Holiday Rentals in Chicago

13982 available vacation rental offers

7 nights
2
1
  • tripcom
  • booking
  • airbnb
  • tripadvisor
  • klook
  • agoda
  • expedia
  • hotelscom
  • hotelscombined
  • eztravel
  • makemytrip
  • rakutentravel
Chicago holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Chicago holiday rentals: compare the best deals

Best family friendly Chicago holiday rentals

Among the 13982 accommodations in Chicago, here are the 4 best family friendly rentals

Iconic Downtown Penthouses Getaway + City Views - Chicago
No reviews

Iconic Downtown Penthouses Getaway + City Views

apartment, Chicago
This luxury duplex apartment in Chicago's Central Loop offers unparalleled access, being just 200 metres from Millennium Park and 'The Bean', with Michigan Avenue's premier shopping a 5-minute walk away.
This family-friendly residence accommodates up to 15 guests across seven bedrooms and seven bathrooms, boasting a fully-equipped chef's kitchen, a balcony with park views, and access to extensive building amenities including indoor and outdoor swimming pools and a fitness centre.
1 Free Parking, Gym, Balcony, Sleeps 10 - Chicago
No reviews

1 Free Parking, Gym, Balcony, Sleeps 10

apartment, Chicago
This West Loop flat is a 5-minute walk from Fulton Market and offers driving distances of 1.3 kilometres to the city centre, 2.1 kilometres to Millennium Park, 2.2 kilometres to Navy Pier, 2.2 kilometres to The Art Institute of Chicago, and 2.9 kilometres to The Field Museum.
This 105 square metre apartment sleeps up to 10 guests across three bedrooms, featuring a king bed, two double beds, a full bunk bed, a private balcony, a fully equipped kitchen with a Keurig coffee maker, high-speed Wi-Fi, a 65-inch Smart TV, and an in-unit washer/dryer.
Luxury Soho Styled Two-level Townhouse - Old Town - Chicago
10 22 reviews

Luxury Soho Styled Two-level Townhouse - Old Town

apartment, Chicago
This three-bedroom, three-bathroom duplex townhouse is situated in Chicago's Old Town, a five-minute walk from the beach and next to the Second City comedy club.
The 207 square metre property sleeps up to 14 guests, boasting a chef's kitchen with Gaggenau appliances, a terrace, parking, and excellent guest reviews.
The Roscoe Village Guesthouse - Chicago
9.8 131 reviews

The Roscoe Village Guesthouse

apartment, Chicago
This Roscoe Village apartment, near the CTA Brown Line and less than 1.6km from Wrigley Field, offers easy access to Chicago's city centre via a 30-minute train journey.
The three-bedroom, one-bathroom flat sleeps six guests and includes a fully equipped kitchen, free in-unit laundry, 600 Mbps Wi-Fi, and free street parking; nearby amenities include numerous restaurants, boutiques, and a Starbucks.

Best Chicago holiday rentals with parking

Walk To Wrigley * Garage Parking* Peaceful Patio - Chicago
9.9 203 reviews

Walk To Wrigley * Garage Parking* Peaceful Patio

apartment, Chicago
This three-bedroom Chicago apartment is situated near Wrigleyville, a short 1.6km walk from the Brown Line, offering easy access to numerous bars and restaurants.
The 3-bedroom flat sleeps six guests, features a fully equipped kitchen with modern appliances, in-unit laundry, a private backyard patio with barbecue, and free garage parking; a smart TV and sleeper sofa provide added comfort.
6br Walk To Wrigley | Sleeps 15 | Bar + Game Room - Chicago
9.8 100 reviews

6br Walk To Wrigley | Sleeps 15 | Bar + Game Room

apartment, Chicago
This jungle-themed Airbnb in Chicago's Wrigleyville neighbourhood is a 10-minute walk (approximately 0.8 km) from Wrigley Field.
Sleeping up to 19 guests, this six-bedroom, three-bathroom house boasts two kitchens, a basement games room with bar and ping pong table, two living rooms with 55-inch smart TVs, and parking for two cars; laundry facilities are also available.
Avondale Coach House - Chicago
9.9 78 reviews

Avondale Coach House

apartment, Chicago
This Avondale coach house apartment in Chicago's Northwest Side offers convenient access to public transport for downtown and O'Hare International Airport travel, being within walking distance of local amenities.
The self-contained second-floor flat features a queen-size bed, full kitchen with dishwasher, bathroom with shower, and comfortably accommodates four guests, with a private entrance and garden access.
Luxury Penthouse Loft W/terrace  507 | River North - Chicago
9.9 30 reviews

Luxury Penthouse Loft W/terrace 507 | River North

apartment, Chicago
This brand new penthouse duplex loft in Chicago's River North district is situated 320 metres from Michigan Avenue and 960 metres from Lake Michigan, offering prime access to nightlife, restaurants, and shopping.
This spacious designer apartment accommodates up to 10 guests with two living areas, a chef's kitchen, a private terrace with city views, and secure parking nearby, making it ideal for families and pet owners seeking a comfortable stay.

Frequently asked questions about holiday rentals in Chicago

  • What should a first-time visitor not miss in Chicago, IL?

    You've got to see the iconic Willis Tower, stroll along Navy Pier, and catch a show in the historic Chicago Theatre. These are must-dos for any first-time visitor.
  • What are the best Airbnb and vacation rentals in Chicago?

  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant and central location, you could look at Lincoln Park. It's close to the lakefront, museums, and has great restaurants and shops. Wicker Park is also trendy with a cool vibe and plenty of independent businesses.
  • What are the most popular Airbnbs in Chicago?

  • What are the top family-friendly attractions in Chicago, IL?

    The Lincoln Park Zoo is a free attraction with lots to see, and the Shedd Aquarium is a great place for kids to learn about marine life. The Field Museum is also a hit with families, especially the Sue the T-Rex exhibit.
  • What are the best vacation rentals with a pool in Chicago?

  • When is the best time to book a vacation rental in Chicago, IL?

    You'll want to book your vacation rental in advance, especially if you're travelling during peak season, which is typically from May to October. You can find good deals outside of these months, but you might miss out on some of the best weather.
  • What are the best rentals for families and kids in Chicago?

  • What events or festivals should visitors check out in and around Chicago, IL?

    Chicago has a great festival scene. The Taste of Chicago in July is a must-see for foodies, and the Chicago Blues Festival in June is a great way to experience the city's musical heritage. The Air and Water Show in August is also a popular event.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago?

  • What are the best budget-friendly activities in Chicago, IL?

    You can explore the city for free by walking or cycling along the Lakefront Trail. Visiting the free museums like the Art Institute of Chicago on Tuesdays after 5pm is a great way to save money. The Millennium Park is a great place to spend a sunny afternoon and soak up the atmosphere.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a taste of Chicago's famous deep-dish pizza, head to Lou Malnati's or Pizzeria Bebu. For a more casual experience, try a Chicago-style hot dog from Portillo's. If you're looking for something more upscale, try Alinea, which offers a modern take on American cuisine.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a great option for both walking and cycling, offering stunning views of Lake Michigan. The 606 is a popular elevated trail that winds through the city's diverse neighbourhoods. For a more scenic route, try the North Shore Channel Trail, which follows a historic canal.
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, there are lots of pet-friendly places in Chicago! You can walk your dog along the Lakefront Trail, or visit the dog-friendly restaurants and cafes in the city. The Lincoln Park Zoo is also pet-friendly, as are many of the parks and green spaces.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy than a hotel room, and are often a more affordable option for families or groups. You can also find rentals in different neighbourhoods, giving you a more local experience.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a great sports city! You can catch a baseball game at Wrigley Field, a basketball game at the United Center, or a football game at Soldier Field. The city also has a number of other sporting facilities, including golf courses, tennis courts, and swimming pools.

Popular destinations

Best Chicago holiday rentals with a balcony

Comfy 4 Bedroom Apartment In The Center Of Chicago! 15 Mins From Downtown! - Chicago
8.9 80 reviews

Comfy 4 Bedroom Apartment In The Center Of Chicago! 15 Mins From Downtown!

apartment, Chicago
This four-bedroom flat is located in a diverse area of Chicago, just under 5 kilometres from the expressway and 10 kilometres from Lake Shore Drive, offering easy access to the city centre. It has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The property has spacious rooms and comfortably sleeps up to eight guests. It is fully equipped with a kitchen, air conditioning, parking, Wi-Fi and other amenities for a comfortable stay.
Spacious Modern 3br  Topfloor + Parking - Chicago
10 9 reviews

Spacious Modern 3br Topfloor + Parking

apartment, Chicago
This Edgewater Glen flat in Chicago offers a rare private deck and shared garden with a fire pit, located just 800 metres from Lake Michigan beaches and a 15-minute Red Line journey to the city centre.
This newly renovated 140 square metre residence accommodates up to five guests and features three bedrooms, a fully equipped kitchen, individual climate control in each room, and private garage parking with EV charging.
Stunning 6 Br Home * Chicago * Centrally Located - Chicago
9.7 191 reviews

Stunning 6 Br Home * Chicago * Centrally Located

apartment, Chicago
This six-bedroom house is located in Albany Park, a family-friendly neighbourhood just 16 kilometres from downtown Chicago, 10 kilometres from Wrigley Field and 10 kilometres from O'Hare Airport. This property has been rated excellent for location, cleanliness and user satisfaction.
The house features large common areas, a chef's kitchen with a five-person island, and spacious bedrooms. This home boasts a fully equipped kitchen, a Jacuzzi, a garden, parking, air conditioning, a laundry room, fast Wi-Fi, Smart TVs, Sonos speakers, Alexa and comfortable bedding.
Spacious 4br West Loop Retreat With Optional Parking - Chicago
No reviews

Spacious 4br West Loop Retreat With Optional Parking

apartment, Chicago
This four-bedroom West Loop flat is situated 1.9 kilometres from Union Station and 2.6 kilometres from the United Center, offering convenient access to public transport and major attractions.
This spacious dwelling, covering 186 square metres, accommodates up to 21 guests with four bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher and microwave, air conditioning, WiFi, and an outdoor seating area, with optional private parking available.

Best Chicago holiday rentals with air conditioning

2br Avondale Apt: Free Parking + Steps To Blueline - Chicago
9.9 22 reviews

2br Avondale Apt: Free Parking + Steps To Blueline

apartment, Chicago
This modern 2-bedroom flat in Chicago offers excellent access to the city, situated just minutes from downtown and Logan Square, with immediate access to the Blue Line and free on-site parking, approximately 100 metres from the nearest Blue Line station.
This newly renovated urban oasis accommodates up to six guests and features a fully equipped kitchen, in-unit washer/dryer, central air conditioning, and partial backyard access, with the Blue Line providing swift journeys to central Chicago and nearby Logan Square boasting numerous dining options.
Wicker Park Apartment W/ 2 Beds! - Chicago
9.6 25 reviews

Wicker Park Apartment W/ 2 Beds!

apartment, Chicago
This one-bedroom flat in Chicago's North Side is situated close to popular dining and entertainment, with the Blue Line L Train approximately 300 metres away for excellent city access.
This private apartment accommodates up to four guests and features a fully equipped kitchen, a dedicated workspace, and two queen beds, though guests should be aware of potential city and L Train noise due to its busy street location.
Explore Chicago! | King Bd Near Train | Near Shops - Chicago
9.5 53 reviews

Explore Chicago! | King Bd Near Train | Near Shops

apartment, Oak Park
This Oak Park flat, a short walk (0.8km) from the Green Line CTA train station and a few blocks from Historic Downtown Oak Park, offers easy access to Chicago and Frank Lloyd Wright's architecture (a 1.6km drive).
The first-floor apartment, sleeping two guests in a king-size bed, features a fully equipped kitchen, 50" smart TV, fast Wi-Fi, radiant floor heating (68-71°F), and is ideal for those with mobility concerns due to its only three steps to access.
Your Home In Roscoe Village - Chicago
9.4 86 reviews

Your Home In Roscoe Village

apartment, Chicago
This Roscoe Village flat, in a central location offering easy access to local amenities and public transport, provides a convenient base for exploring Chicago.
The two-bedroom, one-bathroom apartment sleeps six guests and features a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and excellent guest reviews; nearby recreational activities include various sports facilities (distances unspecified).
©2026 cozycozy.com