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.

100 Yr. Old Chicago Brick Craftsman With Yard, Near Beach And Loyola! - Chicago, IL
10 178 reviews

100 Yr. Old Chicago Brick Craftsman With Yard, Near Beach And Loyola!

apartment, Chicago
This charming three-bedroom flat is situated in a historic Chicago neighbourhood, just 3 kilometres from Lake Michigan and a 2.4 kilometre walk to Wrigleyville. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 139 square metre apartment comfortably accommodates up to eight guests and features a spacious layout with a sunroom and a dining room that can seat up to 10 people. Guests can enjoy a fully equipped kitchen, a charming backyard, parking facilities, and family-friendly amenities such as a baby gate and toddler dishes.
Garage Parking! Walk To Logan Square Station Plus Great Local Restaurants And Bars - Chicago, IL
9.5 335 reviews

Garage Parking! Walk To Logan Square Station Plus Great Local Restaurants And Bars

apartment, Chicago
This three-bedroom duplex apartment is situated in Chicago's Logan Square, a short walk from the Logan Square Blue Line station, offering easy access to Chicago's attractions.
The property boasts a duplex layout, sleeping up to seven guests, and includes amenities such as a fully equipped kitchen with dishwasher, garage parking, and essential toiletries; nearby restaurants and bars provide ample entertainment options.
Remodeled Boho Avondale Getaway - Sleeps 6 - Chicago, IL
No reviews

Remodeled Boho Avondale Getaway - Sleeps 6

apartment, Chicago
This 65 square meter garden flat is situated in Chicago's Avondale district, a developing area approximately 15 minutes by public transport from the city centre.
The property offers a modern boho-style decor, accommodates up to six guests with two queen beds, a sleeper sofa, and two twin air mattresses, and includes an in-unit washer/dryer, free street parking, and a shared garden, with entertainment provided by a classic arcade machine and wall-mounted games.
The Roscoe Village Guesthouse - Chicago, IL
9.4 20 reviews

The Roscoe Village Guesthouse

apartment, Chicago
This Roscoe Village guesthouse in Chicago is situated 2.4 kilometres from Wrigley Field and within 8 kilometres of Lincoln Park Zoo and other key attractions including 360 Chicago and the United Centre.
This three-bedroom apartment offers 111 square metres of space, sleeping up to six guests, and features a fully equipped kitchen with a dishwasher, air conditioning, and a private entrance; towels and bed linen are provided.

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.

Penthouse Level, Stunning Wrigley Stay - Chicago, IL
9.4 154 reviews

Penthouse Level, Stunning Wrigley Stay

apartment, Chicago
This two-bedroom flat is located in Chicago's Lakeview neighbourhood, just a 9-minute walk from Wrigley Field and a short drive from Fullerton Beach. The apartment has excellent user, location and cleanliness ratings.
The 110 square metre flat has a fully equipped kitchen, a terrace with city views and a garden. Guests can enjoy free Wi-Fi, air conditioning, a flat-screen TV, and a dining area.
Premier 4br Art Deco Suite With Garage. - Chicago, IL
10 5 reviews

Premier 4br Art Deco Suite With Garage.

apartment, Chicago
This detached house is located in Chicago's Lakeview district, 3 minutes on foot from the Addison Red Line station and a stone's throw from Wrigley Field.
Spanning 111 square metres over two levels, this property accommodates up to eight guests with four bedrooms, two bathrooms, and amenities including a pool table, fire pit lounge, private office, and Smart TVs in every room.
Two-story Stunner In Iconic Old Town Chicago By Allset Turnover - Chicago, IL
9.6 146 reviews

Two-story Stunner In Iconic Old Town Chicago By Allset Turnover

apartment, Chicago
This Old Town Chicago condo is located blocks from the North and Wells intersection, offering easy access to the Second City comedy club and other attractions in the area.
The three-bedroom, three-bathroom property sleeps eight guests and features a fully equipped chef's kitchen, a living room, a dedicated workspace, and a terrace/balcony plus garden; street parking is available or can be pre-booked via apps such as SpotHero or ParkWhiz.
South Loop · 3 Kings · Steps From Mccormick Place - Chicago, IL
8.8 8 reviews

South Loop · 3 Kings · Steps From Mccormick Place

apartment, Chicago
This family-friendly flat is situated in downtown Chicago, a mere 800 metres from McCormick Place and within easy reach of the State Street shopping district, with the Cermak-McCormick Place metro station 880 metres away and Cermak-Chinatown metro station 1.2 kilometres distant.
This 167 square metre residence accommodates up to eight guests across three bedrooms and two bathrooms, featuring air conditioning, a dedicated workspace, a fully equipped kitchen with a fridge, microwave and dishwasher, and on-site laundry facilities.

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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.

Premier Luxe Retreat | Free Parking - Chicago, IL
10 8 reviews

Premier Luxe Retreat | Free Parking

apartment, Oak Park
This stylish second-floor flat in Oak Park is conveniently located within walking distance of the Frank Lloyd Wright Home and Studio and the Ernest Hemingway Birthplace Museum, with downtown Chicago accessible via a 15-minute drive and public transport options a 15- to 20-minute walk away.
This one-bedroom apartment accommodates up to five guests with a king-size bed, two rollaway beds, and a sofa bed, featuring a fully equipped kitchen, high-speed Wi-Fi, 4K Smart TVs, air conditioning, and dedicated parking, with coin-operated laundry facilities on-site.
Centrally Located Condo With Parking And Deck! - Chicago, IL
9.5 104 reviews

Centrally Located Condo With Parking And Deck!

apartment, Chicago
This four-bedroom apartment is ideally situated in a prime Chicago neighbourhood, just a short walk from restaurants, bars, shops, and cultural attractions, and a few blocks from the train station connecting to O'Hare Airport, located 27 kilometres away. The property has received excellent ratings for location, cleanliness, and user experience.
The apartment is spread across two levels, accommodating up to 12 guests, and features a spacious living area, a fully equipped kitchen, and a comfortable bar area with a projector screen. Amenities include parking for two vehicles, guest parking permits, a fireplace, and air conditioning.
Charming And Quite 2nd Floor Apartment In Logan Sq - Chicago, IL
9.8 63 reviews

Charming And Quite 2nd Floor Apartment In Logan Sq

apartment, Chicago
This Logan Square duplex flat is situated in a quiet neighbourhood, minutes from downtown Chicago and within easy reach of public transport.
The self-contained property offers a private master bedroom and bathroom, a dedicated workout room, and sleeps up to six guests, with a folding bed providing flexible sleeping arrangements; nearby Logan Square boasts diverse dining and entertainment options.
Charming Chicago Apt - Chicago, IL
8.2 24 reviews

Charming Chicago Apt

apartment, Chicago
This Chicago apartment is situated near the United Centre, approximately 3.2km away, offering easy access to attractions such as the Willis Tower and Union Station, both within a 6.4km radius.
The 93 square metre flat comprises two bedrooms, two bathrooms, sleeps up to ten guests, and includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, parking, and free Wi-Fi.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

River North 1br W Gym Pool Roof Nr Riverwalk Chi-821 - Chicago, IL
No reviews

River North 1br W Gym Pool Roof Nr Riverwalk Chi-821

apartment, Chicago
This one-bedroom flat in Chicago's River North district is less than 1 kilometre from the Shops at Northbridge and 1.7 kilometres from Union Station, placing you close to the city centre and iconic sights such as the Willis Tower, which is a 17-minute walk away.
This 66 square metre apartment accommodates up to three guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, and access to building amenities including a gym and pool.
Departamento En ÁRea De Chicago - Chicago, IL
9.6 117 reviews

Departamento En ÁRea De Chicago

apartment, Cicero
This Cicero apartment, situated 2.4 kilometres from the Pink Line 'L' station (offering a 30-minute journey to Chicago city centre) and 6.4 kilometres from Midway International Airport, provides easy access to both local amenities and Chicago attractions.
The one-bedroom, one-bathroom flat sleeps up to six guests and includes free on-site parking, air conditioning, a fully equipped kitchen, and is within walking distance of a supermarket, bakery, and other local businesses.
Flexible Apt. For 8 By Oak Park-chi - Chicago, IL
9.9 215 reviews

Flexible Apt. For 8 By Oak Park-chi

apartment, Chicago
This three-bedroom flat is situated in a quiet residential neighbourhood just north of Oak Park, a suburb of Chicago, and is easily accessible by car or public transport, with the city centre just 8km away. The property has received excellent ratings for cleanliness, location and user experience.
The 96 square metre apartment comfortably sleeps up to eight guests in a variety of bed configurations, including a flexible room with either two twin-XL beds or one king-sized bed. The property is fully equipped with everything you need, including kitchen appliances, cookware, linens, toiletries, laundry facilities, two travel cots, and allergy-free bedding.
A Whimsical Fairy-tale Loft In Ravenswood Chicago - Chicago, IL
10 362 reviews

A Whimsical Fairy-tale Loft In Ravenswood Chicago

apartment, Chicago
This Ravenswood, Chicago flat is situated above a tavern and coffee house, offering convenient access to local amenities and various Chicago neighbourhoods.
The third-floor, two-bedroom apartment sleeps four, featuring a pull-out sofa, semi-private bedrooms (no doors), a kitchen with fridge, freezer and microwave, air conditioning, and excellent guest reviews.
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