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.

Stylish 2-bedroom Wicker Park Apartment - Chicago, IL
9.9 123 reviews

Stylish 2-bedroom Wicker Park Apartment

apartment, Chicago
This Wicker Park flat is conveniently located near the 606 trail and a short walk from the Blue Line, offering easy access to Chicago's city centre and O'Hare International Airport.
The two-bedroom, two-bathroom apartment sleeps four, features a chef's kitchen with modern appliances including a dishwasher, and offers in-unit laundry, a smart TV, and keyless entry; nearby attractions include Wicker Park's numerous bars, restaurants, and boutiques.
5 Bedroom With 5 Beds And 2 Bathrooms - Chicago, IL
10 11 reviews

5 Bedroom With 5 Beds And 2 Bathrooms

apartment, Oak Park
This Oak Park apartment, situated one block from Madison Street and a short walk from the Blue and Green Line trains, offers easy access to Oak Park's attractions and is approximately 10km from major Chicago attractions such as the Art Institute of Chicago, the Field Museum, and the United Centre.
This five-bedroom, two-bathroom dwelling, boasting a 178 square metre floor area, includes a garden, parking, and modern amenities such as a dishwasher and air conditioning, comfortably accommodating six guests.
King Sleep Number Bed  Prime Location - Chicago, IL
10 12 reviews

King Sleep Number Bed Prime Location

apartment, Elmwood Park
This Elmwood Park condo, near the train station providing easy access to Chicago city centre, offers convenient proximity to Central Park, The Brickyard, and Cinemark Melrose Park.
Sleeping up to seven guests, this two-bedroom, one-bathroom apartment features a king-size bed, queen-size bed, full-size daybed, full-size sofa bed, full kitchen with high-end appliances (including an air fryer and rice cooker), on-site parking, and a coin-operated laundry with complimentary tokens.
Southwest Side Oasis- Welcoming And Bright Apt - Chicago, IL
9.2 65 reviews

Southwest Side Oasis- Welcoming And Bright Apt

apartment, Chicago
This family-friendly Chicago flat, situated in a neighbourhood convenient to restaurants and a short drive (approximately 0.8 km) from grocery stores and pharmacies, offers easy access to local parks and a large playground.
The two-bedroom apartment, sleeping five guests comfortably in a queen bed and bunk beds, features a private patio, free on-street parking, a fully equipped kitchen, and a separate entrance with a keypad.

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.

Spacious 2br South Loop With Skyline View, Optional Parking And Gym Access Near Mccormick Place And - Chicago, IL
No reviews

Spacious 2br South Loop With Skyline View, Optional Parking And Gym Access Near Mccormick Place And

apartment, Chicago
Book this Holiday rental. You will be based in Chicago.
Facilities and services: air conditioning, a fridge and a washing machine. Take advantage of the Free Parking with this accommodation.
Secret Gallery On The Park - 2bd/1ba - Chicago, IL
8.0 1 review

Secret Gallery On The Park - 2bd/1ba

apartment, Chicago
This two-bedroom flat is located 1.4 kilometres from the city centre, offering a 18-minute walk to Oak Street Beach and convenient access to attractions such as Water Tower Chicago and the Chicago Museum of Contemporary Art.
This apartment, covering 80 square metres and accommodating up to six guests, features a fully equipped kitchen with a fridge and microwave, air conditioning, a private balcony, and complimentary WiFi, with a washing machine also provided for guest use.
W Loop 1br W Pool Gym Lounge Nr L Chi-750 - Chicago, IL
No reviews

W Loop 1br W Pool Gym Lounge Nr L Chi-750

apartment, Chicago
This West Loop flat is conveniently located a 1.9km walk from Union Station and 1.3km from the Willis Tower, offering easy access to Chicago's key attractions and public transport.
The 58 square metre one-bedroom apartment sleeps five, features a balcony, a fully equipped kitchen with dishwasher, and access to a rooftop pool and fitness centre.
Explore Fulton Market + Retreat In Modern Comfort - Chicago, IL
10 1 review

Explore Fulton Market + Retreat In Modern Comfort

apartment, Chicago
This 125 square metre city flat is situated in downtown Chicago, a 9-minute walk from Ashland metro station and 14 minutes from Racine station, with Union Park a mere 5-minute walk away.
This two-bedroom, two-bathroom flat for five guests offers air conditioning, Wi-Fi, a full kitchen with a microwave and fridge, a balcony, on-site parking, and access to a communal swimming pool and hot tub.

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.

2 Bedroom 3 Beds  1 Bath Apartment In Berwyn - Chicago, IL
9.7 167 reviews

2 Bedroom 3 Beds 1 Bath Apartment In Berwyn

apartment, Berwyn
This Berwyn apartment is conveniently situated on Route 66, a short 1.6-2.4 km walk from the Metra station providing easy access to Chicago, and within walking distance of local restaurants, auto repair shops, and a Walgreens.
The two-bedroom, one-bathroom flat sleeps up to six guests comfortably, thanks to an inflatable bed, and boasts a fully equipped kitchen, air conditioning, parking, and internet access; its photo-ready interior is also perfect for personal photoshoots.
Cozy Modern Avondale Getaway Close To Everything - Chicago, IL
9.6 35 reviews

Cozy Modern Avondale Getaway Close To Everything

apartment, Chicago
This two-bedroom flat in Chicago's Avondale district is situated a stone's throw from the junction of Belmont and California Avenues, providing straightforward access to public transport and local amenities.
This extensively renovated apartment accommodates up to five guests and features a modern kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and an in-unit washer and dryer, with a dedicated office suite for remote working.
Andersonville Garden Living - Chicago, IL
9.7 149 reviews

Andersonville Garden Living

apartment, Chicago
This Chicago garden flat, conveniently located off Clark Street near Coffee Studio and Little Bad Wolf, offers easy access to shops and restaurants.
The one-bedroom apartment sleeps three, boasting a brand-new kitchen and bathroom, two full-size beds (one in a private bedroom, one in a living room nook), two Ashley Furniture reclining leather couches, a smart TV with Netflix, private laundry access, and free street parking.
Modern 2 Bedrooms With Free Parking Spot - Chicago, IL
10 49 reviews

Modern 2 Bedrooms With Free Parking Spot

apartment, Chicago
This apartment is situated in Chicago, within easy reach of the city’s attractions. It has consistently received excellent ratings for location, cleanliness and user experience.
The flat has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen with a fridge, freezer and dishwasher, as well as air conditioning for your comfort.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Mccormick Place Cozy Studio W/ Parking | Sleeps 4 - Chicago, IL
9.6 172 reviews

Mccormick Place Cozy Studio W/ Parking | Sleeps 4

apartment, Chicago
This Michigan Avenue studio apartment is ideally located in Chicago's South Loop, a short walk (less than 1km) from McCormick Place and close to public transport links, offering easy access to the Museum Campus and Soldier Field (both within a short Uber ride).
The self-catering apartment boasts a modern layout, sleeping up to four guests, and includes a fully equipped kitchen, a 4K smart TV with streaming services, and access to a fitness centre and laundry facilities; optional parking is available for £23 per day.
Modern Studio Apartment In Lakeview - Chicago, IL
9.7 94 reviews

Modern Studio Apartment In Lakeview

apartment, Chicago
This Lake View studio apartment is ideally located near the Brown Line CTA, approximately 3.2 kilometres from Wrigleyville and Boystown.
The self-contained unit sleeps two, features a fully equipped kitchen including a dishwasher, a 50" Roku TV with streaming services, and offers convenient access to a coin-operated laundry room and optional private garage parking.
Modern 2br Gem: Mins From Downtown & Laundry - Chicago, IL
9.3 102 reviews

Modern 2br Gem: Mins From Downtown & Laundry

apartment, Chicago
This two-bedroom Chicago apartment enjoys a prime location approximately 1.6km from the United Center and 4.8km from the Loop, offering easy access to numerous attractions and transport links including Union Station.
The 2-bedroom flat sleeps six, features a fully equipped kitchen with dishwasher, in-unit laundry, Roku TVs, fast WiFi, and a smart lock; nearby amenities include the West Loop and Gold Coast neighbourhoods.
Central Downtown Location-modern 2br Condo - Chicago, IL
9.5 173 reviews

Central Downtown Location-modern 2br Condo

apartment, Chicago
This Chicago city centre condo is situated a short walk from the Chicago Riverwalk and Michigan Avenue, offering easy access to Millennium Park, the Magnificent Mile, Willis Tower, and the Art Institute of Chicago.
The fourteenth-floor apartment boasts two bedrooms, one bathroom, sleeps five guests, includes a balcony with city views, and benefits from building amenities such as a swimming pool, fitness centre, and secure parking.
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