This Chicago apartment rental is situated in the Wicker Park neighbourhood, on Milwaukee Avenue, offering easy access to the area's shops, restaurants, and nightlife. The two-bedroom, one-bathroom flat sleeps five guests, features a fully equipped kitchen with appliances including a dishwasher and in-unit laundry, and boasts king and queen bedrooms with en-suite TVs.
This Chicago apartment rental is conveniently located on the border of Logan Square and Avondale neighbourhoods, offering easy access to both areas' diverse restaurants and shops. The one-bedroom flat sleeps two, features a private patio, kitchen with fridge and microwave, and includes air conditioning, parking, and internet access; nearby attractions include Logan Square's farmers' markets.
This Chicago apartment rental is located in Little Village, a 10-minute drive (approx. 4.8km) from the city centre, 4.8km from Little Italy and Chinatown, and a 15-minute drive (approx. 11.2km) from Millennium Park and Soldier Field. The one-bedroom flat sleeps five guests comfortably, offering a full kitchen, washer/dryer, in-unit entertainment (two smart TVs, Pac-Man arcade game, board games), a mini-patio with grill, and enhanced security features including keyless entry.
This Pilsen flat, in Chicago's Mexican heritage neighbourhood, offers convenient access to local taquerias and cultural attractions. The self-catering apartment features a newly remodelled bathroom, a pull-out sofa accommodating four guests, high-speed Wi-Fi, and a private garden.
Amazing Modern Condo, *3 Bed & *2bath In Chicago!!
apartment - Chicago
This Ravenswood Manor flat offers convenient access to Lincoln Park, Lakeview, and the Chicago city centre, with Wrigleyville a short 1.6km drive away. Sleeping up to six guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen including a dishwasher, free street parking, and a private garden; nearby attractions include numerous restaurants and shops.
This Lincoln Park flat is conveniently located within walking distance of Lincoln Park Zoo and numerous restaurants and shops. The 74 square metre (800 square feet) self-catering property sleeps four, featuring a king-size bed, a convertible daybed, a queen air mattress, a fully equipped kitchen, and a terrace.
This Chicago apartment, located in a residential area near the Healy Metra station (providing a 15-minute train journey to Union Station) and approximately 1.6km from the Logan Square Blue Line 'L' station, offers easy access to downtown Chicago and other areas. The first-floor flat comprises two bedrooms, one bathroom, and accommodates four guests, featuring a fully equipped kitchen with modern appliances, a garden, parking, and excellent user ratings; nearby amenities include numerous bars and restaurants.
This Chicago flat offers a 15-minute drive to the city centre, with local amenities including restaurants, shops, public transport, the 4DX cinema, the Salt Shed, and attractions such as the 'Messi Experience Chicago', Whirley Ball, and a bowling alley within walking distance, and is 14 kilometres from Cubs Stadium. This two-bedroom flat accommodates up to five guests, featuring a full kitchen with a fridge, freezer, and microwave, air conditioning, on-site parking, a fitness centre, and allows pets, providing a comfortable base for exploring Chicago's entertainment and attractions.
This Chicago apartment, near Loyola University Chicago, is a 15-minute walk from the university and within 7km of Wrigley Field, Lincoln Park Zoo, and the city centre. The 84-square-metre one-bedroom flat offers free Wi-Fi, private parking, a fully equipped kitchen, and sleeps up to seven guests.
This two-bedroom flat for rent offers convenient access to O'Hare International Airport and downtown Chicago, situated a short stroll from the Blue Line train station. This pet-friendly accommodation can host up to seven guests and features a fully equipped kitchen with a microwave, a private balcony with a barbecue, an in-unit laundry, and fitness equipment.
This Chicago flat is located near the city centre, offering convenient access to key attractions such as the United Centre (4.5 km), Union Station (6.9 km), and Grant Park (8 km). This spacious two-bedroom, two-bathroom flat, covering 130 square metres and accommodating up to 11 guests, features a fully equipped kitchen, free WiFi, and air conditioning, with private host management ensuring a personal touch while strictly prohibiting stag and hen parties.
King Bed| Near Downtown & United Ctr+walk To Train
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.
Best family friendly Chicago, IL vacation rentals
Among the 13982 accommodations in Chicago, IL, here are the 4 best family friendly rentals
This West Town apartment, a 130 square metre (1400 square foot) property, is situated in Chicago's West Town district, conveniently located within a 24-32 km radius of the city centre, O'Hare International Airport, Navy Pier, Millennium Park, the Field Museum, and the Art Institute of Chicago. The spacious dwelling boasts three bedrooms, two bathrooms, and sleeps up to 14 guests comfortably, offering a fully equipped kitchen, a games room with a pool table and arcade machine, two free on-site parking spaces, and in-unit laundry facilities.
This two-bedroom flat boasts a prime Downtown Chicago location, just 1.29 kilometres from the Field Museum and a 10-minute walk to Grant Park, placing you within easy reach of the CIBC Theatre, DePaul University, the Art Institute of Chicago, and the Chicago Symphony Orchestra. This 63 square metre apartment accommodates up to seven guests with a fully equipped kitchen including an oven, air conditioning, free WiFi, and an on-site fitness centre, ensuring a comfortable and convenient stay.
This Chicago flat offers convenient access to McCormick Place, just a 5-minute drive away, and the city centre, The Loop, within 10-15 minutes, with excellent links to public transport and Lake Shore Drive. This family-friendly apartment accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, complimentary Wi-Fi, a fitness centre, and secure parking, with a 24/7 virtual concierge service and pet-friendly options available.
Relax And Enjoy Chicago In An Updated And Private Apartment In Roscoe Village
apartment - Chicago
This Roscoe Village flat is located 1.6km west of Wrigley Field and 3.2km west of Lake Michigan, offering easy access to Chicago's iconic attractions. The one-bedroom apartment sleeps four, features a fully equipped kitchen with high-end appliances, a private garden, heated floors, and complimentary Wi-Fi; guests can also enjoy barbecue facilities in the landscaped backyard.
Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
house - Chicago
This one-bedroom flat is situated in the Armitage/Sheffield neighbourhood, a short walk from the Brown and Red Line stations, making it easy to explore Chicago's main attractions, including Millennium Park, just 2km away. The property has received excellent ratings for its location, cleanliness and overall experience. The flat offers a spacious living room, a comfortable king-size bed and a large dining table, perfect for enjoying a meal with your travel companion. The kitchen is fully equipped with a fridge, freezer, microwave oven and dishwasher, and the flat also benefits from air conditioning, a garden and free parking.
This Lincoln Park holiday home in Chicago is ideally situated 1.9km from North Avenue Beach and 1.2km from Wrigley Field. The 93 square metre property offers three queen-size beds sleeping six, a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, and a private patio; guests can easily access Lincoln Park Zoo (2.6km).
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.
This apartment is situated in the Rogers Park neighbourhood on Chicago's north side, just 3.5 kilometres from Lake Michigan and within walking distance of the Morse and Loyola Red Line train stations, offering easy access to the city's main attractions. The apartment has received excellent ratings for location, cleanliness, and overall experience. The apartment provides a full kitchen, one full bathroom, and a half bathroom, providing ample space for guests. The apartment also offers free street parking, Wi-Fi, a Smart TV, self-serve laundry, and a welcome basket, along with access to a shared deck, patio, and side yard.
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.
The Avondale Guesthouse is situated in the Avondale neighbourhood of Chicago, just a short distance from Wrigley Field and Lincoln Park Zoo, making it a great base for exploring the city. The guesthouse consistently receives excellent ratings for its cleanliness, location, and overall user experience. The property has three bedrooms, accommodating up to six guests, and is ideal for families or groups of friends. You can enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, and a private patio, as well as explore the neighbourhood by bike or relax in the garden.
Spacious South Loop 2br Apartment Near Mccormick Place, Soldier Field & Downtown Chicago
apartment - Chicago
Apartment listing. You will be in Chicago. Facilities and services: a terrace, an iron and air conditioning. Enjoy free parking with this accommodation in Chicago!
This three-bedroom house is situated in Chicago, just five miles from the city centre and a short distance from the United Center. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers. The house provides 139 square metres of space, accommodating up to five guests. It features a fully equipped kitchen, a private patio and garden, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Downtown Mich Ave, Grant Park, Museums 2bd-2ba #20
house - Chicago
This downtown Chicago holiday home is located a 10-minute walk from the Field Museum of Natural History and 1.4 kilometres from Grant Park, placing it conveniently close to the Art Institute of Chicago (1.4 kilometres), the Chicago Symphony Orchestra, DePaul University, and the Adler Planetarium & Astronomy Museum. This 98 square metre, 2-bedroom, 2-bathroom apartment accommodates up to 8 guests and features a private patio with lake views, a well-equipped kitchen, air conditioning, complimentary Wi-Fi, and access to a shared lounge and sun terrace.
Best Chicago, IL vacation rentals with air conditioning
This Bronzeville flat is situated 2.4 kilometres south of McCormick Place and 4.8 kilometres north of Hyde Park, offering easy access to public transport and local amenities. The one-bedroom garden apartment features a kitchenette with fridge, microwave, and dishwasher, off-street parking, Wi-Fi, and is ideal for a couple's Chicago weekend break.
Private, Charming, Coach House Loft In Andersonville
house - Chicago
This meticulously renovated Chicago loft, ideal for couples, offers a unique blend of Midwest farmhouse and industrial styles and is situated in a residential area with easy street parking, though its precise distance from specific Chicago landmarks requires further clarification. The 1-bathroom apartment features an open-plan kitchen with modern appliances (fridge, microwave, dishwasher), secure keyless entry, and accommodates two guests; nearby attractions and activities will depend on its exact location within the city.
This three-bedroom Pilsen apartment is situated approximately 1.6km from downtown Chicago, offering easy access to the neighbourhood's cultural attractions and a short journey to the city's major landmarks. The 3-bedroom, 2-bathroom dwelling sleeps 5 guests and features a fully equipped kitchen, high-speed Wi-Fi, smart TVs, in-unit laundry, parking, and keyless entry; plus added extras such as games, books, and umbrellas are provided.
This three-bedroom apartment is located in Chicago's Logan Square neighbourhood, close to family-run restaurants and the 606 trail. The 3-bedroom property, sleeping up to six guests, features a fully equipped kitchen, in-unit laundry, a private patio, and ample free street parking with provided permits.