Best Holiday rentals and Airbnb offers in Chicago, IL
9.6 16 reviews
The Morgan - West Loop/fulton Market Designer Flat
apartment, Chicago
This one-bedroom flat is located in Chicago's West Loop/Fulton Market district, 100 metres from the Morgan Green/Pink line 'L' train station, offering direct access to the area's restaurants, bars, and shops. This modern apartment sleeps two and features a king-sized bed, a walk-in shower with a rainfall showerhead, free in-building laundry, and complimentary access to The Metropolitan members' club in the Willis Tower.
9.6 77 reviews
Kasa | Large Studio Near Gold Coast | River North
apartment, Chicago
This Chicago studio apartment is ideally situated between Old Town and River North, less than 1.6km from the Museum of Contemporary Art and the Wrigley Building. The pet-friendly self-catering unit, sleeping two guests, boasts a gourmet kitchen, in-unit laundry, high-speed Wi-Fi, and access to a fitness centre, resident lounge, and business centre within a LEED Silver certified building.
9.5 16 reviews
Cozy Studio Near Loyola & Lakefront W Gym
apartment, Chicago
This Rogers Park studio flat is conveniently located near Loyola University Chicago and Lake Michigan, offering easy access to downtown Chicago via the Red Line. The modern studio apartment, sleeping up to two guests, features a kitchenette with fridge, freezer, microwave, and dishwasher, plus parking and air conditioning; nearby attractions include local shops and diverse restaurants.
10 6 reviews
Newly Renovated 3br 2ba In Heart Of Andersonville
apartment, Chicago
This fully renovated three-bedroom flat in Chicago's Andersonville district is a seven-minute walk to the lakefront and beaches, placing you close to the shops and eateries on Clark Street. This modern condo accommodates six guests and features a fully equipped kitchen with a wine cooler, spa-like bathrooms with heated towel racks, and in-unit laundry, with convenient street parking and public transport links nearby.
9.9 47 reviews
Bridgeport Garden Studio
apartment, Chicago
This newly renovated basement studio apartment is situated near Guaranteed Rate Field in a quiet residential area of Chicago, a short walk from the Ramova Theatre and approximately 3.2 kilometres from the city centre. The self-contained apartment, sleeping up to two guests, features a kitchenette, private bathroom, free laundry facilities (shared), and excellent transport links to downtown Chicago.
No reviews
2br Newly Furnished Modern Apt Near O'hare
apartment, Chicago
This Cook County flat offers convenient access to O'Hare International Airport (ORD), approximately 16 kilometres away, and the Donald E. Stephens Convention Centre, also around 16 kilometres distant, with Presence Resurrection Medical Centre a mere 800 metres from your doorstep. This three-bedroom, one-bathroom property accommodates up to five guests, features a fully equipped kitchen with a coffee maker, a comfortable living area with a 55-inch 4K Smart TV, a dedicated workspace, and in-building coin-operated laundry facilities, with free street parking available.
10 5 reviews
Bright 2 Bedroom On Quiet Street
apartment, Chicago
This two-bedroom garden flat is located in a quiet Oak Park neighbourhood, close to Oak Park Hospital and Insight Hospital, offering easy access to Chicago. The 2-bathroom property sleeps four guests and features a fully equipped kitchen with fridge, freezer, and microwave, plus free street parking and ceiling fans in both bedrooms.
9.8 74 reviews
Stylish Northside Retreat
apartment, Chicago
This two-bedroom Chicago apartment is situated on the North Side, offering convenient access to local shops and public transport. The 4-guest flat features a fully equipped kitchen, high-speed Wi-Fi, and free street parking, ensuring a comfortable stay.
9.2 236 reviews
Lux 2 Bdr In Ravenswood Close To Wrigley|downtown
apartment, Chicago
This Chicago apartment, ideal for exploring the city, offers excellent location ratings and is within easy walking distance of numerous shops, cafes, restaurants, and bars; its precise location within Chicago is unspecified. Sleeping up to six guests in two bedrooms and one bathroom, this self-catering flat features a well-equipped kitchenette, laundry facilities, a Roku smart TV, Wi-Fi, air conditioning, and a porch; ample amenities ensure a comfortable stay.
9.9 74 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.
9.4 19 reviews
Gold Coast, Downtown Chicago, Sleeps 20
apartment, Chicago
This five-bedroom, three-bathroom duplex flat is located in Chicago's Gold Coast district, offering prime access to the Downtown/Loop corridor, just 1.2 kilometres from Millennium Park. This pet-friendly accommodation sleeps up to 18 guests, featuring a modern kitchen with granite countertops, a private rear deck, and in-unit laundry facilities.
10 248 reviews
2-story Penthouse -Views, Fireplace, Pool, Gym
apartment, Chicago
This penthouse flat is situated in the heart of downtown Chicago, offering breathtaking views of the city skyline and Lake Michigan. It has consistently received excellent ratings for its cleanliness, location, and overall experience. The spacious two-storey property boasts 179 square metres of living space and comfortably accommodates up to seven guests. Residents can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, spa, fitness centre, and a terrace with panoramic views.
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.
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.
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.
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.
Best Chicago, IL holiday rentals with air conditioning
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.
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.
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.
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.
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?
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?
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.
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.
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.
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.
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.
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.
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.
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.
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.
9.7 87 reviews
The Uptown Studio Retreat
apartment, Chicago
9.7 17 reviews
3 Flat Building Downtown - With Private Patios
apartment, Chicago
9.5 159 reviews
Cozy Blue 2br Apt W Free Parking/9 Min From Mdw
apartment, Chicago
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.
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.
9.7 42 reviews
Complete 1br Fully Furnished Home
apartment, Chicago
10 1 review
Sleeps 15 Game Room Theater Gym
apartment, Chicago
10 9 reviews
Premier 3br Art Deco Retreat With Garage.
apartment, Chicago
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.
No reviews
Blueground | Near North, Pool, Nr Millennium Park
apartment, Chicago
10 4 reviews
West Loop Ph: Unmatched Views & Private Deck
apartment, Chicago
No reviews
Downtown Penthouse 3bd Views Parking Gym #2
apartment, Chicago
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.
9.8 34 reviews
South Loop Suite (Indoor Pool Fitness Center)
apartment, Chicago
9.6 25 reviews
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna In Central Chicago, 8-12 Guests