Apartment rentals in Chicago

10028 available apartment offers

7 nights
2
1
  • booking
  • agoda
  • airbnb
  • tripcom
  • hotelscom
  • tiket
  • expedia
  • hotelmix
  • traveloka
  • trivago
  • tripadvisor
  • kayak
Chicago apartments
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Apartments in Chicago

Best family-friendly Chicago holiday apartments

Among the 10028 accommodations in Chicago, here are the 4 best family friendly apartments

Light And Bright 3bd Duplex In Avondale, Chicago - Chicago
9.8 99 reviews
Chicago
03/07 – 05/07
IDR 7294242/total: IDR 14588484 (2 )

Light And Bright 3bd Duplex In Avondale, Chicago

1 2
apartment , Chicago
This three-bedroom, two-bathroom Chicago duplex is ideally located in a trendy area spanning Avondale, Bucktown, and Logan Square, a short distance from Chicago's city centre.
The 3-bedroom dwelling boasts a top/bottom layout, sleeping up to six guests and offering in-unit laundry, a fully equipped kitchen with dining area, two entertainment areas with TVs (including a 55" Roku TV), and a garden with parking.
Group-friendly 5br Suite Near Mccormick |Sleeps 12 - Chicago
9.5 65 reviews
Chicago
30/06 – 05/07
IDR 12547533/total: IDR 62737665 (5 )

Group-friendly 5br Suite Near Mccormick |Sleeps 12

1 10
apartment , Chicago
This luxurious five-bedroom apartment is located in Chicago's South Loop, a short walk (approximately 0.8 km) from McCormick Place and close to a subway station, offering easy access to Soldier Field and the Museum Campus.
The 260 sq m property boasts a spacious layout ideal for large groups (sleeping up to 12), featuring five queen-size beds, a pool table, a 70" Smart HDTV, and a fully equipped kitchen, plus building amenities including a fitness centre and EV charging points.
Fun 3br Apt With Games 10 Min Downtown - King Bed - Chicago
9.7 151 reviews
Chicago
21/07 – 23/07
IDR 3754918/total: IDR 7509836 (2 )

Fun 3br Apt With Games 10 Min Downtown - King Bed

1 7
apartment , Chicago
This spacious Chicago apartment, ideal for families or large groups, is situated in a residential area approximately 5.6km from the city centre, a short drive from Millennium Park and Soldier Field, and close to Guaranteed Rate Field.
The 88 square metre property sleeps 8-10 guests and boasts three bedrooms, one bathroom, a fully equipped kitchen, free high-speed Wi-Fi, and entertainment features including four smart TVs and classic arcade games.
Medical District 2br With Jacuzzi & Parking - Chicago
9.7 14 reviews
Chicago
30/07 – 02/08
IDR 15438460/total: IDR 46315380 (3 )

Medical District 2br With Jacuzzi & Parking

2 2
apartment , Chicago
This Chicago apartment is ideally located near the city centre and the Medical District, within 1.8km of the United Centre and under 4km of Union Station, the Willis Tower, and DePaul University.
The 111 square metre flat offers two bedrooms, two bathrooms, sleeps seven, and includes free Wi-Fi, on-site parking, a fully equipped kitchen with dishwasher, and a fireplace.

Best Chicago holiday apartments with a balcony

Downtown Penthouse Lake Views Gym, Parking #1 - Chicago
Chicago
20/07 – 11/08
IDR 19903163/total: IDR 437869586 (22 )

Downtown Penthouse Lake Views Gym, Parking #1

2 1
apartment , Chicago
This downtown Chicago flat offers spectacular lake views from a spacious balcony, situated a mere 720 metres from DePaul University and 1.8 kilometres from the city centre, placing it steps from Grant Park and the Art Institute of Chicago.
This well-appointed two-bedroom flat, covering 103 square metres, accommodates up to nine guests and features a full kitchen with a fridge, microwave, and dishwasher, plus on-site amenities including a fitness centre and free WiFi.
2-car Parking, Pingpong, Arcade, 3 Floors! - Chicago
10 2 reviews
Chicago
21/07 – 26/07
IDR 10742155/total: IDR 53710775 (5 )

2-car Parking, Pingpong, Arcade, 3 Floors!

3 6
apartment , Chicago
This West Town apartment, a 130 square metre (1400 square foot) property, is situated in Chicago's West Town district, conveniently located within a 24-32 km radius of the city centre, O'Hare International Airport, Navy Pier, Millennium Park, the Field Museum, and the Art Institute of Chicago.
The spacious dwelling boasts three bedrooms, two bathrooms, and sleeps up to 14 guests comfortably, offering a fully equipped kitchen, a games room with a pool table and arcade machine, two free on-site parking spaces, and in-unit laundry facilities.
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests - Chicago
9.4 23 reviews
Chicago
26/06 – 30/06
IDR 12336072/total: IDR 49344288 (4 )

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests

4 4
apartment , Chicago
Mayor's Manor, a spacious apartment in Chicago's Bridgeport neighbourhood, offers convenient access to local amenities and is within a reasonable distance of attractions such as Michigan Avenue, Navy Pier, and the Field Museum.
This 186-square-metre (1999 square-foot) property boasts four bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, a game room with projector screens, an in-house bar, a large deck with a hot tub, and a private garden; nearby activities include boating, swimming and rock climbing.
Beautiful, Cozy, Stylish Bucktown, Wicker Park House, Perfect Chicago Location. - Chicago
Chicago
01/08 – 31/10
IDR 15878095/total: IDR 1444906645 (91 )

Beautiful, Cozy, Stylish Bucktown, Wicker Park House, Perfect Chicago Location.

3 2
apartment , Chicago
This West Town family-friendly house, ideal for Chicago city breaks, is located less than 1.6km from The Salt Shed and Humboldt Park, and under 4.8km from both the United Centre and Michigan Avenue.
Sleeping up to 10 guests, this three-bedroom property boasts a fully equipped kitchen, balcony, garden, spa, concierge service, parking, and free Wi-Fi; nearby attractions include Damen and Division train stations.

Destinations nearby

Best Chicago holiday apartments with parking

Peaceful Pilsen Garden Apt - Chicago
Chicago
24/07 – 24/08
IDR 1699328/total: IDR 52679168 (31 )

Peaceful Pilsen Garden Apt

1 1
apartment , Chicago
This Peaceful Pilsen Garden Apt is situated in Chicago's Pilsen district, 4.2 kilometres from the United Center and within 6.9 kilometres of Union Station and Willis Tower.
This 93 square metre flat offers a private garden and terrace, a fully equipped kitchen, and air conditioning, with parking available and a check-out time between 8 AM and 12 PM.
Retro Disco Cowboy Fun, Walk To Wrigley, Restaurants/bars! 15 Mins To Downtown! - Chicago
9.6 8 reviews
Chicago
23/06 – 25/06
IDR 12070892/total: IDR 24141784 (2 )

Retro Disco Cowboy Fun, Walk To Wrigley, Restaurants/bars! 15 Mins To Downtown!

6 10
apartment , Chicago
This six-bedroom house in Lakeview, Chicago, is located close to Wrigley Field and a short distance from Lake Michigan and Millennium Park.
The property, ideal for large groups, boasts a unique Disco Cowboy theme, six bedrooms, two bathrooms, and amenities including a fridge, microwave, dishwasher, and air conditioning; guests can enjoy nearby Wrigleyville's nightlife, subject to the property's strict quiet hours.
Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2s - Chicago
8.9 34 reviews
Chicago
04/07 – 06/07
IDR 11816671/total: IDR 23633342 (2 )

Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2s

2 7
apartment , Chicago
This River North flat, 2.4km from Ohio Street Beach and 2.7km from North Avenue Beach, offers easy access to attractions such as 360 Chicago and the Shops at Northbridge.
The 74 square metre, two-bedroom, two-bathroom apartment sleeps 19 guests and features a fully equipped kitchen, in-unit laundry, private rooftop access, and free Wi-Fi.
4br Bright City Retreat-sleeps 12-garage Parking - Chicago
10 1 review
Chicago
08/07 – 13/07
IDR 17495508/total: IDR 87477540 (5 )

4br Bright City Retreat-sleeps 12-garage Parking

5 10
apartment , Chicago
This expansive flat is situated in Chicago's Belmont Cragin district, offering convenient access to cultural attractions and major event venues.
Boasting 186 square meters of living space, this family-friendly five-bedroom apartment accommodates up to 12 guests and features a fully equipped kitchen, three bathrooms, high-speed WiFi, on-site parking, and a terrace/balcony.

Best Chicago holiday apartments with air conditioning

Spacious 1br Apartment In A Central Location - Chicago
9.9 305 reviews
Chicago
23/07 – 25/07
IDR 2461357/total: IDR 4922714 (2 )

Spacious 1br Apartment In A Central Location

1 2
apartment , Chicago
This Avondale flat is ideally located near the Chicago Blue Line, offering swift access to O'Hare International Airport and Chicago's city centre (both within 3.2 km), and a bus journey to Wrigley Field (also 3.2 km).
The one-bedroom, one-bathroom apartment sleeps three, featuring a spacious attic layout with skylights, keyless entry, ample street parking, and blackout blinds; nearby attractions include the Blue Line and Wrigley Field.
The Holiday House By The Lake! 2br/2bth - Chicago
9.9 84 reviews
Chicago
28/07 – 31/07
IDR 5180229/total: IDR 15540687 (3 )

The Holiday House By The Lake! 2br/2bth

1 2
apartment , Chicago
This Chicago apartment, near Loyola University and the Red Line, enjoys a superb location steps from the beach and within easy walking distance of local amenities.
The two-bedroom, two-bathroom flat sleeps five, offering a well-equipped kitchen, laundry facilities, smart TVs, and access to a shared patio with a fire pit and lake views, plus rentable paddleboards and kayaks (May-October).
City View 3br Condo/garage Parking/rooftop Deck - Chicago
9.5 73 reviews
Chicago
28/06 – 05/07
IDR 9581991/total: IDR 67073937 (7 )

City View 3br Condo/garage Parking/rooftop Deck

1 5
apartment , Chicago
This Wicker Park apartment in Chicago offers easy access to downtown via public transport and is close to Wicker Park's restaurants and shops.
Sleeping up to 12 guests, this three-bedroom property features two bathrooms, a loft with a queen bed, two balconies, a shared patio with a gas fire pit, a fully equipped kitchen with granite island, flat-screen TVs, and an arcade machine; garage parking is included.
West Town Modern Garden 1 - Chicago
9.5 97 reviews
Chicago
28/07 – 31/07
IDR 2970397/total: IDR 8911191 (3 )

West Town Modern Garden 1

1 2
apartment , Chicago
This stylish, newly renovated one-bedroom apartment is centrally located in Chicago, offering easy access to Wicker Park, Logan Square, Humboldt Park, and Fulton Market, and is within a few kilometres of the city centre.
The 1-bathroom flat, sleeping up to four guests, boasts two private entrances, a fully equipped kitchen (fridge, freezer, microwave), air conditioning, parking, and is near large public parks; registration number R23000104954.
©2026 cozycozy.com