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

Browse Holiday Rentals near the Historic Centre in Chicago, IL

Reconnect with your partner at secluded holiday rentals for couples in Chicago, IL, offering intimate settings for a city break.

Cabin 101 By 747 Lofts - Chicago, IL
9.6 173 reviews

Cabin 101 By 747 Lofts

apartment, Chicago
This studio apartment is conveniently located near the Blue Line L, offering easy access to downtown Chicago and the bustling West Loop neighbourhood. The property has received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay.
The studio is ideal for a group of up to three guests and features a modern kitchen, a bathroom with a spa bath, and in-unit laundry facilities. Guests can enjoy convenient access to local amenities, including restaurants, bars, and shops, all within walking distance.
Spacious 3br Unit W/ Skyline Views Near Mccormick - Chicago, IL
9.5 95 reviews

Spacious 3br Unit W/ Skyline Views Near Mccormick

apartment, Chicago
This three-bedroom, two-bathroom Chicago apartment is located in the South Loop, a short walk from McCormick Place and within a few kilometres of the Museum Campus and the city centre.
Sleeping up to ten guests, this family-friendly flat boasts a fully equipped kitchen, in-unit laundry, 4K smart TVs, access to a fitness centre, and parking (optional, at £24 per day), offering comfortable accommodation near many attractions.
Lovely Gold Coast Apartment - Chicago, IL
9.4 40 reviews

Lovely Gold Coast Apartment

apartment, Chicago
This Gold Coast apartment offers exceptional access to Chicago's attractions, being within a short walk (less than 1.6 km) of Oak Street Beach and the Magnificent Mile, and close to the Clark/Division Red Line station.
The one-bathroom flat sleeps four guests and includes a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, and access to a fitness centre; numerous dining and entertainment options are nearby.
Plymouth Collection: 3bd 2ba With Gym & Rooftop - Chicago, IL
9.0 6 reviews

Plymouth Collection: 3bd 2ba With Gym & Rooftop

apartment, Chicago
This studio flat is located in Chicago's historic Printers Row, a district south of The Loop, placing it within a few hundred metres of Printers Row cafés, Millennium Park, and downtown attractions.
This newly renovated flat, accommodating up to six guests, offers a full kitchen, in-unit laundry, and access to building amenities including a fitness centre and a rooftop with grills and city views.

Best Chicago, IL holiday rentals with air conditioning

Historic Hales Mansion Near Frank Lloyd Wright - Chicago, IL
10 7 reviews

Historic Hales Mansion Near Frank Lloyd Wright

castle, Oak Park
This Tudor Revival mansion, situated in North Oak Park within walking distance of Oak Park's town centre, offers a unique castle-like experience.
Sleeping up to 16 guests, this four-bedroom, three-bathroom property boasts a performance hall, formal dining room, jacuzzis, four fenced second-floor porches, on-site parking for three vehicles, and event catering equipment (100 chairs, 100 place settings), with additional rooms and beds available on request; all proceeds benefit the Language and Music School's scholarship fund.
Downtown 3bd Penthouse Lake Mich Views Plus Gym #13 - Chicago, IL
9.5 2 reviews

Downtown 3bd Penthouse Lake Mich Views Plus Gym #13

apartment, Chicago
This downtown Chicago penthouse offers direct Lake Michigan views and is located 1.1 kilometres from DePaul University and 1.1 kilometres from the Art Institute of Chicago, a 10-minute walk from Grant Park.
This spacious 3-bedroom flat, accommodating up to 9 guests, features a balcony with lake vistas, a fully equipped kitchen, air conditioning, free WiFi, and access to an on-site fitness centre.
The Luxe Haven | 1br | Near City | Free Parking - Chicago, IL
8.9 53 reviews

The Luxe Haven | 1br | Near City | Free Parking

apartment, Chicago
This Chicago apartment, a short distance from the Loop, offers easy access to attractions such as Chinatown (3.2km), McCormick Place (4.8km), and Millennium Park (4.8km).
The one-bedroom flat sleeps three, features a fully equipped kitchen, in-unit laundry, and 50-inch smart TV, plus a sofa bed and amenities including toiletries and Wi-Fi.
Rustic Sanctuary - Chicago, IL
10 47 reviews

Rustic Sanctuary

apartment, Chicago
This two-bedroom Chicago apartment, near the United Centre, offers easy access to downtown Chicago via public transport.
Sleeping seven guests, the property includes a kitchen with dishwasher, air conditioning, a jacuzzi, garden, parking and excellent guest reviews; nearby attractions include numerous restaurants and shops.

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.

Popular destinations

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.

43rd-floor Luxury Escape + Lake Views - Chicago, IL
No reviews

43rd-floor Luxury Escape + Lake Views

apartment, Chicago
This 2-bedroom flat is situated in Chicago's South Loop, a 5-minute walk from Grant Park and a 7-minute walk from the Art Institute of Chicago, offering convenient access to the Museum Campus and a notable culinary scene.
Guests can enjoy panoramic lake views from the 43rd floor, access to extensive building amenities including multiple swimming pools, a fitness centre, and a hot tub, as well as a fully equipped kitchen and Smart TVs for their stay.
Spacious Oak Park Home, 11 Mi To Downtown Chicago! - Chicago, IL
9.3 68 reviews

Spacious Oak Park Home, 11 Mi To Downtown Chicago!

house, Oak Park
This comfortable house is situated in Oak Park, just 18 kilometres from downtown Chicago and 14 kilometres from the United Center, offering easy access to the city's attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious three-bedroom home, spanning 223 square metres, comfortably accommodates up to six guests. The house boasts a well-equipped kitchen, laundry facilities, a garden, and parking, ensuring a comfortable and enjoyable stay.
1 Garage Parking/skyline Rooftop/pingpong/balcony - Chicago, IL
10 2 reviews

1 Garage Parking/skyline Rooftop/pingpong/balcony

apartment, Chicago
This West Loop apartment is ideally situated 0.5km from Fulton Market and within 1.3-1.6km of Chicago's Millennium Park and Navy Pier.
This 111 square metre Chicago flat boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, in-unit laundry, and a private balcony with stunning city views; heated garage parking is also provided.
Edgewater Gem By The Lake! 2br With Parking & Gym - Chicago, IL
9.6 5 reviews

Edgewater Gem By The Lake! 2br With Parking & Gym

apartment, Chicago
This Edgewater flat is situated a short walk from the CTA Red Line's Granville Station and the Chicago lakefront, offering easy access to Loyola University and downtown.
This 93 square meter flat provides accommodation for up to four guests with two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a balcony, and included garage parking.

Neighborhoods and points of interest 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.

Trendy Roscoe Village 3bd/2b W/fireplace~ Cozy Hm2 - Chicago, IL
9.8 78 reviews

Trendy Roscoe Village 3bd/2b W/fireplace~ Cozy Hm2

apartment, Chicago
This Roscoe Village apartment, in Chicago, Illinois, offers a family-friendly stay with easy access to local businesses and public transport.
The three-bedroom, two-bathroom dwelling sleeps eight guests and includes a fully equipped kitchen, garden, parking, and internet access; nearby attractions include various restaurants, shops, and parks.
Livn West Loop Chicago King Studio - Chicago, IL
10 5 reviews

Livn West Loop Chicago King Studio

studio, Chicago
This newly renovated king studio is located in Chicago's West Loop Gate, a short walk from Union Station and Willis Tower, providing excellent access to the city centre.
This 42 square meter apartment accommodates two guests and features a fully equipped kitchen, in-unit washer and dryer, and secure elevator access, with dining and public transport within easy reach.
"Modern Comfort, Urban Charm" - Chicago, IL
No reviews

"Modern Comfort, Urban Charm"

apartment, Chicago
This two-bedroom, two-bathroom apartment in Chicago's West Ridge neighbourhood is conveniently located approximately 4 kilometres from Lake Michigan and 6 kilometres from Wrigley Field.
The 10-guest property offers self-catering facilities including a fully equipped kitchen, in-unit laundry, and amenities such as Wi-Fi and a smart TV; nearby attractions include the Chicago Theatre, Art Institute of Chicago, and the Field Museum.
Downtown 2bd Gym Near Park Lake Museums #4 - Chicago, IL
10 1 review

Downtown 2bd Gym Near Park Lake Museums #4

apartment, Chicago
This downtown Chicago flat, a 2-bedroom, 1-bathroom property, is situated an 11-minute walk from DePaul University, 720 metres from the Art Institute of Chicago, and a 10-minute walk from Grant Park.
This family-friendly apartment offers 63 square metres of space, accommodates up to 8 guests, and includes a kitchen with a fridge and microwave, air conditioning, and complimentary WiFi, with a fitness centre also available.

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.

The Uptown Studio Retreat - Chicago, IL
9.7 87 reviews

The Uptown Studio Retreat

apartment, Chicago
3 Flat Building Downtown - With Private Patios - Chicago, IL
9.7 17 reviews

3 Flat Building Downtown - With Private Patios

apartment, Chicago
Cozy Blue 2br Apt W Free Parking/9 Min From Mdw - Chicago, IL
9.5 159 reviews

Cozy Blue 2br Apt W Free Parking/9 Min From Mdw

apartment, Chicago
Sun Drenched 2 Bedroom 1 Bath With Kitchen & W/d - Chicago, IL
9.9 260 reviews

Sun Drenched 2 Bedroom 1 Bath With Kitchen & W/d

apartment, Chicago

Handpicked Luxury Holiday Rentals in Chicago, IL

There is much to be said for a well-chosen luxury holiday rental or Airbnb in Chicago, IL. Discover wonderful rooms and locations worth the trip. Start comparing now.

4bdrm Gorgeous Apt Pilsen Private Prking Available - Chicago, IL
9.6 308 reviews

4bdrm Gorgeous Apt Pilsen Private Prking Available

apartment, Chicago

Our Favourite Dog-Friendly Self-Catering Holiday Rentals in Chicago, IL

Your dog is as welcome as you are. These pet-friendly holiday rental and Airbnbs in Chicago, IL provide easy access to local dog parks and city walks. See what's available.

Complete 1br Fully Furnished Home - Chicago, IL
9.7 42 reviews

Complete 1br Fully Furnished Home

apartment, Chicago
Sleeps 15  Game Room  Theater  Gym - Chicago, IL
10 1 review

Sleeps 15 Game Room Theater Gym

apartment, Chicago
Premier 3br Art Deco Retreat With Garage. - Chicago, IL
10 9 reviews

Premier 3br Art Deco Retreat With Garage.

apartment, Chicago
South Loop 2br Corner Unit With Natural Light, Optional Parking And Guest Access Near Downtown Chicago And Mccormick Place - Chicago, IL
9.0 4 reviews

South Loop 2br Corner Unit With Natural Light, Optional Parking And Guest Access Near Downtown Chicago And Mccormick Place

apartment, Chicago

Compare Holiday Rentals with a Pool in Chicago, IL

These holiday rentals and Airbnbs in Chicago, IL include a pool, so a proper swim in the heart of the city is always on the cards.

Blueground | Near North, Pool, Nr Millennium Park - Chicago, IL
No reviews

Blueground | Near North, Pool, Nr Millennium Park

apartment, Chicago
West Loop Ph: Unmatched Views & Private Deck - Chicago, IL
10 4 reviews

West Loop Ph: Unmatched Views & Private Deck

apartment, Chicago
Downtown Penthouse 3bd Views Parking Gym #2 - Chicago, IL
No reviews

Downtown Penthouse 3bd Views Parking Gym #2

apartment, Chicago
Luxury Designer Penthouse 3803 | Pool | Gold Coast - Chicago, IL
10 6 reviews

Luxury Designer Penthouse 3803 | Pool | Gold Coast

apartment, Chicago

Top-Rated Self-Catering Holiday Rentals with a Jacuzzi in Chicago, IL

A hot tub to come back to after a day in Chicago, IL changes the whole feel of a stay. These holiday rentals are ready for you. Choose the one that suits you best.

South Loop Suite (Indoor Pool  Fitness Center) - Chicago, IL
9.8 34 reviews

South Loop Suite (Indoor Pool Fitness Center)

apartment, Chicago
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests - Chicago, IL
9.6 25 reviews

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests

apartment, Chicago
Streeterville Junior 1 Bed With Skyline Views - Chicago, IL
10 1 review

Streeterville Junior 1 Bed With Skyline Views

apartment, Chicago
H&h 1896 - Spacious, Fully Stocked, & Free Parking - Chicago, IL
9.9 113 reviews

H&h 1896 - Spacious, Fully Stocked, & Free Parking

apartment, Chicago
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