Best apartment offers in Chicago, IL

10028 available apartment offers

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Chicago, IL apartments
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10028 Holiday apartments Chicago, IL

Best family friendly Chicago, IL Holiday Apartments and Self Catering Accommodations

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

Grant Park 2br Condo With Balcony Skyline View & Gym In Chicago Downtown - Chicago, IL
10 1 review
Chicago, IL
30/07 – 03/08
1045 €/nighttotal: 4180 € (4 )

Grant Park 2br Condo With Balcony Skyline View & Gym In Chicago Downtown

2 7
apartment , Chicago
This two-bedroom flat is located in downtown Chicago, a 10-minute walk from DePaul University and within 2 kilometres of the city centre, with Grant Park and the Art Institute of Chicago mere steps away.
This 112 square metre apartment accommodates up to 13 guests and offers a balcony with skyline views, on-site amenities including a shared lounge and billiards, free WiFi, and private parking.
Gilded Age Gold Coast Mansion With Parking, Deck, Fireplaces - Chicago, IL
9.6 10 reviews
Chicago, IL
07/08 – 09/08
3864 €/nighttotal: 7728 € (2 )

Gilded Age Gold Coast Mansion With Parking, Deck, Fireplaces

6 12
apartment , Chicago
This Gold Coast mansion, a historic Gilded Age Romanesque Revival property, is situated a short walk from Rush Street, Division Street, Oak Street Beach, and Michigan Avenue.
This six-bedroom residence sleeps up to 26 guests, offering a fully equipped kitchen, two sets of laundry facilities, free Wi-Fi, and a garage with one parking space, plus additional amenities including a worry-free cleaning package.
Aloha Tropical Penthouse In Wicker Park Sleeps 14 - Chicago, IL
9.8 214 reviews
Chicago, IL
23/06 – 25/06
492 €/nighttotal: 984 € (2 )

Aloha Tropical Penthouse In Wicker Park Sleeps 14

1 10
apartment , Chicago
This Chicago penthouse apartment is situated in Wicker Park, one block from the Milwaukee/Damen/North Blue Line station, offering easy access to the city's attractions.
Sleeping up to 14 guests in a four-bedroom, two-bathroom dwelling, this luxury property boasts a fully equipped kitchen, fitness centre, garden, and parking (additional fee applies), alongside amenities such as sound machines for a peaceful stay.
Sleeps 12! - Huge 3br/2ba Rogers Park Oasis - Chicago, IL
8.6 21 reviews
Chicago, IL
12/07 – 17/07
218 €/nighttotal: 1090 € (5 )

Sleeps 12! - Huge 3br/2ba Rogers Park Oasis

3 5
apartment , Chicago
This three-bedroom Chicago apartment, sleeping eight, offers a serene atmosphere and is conveniently located in an unspecified area of the city; further details regarding proximity to specific landmarks are needed to determine precise distances.
The property includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, a garden, parking, and benefits from excellent user ratings; additional information on the apartment's size and interior design features is required for a complete description.

Best Chicago, IL holiday apartments with a balcony

South Loop 2br Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College - Chicago, IL
9.0 3 reviews
Chicago, IL
21/09 – 24/09
269 €/nighttotal: 807 € (3 )

South Loop 2br Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College

2 2
apartment , Chicago
This McCormick Place apartment offers a convenient base for exploring Chicago's Museum Campus, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of both the Art Institute of Chicago and the Chicago Symphony Orchestra.
This 84-square-metre two-bedroom, two-bathroom flat comfortably sleeps six guests and boasts amenities including a fitness centre, terrace, parking, and free Wi-Fi; luggage storage is also available.
Spacious Historic Apartments In Lakeview Chicago - Walk To Wrigley, Nightlife, Shops, Hospitals - Chicago, IL
8.8 26 reviews
Chicago, IL
13/09 – 16/09
367 €/nighttotal: 1101 € (3 )

Spacious Historic Apartments In Lakeview Chicago - Walk To Wrigley, Nightlife, Shops, Hospitals

3 2
apartment , Chicago
This Lakeview apartment, a short walk from Wrigley Field and 2.7km from Fullerton Beach, offers easy access to Lincoln Park Zoo (3.2km) and Chicago's downtown area (6.4-7.4km).
The self-catering flat features a fully equipped kitchen, private patio, air conditioning, free Wi-Fi, and accommodates families with amenities including a baby safety gate, all within easy reach of local attractions.
The Banksy-king Bed-firepit-rooftop-united Center - Chicago, IL
10 5 reviews
Chicago, IL
01/08 – 08/08
1022 €/nighttotal: 7154 € (7 )

The Banksy-king Bed-firepit-rooftop-united Center

4 10
apartment , Chicago
This apartment is situated in Chicago's Near West Side, a 13-minute walk from United Center and a 5-minute drive from Merchandise Mart, offering a convenient location for exploring the city. The apartment is within easy reach of major sporting events, cultural attractions, and public transport.
The property has four bedrooms and two bathrooms, providing ample space for up to 12 guests. The apartment is equipped with a modern kitchen, a private garden and terrace, a washer and dryer, and a range of other amenities perfect for a comfortable stay.
Entire Apt In Heart Of Chicago - Chicago, IL
Chicago, IL
02/10 – 05/10
355 €/nighttotal: 1065 € (3 )

Entire Apt In Heart Of Chicago

2 4
apartment , Chicago
This Chicago flat is located in Lakeview, offering convenient access to the Chicago Theatre, Art Institute of Chicago, Michigan Avenue shopping, Navy Pier, the Field Museum of Natural History, and the Chicago Museum of Science and Industry.
This two-bedroom flat sleeps up to six guests, featuring a queen bed in each bedroom and a sofa bed in the living area, with amenities including air conditioning, WiFi, and a microwave oven, plus a bathtub for relaxation.

Frequently asked questions about apartment rentals in Chicago, IL

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    You can't miss the iconic Willis Tower for its views of the city. A visit to Millennium Park is a must, with the Cloud Gate sculpture (aka 'The Bean') and Crown Fountain. And no trip to Chicago is complete without a walk along Navy Pier, especially at night when the Ferris wheel lights up.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, trendy atmosphere, check out Wicker Park or Bucktown. If you prefer a more relaxed vibe with easy access to nature, consider Lincoln Park or Lakeview. And for a more budget-friendly option, Logan Square or Pilsen are popular choices.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    The Art Institute of Chicago is a must-see for art lovers, with works from Monet, Picasso, and Van Gogh. For history buffs, the Field Museum houses dinosaur skeletons and ancient artifacts. And the Museum of Science and Industry offers interactive exhibits on everything from transportation to space exploration.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of Lincoln Park. The city also boasts a world-class food scene, with deep-dish pizza, hot dogs, and Italian beef sandwiches being local favourites. And don't forget the vibrant music scene, with blues, jazz, and rock all having strong roots in the city.
  • What are the best apartments for families and kids in Chicago, IL?

  • Where can you find the best local markets and street food in Chicago, IL?

    The Maxwell Street Market is a great place to find a mix of local crafts, produce, and street food vendors. For a more upscale experience, head to the Green City Market in Lincoln Park, which features local and organic produce, artisanal goods, and prepared foods. And for a taste of Mexican cuisine, check out the Pilsen Food Truck Festival.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a well-developed public transportation system, with the 'L' (elevated train) and buses covering most of the city. The 'L' is particularly convenient for getting around downtown and the surrounding neighbourhoods. You can purchase a Ventra card for easy fare payments.
  • What are the best apartments with parking in Chicago, IL?

  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    In the summer, the Chicago Blues Festival is a must-see, while the Taste of Chicago food festival is a great way to sample local cuisine. In the autumn, the Chicago Marathon draws crowds of runners and spectators. And in the winter, the Christkindlmarket brings a touch of European charm to the city with its festive decorations and traditional treats.
  • What amenities are typically included in apartments in Chicago, IL?

    Most apartments in Chicago come with basic amenities like central heating and air conditioning, in-building laundry facilities, and sometimes a fitness centre. Some high-end buildings may offer additional amenities like swimming pools, rooftop decks, and concierge services.

Destinations nearby

Best Chicago, IL holiday apartments with parking

Sunny, Spacious, 3br 1ba Davlin Inn Chicago - Chicago, IL
9.4 7 reviews
Chicago, IL
06/07 – 28/07
390 €/nighttotal: 8580 € (22 )

Sunny, Spacious, 3br 1ba Davlin Inn Chicago

3 3
apartment , Chicago
This Chicago apartment, located in the Davlin Inn area, is approximately 8-11 kilometres from attractions such as Wrigley Field, Lincoln Park Zoo, the United Centre, and 360 Chicago Observation Deck.
The 117 square metre property offers a spacious three-bedroom layout sleeping up to nine guests, complete with a fully equipped kitchen, private patio with fireplace, barbecue facilities, and on-site children's playground.
Modern 1br Free Parking Spot - Chicago, IL
Chicago, IL
23/07 – 27/07
294 €/nighttotal: 1176 € (4 )

Modern 1br Free Parking Spot

1 2
apartment , Chicago
This modern one-bedroom apartment in Chicago's Wrigleyville neighbourhood is located 1.8km from Wrigley Field and within a few kilometres of Lincoln Park Zoo and Fullerton Beach.
The 46-square-metre flat offers a fully equipped kitchen, in-unit laundry, free Wi-Fi, private entrance, parking, and sleeps up to five guests, with nearby access to a casino.
5br/3ba/3tv's/prkg4-5cars/13ppl - Chicago, IL
10 53 reviews
Chicago, IL
18/09 – 21/09
794 €/nighttotal: 2382 € (3 )

5br/3ba/3tv's/prkg4-5cars/13ppl

1 8
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.
The Original Wrigleyville Coach House- Private 2 Story House In Heart Of City - Chicago, IL
9.8 237 reviews
Chicago, IL
07/10 – 14/10
1330 €/nighttotal: 9310 € (7 )

The Original Wrigleyville Coach House- Private 2 Story House In Heart Of City

3 8
apartment , Chicago
This detached house is located in the Lakeview neighbourhood, just a short walk from Wrigley Field and a few blocks from Lincoln Avenue and Southport Avenue, offering easy access to restaurants, bars, shops, and entertainment. The property has received excellent ratings for user experience, location, and cleanliness.
The house spans 107 square metres (1,150 square feet) and features three bedrooms, two bathrooms, a fully equipped kitchen, flat-screen TVs, high-speed internet, and a garden. Guests can enjoy access to game tickets for various Chicago sports teams, VIP parking passes for Wrigley Field, and nearby amenities like a Target Express, local coffee shops, and a YMCA.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Edgewater Studio On Paulina - Chicago, IL
9.9 126 reviews
Chicago, IL
24/10 – 01/11
109 €/nighttotal: 872 € (8 )

Edgewater Studio On Paulina

1 2
apartment , Chicago
This Chicago garden flat is situated in Edgewater, a short walk from Andersonville's shops and restaurants.
The self-contained studio sleeps three, includes a kitchenette, in-unit laundry, and a large walk-in wardrobe.
Logan Square Apartment! - Chicago, IL
9.8 387 reviews
Chicago, IL
04/07 – 06/07
196 €/nighttotal: 392 € (2 )

Logan Square Apartment!

1 3
apartment , Chicago
This apartment is located in the lively Logan Square neighbourhood, just a short walk from popular bars and restaurants like Logan 11 Bar, The Boiler Room, and The Chicago Diner. It has excellent user, location, and cleanliness ratings.
The flat offers one bedroom and one bathroom, comfortably accommodating up to seven guests. Amenities include a kitchen with a fridge and microwave, air conditioning, and Wi-Fi, making it ideal for exploring the city and enjoying a comfortable stay.
Game Day Stay Steps To Wrigley Garage - Chicago, IL
10 1 review
Chicago, IL
05/10 – 06/10
823 €/nightfor 1 night

Game Day Stay Steps To Wrigley Garage

3 5
apartment , Chicago
This Wrigleyville flat offers a prime Chicago location, just a 2-minute walk from Wrigley Field and 3.9 kilometres from Lincoln Park Zoo.
This spacious 3-bedroom property boasts 102 square metres of living space, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, a fireplace, and on-site parking for up to 12 guests.
Modern Apt. In Walkable Irving Park Neighborhood - Chicago, IL
9.8 49 reviews
Chicago, IL
01/08 – 30/09
101 €/nighttotal: 6060 € (60 )

Modern Apt. In Walkable Irving Park Neighborhood

1 2
apartment , Chicago
This ground-floor flat is located in Chicago's Irving Park neighbourhood, a 2.4km walk or 6.4km drive from the Blue Line, offering easy access to the city centre and O'Hare International Airport.
The two-bedroom apartment, sleeping four, features a queen and full bed plus a futon, a fully equipped kitchen with fridge, freezer and microwave, 1000 Mbps internet, and access to a shared laundry room; optional garage parking is available at an extra cost.
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