chicago's Wrigley Field - Chicago, IL
10 216 reviews

Roscoe Village Inn -Guesthouse - Walk To Chicago's Wrigley Field

apartment, Chicago
This Roscoe Village flat is situated in Chicago's North Center district, 8 kilometres north of the Loop and a short walk from Wrigley Field.
This 84 square metre apartment offers two bedrooms, one bathroom, and accommodation for four guests, featuring a kitchen with a fridge, microwave, and dishwasher, plus air conditioning, a garden, spa, and parking.
Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio! - Chicago, IL
9.5 113 reviews

Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio!

apartment, Chicago
This four-bedroom Chicago house, situated less than 6.4 km from the city centre, offers easy access to major attractions.
The spacious property sleeps ten guests, boasting a fully equipped kitchen, six 55" Smart TVs, a private patio with Solostove and smoker, and free on-street parking; breed restrictions and fees apply for pets.

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.

Luxury Downtown Penthouse With Private Rooftop - Chicago, IL
No reviews

Luxury Downtown Penthouse With Private Rooftop

apartment, Chicago
Apartment listing. Your accommodation will be based in Chicago.
Services and facilities: a kitchen, a washing machine and a terrace. Take advantage of the air conditioning in this apartment in Chicago.
Modern 3br Apartment Near North Ave Shops - Chicago, IL
9.6 4 reviews

Modern 3br Apartment Near North Ave Shops

apartment, Chicago
This spacious three-bedroom flat is situated in Chicago's Old Town/Lincoln Park/Clybourn Corridor area, placing you a short walk from the Second City Theatre and a few kilometres from Lincoln Park Zoo and the lakefront via the North Branch Trail.
This 90-square-metre residence accommodates up to eight guests with three bedrooms, two bathrooms, a fully equipped kitchen featuring stainless steel appliances, and in-unit laundry facilities, all offering city views and individually controlled air conditioning.
Home Away From Home Unit. - Chicago, IL
No reviews

Home Away From Home Unit.

apartment, Chicago
This three-bedroom flat is located in Chicago's West Town district, placing it 4.8 kilometres from Millennium Park and 4.2 kilometres from Lake Michigan, with the Field Museum of Natural History and the Museum of Science and Industry also within easy reach.
This residence offers accommodation for up to six guests and includes internet, air conditioning, a balcony, and parking, providing a comfortable base for exploring attractions such as the United Center and Wrigley Field.
Wrigleyville Retreat  1br  Sleeps 6  Full Kitchen - Chicago, IL
10 4 reviews

Wrigleyville Retreat 1br Sleeps 6 Full Kitchen

apartment, Chicago
This 84 square metre flat in Chicago's Lakeview district offers a prime location just 100 metres from the iconic Wrigley Field, placing you a short walk from local eateries and entertainment.
This newly remodelled one-bedroom unit accommodates up to six guests with a fully equipped kitchen, air conditioning, high-speed Wi-Fi, and private entry, whilst being conveniently situated near CTA transport links for easy exploration of Downtown Chicago and the lakefront.

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.

Kasa | Explore The Neighborhood-mag Mile | Chicago - Chicago, IL
9.6 304 reviews

Kasa | Explore The Neighborhood-mag Mile | Chicago

apartment, Chicago
This Chicago apartment offers a prime downtown location, steps from Oak Street Beach and a short walk from Michigan Avenue and Millennium Park.
The self-catering flat, sleeping two guests, includes a full kitchen with dishwasher, in-unit laundry, high-speed Wi-Fi, and on-site parking (fees apply); pets are welcome (restrictions apply).
Cozy 1-bedroom Garden Apartment Near Midwayairport - Chicago, IL
9.2 159 reviews

Cozy 1-bedroom Garden Apartment Near Midwayairport

apartment, Chicago
This stylish Chicago apartment, registered as R24000117322, is conveniently located near the Pulaski Orange Line station, offering easy access to Chicago's public transport network via a 1.9km walk.
The one-bedroom flat sleeps two guests and features a fully equipped kitchen (fridge, freezer, microwave), air conditioning, parking, and added comforts such as a white noise machine; nearby attractions are easily accessible via the Orange Line.
5br/3ba/large Game Room-private Parking For 5 Cars - Chicago, IL
10 65 reviews

5br/3ba/large Game Room-private Parking For 5 Cars

apartment, Chicago
This spacious five-bedroom, three-bathroom house is situated in Jefferson Park, Chicago, approximately 16 kilometres northwest of the city centre, offering easy access to public transport links and major airports such as O'Hare International Airport (14.5 km) and Midway International Airport (30.5 km).
The 311-square-metre property sleeps up to 13 guests, boasting a large games room with air hockey, a pool table, cornhole, and foosball, plus modern amenities including heated floors, a reverse osmosis water system, and a private garden with BBQ grills; discounted weekday rates are available.
Exquisite Rogers Park 1bd/1bath Apt. Near Evanston - Chicago, IL
9.7 72 reviews

Exquisite Rogers Park 1bd/1bath Apt. Near Evanston

apartment, Chicago
This one-bedroom flat is situated in Rogers Park, a diverse neighbourhood in Chicago, just a short drive from the Howard Station, which provides easy access to the Red, Yellow, and Purple Lines. The apartment has received excellent ratings for location, cleanliness, and user experience.
The flat can comfortably accommodate up to three guests and includes a sleeper sofa for additional sleeping space. Amenities include a fully equipped kitchen, air conditioning, gated parking, and access to a shared laundry facility.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Cubbies Dream! Half A Block To Wrigley! You Can Feel The Excitement In The Air On Game Days! Condo - Chicago, IL
9.6 286 reviews

Cubbies Dream! Half A Block To Wrigley! You Can Feel The Excitement In The Air On Game Days! Condo

apartment, Chicago
This Wrigleyville apartment is situated a mere 0.8 kilometres from Wrigley Field and a short walk from the 'L' train, offering easy access to Chicago's iconic baseball stadium and excellent transport links.
The two-bedroom, two-bathroom flat sleeps up to six guests comfortably, features a private deck with pre-game views of Wrigley Field, and includes amenities such as a fully equipped kitchen, Wi-Fi, and pet-friendly options (one pet allowed, additional fee applies).
City Center, River North Condo Huge 3br, Patio, Parking(2x) - Chicago, IL
10 209 reviews

City Center, River North Condo Huge 3br, Patio, Parking(2x)

apartment, Chicago
This Chicago apartment is situated in the River North neighbourhood, just a short walk from the Magnificent Mile, Lake Michigan, and Navy Pier. The area is known for its lively atmosphere, with plenty of shops, restaurants, and bars within easy reach. The apartment has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The apartment is spacious, covering 167 square metres and comfortably accommodating up to 10 guests. It features a fully equipped kitchen, a games room with board games and a shuffleboard table, a private patio with a barbecue, and secure gated parking.
Modern 2 Bedroom Apt In Heart Of Bronzeville - Chicago, IL
9.9 118 reviews

Modern 2 Bedroom Apt In Heart Of Bronzeville

apartment, Chicago
This newly renovated two-bedroom apartment is situated near Chicago's public transport links, a short 16km drive from Downtown Chicago and its major attractions.
The 2-bedroom, 1-bathroom flat sleeps four guests and offers a modern interior, a garden, parking, and all essential amenities including a fridge, freezer and microwave; enjoy nearby restaurants and shops.
Apartment In Cicero - Chicago, IL
10 3 reviews

Apartment In Cicero

apartment, Cicero
This Cicero flat offers excellent access to downtown Chicago, just a short drive away, and is within walking distance of local restaurants and grocery stores, making it ideal for weekend getaways, business trips, or family holidays.
This three-bedroom flat accommodates up to six guests and features air conditioning, a microwave oven, and parking, with convenient street parking available though guests should note street cleaning schedules.
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