Vacation rentals in Chicago

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Chicago vacation rentals
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Best Vacation rentals and Airbnb offers in Chicago

Top-Rated Vacation Rentals near the City Center in Chicago

From vibrant downtown areas to historic streets, these Chicago vacation rentals put you close to everything worth seeing.

River North Rooftop With In And Out Parking 6 - Chicago
9.0 2 reviews

River North Rooftop With In And Out Parking 6

apartment, Chicago
This downtown Chicago condo offers prime access to Michigan Avenue, just a 10-minute walk away, and the Chicago Riverwalk, 14 minutes on foot, with the Merchandise Mart and Grand subway stations conveniently located within a 6-minute walk.
This 1230 sq ft rental sleeps up to 7 guests, featuring 2 bedrooms and 2 bathrooms, a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, covered parking, and on-site fitness and barbecue facilities.
Cozy 2 Bed Pilsen Condo - Chicago
10 12 reviews

Cozy 2 Bed Pilsen Condo

apartment, Chicago
This Chicago apartment is conveniently located between the vibrant neighborhoods of Pilsen and Chinatown, offering easy access to diverse dining, shopping, and entertainment options. Guests consistently rate the apartment excellent for location, cleanliness, and overall experience.
This comfortable 2-bedroom, 1-bathroom apartment can comfortably accommodate up to 6 guests. Enjoy amenities like air conditioning, parking, and a kitchen equipped with a fridge, perfect for a relaxing and enjoyable stay in Chicago.
City Center Oasis: 3br/2ba︎ Patio︎ Parking(2x) ︎ - Chicago
10 207 reviews

City Center Oasis: 3br/2ba︎ Patio︎ Parking(2x) ︎

apartment, Chicago
This Chicago apartment is located in the River North neighborhood, just steps from the Magnificent Mile, Lake Michigan, and Navy Pier, putting you in the heart of the city's action. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The spacious 1800 square foot apartment comfortably accommodates up to 10 guests with its 3 bedrooms and 2 bathrooms. It's fully equipped with a kitchen, a gameroom, a private patio with a grill, and gated parking, offering everything you need for a memorable Chicago getaway.
Spacious & Stylish 2br-2ba Apt Steps From The Bean - Chicago
9.6 272 reviews

Spacious & Stylish 2br-2ba Apt Steps From The Bean

apartment, Chicago
This Chicago apartment is located in the Loop, just a one-minute walk from Millennium Park, Michigan Avenue, and State Street shopping. It has excellent ratings for location, cleanliness, and user experience.
This two-bedroom, two-bathroom dwelling can accommodate up to 8 guests. Amenities include a kitchen with a fridge, freezer, and microwave, air conditioning, parking, and internet access.

Where to stay in Chicago?

The Loop

The Loop is Chicago's central business district, famous for its architecture and iconic skyscrapers, such as the Willis Tower. Just a short walk from the Loop, you can visit Millennium Park, an urban park featuring the famous sculpture "The Bean". In addition, the area is well connected by public transport, providing easy access to other Chicago attractions.

Gold Coast

Gold Coast is a historic district with beautiful mansions and buildings of neo-gothic and art deco architectural style. Tourists can stroll along the shopping avenue Oak Street, where renowned designer boutiques and luxury jewelry stores are located. Lincoln Park and the famous Lincoln Park Zoo are just a few minutes' walk away. Gold Coast is also known for its proximity to the beaches of Lake Michigan.

Wicker Park

Wicker Park is a neighborhood famous for its hipster vibe. It is full of art galleries, vintage venues and independent coffee shops. In addition, the location is notable for Wicker Park, a stunning green space that offers enriching outdoor recreational opportunities, such as a skating rink, playground and more.

Lakeview

Lakeview is a Lake Michigan neighborhood known for its lively nightlife, with an abundance of bars, clubs and restaurants to suit all tastes. You can also enjoy Lake Michigan, stroll down Broadway Avenue, where there are theaters and thrift stores, and visit Wrigley Field, the flagship stadium of the Chicago Cubs.

Lincoln Park

Lincoln Park is a neighborhood located north of downtown Chicago. It is known for having classic and refined style houses and apartments, with brick and stone facades. It is an ideal place for those seeking elegance and nature, with a variety of parks, gardens and ponds. It also has several places of interest, such as the Lincoln Park Zoo, the Lincoln Park Conservatory and the Chicago History Museum.

West Loop

The West Loop, once an industrial hub, has transformed into the culinary capital of Chicago, featuring a wide range of top-rated restaurants and chic bars. Additionally, the Fulton Market District is located in the neighborhood. Apart from its stylish ambience, the West Loop is recognized for its reinvigorated industrial architecture.

Logan Square

Logan Square is a diverse neighborhood in Chicago. This neighborhood is noted for its arts scene and its wide variety of ethnic restaurants, bars and cafes. It has several points of interest, such as the Logan Square Farmers Market, a market that offers local and organic produce every Sunday; the Logan Theatre and the Comfort Station, a former trolley station converted into a cultural space.

Hyde Park

Hyde Park, positioned in the south of Chicago downtown, houses the University of Chicago and the notable Rockefeller Memorial Chapel. Additionally, the neighborhood is also home to the Oriental Museum and the Museum of Science and Industry at the university. Besides, Hyde Park is renowned for its captivating Jackson Park and the Palace of Fountains.

Pilsen

Pilsen is a neighborhood famous for its large Mexican population. The city is historically decorated with many murals created by local artists that adorn its streets contributing to its distinctive and artistic atmosphere. In addition, Pilsen boasts the National Museum of Mexican Art, which exhibits numerous works of art created by artists of Mexican and Latin American descent.

Best Chicago vacation rentals with air conditioning

Blueground | The Loop, Pool & Gym, Nr Park - Chicago
No reviews

Blueground | The Loop, Pool & Gym, Nr Park

apartment, Chicago
This furnished Chicago Loop apartment, near the Art Institute of Chicago and Chicago Theatre, offers easy access to major attractions.
This 860-square-foot unit features one bedroom, one bathroom, accommodates two guests, and includes in-unit laundry, a modern kitchen with dishwasher, a swimming pool, and a pet-friendly policy.
Wrigleyville 2 Bed 2 Bath + Office Newly Rehabbed - Chicago
10 105 reviews

Wrigleyville 2 Bed 2 Bath + Office Newly Rehabbed

apartment, Chicago
This Wrigleyville apartment rental is located steps from Wrigley Field and Clark Street, offering easy access to Chicago's North Side attractions.
The two-bedroom, two-bathroom unit, featuring a dedicated office and a master suite with a skylight and marble shower, comfortably accommodates four guests and includes a full kitchen with modern appliances, free street parking, and high ceilings.
Delightful 2-bedroom Building With Ac In Vibrant Chicago - Chicago
No reviews

Delightful 2-bedroom Building With Ac In Vibrant Chicago

apartment, Chicago
This 2-bedroom, 1-bathroom apartment in Chicago's South Shore neighborhood is located 0.5 miles from Lake Michigan and Grant Park, and within 2 miles of the Museum of Science and Industry and the Field Museum of Natural History.
This accommodation accommodates up to 2 guests and features air conditioning, internet, and is conveniently located 2 miles from McCormick Place and 3 miles from Lincoln Park Zoo.
Chi-town Ultimate Hideout 1-2-3 - Chicago
9.0 2 reviews

Chi-town Ultimate Hideout 1-2-3

house, Berwyn
This Berwyn vacation home, located approximately 5.6 miles from Midway International Airport and 9-11 miles from attractions like the United Center and Guaranteed Rate Field, offers easy access to Chicago's highlights.
This 2,900-square-foot house features five bedrooms, three bathrooms, and accommodates up to 22 guests, boasting a fully equipped kitchen, free Wi-Fi, air conditioning, a patio, and a washing machine.

Frequently Asked Questions about vacation rentals in Chicago

  • What should a first-time visitor not miss in Chicago, IL?

    You definitely can't miss a visit to Millennium Park and seeing Cloud Gate, also known as "The Bean." The Art Institute of Chicago is another must-see for any art lover. And of course, no trip to Chicago is complete without a deep-dish pizza, so be sure to try one at Lou Malnati's or Pizzeria Bebu.
  • What are the best Airbnb and vacation rentals in Chicago?

  • What's the best district to book a vacation rental in Chicago?

    The best district to book a vacation rental in Chicago is the Magnificent Mile. It offers a central location with easy access to popular attractions, shopping, and dining options.
  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant and walkable neighborhood with tons of restaurants and shops, check out Wicker Park or Bucktown. If you want to be close to the lakefront and beaches, consider Lincoln Park or Lakeview. For a more historic feel, try the Gold Coast or River North.
  • What are the most popular Airbnbs in Chicago?

  • Where can families find local cuisine in Chicago?

    Chinatown and Pilsen are great neighborhoods for trying local cuisine.
  • What are the top family-friendly attractions in Chicago, IL?

    The Lincoln Park Zoo is a great free option with plenty of animals for kids to see. The Shedd Aquarium is a bit more expensive, but it's a fantastic experience with a wide variety of marine life. And the Field Museum is always a hit with dinosaur exhibits and other fascinating displays.
  • What are the best vacation rentals with a pool in Chicago?

  • Are there any playgrounds or parks in Chicago suitable for families?

    Grant Park and Millennium Park have playgrounds and parks suitable for families.
  • When is the best time to book a vacation rental in Chicago, IL?

    The best time to book a vacation rental in Chicago is usually in the shoulder seasons, like spring or fall. You'll get better deals and avoid the crowds of summer. If you're looking for the best weather, June to August is the warmest, but expect higher prices and more tourists.
  • What are the best rentals for families and kids in Chicago?

  • Which restaurants in Chicago offer the best traditional local cuisine?

    The best restaurants in Chicago for traditional local cuisine include Lou Malnati's for deep-dish pizza, Portillo's for Chicago-style hot dogs, and The Publican for delicious pork dishes.
  • What events or festivals should visitors check out in and around Chicago, IL?

    Chicago has events all year round. In the summer, you can catch the Chicago Blues Festival or the Taste of Chicago. In the fall, there's the Chicago Marathon and the Magnificent Mile Lights Festival. And in the winter, the Christkindlmarket is a fun holiday tradition.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago?

  • What are the must-try local dishes in Chicago?

    Must-try local dishes in Chicago include the iconic Chicago-style deep-dish pizza, Italian beef sandwiches, and Garrett Popcorn's famous Chicago Mix.
  • What are the best budget-friendly activities in Chicago, IL?

    Take a walk or bike ride along the Lakefront Trail, which stretches for miles along Lake Michigan. Visit the free museums, like the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry. And enjoy a picnic in Millennium Park, where you can also see Cloud Gate and Crown Fountain.
  • What are the local expectations around tipping at restaurants and food stalls in Chicago?

    In Chicago, it's customary to tip around 15-20% at restaurants and food stalls. However, always check the bill for any included gratuity, especially for larger groups.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a popular choice for walking and biking, offering stunning views of Lake Michigan. For a more urban experience, try the 606, a former railway line transformed into a scenic park. And for a historical journey, walk the Chicago Riverwalk, which offers views of the city's iconic architecture.
  • Yes, famous stadiums like Wrigley Field and Soldier Field offer tours and behind-the-scenes experiences.

    Are there any famous stadiums or sports arenas that offer tours or behind-the-scenes experiences in Chicago?
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, there are many pet-friendly attractions in Chicago. The Lincoln Park Zoo is dog-friendly, and many restaurants and cafes have outdoor patios where you can bring your furry friend. You can also find dog parks throughout the city.
  • Are there museums or landmarks related to famous athletes or sporting moments in Chicago?

    Chicago has the Chicago Sports Museum and the Michael Jordan statue outside the United Center.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy than a hotel room. You can also save money by cooking your own meals. And you can often find rentals in convenient locations, close to attractions and public transportation.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a great city for sports fans. You can catch a Cubs game at Wrigley Field, a White Sox game at Guaranteed Rate Field, or a Bulls game at the United Center. The city is also home to the Blackhawks (hockey), the Bears (football), and the Fire (soccer).

Popular destinations

Guest-Favorite Vacation Rentals with a Terrace in Chicago

Take in sweeping views of the Chicago River or the iconic skyline from your private balcony. These vacation rentals offer the perfect outdoor space to enjoy a morning coffee or an evening drink above the vibrant city streets.

Downtown Mich Ave #10 | Gym+rooftop - Chicago
9.4 14 reviews

Downtown Mich Ave #10 | Gym+rooftop

apartment, Chicago
This penthouse apartment is located in downtown Chicago on Michigan Avenue, directly overlooking Grant Park and Lake Michigan, just a short walk from popular attractions like The Bean, Soldier Field, and the Art Institute of Chicago. The apartment has received excellent user ratings and offers convenient access to public transportation with the Red "L" subway just three blocks away.
This one-bedroom, one-bathroom apartment features a modern design with a spacious 600 square feet layout that can accommodate up to four guests. Enjoy amenities like a fully equipped kitchen, a private terrace, a shared rooftop deck with city views, and an on-site gym, along with convenient features like a washer and dryer in the unit, contact-free check-in, and pet-friendly accommodations.
Downtown Elmhurst Luxury Apartments Near Metra & O'hare With Pool, Gym, Parking & Theater - Chicago
10 1 review

Downtown Elmhurst Luxury Apartments Near Metra & O'hare With Pool, Gym, Parking & Theater

apartment, Elmhurst
This Elmhurst condo is located 6.2 miles from Chicago O'Hare International Airport and is a 16-mile drive to the United Center.
This stylish apartment features a king bed, a fully equipped kitchen with a dishwasher and microwave, air conditioning, WiFi, a swimming pool, fitness center, and private parking, with barbecue facilities and a fireplace on the terrace.
Fulbrix Bright Designer Apartments With West Loop Views - Chicago
No reviews

Fulbrix Bright Designer Apartments With West Loop Views

apartment, Chicago
Vacation rental listing. Your accommodation will be based in Chicago.
Services and facilities: air conditioning, a washing machine and a swimming pool. Take advantage of the garden in this apartment!
Cozy 2-bedroom Apartment In Pilsen Chicago - Chicago
10 4 reviews

Cozy 2-bedroom Apartment In Pilsen Chicago

apartment, Chicago
This 2-bedroom, 1-bathroom apartment in Chicago's Lower West Side offers excellent walkability to the Pink Line train and bus stops, with downtown Chicago just a 15-minute drive away, providing convenient access to attractions like Michigan Avenue, Navy Pier, the Field Museum of Natural History, and the Museum of Science and Industry, as well as event venues such as the United Center and McCormick Place. Guests will enjoy private full apartment access with a keypad entry, a full kitchen, living room, and complimentary Wi-Fi, with numerous dining options available in the neighborhood and a guest capacity of six.

Neighborhoods and points of interest in Chicago

Choose the Right Family-Friendly Vacation Rentals in Chicago

Find a spacious home base near Millennium Park or the Shedd Aquarium. These rentals offer plenty of room for the kids and easy access to the Lakefront Trail, ensuring a smooth and entertaining stay for all ages.

The Urban Oasis | Outdoor Lounge  Sleeps 10+ - Chicago
9.8 28 reviews

The Urban Oasis | Outdoor Lounge Sleeps 10+

apartment, Chicago
This modern Chicago apartment is conveniently located in the South Loop, within walking distance of several popular neighborhoods and a short drive from major attractions like McCormick Place and Millennium Park. This rental has excellent user ratings, making it a popular choice for travelers. The spacious apartment comfortably accommodates up to 10 guests with four bedrooms and two bathrooms. Enjoy a fully equipped kitchen, a private terrace, free street parking, and the convenience of being close to Lake Michigan and the city's vibrant cultural scene.
Victorian Mansion In Garfield Park - Chicago
9.5 61 reviews

Victorian Mansion In Garfield Park

house, Chicago
This Chicago vacation rental is located just 5 miles from downtown and 2.3 miles from the United Center, offering easy access to the city's attractions. The property boasts excellent ratings for user experience, location, and cleanliness, making it a top choice for travelers.
This 3-bedroom home offers 1500 square feet of space, comfortably accommodating up to 5 guests. Enjoy modern amenities including a fully equipped kitchen, air conditioning, and a private balcony or patio, perfect for relaxing after a day of exploring the city.
The Woodlawn Grey  - Large 3bd/3ba Apt By Uchicago - Chicago
9.6 128 reviews

The Woodlawn Grey - Large 3bd/3ba Apt By Uchicago

apartment, Chicago
This spacious 3-bedroom apartment is located on a quiet block steps away from the University of Chicago campus, within easy reach of major attractions and transportation. It has excellent user, location, and cleanliness ratings.
The apartment has three bedrooms, three bathrooms, and a living room with a 4K Smart TV. It can accommodate up to 6 guests. The apartment is well-equipped with a kitchen that includes cooking supplies, appliances, microwave, toaster, and coffee/tea. It also has convenient amenities such as an in-unit washer and dryer, charging station for devices, and high-speed Wi-Fi.
Top Floor Escape | Modern Amenities | Lush Garden - Chicago
9.9 498 reviews

Top Floor Escape | Modern Amenities | Lush Garden

apartment, Chicago
This top-floor apartment is located on a quiet street in Chicago's Logan Square neighborhood, just a short walk from Milwaukee Avenue's restaurants and shops. It has excellent user, location, and cleanliness ratings. This two-bedroom, two-bathroom rental can comfortably accommodate up to five guests. Amenities include a modern kitchen with stainless steel appliances, a soaking tub, in-unit laundry, high-speed internet, and a private garden.

Best Chicago vacation rentals with parking

Peaceful & Airy Modern-chic Condo In Trendy Pilsen - Chicago
9.8 483 reviews

Peaceful & Airy Modern-chic Condo In Trendy Pilsen

apartment, Chicago
*New* Luxury Wrigley Penthouse, Free Parking - Chicago
9.9 59 reviews

*New* Luxury Wrigley Penthouse, Free Parking

apartment, Chicago
Lovely Top Floor Apt In Logan Sq - Chicago
10 37 reviews

Lovely Top Floor Apt In Logan Sq

apartment, Chicago
Skylit Boho Retreat In Wicker Park - Chicago
9.4 253 reviews

Skylit Boho Retreat In Wicker Park

apartment, Chicago

Our Favorite 5-Star Vacation Rentals in Chicago

Experience the Gold Coast lifestyle in these premier rentals featuring designer finishes and high-end amenities. These upscale homes place you moments from the Magnificent Mile and the city’s finest Michelin-starred dining.

Talman Ave - Chicago
9.9 63 reviews

Talman Ave

apartment, Chicago

Top-Rated Pet-Friendly Vacation Rentals in Chicago

Explore the city with your dog from rentals located near the green stretches of Grant Park or Lincoln Park. These pet-friendly vacation rentals provide easy access to urban walking paths and local dog beaches along Lake Michigan.

City Villa Sleeps 10-20 Free Tv & Parking - Chicago
9.5 16 reviews

City Villa Sleeps 10-20 Free Tv & Parking

apartment, Chicago
Spacious Centrally Located West Loop Loft - Chicago
9.8 326 reviews

Spacious Centrally Located West Loop Loft

apartment, Chicago
Spacious Studio For 2 Close To Wrigley & Boystown - Chicago
No reviews

Spacious Studio For 2 Close To Wrigley & Boystown

apartment, Chicago
Chicago Boutique Hideaway Private Deck, Fire Pit - Chicago
8.3 3 reviews

Chicago Boutique Hideaway Private Deck, Fire Pit

apartment, Chicago

Search Vacation Rentals with Swimming Pool in Chicago

Make a morning swim part of your routine with a luxury rental or Airbnb featuring an on-site pool. It’s the perfect way to recharge after a day of meetings or sightseeing at Navy Pier and the Art Institute.

Spacious 2br In The Loop Downtown Resort Amenities - Chicago
8.6 4 reviews

Spacious 2br In The Loop Downtown Resort Amenities

apartment, Chicago
Penthouse Paradise Executive Elegance  Elevated Amenities  Sleeps 6 - Chicago
No reviews

Penthouse Paradise Executive Elegance Elevated Amenities Sleeps 6

apartment, Chicago
Beautiful Corner 2 Bedroom In The Loop | Roof Deck - Chicago
9.4 1558 reviews

Beautiful Corner 2 Bedroom In The Loop | Roof Deck

apartment, Chicago
Blueground River North Pool Gym Nr Mile Chi-1141 - Chicago
No reviews

Blueground River North Pool Gym Nr Mile Chi-1141

apartment, Chicago

Explore Vacation Rentals with Jacuzzi in Chicago

Unwind in a private hot tub after a day of exploring the Loop or the boutiques in Wicker Park. These top-rated rentals offer a quiet sanctuary to relax while soaking in the energy of the city.

Promo 10% Weekly And 15% Monthly! Jacuzzi, King Beds, Easy Access To Dt Chicago! - Chicago
9.4 23 reviews

Promo 10% Weekly And 15% Monthly! Jacuzzi, King Beds, Easy Access To Dt Chicago!

apartment, Westchester
Explore Fulton Market + Retreat In Modern Comfort - Chicago
10 2 reviews

Explore Fulton Market + Retreat In Modern Comfort

apartment, Chicago
The Hotel & Athletic Club At Midtown - Chicago
8.9 1369 reviews

The Hotel & Athletic Club At Midtown

resort, Chicago
Sweet Home Chicago- 3 Br, 2.5 Ba + Game Room, Hot Tub, Near O'hare, Rosemont - Chicago
No reviews

Sweet Home Chicago- 3 Br, 2.5 Ba + Game Room, Hot Tub, Near O'hare, Rosemont

apartment, Dunning
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