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.

Beautifully Renovated House 10 Mins From Downtown - Chicago, IL
9.6 57 reviews
Chicago, IL
30/06 – 05/07
£605/nighttotal: £3025 (5 )

Beautifully Renovated House 10 Mins From Downtown

1 10
apartment , Chicago
This six-bedroom, five-bathroom house in Chicago's Bronzeville neighbourhood offers easy access to public transport and is within walking distance of Lake Michigan.
Sleeping up to fourteen guests, the recently renovated property boasts a fully equipped kitchen, garden, parking, and excellent guest reviews; nearby attractions include parks and architecturally significant buildings.
Spacious 2br Group Stay Near Mccormick Place & Wintrust Arena - Chicago, IL
9.4 6 reviews
Chicago, IL
20/08 – 19/09
£254/nighttotal: £7620 (30 )

Spacious 2br Group Stay Near Mccormick Place & Wintrust Arena

2 2
apartment , Chicago
This 88 square metre, two-bedroom flat is situated in Chicago's South Loop, offering excellent proximity to McCormick Place and Wintrust Arena, a mere 7-minute walk away, and Soldier Field and Museum Campus, accessible within a 5-minute drive.
Accommodating up to eight guests, this spacious suite boasts modern furnishings, high ceilings, a fully equipped kitchen, on-site fitness centre, and in-unit laundry facilities, all secured by 24/7 surveillance.
Experience Chicago Living Near\nunited Center - Chicago, IL
8.8 30 reviews
Chicago, IL
09/09 – 14/09
£162/nighttotal: £810 (5 )

Experience Chicago Living Near\nunited Center

3 3
apartment , Chicago
This two-bedroom flat is situated in the Austin neighbourhood, about 10 miles west of downtown Chicago, offering a more residential atmosphere than the bustling city centre. It has received excellent user ratings, making it a popular choice for travellers.
The flat is suitable for up to five guests, with two bedrooms and a bathroom, plus a sunroom and a living room with three large sofas. The kitchen features modern appliances, including a fridge, microwave, and dishwasher, and there is also air conditioning, internet, and a swimming pool.
Retro 2 Bedroom Bungalow In Chicago (Avondale) - Chicago, IL
9.9 85 reviews
Chicago, IL
17/07 – 26/07
£180/nighttotal: £1620 (9 )

Retro 2 Bedroom Bungalow In Chicago (Avondale)

1 2
apartment , Chicago
This Avondale apartment, situated in Chicago's northwest side near Milwaukee Avenue, offers easy access to diverse culinary options including Mexican restaurants and Polish delis, plus attractions such as The Brewed coffee shop and The Insect Asylum.
This top-floor, two-bedroom flat sleeps four guests, featuring a full kitchen with dishwasher, air conditioning, free on-street parking nearby on Barry Street, and a pet-friendly policy (fee applies).

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.

Lux 5br Near Downtown | Rooftop +Garage + Spa Bath - Chicago, IL
9.9 107 reviews
Chicago, IL
26/08 – 30/08
£817/nighttotal: £3268 (4 )

Lux 5br Near Downtown | Rooftop +Garage + Spa Bath

1 13
apartment , Chicago
This luxurious four-storey house is located in Humboldt Park, Chicago, approximately 8 kilometres from the city centre.
The 370 sqm property boasts five ensuite bedrooms, sleeping up to 16 guests, and features a chef's kitchen, rooftop deck with Chicago skyline views, a games room, and ample outdoor space.
Quiet Oasis Only Minutes From Downtown - Friendly Neighborhood! Apts - Chicago, IL
9.9 286 reviews
Chicago, IL
26/08 – 30/08
£352/nighttotal: £1408 (4 )

Quiet Oasis Only Minutes From Downtown - Friendly Neighborhood! Apts

2 2
apartment , Chicago
This charming two-bedroom flat is located in Ukrainian Village, a friendly neighbourhood on Chicago's near West side, just a short walk from the lively restaurants and bars on Division Street and a 10-15 minute drive from the city centre. The apartment has received excellent ratings for its location, cleanliness and overall experience.
The flat offers ample space for up to four guests with a private garden for relaxing. It comes equipped with a kitchen, a terrace, air conditioning and parking, along with internet access and the option to bring your pet.
Modern 6 Br 3 Baths 11 Beds Sleeps 17 Birthday - Chicago, IL
Chicago, IL
26/08 – 30/08
£767/nighttotal: £3068 (4 )

Modern 6 Br 3 Baths 11 Beds Sleeps 17 Birthday

6 13
apartment , Chicago
This spacious six-bedroom, three-bathroom flat offers a prime central Chicago location, placing you within easy reach of iconic landmarks such as Millennium Park and the Art Institute of Chicago, with public transport readily available for exploring the city.
Accommodating up to sixteen guests, this modern apartment boasts air conditioning and a fully equipped kitchen, providing a comfortable and convenient base for discovering Chicago's dining, entertainment, and cultural attractions.
Spacious Modern 3br  Topfloor + Parking - Chicago, IL
10 7 reviews
Chicago, IL
18/09 – 20/09
£294/nighttotal: £588 (2 )

Spacious Modern 3br Topfloor + Parking

3 2
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.

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.

Two-story Stunner In Iconic Old Town Chicago By Allset Turnover - Chicago, IL
9.5 132 reviews
Chicago, IL
08/10 – 12/10
£1296/nighttotal: £5184 (4 )

Two-story Stunner In Iconic Old Town Chicago By Allset Turnover

2 2
apartment , Chicago
This Old Town Chicago condo is located blocks from the North and Wells intersection, offering easy access to the Second City comedy club and other attractions in the area.
The three-bedroom, three-bathroom property sleeps eight guests and features a fully equipped chef's kitchen, a living room, a dedicated workspace, and a terrace/balcony plus garden; street parking is available or can be pre-booked via apps such as SpotHero or ParkWhiz.
The Banksy-king Bed-firepit-rooftop-united Center - Chicago, IL
10 5 reviews
Chicago, IL
31/07 – 03/08
£1515/nighttotal: £4545 (3 )

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

4 8
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.
Gothic-meets-mid-century 2br In Lakeview | Statment Kitchen + Dining For 4 - Chicago, IL
Chicago, IL
17/09 – 17/12
£238/nighttotal: £21658 (91 )

Gothic-meets-mid-century 2br In Lakeview | Statment Kitchen + Dining For 4

2 1
apartment , Chicago
This Lakeview coach house, offering a private hideaway, is located on a quiet, tree-lined street just 800 metres from the brown line 'L' train for downtown Chicago access and a short drive or transit ride to Wrigley Field.
This 70 square metre flat accommodates up to four guests with two bedrooms and one bathroom, featuring a stylish gothic and mid-century modern interior, a striking emerald kitchen, and is within walking distance of Lakeview's shops, restaurants, and nightlife.
Gilded Age Gold Coast Mansion With Parking, Deck, Fireplaces - Chicago, IL
9.6 10 reviews
Chicago, IL
21/08 – 23/08
£3284/nighttotal: £6568 (2 )

Gilded Age Gold Coast Mansion With Parking, Deck, Fireplaces

6 7
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.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Sunny Studio W/ Skyline View And Parking - Chicago, IL
9.9 38 reviews
Chicago, IL
29/06 – 02/07
£96/nighttotal: £288 (3 )

Sunny Studio W/ Skyline View And Parking

1 2
apartment , Chicago
This stylish attic studio flat is situated in Chicago's Pilsen neighbourhood, a short walk from 18th Street's restaurants, nightlife, and a park with an outdoor swimming pool.
The property offers a queen-size bed and a sofa bed sleeping three, boasting a private porch with downtown Chicago views, on-site parking (subject to availability), and convenient access to public transport; it includes amenities such as air conditioning, Wi-Fi, and a fully equipped kitchen.
Huge 1500sqft 3br | Uchicago, Golf Course & Beach - Chicago, IL
10 5 reviews
Chicago, IL
03/07 – 05/07
£247/nighttotal: £494 (2 )

Huge 1500sqft 3br | Uchicago, Golf Course & Beach

1 5
apartment , Chicago
This spacious flat in Chicago's South Shore district is conveniently located a mere 500 metres from the University of Chicago and the Obama Presidential Center, with downtown Chicago accessible within a 32-kilometre drive.
Offering 140 square metres of living space for up to eight guests, this residence boasts three bedrooms, 1.5 bathrooms, and includes essential amenities such as air conditioning, Wi-Fi, and a fully equipped kitchen, whilst being only 800 metres from Jackson Park Golf Course and 640 metres from 71st Street Beach.
Brand New 2 Bed 2 Bath Apartment In Lincoln Square - Chicago, IL
9.9 129 reviews
Chicago, IL
07/10 – 12/10
£438/nighttotal: £2190 (5 )

Brand New 2 Bed 2 Bath Apartment In Lincoln Square

1 3
apartment , Chicago
This family-friendly apartment in Lincoln Square, Chicago, is situated three houses from the Chicago River and a short walk from the Brown Line CTA station, offering easy access to the city's transport network.
The 150-square-metre (approximately 1600 sq ft) property boasts two bedrooms, two bathrooms, and sleeps six, featuring a fully equipped kitchen, in-unit laundry, a dedicated home office, and amenities for infants upon request; nearby Lincoln Square offers shops, restaurants, and breweries.
3br Spacious Home Away From Home. Coziest Neighborhood In Chicago. - Chicago, IL
9.9 144 reviews
Chicago, IL
13/08 – 16/08
£250/nighttotal: £750 (3 )

3br Spacious Home Away From Home. Coziest Neighborhood In Chicago.

3 2
apartment , Chicago
This three-bedroom flat is situated in a neighbourhood close to the lakefront, offering easy access to the lake and nearby parks. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property spans 111 square metres and comfortably accommodates up to six guests. Amenities include a fully equipped kitchen, a private back porch, and a range of extras such as coffee, toiletries, and plenty of towels and crockery.
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