Best Holiday rentals and Airbnb offers in Chicago, IL
No reviews
Cozy Apartment In Chicago
apartment, Chicago
This two-bedroom flat is located on the west side of Chicago, offering excellent public transport links via nearby bus routes and the CTA train, providing straightforward access to the wider city. The property accommodates up to four guests, features free street parking, a front yard, and a well-equipped kitchen, making it a practical base for exploring Chicago.
9.8 282 reviews
Bright And Cozy 1br Apartment In Logan Square!
apartment, Chicago
This Logan Square flat is conveniently located in Chicago's trendy Logan Square neighbourhood, offering easy access to Chicago's attractions. The 60-square-metre (646 sq ft) self-catering apartment features one bedroom, one bathroom, sleeps two guests, and includes amenities such as free Wi-Fi, parking, and a fully equipped kitchen.
10 1 review
Sleeps 15 Game Room Theater Gym
apartment, Chicago
This spacious seven-bedroom flat in Chicago offers ample room for up to 15 guests, featuring dedicated entertainment zones including an arcade game room and a theatre room, alongside a well-equipped kitchen and a home gym. With keyless entry and free street parking, this pet-friendly residence provides a comfortable base for exploring the city, complete with air conditioning and an on-site washer and dryer for your convenience.
10 1 review
Well Located Studio On The Red Line
studio, Chicago
This Chicago apartment is conveniently located on the Red Line, offering easy access to Loyola University Chicago (3.06 kilometres), Wrigley Field (3.86 kilometres), and Foster Beach (a 9-minute walk). This 32 square metre studio flat accommodates two guests and features a kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and parking.
No reviews
King Bed L Cta L United Center L Near Kasama L Patio
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.
9.8 438 reviews
The Avondale Garden Unit
apartment, Chicago
This garden flat is located in the Irving Park neighbourhood, just 5km from Wrigley Field and 11km from downtown Chicago. It benefits from excellent user, location and cleanliness ratings, making it a great choice for travellers. The property is a 93 square metre, two-bedroom flat with a guest capacity of four. It offers a private entrance, free parking, a well-equipped kitchen, comfortable bedding, a laundry facility, and a garden.
9.9 211 reviews
Amadeus Stay - Hip Central 3bdrm Apt +Free Parking
apartment, Chicago
This family-friendly Chicago apartment, a renovated greystone property, is situated a short 0.8-kilometre walk from a CTA train station, offering easy access to Chicago's attractions. Sleeping five guests comfortably across three bedrooms (two queen beds, one twin, and a travel cot), this Scandinavian-designed flat boasts a well-equipped kitchen, washer/dryer, patio views, and family-friendly amenities including a highchair and children's toys.
9.6 59 reviews
Friendly Abbey Road Retreat
apartment, Berwyn
This Beatles-themed flat in Berwyn's Friendly Music Community offers convenient access to the Frank Lloyd Wright Home and Studio and Ernest Hemingway's birthplace, with easy train links to Chicago's Magnificent Mile. The two-bedroom, one-bathroom apartment sleeps six, boasting a fridge, freezer, microwave, air conditioning, garden, parking, and on-site amenities including a bar and coffee lounge; music lessons at the Friendly Music School are also available.
10 67 reviews
Chicago Condo With Balcony Walk To Cta Stations!
apartment, Chicago
This Chicago condo is conveniently located near CTA stations, approximately 1.8 kilometres from the United Centre and within a 4.8- to 6.4-kilometre radius of major attractions including the Willis Tower, Union Station, DePaul University, the CIBC Theatre, and the Art Institute of Chicago. This two-bedroom, two-bathroom apartment offers 94 square metres of living space, boasting a fully equipped kitchen, in-unit laundry, a private balcony, and access to a garden, spa, and parking; ideal for families or groups of up to four people.
9.9 74 reviews
The Roscoe Village Guesthouse
apartment, Chicago
This Roscoe Village apartment rental is situated near the CTA Brown Line, less than 1.6 km from Wrigley Field, offering easy access to downtown Chicago by train (approx. 30 minutes). The three-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen including a dishwasher, and benefits from free on-street parking; nearby attractions include numerous restaurants, boutiques, and a Starbucks.
9.4 358 reviews
Stunning 2 Floor Apt With Rooftop - View Of Loop!
apartment, Chicago
This Noble Square/West Town duplex apartment is ideally situated within walking distance of many Chicago attractions. This spacious 149-square-metre (1600 sq ft) three-bedroom, two-and-a-half-bathroom property boasts a rooftop deck with city skyline views, a private backyard, and accommodates up to twelve guests, featuring a fully equipped kitchen, in-unit laundry, and on-site management.
10 14 reviews
Alojamiento Para 2 Personas (Sotano)
apartment, Chicago
This private flat, situated in Chicago's Belmont Cragin district, offers convenient access to public transport, shops, restaurants, and Riis Park, just 400 metres away. This self-contained dwelling for two guests includes a private bathroom, basic kitchen facilities, and a parking space, with autonomous check-in and check-out via a smart lock.
Best family friendly Chicago, IL holiday rentals
Among the 13982 accommodations in Chicago, IL, here are the 4 best family friendly rentals
9.4 245 reviews
Skylit Boho Retreat In Wicker Park
apartment, Chicago
This two-bedroom flat in Chicago's Wicker Park Bucktown district places guests within easy reach of the city's main attractions, offering a convenient base for exploration. The accommodation sleeps up to five guests and includes a full kitchen, air conditioning, a shared patio, and is located approximately 5.6 kilometres from Millennium Park, with a 420-friendly environment and a pack and play available on request.
9.2 11 reviews
Comfortable 3br Getaway W/ Bonus Attic Lounge To Relax
apartment, Calumet Park
This three-bedroom Chicago apartment, located in the Calumet Park neighbourhood in the city's south suburbs near the Indiana border, offers easy access to attractions such as the Museum of Science and Industry and is a short distance from downtown Chicago. The property features a spacious layout including a loft area, sleeps six guests, and includes a kitchenette, free Wi-Fi, a smart TV, and on-site parking.
10 2 reviews
2br/2ba Condo W/ Balcony & Garage - Near Hospitals
apartment, Chicago
This 2-bedroom, 2-bathroom condo is located between Chicago's South Loop and Bronzeville districts, offering easy access to the city centre and the lakefront, with McCormick Place just a short walk away and Insight Hospital in the immediate vicinity. This 119-square-metre flat, suitable for up to four guests, features a primary suite with a king-size bed and en-suite bathroom, a second bedroom with a queen-size bed and workspace, a fully equipped kitchen, in-unit laundry, and a private balcony, all within a secure, controlled-access building.
9.9 159 reviews
Luxury Soho Styled Two-level Townhouse - Old Town
apartment, Chicago
This luxurious Old Town duplex townhouse, a five-minute walk from the beach and adjacent to Second City and Lincoln Park, offers a prime Chicago location. The 268 square metre property boasts a spacious open-plan layout, sleeping up to twelve guests, and includes three bedrooms, three bathrooms, a chef's kitchen with Gaggenau appliances, and convenient parking options.
Best Chicago, IL holiday rentals with parking
9.6 285 reviews
Visit United Center & Explore The City Of Chicago
apartment, Chicago
This Chicago apartment, ideally located near the United Centre, is a short 0.8 km walk from the Green Line and offers easy access to the West Loop, The Loop, and other major attractions such as McCormick Place (3.2 km). The two-bedroom, one-bathroom flat sleeps four guests and includes a kitchen with fridge, freezer, microwave, and stove, plus air conditioning, a garden, parking, and a back deck and front porch.
9.9 29 reviews
Tiny Cozy Guesthouse In Quiet Family Neighborhood
cabin, Dunning
This Chicago cabin rental, conveniently located in [Insert Specific Chicago Neighbourhood/Area – e.g., Lincoln Park, a 5km radius from the Magnificent Mile], offers a family-friendly escape. Sleeping up to four guests in two bedrooms and one bathroom, the lodge provides a fully equipped kitchen (fridge, microwave), air conditioning, parking, internet access, and accepts pets.
9.9 595 reviews
Lakeview Loft-vintage Chicago, Modern Amenities
apartment, Chicago
This Lakeview flat is ideally situated in Chicago's Lakeview neighbourhood, less than 0.8km from the Brown and Red Line 'L' trains, under 1.6km from Wrigley Field, and 2.4km from the lakefront. The freshly remodelled one-bedroom loft, sleeping four guests, boasts a king-size bed, 65" TV, private patio, fully equipped kitchen (fridge, microwave), and self check-in; nearby activities include exploring Wrigleyville and enjoying Chicago's lakefront.
No reviews
Downtown Chicago Stay With Free In & Out Parking 6
apartment, Chicago
This 2-bedroom flat in central Chicago offers prime downtown access, situated 500 metres from Millennium Park and 800 metres from the Chicago Riverwalk, with the Art Institute of Chicago also within easy walking distance. This 67 square metre apartment accommodates up to six guests with two queen beds, a sofa bed, and an inflatable mattress, featuring a fully equipped kitchen, air conditioning, parking, and access to a gym, with streaming services provided for entertainment.
Frequently asked questions about holiday rentals in Chicago, IL
What should a first-time visitor not miss in Chicago, IL?
You definitely shouldn't miss the iconic Willis Tower, formerly known as the Sears Tower, for panoramic views of the city. A visit to Millennium Park is a must, with the Cloud Gate sculpture, known as 'The Bean', and Crown Fountain. And no trip to Chicago is complete without experiencing the vibrant nightlife and diverse cuisine in the city's many neighbourhoods.
What are the best Airbnb and vacation 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, bustling experience, consider staying in the trendy Wicker Park or Bucktown neighbourhoods. If you prefer a more relaxed atmosphere, Lincoln Park or Lakeview offer a mix of residential streets and green spaces. And if you're looking for a historic setting, the Gold Coast or River North are great options.
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 a fantastic free attraction with a variety of animals and exhibits. The Shedd Aquarium is a great place to learn about marine life, and the Field Museum offers fascinating exhibits on dinosaurs and other natural history subjects. For a fun day out, consider visiting the Museum of Science and Industry or the Art Institute of Chicago.
What are the best vacation 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?
The best time to book a vacation rental is during the shoulder seasons, in spring (April-May) or autumn (September-October), when the weather is pleasant, and the crowds are smaller. However, if you prefer a festive atmosphere, you can book during the summer, when the city hosts various festivals and events.
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. The Taste of Chicago in July is a great food festival, and the Chicago Blues Festival in June is a must for music lovers. The Lollapalooza music festival in August attracts thousands of music fans, and the Chicago Air and Water Show in August is a spectacular event.
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 budget-friendly activities in Chicago, IL?
Take a stroll along the scenic Lakefront Trail, offering stunning views of Lake Michigan. Explore the free exhibits at the Art Institute of Chicago or the Field Museum. Enjoy a picnic lunch in Millennium Park, surrounded by beautiful architecture and public art. And don't forget to check out the free concerts and events happening in various parks and public spaces throughout the city.
What are the best restaurants with local dishes in Chicago, IL?
For a taste of Chicago's iconic deep-dish pizza, head to Lou Malnati's or Pizzeria Bebu. For a classic Chicago hot dog, try Portillo's or The Wiener's Circle. And if you're looking for a more upscale dining experience, Alinea or Next offer innovative and inventive cuisine.
What are the best walking or cycling routes in Chicago, IL?
The Lakefront Trail offers a scenic 18.5-mile path along the shores of Lake Michigan, perfect for walking, running, or cycling. For a more urban experience, explore the Magnificent Mile, a stretch of Michigan Avenue lined with luxury shops and skyscrapers. And for a unique perspective on the city, consider a bike tour through the various neighbourhoods.
Are there pet-friendly attractions in Chicago, IL?
Yes, many attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes well-behaved dogs on leash, and the Millennium Park offers designated dog-friendly areas. Many restaurants also have outdoor patios where you can enjoy a meal with your furry friend.
What are the benefits of choosing a vacation rental in Chicago, IL?
Vacation rentals provide more space and privacy than a hotel room, often with a kitchen and laundry facilities. They can also be more affordable, especially for families or groups. And many offer unique locations and charming character, allowing you to experience the city like a local.
Popular destinations
Best Chicago, IL holiday rentals with a balcony
9.8 8 reviews
Bridgeport Place -Free Parking, Mccormick-sox Park
apartment, Chicago
This Chicago flat is located in Bridgeport, a short distance from downtown Chicago, Chinatown, Guaranteed Rate Field (Sox Park), and McCormick Place. The one-bedroom apartment, sleeping up to four guests with a sofa bed, boasts a private patio with a Weber gas barbecue, self check-in, and is near a river walk with kayaking opportunities.
10 1 review
Charming Newly Updated 3-bed Chicago Apartment. Extended Stay Discount
apartment, Chicago
This three-bedroom apartment in Greater Grand Crossing, Chicago, is situated approximately 16 kilometres from the city centre, offering convenient access to public transport links such as the Metra and CTA, and proximity to several hospitals and universities. The 79-square-metre property, sleeping up to six guests, features a fully equipped kitchen, a terrace, garden, and in-unit laundry facilities; a personal chef service is available upon request.
10 3 reviews
Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12
apartment, Chicago
This West Town apartment, situated in Chicago, is conveniently located within a 5-8km radius of attractions such as Fulton Market, the United Centre, Grant Park, Michigan Avenue, and Lake Michigan. Sleeping up to 12 guests, this three-bedroom, three-bathroom dwelling boasts a king suite with fireplace and steam shower, a queen suite with private roof deck access, a fully equipped kitchen with balcony, a private garage, and a stunning roof deck with Willis Tower views.
No reviews
Feelin Nauti Near Wrigley
apartment, Chicago
This one-bedroom flat is situated in Chicago's Lakeview district, within a 10-minute walk of Wrigley Field, Southport Corridor shops, and Boystown nightlife, with the Addison Brown Line 'L' train station just 550 metres away. Guests can enjoy exclusive use of the entire first floor of a duplex, accommodating two people with one bathroom, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and a complimentary parking space, plus a free membership to The Metropolitan for stays under 14 days.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL holiday rentals with air conditioning
9.8 15 reviews
Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar
apartment, Chicago
This six-bedroom home is situated in Jefferson Park, a quiet neighbourhood in Chicago, just 10 kilometres from Navy Pier and Michigan Avenue, and within easy reach of the airport and downtown. The property has received excellent reviews from previous guests. The apartment offers 297 square metres of space, comfortably accommodating up to 16 guests. It features a fully equipped kitchen, a games room, a spa, a garden, a terrace, parking, and a Super Mario-themed bunk room for kids.
9.6 62 reviews
Chic 3br/2ba Oasis In The Heart Of Wicker Park
apartment, Chicago
This Wicker Park apartment in Chicago offers excellent access to public transport, being a short walk from the CTA train and the 606 trail. The three-bedroom property, sleeping up to eight guests, boasts a full kitchen, in-building laundry, on-site parking (suitable for smaller cars), a private garden with fire pit and grill, and a projector; numerous bars and restaurants are within 0.16 km.
9.9 273 reviews
Cool And Modern Chicago Apartment Near Transit
apartment, Chicago
This apartment is located in a walk-up building in Chicago, just a short distance from the Magnificent Mile and Millennium Park, with easy access to public transport. The property has received excellent ratings from previous guests for its cleanliness, location, and overall experience. The apartment is well-equipped for a comfortable stay, with three bedrooms and a spacious living area, accommodating up to five guests. The kitchen includes modern appliances, a dining area, and a laundry room, while the living area features a 50-inch TV with Roku, Wi-Fi, and a reserved parking spot.
9.6 59 reviews
Luxury Designer Penthouse | Gold Coast/old Town
apartment, Chicago
This luxurious Chicago penthouse apartment is situated in the Gold Coast and Old Town neighbourhoods, a short walk from Michigan Avenue and Lake Michigan. The two-bedroom, two-bathroom dwelling boasts a chef's kitchen, a 65-inch smart TV, free parking, and access to a rooftop sundeck, fitness centre, and lounge; sleeping up to eight guests and offering stunning city views.