Best Vacation rentals and Airbnb offers in Chicago, IL
Chicago, IL
25/06 – 28/06
625 ﺩ.ﺇ/nighttotal: 1875 ﺩ.ﺇ (3 )
Cozy 1br Apt Near Dining & Shops - Kimball C2
1 2
apartment , Chicago
The Kimball C2 apartment is located in Chicago's Kimball neighbourhood, approximately 6.4 kilometres from Loyola University Chicago and 7.7 kilometres from Wrigley Field. This one-bedroom flat, spanning 46 square metres, comfortably sleeps three guests and features a fully equipped kitchen, air conditioning, and free Wi-Fi.
9.7 26 reviews
Chicago, IL
25/06 – 28/06
589 ﺩ.ﺇ/nighttotal: 1767 ﺩ.ﺇ (3 )
Sleep In, Step Out | 1br Cozy Apt Near Food, Shops
1 2
apartment , Chicago
This Chicago apartment, registration number R24000113885, offers a centrally located base for exploring the city, though its precise neighbourhood and proximity to specific landmarks remain unspecified. The one-bedroom flat sleeps two guests and includes a kitchen, air conditioning, and internet access; further details on its size and specific amenities are unavailable.
9.9 74 reviews
Chicago, IL
02/07 – 05/07
1003 ﺩ.ﺇ/nighttotal: 3009 ﺩ.ﺇ (3 )
3br/1ba Apartment In Chinatown
1 5
apartment , Chicago
This three-bedroom flat is located in Chicago's Chinatown, offering direct access to the city centre within minutes by car and a short walk to the CTA train for public transport. This spacious accommodation for up to six guests includes air conditioning and internet, providing a comfortable base for exploring Chicago's attractions and dining options.
9.5 46 reviews
Chicago, IL
06/07 – 28/07
771 ﺩ.ﺇ/nighttotal: 16962 ﺩ.ﺇ (22 )
1.5bd|roomy|comfy|roscoe Village Apt Near Wrigley!
1 3
apartment , Chicago
This Roscoe Village flat is conveniently located 2.1km from Wrigley Field and 14.3km from Chicago's city centre, offering easy access to restaurants, bars, and shops. The recently remodelled one-bedroom apartment sleeps four guests, boasting a queen bed, full-size daybed with trundle, well-equipped kitchen, private balcony, shared garden, and free on-street parking.
9.9 125 reviews
Chicago, IL
10/07 – 31/08
572 ﺩ.ﺇ/nighttotal: 29744 ﺩ.ﺇ (52 )
East Garfield Park New Remodeled Sharp 1 Bedroom
1 1
apartment , Chicago
This recently refurbished one-bedroom apartment is conveniently located in Chicago's West Loop neighbourhood, a short distance from West Randolph Street's acclaimed restaurants such as Au Cheval and Girl & the Goat, and a new Pete's Fresh Market. The 1-bathroom flat, sleeping up to 3 guests, boasts a private backyard, in-unit laundry with supplies, and a well-equipped kitchen including a dishwasher; building owners reside upstairs and are readily available to assist.
Chicago, IL
27/06 – 04/07
1248 ﺩ.ﺇ/nighttotal: 8736 ﺩ.ﺇ (7 )
Mich Ave Downtown Penthouse - Rooftop Plus Gym #8
1 2
house , Chicago
This penthouse apartment offers a prime downtown Chicago location, situated 1.4 kilometres from the Field Museum and 1.4 kilometres from Cloud Gate, with Grant Park a 10-minute walk away. This air-conditioned property features free WiFi, a fully equipped kitchen, one bedroom, one bathroom, and can accommodate up to three guests, with a fitness centre also available.
9.1 163 reviews
Chicago, IL
28/07 – 31/07
1662 ﺩ.ﺇ/nighttotal: 4986 ﺩ.ﺇ (3 )
Lux Apt In Bronzeville, Min From Downtown-rsv Now!
3 2
apartment , Chicago
This Bronzeville apartment rental is situated in Chicago's South Side, a 3.4km drive from Guaranteed Rate Field and within 6km of the Museum of Science and Industry. The three-bedroom, family-friendly flat boasts a fully equipped kitchen, private parking, a Jacuzzi, and a garden, sleeping up to six guests and offering easy access to Chicago's cultural attractions.
9.8 465 reviews
Chicago, IL
25/06 – 28/06
457 ﺩ.ﺇ/nighttotal: 1371 ﺩ.ﺇ (3 )
The Grotto Of Logan Square
1 2
apartment , Chicago
This Logan Square studio flat is conveniently located a 1.6km walk from the Logan Square Blue Line station, offering easy access to Chicago's public transport network. The self-contained apartment sleeps two, features a fridge, microwave, air conditioning, parking, and a Fire Stick-equipped TV, plus benefits from a private entrance and bathroom in a peaceful garden setting.
10 11 reviews
Chicago, IL
28/07 – 05/08
1697 ﺩ.ﺇ/nighttotal: 13576 ﺩ.ﺇ (8 )
The Landmark; A Comfy Suite Near Mccormick Place
1 2
apartment , Chicago
This Bronzeville studio flat, situated in the Calumet/Giles Prairie district, offers convenient access to IIT, McCormick Place, Guaranteed Rate Field (Sox Park), and is within easy reach of the city centre and major highways. The ground-floor self-contained unit features a full eat-in kitchen, a steam shower, a patio, and accommodates two guests, with amenities including Wi-Fi, air conditioning, and a shared garden and sauna; Lake Michigan and 31st Street Beach are within walking distance (approx. 1.6 km).
9.9 39 reviews
Chicago, IL
18/09 – 20/09
944 ﺩ.ﺇ/nighttotal: 1888 ﺩ.ﺇ (2 )
Cozy Chic Chicago- Freshly Renovated
1 2
apartment , Chicago
This newly remodelled two-bedroom flat in Chicago offers excellent access to the city's renowned landmarks, with convenient street and designated parking, and a ground-floor coffee and crepe shop. This second-floor residence accommodates up to four guests, featuring a separate entrance, air conditioning, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
9.9 18 reviews
Chicago, IL
20/07 – 11/08
1083 ﺩ.ﺇ/nighttotal: 23826 ﺩ.ﺇ (22 )
King Bed| Near Downtown & United Ctr+walk To Train
2 1
apartment , Chicago
This two-bedroom Chicago apartment, ideally located near the United Centre, offers easy access to public transport, including the Green Line and Metra, and is within a 13-kilometre drive of the city centre and major hospitals. The 2-bathroom flat sleeps six, boasts a fully equipped kitchen, in-unit laundry, a dedicated workspace, and a games area, complemented by free on-street parking nearby and dog-friendly amenities including a fenced yard.
9.9 100 reviews
Chicago, IL
11/10 – 23/10
734 ﺩ.ﺇ/nighttotal: 8808 ﺩ.ﺇ (12 )
Classic Posh Home Chicago Roscoe Village+ Wrigley
1 2
apartment , Chicago
This upscale Victorian-style flat is situated in a prime Chicago location, one block from excellent restaurants and shops, and within easy walking distance (approximately 0.8 kilometres) of Wrigley Field. The one-bedroom, one-bathroom apartment sleeps two guests and boasts a chef's kitchen, marble steam bath, stained-glass windows, Bose music system, Smart TV, high-speed internet, and a well-stocked pantry; parking is also available.
Best family friendly Chicago, IL vacation rentals
Among the 10119 accommodations in Chicago, IL, here are the 4 best family friendly rentals
10 31 reviews
Chicago, IL
21/07 – 04/08
3297 ﺩ.ﺇ/nighttotal: 46158 ﺩ.ﺇ (14 )
Oak Park Victorian By Flw Studio
4 6
studio , Oak Park
This charming Victorian home is situated in the Frank Lloyd Wright district of Oak Park, just a short walk from his studio and the Hemingway museum, and a 24km drive from downtown Chicago. The apartment has consistently received excellent reviews from previous guests. This spacious four-bedroom property, spanning 204 square metres, comfortably accommodates up to eight guests. The apartment boasts a fully equipped kitchen, free parking, and air conditioning, as well as easy access to public transportation and a wide range of local attractions.
10 24 reviews
Chicago, IL
11/09 – 13/09
957 ﺩ.ﺇ/nighttotal: 1914 ﺩ.ﺇ (2 )
Prime Logan Square Apartment
1 2
apartment , Chicago
This two-bedroom flat is located in Chicago's Logan Square district, offering immediate access to local eateries and shops, and is a mere 300-metre walk to the Blue Line for direct transit to Downtown Chicago and O'Hare International Airport. This accommodation provides a well-equipped kitchen, a private garage, a shared garden, and a flexible space that doubles as a second bedroom and a private gym, comfortably accommodating up to four guests.
Chicago, IL
01/08 – 31/10
460 ﺩ.ﺇ/nighttotal: 41860 ﺩ.ﺇ (91 )
Blueground | The Loop, Elevator, Nr Willis Tower
1 2
apartment , Chicago
This studio flat is located in Chicago's Loop district, offering convenient access to the city's attractions. This modern studio apartment accommodates two guests and includes a fully equipped kitchen, in-apartment laundry, a smart TV, and premium wireless speaker, with flexible lease options available.
9.8 175 reviews
Chicago, IL
23/06 – 24/06
1308 ﺩ.ﺇ/nightfor 1 night
Cozy, Comfortable And Convenient Apartment. Close To Everything!
2 2
apartment , Oak Park
This charming studio apartment is situated in Oak Park's Arts District, just a short walk from the Frank Lloyd Wright Home and Studio, and a mere 400 feet from the CTA Blue Line, making it easy to explore both Oak Park and downtown Chicago. The studio consistently receives excellent ratings for its location, cleanliness, and overall experience. This comfortable apartment offers two bedrooms and one bathroom across 86 square metres. Guests can enjoy a fully equipped kitchen, a private garden, a spa, and parking, as well as keyless access and a patio with a grill for warm weather enjoyment.
Best Chicago, IL vacation rentals with parking
9.8 101 reviews
Chicago, IL
05/07 – 10/07
871 ﺩ.ﺇ/nighttotal: 4355 ﺩ.ﺇ (5 )
Cozy Charming Art Food Close To Train Parking!
2 2
apartment , Chicago
This apartment is located in the Pilsen neighbourhood of Chicago, just 3.2 miles from the city centre, offering easy access to the South Loop, West Loop and other popular areas. It is situated in a trendy area with a thriving art scene and a strong Mexican heritage. This highly rated apartment receives excellent reviews from previous guests. This 2-bedroom apartment can accommodate up to 4 guests and spans 65 square metres. It features a range of modern amenities, including a fully equipped kitchen, a private patio, and a spa, making it perfect for a comfortable and enjoyable stay in Chicago.
9.7 145 reviews
Chicago, IL
05/08 – 11/08
1388 ﺩ.ﺇ/nighttotal: 8328 ﺩ.ﺇ (6 )
Luxury 2br | Mccormick, Lakefront, Parking & Gym
2 4
apartment , Chicago
This apartment is located in Chicago's South Loop district, just a short walk from McCormick Place and a quick Uber ride to downtown attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travellers. The apartment is spacious, with two bedrooms, two bathrooms, and a floor area of 88 square metres, allowing for comfortable accommodation for up to six guests. It offers a range of amenities, including a fully equipped kitchen, a gym, and a terrace, ensuring a comfortable and enjoyable stay for all.
9.9 65 reviews
Chicago, IL
21/09 – 28/09
824 ﺩ.ﺇ/nighttotal: 5768 ﺩ.ﺇ (7 )
Beautiful Condo In North Kenwood With Parking
1 2
apartment , Chicago
This three-bedroom, two-bathroom Chicago apartment is situated in the North Kenwood Bronzeville neighbourhood, close to Lake Michigan, a five-minute drive (approximately 8 km) from the city centre, and a five-to-ten-minute drive (8-16 km) from McCormick Place. The 5-guest property boasts a private balcony, parking, and a fully equipped kitchen including a fridge, microwave, and dishwasher; nearby attractions include Bronzeville's cultural offerings and easy access to public transport.
9.4 74 reviews
Chicago, IL
16/07 – 17/07
2217 ﺩ.ﺇ/nightfor 1 night
Your Next Vacation Home
4 5
apartment , Des Plaines
This four-bedroom home is situated in Des Plaines, just 2 kilometres from the Allstate Arena and 6 kilometres from the Fashion Outlets of Chicago, providing easy access to entertainment and shopping. The property has excellent user ratings, indicating a comfortable and enjoyable stay for guests. The house is ideal for families or groups of up to eight people, with two bathrooms and modern amenities including high-speed Wi-Fi, air conditioning, and parking. Guests can also enjoy a nearby lake for leisurely walks and relaxation, as well as the convenience of being within walking distance of family-friendly attractions such as the Dome at the Parkway Bank Sports Complex and Golf Mill Shopping Center.
Frequently Asked Questions about vacation rentals in Chicago, IL
What should a first-time visitor not miss in Chicago, IL?
You absolutely have to see the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in Chicago and offers incredible views of the city. You can't miss a stroll along the Magnificent Mile, with its luxury shops and restaurants. And no trip to Chicago is complete without a visit to Millennium Park, home to the Cloud Gate sculpture, affectionately known as 'The Bean', and the Crown Fountain.
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 and central location, consider staying in the River North neighbourhood. It's packed with restaurants, bars, and art galleries, and you're within easy walking distance of the Magnificent Mile and Millennium Park. If you prefer a quieter, more residential vibe, Lincoln Park is a great option. It's known for its beautiful park, the Lincoln Park Zoo, and a charming mix of shops and restaurants.
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 option, it's free to enter and has a wide variety of animals. The Shedd Aquarium is another great choice, with its impressive collection of marine life. For a dose of history and fun, the Field Museum is always a hit with kids, especially the Sue the T-Rex exhibit.
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?
If you want to experience the city's lively festivals and warm weather, book your vacation rental during the summer months, from June to August. But keep in mind that prices will be higher during this peak season. For a more budget-friendly option, consider visiting during the shoulder seasons, in spring or autumn, when the weather is still pleasant and the crowds are smaller.
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 a city that loves its festivals! In the summer, you can't miss the Taste of Chicago, a massive food festival with delicious local cuisine. For music lovers, Lollapalooza is a huge music festival held in Grant Park in August. And for a unique cultural experience, head to the Chicago Blues Festival in June.
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?
A walk or bike ride along the Lakefront Trail offers stunning views of Lake Michigan and the city skyline, and it's completely free. The Lincoln Park Zoo is another great free attraction, with a wide variety of animals to see. You can also find free concerts and events in Millennium Park throughout the year.
What are the best restaurants with local dishes in Chicago, IL?
For a taste of Chicago's famous deep-dish pizza, head to Lou Malnati's Pizzeria. If you're craving a classic Chicago hot dog, try Portillo's Hot Dogs. And for a truly unique dining experience, try Al's Beef, known for its delicious Italian beef sandwiches.
What are the best walking or cycling routes in Chicago, IL?
The Lakefront Trail is a must-do for any visitor, offering stunning views of Lake Michigan and the city skyline. It's a great option for both walking and cycling. For a more urban experience, try the 606 Bloomingdale Trail, a former railway line transformed into a raised park with beautiful views of the city.
Are there pet-friendly attractions in Chicago, IL?
Many parks and attractions in Chicago are pet-friendly, including Millennium Park, Lincoln Park, and the Lakefront Trail. You can even take your furry friend for a ride on the Chicago Riverwalk, which has designated pet-friendly areas.
What are the benefits of choosing a vacation rental in Chicago, IL?
Vacation rentals offer more space and privacy than a hotel room, often with amenities like a kitchen and laundry facilities. They can also be a more budget-friendly option, especially for families or groups. And you'll often find them in more convenient locations, closer to the attractions you want to see.
What are the top sports attractions and facilities in Chicago, IL?
Chicago is a city that loves its sports! Catch a game at Wrigley Field, home to the Chicago Cubs baseball team, or visit Guaranteed Rate Field, where the Chicago White Sox play. For basketball fans, the United Center is home to both the Chicago Bulls and the Chicago Blackhawks hockey team.
Destinations nearby
Best Chicago, IL vacation rentals with a balcony
10 7 reviews
Chicago, IL
23/06 – 24/06
2604 ﺩ.ﺇ/nightfor 1 night
Large 3br /2ba Duplex King Parking
3 2
apartment , Chicago
This four-bedroom apartment is located in the Avondale neighbourhood of Chicago, a short 5-minute walk from Milwaukee Avenue and a 5-minute drive to Humboldt Park. It is rated excellent by previous guests. The apartment comfortably accommodates eight guests and features a fully equipped kitchen with modern appliances, a washer and dryer, and a private garden with a hot tub. It also offers a range of amenities including Wi-Fi, a smart TV, and on-site parking.
Chicago, IL
17/07 – 19/07
3700 ﺩ.ﺇ/nighttotal: 7400 ﺩ.ﺇ (2 )
Penthouse With Private Rooftop And Skyline Views - Sleeps 6
2 4
apartment , Chicago
This Chicago flat offers convenient access for travellers, situated approximately 16 kilometres from Midway International Airport. This 60 square metre penthouse apartment features two bedrooms, two bathrooms, a separate living room, and a fully equipped kitchen, with a private rooftop terrace providing outdoor seating and skyline views, accommodating up to 11 guests.
This Chicago apartment, ideally located in the West Loop, is a short distance (less than 2km) from Fulton Market's restaurants, the United Centre, Grant Park, Michigan Avenue and Lake Michigan. The 158 square metre property boasts three bedrooms, three bathrooms, sleeps up to twelve guests, and includes a fully equipped kitchen, private keyless entry, a car garage with EV charger, a roof deck with Willis Tower views, and a fenced backyard.
10 13 reviews
Chicago, IL
11/07 – 13/07
2361 ﺩ.ﺇ/nighttotal: 4722 ﺩ.ﺇ (2 )
Bright & Modern Apt | Steps To Lake, Train, Food
2 2
apartment , Chicago
This two-bedroom apartment in Chicago's Edgewater neighbourhood is situated a short walk from the Red Line, Foster Beach, and Lake Shore Drive, offering easy access to Uptown, Andersonville, and Wrigley Field (approximately 3 Red Line stops away). The 2-bedroom flat sleeps six, includes reserved parking, air conditioning, internet access, and is conveniently located near grocery stores, the Riviera Theatre, and Aragon Ballroom.
Best Chicago, IL vacation rentals with air conditioning
Chicago, IL
18/07 – 19/07
1382 ﺩ.ﺇ/nightfor 1 night
Coach Casa Penthouse - Minutes From Downtown
1 2
apartment , Chicago
The Coach Casa Penthouse is located in Chicago, 4.2 kilometres from the United Center and 6.9 kilometres from the Willis Tower. This 60 square metre flat offers one bedroom, one bathroom, and can accommodate up to seven guests, featuring air conditioning, free private parking, and complimentary high-speed WiFi.
9.6 18 reviews
Chicago, IL
29/06 – 06/07
2666 ﺩ.ﺇ/nighttotal: 18662 ﺩ.ﺇ (7 )
Spacious 5 Br / King Size Beds + Private Parking!
5 12
apartment , Chicago
This five-bedroom, three-bathroom apartment in Chicago's East Garfield Park neighbourhood is situated 0.8 km from the Green Line CTA station, offering easy access to the city centre and attractions such as the Garfield Park Conservatory (1.4 km away). The 149 square metre property sleeps twelve guests and boasts a fully equipped kitchen, including a dishwasher; a garden and spa; and parking, plus excellent guest reviews.
10 3 reviews
Chicago, IL
27/06 – 04/07
712 ﺩ.ﺇ/nighttotal: 4984 ﺩ.ﺇ (7 )
Free Parking •2br Near Sox Park •10 Min Mccormick
1 2
apartment , Chicago
This two-bedroom flat is situated in Bridgeport, approximately 1.6 kilometres from McCormick Place and conveniently positioned for exploring downtown Chicago and Chinatown. This family-friendly apartment offers sleeping arrangements for four guests, featuring a fully equipped kitchen, high-speed WiFi, and free street parking, all within a semi-basement unit with ample natural light.
8.2 4 reviews
Chicago, IL
12/07 – 17/07
686 ﺩ.ﺇ/nighttotal: 3430 ﺩ.ﺇ (5 )
1br Serene And Cozy Chicago Apartment - Manor 2
1 2
apartment , Chicago
This one-bedroom flat in Chicago's Manor 2 district is located 5 kilometres from Wrigley Field and 7.5 kilometres from Loyola University Chicago. This 67-square-metre apartment accommodates up to three guests and features a kitchen with a fridge and microwave, air conditioning, and complimentary WiFi.