Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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Best Holiday rentals and Airbnb offers in Chicago, IL

Explore Holiday Rentals for Families in Chicago, IL

Family holidays in Chicago, IL work best when your holiday rental is properly set up with space and city attractions within easy reach.

South Loop 3br Group Comfort Near Downtown, Grant Park, Soldier Field And Mccormick Place - Chicago, IL
9.0 4 reviews
Chicago, IL
01/07 – 05/07
£336/nighttotal: £1344 (4 )

South Loop 3br Group Comfort Near Downtown, Grant Park, Soldier Field And Mccormick Place

3 5
apartment , Chicago
This apartment is situated in McCormick Place, just 2.4 kilometres from the Field Museum of Natural History and 2.9 kilometres from the Art Institute of Chicago, making it ideal for exploring the city's cultural attractions. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment is spacious, offering 111 square metres of living space with three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and luggage storage, ensuring a convenient and comfortable stay.
Sunny Basement - 3 Beds 2 Baths - Chicago, IL
9.5 12 reviews
Chicago, IL
14/07 – 18/07
£218/nighttotal: £872 (4 )

Sunny Basement - 3 Beds 2 Baths

1 5
apartment , Chicago
This three-bedroom, two-bathroom flat in Chicago offers convenient street parking and is situated in a neighbourhood with straightforward access to local attractions.
This basement flat accommodates up to six guests and features a fully equipped kitchen, central air conditioning, and complimentary Wi-Fi, making it suitable for families.
Welcoming 3-bedroom House In Vibrant Chicago - Chicago, IL
Chicago, IL
09/10 – 12/10
£621/nighttotal: £1863 (3 )

Welcoming 3-bedroom House In Vibrant Chicago

3 2
apartment , Chicago
This Ukrainian Village flat, situated in Chicago's West Town district, is a short 800-metre walk to the United Centre and offers convenient access to downtown attractions, Millennium Park, and Lake Michigan.
This three-bedroom, two-bathroom apartment accommodates up to eight guests, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and a patio, with free street parking available.
Enjoy Your Stay, Safe Easy Place. - Chicago, IL
9.8 80 reviews
Chicago, IL
25/06 – 28/06
£187/nighttotal: £561 (3 )

Enjoy Your Stay, Safe Easy Place.

1 4
apartment , Berkeley
This Berkeley apartment, ideal for families, is conveniently located near O'Hare International Airport (approximately 11km) and Chicago's city centre (40km), providing easy access to major transport links.
Sleeping up to six guests in three queen-size beds, this two-bedroom, one-bathroom flat offers free Wi-Fi, parking for two cars, a fully equipped kitchen, and two TVs with Netflix; Level 1 car charging is available on request.

Popular Holiday Rentals with Parking in Chicago, IL

A car park at your holiday rental in Chicago, IL means exploring the city centre is easy every day with no extra faff. Find your perfect stay.

Rogers Park Cozy 1 Bd, 1 Bath Unit. Gated Parking. - Chicago, IL
9.1 35 reviews
Chicago, IL
04/12 – 10/12
£181/nighttotal: £1086 (6 )

Rogers Park Cozy 1 Bd, 1 Bath Unit. Gated Parking.

1 2
apartment , Chicago
This one-bedroom apartment is located in Rogers Park, a lively neighbourhood just a short drive from the Howard station, which connects to the Red, Yellow, and Purple Lines, making it easy to explore the city. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
The apartment offers a spacious layout, ideal for two guests, with a private bedroom, full kitchen, dedicated workspace, and a separate living room. Enjoy free parking on the premises, high-speed internet, air conditioning, and a kitchen equipped with a fridge and microwave oven, allowing you to prepare meals and relax in comfort.
5 Mi To Dtwn: Ukrainian Village Apartment! - Chicago, IL
9.4 12 reviews
Chicago, IL
20/08 – 24/08
£222/nighttotal: £888 (4 )

5 Mi To Dtwn: Ukrainian Village Apartment!

2 2
apartment , Chicago
This West Town apartment in Chicago offers a convenient location near restaurants and museums, less than 1.6km from laundromats and a short drive from Humboldt Park, Lincoln Park Zoo, Wrigley Field, and Chicago's city centre.
The 93 square metre two-bedroom, one-bathroom flat sleeps six guests and features a well-equipped kitchen with stainless steel appliances, a smart TV, board games, free Wi-Fi, and central air conditioning and heating.
Modern 3br Apartment Near North Ave Shops - Chicago, IL
Chicago, IL
30/06 – 01/10
£378/nighttotal: £35154 (93 )

Modern 3br Apartment Near North Ave Shops

3 1
apartment , Chicago
This spacious three-bedroom flat is situated in Chicago's Old Town/Lincoln Park/Clybourn Corridor area, placing you a short walk from the Second City Theatre and a few kilometres from Lincoln Park Zoo and the lakefront via the North Branch Trail.
This 90-square-metre residence accommodates up to eight guests with three bedrooms, two bathrooms, a fully equipped kitchen featuring stainless steel appliances, and in-unit laundry facilities, all offering city views and individually controlled air conditioning.
5 Mins To The United Center! Cozy 2 Bedroom Apartment - Chicago, IL
9.4 18 reviews
Chicago, IL
11/07 – 13/07
£346/nighttotal: £692 (2 )

5 Mins To The United Center! Cozy 2 Bedroom Apartment

2 2
apartment , Chicago
This Chicago apartment rental is situated in the city's Medical District, offering easy access to the United Center (approx. 0.8 km), downtown Chicago (approx. 1.9 km), Grant Park (approx. 1.4 km), and Soldier Field (approx. 1.6 km).
The two-bedroom, one-bathroom flat sleeps three guests and includes amenities such as a fridge, dishwasher, internet access, air conditioning, parking, and is pet-friendly.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You've got to see the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in Chicago and offers amazing views of the city. A trip to Millennium Park is a must, especially to see Cloud Gate, nicknamed 'The Bean'. It's a popular spot for photos and a great place to people-watch.
  • What are the best Airbnb and holiday rentals in Chicago, IL?

  • What kind of vacation rentals can you find in Chicago?

    There's a wide range of vacation rental choices in Chicago to choose from, from houses to downtown apartments and penthouses.
  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant and central location, consider staying in the River North neighbourhood. It's close to the Magnificent Mile, the Chicago Riverwalk, and many restaurants and bars. If you're looking for a more relaxed atmosphere, Lincoln Park is a good option. It's known for its beautiful park, zoo, and quieter streets.
  • What are the most popular Airbnbs in Chicago, IL?

  • What's the best one-day itinerary for Chicago?

    Kick things off Ferris Bueller style at the Art Institute of Chicago for some culture before heading over to "The Bean" at Millennium Park, making sure you leave the park via the BP Bridge, which will give you stunning views of the city's skyline. On the corner of Michigan Avenue and Randolph street, make sure you check out the Chicago Cultural Center for the stunning interior alone (the largest Tiffany stained-glass dome in the world is so worth it!). Cross through Grant Park and visit the Buckingham Fountain before heading south to the amazing Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Head up the Skydeck at Willis Tower (one of the world's tallest buildings) and if you dare, step on the ledge. Head over to the Chicago Riverwalk to find something to eat before hitting one of the famous jazz and blues clubs.
  • What are the top family-friendly attractions in Chicago, IL?

    The Lincoln Park Zoo is free to enter and a great place to spend a day with the kids. You can see all sorts of animals, including lions, tigers, and bears! The Shedd Aquarium is also a popular choice, with a wide variety of marine life. If you're looking for something more interactive, the Museum of Science and Industry is a great option.
  • What are the best holiday rentals with a pool in Chicago, IL?

  • Where should you book a vacation rental in Chicago?

    It really depends on what you want. If you're want to be in the heart of the action, or it's your first visit to the Windy City, then book an apartment or a studio in the Chicago Loop downtown. However, some of the most popular places to book are Lincoln Park and Hyde Park when it comes to vacation rentals.
  • When is the best time to book a vacation rental in Chicago, IL?

    Booking in advance is always a good idea, especially if you're travelling during peak season, which is typically June to August. Prices tend to be higher during these months, so booking early can help you get a better deal. If you're flexible with your dates, you may be able to find better deals during the shoulder seasons, which are April-May and September-October.
  • What are the best rentals for families and kids in Chicago, IL?

  • What are Chicago's special dishes you should try?

    You can't come to Chicago without trying some deep-dish pizza, a Chicago icon. However, there's plenty else to chow down on. Chicago had a large Italian community, so you can try some great Italian-American dishes. If you want something quick to go, grab a spicy Italian beef sandwich from a local street food joint.
  • What events or festivals should visitors check out in and around Chicago, IL?

    Chicago is known for its vibrant festival scene. In the summer, there's the Taste of Chicago, a huge food festival with samples from local restaurants. The Chicago Blues Festival in June is a must for music lovers. There are also many smaller festivals throughout the year, so check the local listings for what's happening during your visit.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago, IL?

  • What is sites are there to see in Chicago?

    There's plenty to keep you on your feet on your next trip to Chicago. If you're an art lover, make sure you pay a visit to the Art Institute of Chicago, which is home to more than 300,000 artworks! But if you want a view that's more than paintings, then get yourself to the top of 360 Chicago for panoramas over the city from this 1000-ft-high observation deck. Millennium Park with its futuristic-looking Cloud Gate (AKA the Bean), is great place to explore. And that's just to get you started!
  • What are the best restaurants with local dishes in Chicago, IL?

    Chicago is famous for its deep-dish pizza, so you have to try it at least once! Lou Malnati's is a popular choice, or you can go for a more traditional thin-crust pizza at Pizzeria Bebu. If you're looking for something different, try a Chicago-style hot dog, which is served on a poppy seed bun with all the toppings.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a great option for both walking and cycling, stretching for 18.5 km along the shores of Lake Michigan. You can also explore the Chicago Riverwalk, a scenic path along the Chicago River with bridges, gardens, and sculptures.
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, many attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes leashed dogs in designated areas. You can also take your furry friend for a walk or cycle along the Lakefront Trail. Many restaurants and cafes also have outdoor seating areas that are pet-friendly.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is home to several professional sports teams, including the Chicago Cubs (baseball), Chicago White Sox (baseball), Chicago Bulls (basketball), and Chicago Blackhawks (ice hockey). You can catch a game at Wrigley Field, Guaranteed Rate Field, United Center, or the United Center. The city also has many parks and recreational facilities for those who want to participate in sports.

Destinations nearby

Top Holiday Rentals with a Balcony in Chicago, IL

A terrace with city skyline views is a fantastic reason to book a holiday rental in Chicago, IL. View our top picks and start comparing now.

4br Bright City Retreat-sleeps 12-garage Parking - Chicago, IL
10 1 review
Chicago, IL
21/08 – 23/08
£934/nighttotal: £1868 (2 )

4br Bright City Retreat-sleeps 12-garage Parking

5 7
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.
Elegant And Chic 2bed 2bath Steps From The Lake! - Chicago, IL
9.1 12 reviews
Chicago, IL
26/07 – 27/07
£475/nightfor 1 night

Elegant And Chic 2bed 2bath Steps From The Lake!

2 2
apartment , Chicago
This stylish Chicago apartment is situated near Lake Michigan, a short 1.9km walk from Loyola University Chicago, offering convenient access to lakefront activities and the city's attractions.
The 167 square metre property boasts one bedroom, two bathrooms, and sleeps seven, featuring a fully equipped kitchen, in-unit laundry, free private parking, a balcony, and a fireplace; nearby Wrigley Field is also within easy reach.
Lakehouse With Rooftop And Views Of Lake. - Chicago, IL
9.4 84 reviews
Chicago, IL
15/07 – 17/07
£683/nighttotal: £1366 (2 )

Lakehouse With Rooftop And Views Of Lake.

3 10
apartment , Chicago
This Chicago bed and breakfast is situated in a residential area close to a tennis court, golf course, beach, playground, and cultural centre, and is within a short drive of the city centre, the University of Chicago, and the Museum of Science and Industry. The 204 square metre guesthouse offers a private terrace with views of the city, a rooftop garden, a full kitchen, a lounge, and a Jacuzzi, making it ideal for both short and long stays.
Chicago 3br Oasis Near Downtown & United Center - Chicago, IL
Chicago, IL
09/07 – 12/07
£391/nighttotal: £1173 (3 )

Chicago 3br Oasis Near Downtown & United Center

3 4
apartment , Chicago
This Chicago three-bedroom flat is located 2.25 kilometres from the United Center and offers convenient access to downtown attractions such as Union Station and the Willis Tower, both 5.15 kilometres away.
This family-friendly residence spans 1000 square metres, features three bedrooms, two bathrooms, and accommodates up to 14 guests with amenities including air conditioning, a fully equipped kitchen with a dishwasher, and free WiFi, plus a balcony and private parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Two Bedroom W Porch In Wicker Park - Chicago, IL
9.9 106 reviews
Chicago, IL
01/08 – 31/08
£191/nighttotal: £5730 (30 )

Two Bedroom W Porch In Wicker Park

1 2
apartment , Chicago
This Wicker Park/West Town flat is situated two blocks (approximately 0.16 km) from the Division Street Blue Line station, offering easy access to O'Hare International Airport and Chicago's city centre.
The two-bedroom, one-bathroom apartment sleeps five, features a furnished porch, a 43" smart TV, and is within easy walking distance of Milwaukee Avenue's bars and restaurants.
New! Large/beautiful Home With 6bds/4bth + Garage! - Chicago, IL
9.9 46 reviews
Chicago, IL
08/07 – 13/07
£862/nighttotal: £4310 (5 )

New! Large/beautiful Home With 6bds/4bth + Garage!

1 10
apartment , Chicago
This six-bedroom Chicago house, situated in a residential area 32-48 km from both Midway and O'Hare International Airports, offers convenient access to the city.
Sleeping up to 12 guests, this spacious property boasts four bathrooms, a fully equipped kitchen with dishwasher, a garden, parking, and amenities including a furnished deck with grill and ping pong table.
King Bed L Cta L United Center L Near Kasama L Patio - Chicago, IL
Chicago, IL
16/09 – 23/09
£342/nighttotal: £2394 (7 )

King Bed L Cta L United Center L Near Kasama L Patio

2 2
house , Chicago
This Chicago residence is situated 2.6 kilometres from the United Center and within 4.5 kilometres of the Chicago Water Tower and Union Station, offering convenient access to downtown attractions.
This property provides accommodation for up to 9 guests across 2 bedrooms, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, complimentary Wi-Fi, air conditioning, a private patio, and parking, with a floor area of 15 square meters.
Stay By Downtown, Mccormick, University Of Chicago - Chicago, IL
10 7 reviews
Chicago, IL
01/08 – 08/08
£693/nighttotal: £4851 (7 )

Stay By Downtown, Mccormick, University Of Chicago

1 10
apartment , Chicago
This Bronzeville house, situated 4 km from McCormick Place and Soldier Field, offers easy access to Chicago's city centre, lakefront, and Navy Pier.
The four-bedroom, three-and-a-half-bathroom property sleeps ten guests and includes a furnished basement, den with fireplace, and ample living space; nearby attractions include the Museum of Science and Industry and the Art Institute of Chicago.
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