Best apartment offers in Chicago, IL

10028 available apartment offers

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Chicago, IL apartments
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10028 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.

6br Apt • Near Lakefront + Red Line Access - Chicago, IL
Chicago, IL
31/07 – 03/08
£1758/nighttotal: £5274 (3 )

6br Apt • Near Lakefront + Red Line Access

1 11
apartment , Chicago
This spacious 6-bedroom flat is conveniently located near Chicago's lakefront, offering easy access to Lake Michigan beaches and the Red Line for city commutes.
This family-friendly apartment accommodates up to 12 guests and features individual air conditioning, a fully equipped kitchen, and keyless self check-in, with coin-operated laundry facilities in the basement.
Blueground | The Loop, Elevator, Nr Willis Tower - Chicago, IL
Chicago, IL
01/08 – 31/10
£93/nighttotal: £8463 (91 )

Blueground | The Loop, Elevator, Nr Willis Tower

1 2
apartment , Chicago
This studio flat is located in Chicago's Loop district, offering convenient access to the city's attractions.
This modern studio apartment accommodates two guests and includes a fully equipped kitchen, in-apartment laundry, a smart TV, and premium wireless speaker, with flexible lease options available.
Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park - Chicago, IL
Chicago, IL
31/07 – 03/08
£1626/nighttotal: £4878 (3 )

Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park

5 11
apartment , Chicago
This spacious five-bedroom, three-bathroom luxury flat is situated in Chicago's Portage Park district, offering a residential setting approximately 13 to 14 kilometres from downtown attractions such as Millennium Park and Skydeck Chicago.
This expansive 204 square metre residence accommodates up to sixteen guests and features an entertainment basement with a home cinema, games, and a gym, alongside a private garden with a hot tub and outdoor games.
Logan Sq 4br Duplex  Garage  Sleeps 8 - Chicago, IL
Chicago, IL
26/06 – 30/06
£745/nighttotal: £2980 (4 )

Logan Sq 4br Duplex Garage Sleeps 8

4 3
apartment , Chicago
This 4-bedroom flat is located in Chicago's Avondale district, offering proximity to Lake Michigan, the Art Institute of Chicago and Wrigley Field.
This well-equipped property accommodates up to 8 guests with 2 bathrooms, a kitchen featuring a microwave oven and dishwasher, and it also provides parking and a terrace.

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.

Edgewater Gem By The Lake! 2br With Parking & Gym - Chicago, IL
10 1 review
Chicago, IL
24/06 – 26/06
£285/nighttotal: £570 (2 )

Edgewater Gem By The Lake! 2br With Parking & Gym

2 2
apartment , Chicago
This Edgewater flat is situated a short walk from the CTA Red Line's Granville Station and the Chicago lakefront, offering easy access to Loyola University and downtown.
This 93 square meter flat provides accommodation for up to four guests with two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a balcony, and included garage parking.
Luxury 6bd/5bth + Roofdeck - Downtown Chicago! - Chicago, IL
9.2 10 reviews
Chicago, IL
08/10 – 12/10
£3297/nighttotal: £13188 (4 )

Luxury 6bd/5bth + Roofdeck - Downtown Chicago!

6 11
apartment , Chicago
This spacious six-bedroom, five-bathroom duplex, offering accommodation for up to fourteen guests, is situated in Downtown Chicago, a mere stone's throw from Old Town and within blocks of Michigan Avenue, the Gold Coast, and River North, placing you close to attractions such as the Chicago Theatre and the Art Institute of Chicago.
This newly finished residence spans 418 square metres and features two fully equipped kitchens, air conditioning, and internet, with ample free street parking available nearby, making it an ideal base for exploring the Field Museum of Natural History and the Chicago Museum of Science and Industry.
Elevated Gem - Sleeps 12 - 20 Mins To Downtown Chicago - Chicago, IL
10 2 reviews
Chicago, IL
25/06 – 26/06
£1017/nightfor 1 night

Elevated Gem - Sleeps 12 - 20 Mins To Downtown Chicago

5 1
apartment , Oak Park
This five-bedroom, three-bathroom flat in Oak Park offers proximity to the Frank Lloyd Wright Historic District (644 metres drive) and Ernest Hemingway's House and Museum (966 metres drive), with the Oak Park Metro Station a 13-minute walk away for convenient travel.
This pet-friendly accommodation for up to 12 guests includes air conditioning, Wi-Fi, a fully equipped kitchen with an oven and microwave, and on-site foosball, with covered parking provided for ease of access.
Spacious 2br Near Univ Of Chicago Home Away From Home - Chicago, IL
Chicago, IL
25/06 – 26/07
£113/nighttotal: £3503 (31 )

Spacious 2br Near Univ Of Chicago Home Away From Home

1 3
apartment , Chicago
This Hyde Park flat is ideally situated for those visiting the University of Chicago, with 63rd Street Beach just 2.1 kilometres away and the Museum of Science and Industry – Chicago 2.4 kilometres distant.
This apartment offers parking, free WiFi, air conditioning, and a private terrace, alongside a fully equipped kitchen and a flat-screen TV for up to 11 guests, with a 11:00 AM check-out.

Frequently asked questions about apartment rentals in Chicago, IL

Destinations nearby

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.

River West, Second Floor Chicago By 747 Lofts - Chicago, IL
9.3 1023 reviews
Chicago, IL
19/08 – 24/08
£215/nighttotal: £1075 (5 )

River West, Second Floor Chicago By 747 Lofts

1 2
hotel , Chicago
The 747 Lofts by RedAwning - River West, Second Floor Chicago is located in the River West neighbourhood, just over 2.5 kilometres from the United Center and 3 kilometres from the Chicago Museum of Contemporary Art. This area is known for its trendy restaurants, independent shops, and lively atmosphere. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers one bedroom and one bathroom, providing a comfortable space for a couple or small family. It features a fully equipped kitchen, free parking, and access to a garden, along with amenities like bed linen, towels, cable TV, and internet access.
Spacious 3br 420 Friendly Apartment Near Mccormick Place, Lakefront And Soldier Field - Chicago, IL
8.8 4 reviews
Chicago, IL
24/07 – 27/07
£589/nighttotal: £1767 (3 )

Spacious 3br 420 Friendly Apartment Near Mccormick Place, Lakefront And Soldier Field

3 8
apartment , Chicago
This three-bedroom apartment near McCormick Place in Chicago offers easy access to attractions such as the Field Museum, Art Institute of Chicago, and Chicago Symphony Orchestra, all within a 3.2-kilometre radius.
The 111-square-metre property features a spacious layout sleeping up to eight guests, boasting a fully equipped kitchen, complimentary Wi-Fi, and optional private parking, plus it's allergy-free and soundproof.
Spacious&modern Condo, Near Dwtn, Secure Parking - Chicago, IL
10 126 reviews
Chicago, IL
17/06 – 21/06
£662/nighttotal: £2648 (4 )

Spacious&modern Condo, Near Dwtn, Secure Parking

1 8
apartment , Chicago
This spacious Chicago apartment, ideal for families or groups, enjoys convenient access to public transport, situated near a bus stop with easy connections to the city centre, United Centre, and McCormick Place.
The 167 sq m (1800 sq ft) property boasts two bedrooms, two bathrooms, sleeps eight to ten guests comfortably, and includes a chef's kitchen, in-unit laundry, free high-speed Wi-Fi, and a parking space with EV charging.
4br/1.5ba+fenced Backyard +Near Mdw+one Level - Chicago, IL
10 43 reviews
Chicago, IL
17/06 – 20/06
£387/nighttotal: £1161 (3 )

4br/1.5ba+fenced Backyard +Near Mdw+one Level

1 8
apartment , Burbank
This Burbank house, situated in a peaceful suburban neighbourhood approximately 20-30km from downtown Chicago and Midway Airport, offers convenient access to local shops and parks.
Sleeping eight guests comfortably, this four-bedroom property boasts a spacious interior with modern finishes, a private garden, driveway parking for five cars, fast Wi-Fi, and a fully equipped kitchen including a fridge, freezer and microwave.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

A Vintage Pink House In The Heart Of Chicago - Chicago, IL
9.9 487 reviews
Chicago, IL
24/07 – 26/07
£288/nighttotal: £576 (2 )

A Vintage Pink House In The Heart Of Chicago

2 2
apartment , Chicago
This East Village flat, a Victorian pink house with a Walk Score of 97, is situated in a residential area of Chicago, offering easy access to the Division Blue Line.
The two-bedroom, one-bathroom apartment sleeps three, features a Stearns & Foster queen-size bed, a gold glitter clawfoot bathtub, and a smart TV with streaming services, plus a garden and parking.
Cozy Comfy Clean 420 Compliant Free Parking Quiet Neighborhood A Guest Favorite! - Chicago, IL
10 125 reviews
Chicago, IL
21/08 – 24/08
£145/nighttotal: £435 (3 )

Cozy Comfy Clean 420 Compliant Free Parking Quiet Neighborhood A Guest Favorite!

3 2
apartment , Chicago
This renovated flat is located in a peaceful, family-friendly neighbourhood in northwest Chicago, just a short distance from downtown attractions like Navy Pier and Michigan Avenue. The property enjoys excellent user ratings and is a popular choice for travellers seeking a comfortable and convenient base for exploring the city.
The three-bedroom apartment spans 93 square metres and can comfortably accommodate up to 10 guests. A range of amenities are provided, including free Wi-Fi, a well-equipped kitchen, a Jacuzzi, a garden, and a spa, ensuring a relaxing and enjoyable stay.
Stylish 2br | Near Downtown, Mccormick & Lakefront - Chicago, IL
8.0 1 review
Chicago, IL
19/06 – 22/06
£271/nighttotal: £813 (3 )

Stylish 2br | Near Downtown, Mccormick & Lakefront

1 3
apartment , Chicago
This Chicago flat is situated in historic Bronzeville, offering a 10-minute drive to McCormick Place and mere minutes from Museum Campus, with Downtown Chicago accessible in 12-15 minutes.
This garden-level suite accommodates four guests across two bedrooms, featuring a fully equipped kitchen, air conditioning, a private garden, and direct access to Armstrong Park and its amenities, just 8 kilometres from Lake Michigan.
Spacious 2br/2ba W/ Free Parking Near Downtown - Chicago, IL
9.5 34 reviews
Chicago, IL
07/10 – 12/10
£249/nighttotal: £1245 (5 )

Spacious 2br/2ba W/ Free Parking Near Downtown

1 3
apartment , Chicago
This 2-bedroom, 2-bathroom condo is situated in historic Bronzeville, offering convenient access to Downtown Chicago, McCormick Place, Hyde Park, and the Museum Campus, all within a few kilometres.
This stylish apartment provides hotel-quality furnishings, a fully equipped kitchen, complimentary on-site parking, and is well-connected by public transport, accommodating up to four guests.
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