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.
Modern Minimalist Studio | Heart Of Gold Coast - Chicago
9.4 31 reviews

Modern Minimalist Studio | Heart Of Gold Coast

apartment, Chicago
This studio apartment is located in Chicago's Gold Coast neighborhood, a 14-minute walk from the Art Institute of Chicago and a 10-minute walk from Michigan Avenue shopping.
This pet-friendly studio offers WiFi, a kitchen with a fridge and microwave, air conditioning, a dedicated workspace, and accommodates up to two guests, with Oak Street Beach just a 5-minute walk away.
Livn West Loop Chicago Queen Studio Apartment - Chicago
9.7 175 reviews

Livn West Loop Chicago Queen Studio Apartment

apartment, Chicago
This stylish loft-style studio is located in Chicago's West Loop, a short walk from Union Station and Willis Tower, and minutes from top dining establishments like Lou Mitchell's and Girl & The Goat.
This newly renovated unit offers a full kitchen with a fridge, freezer, microwave oven, and dishwasher, air conditioning, in-unit laundry, and accommodates up to two guests, with access to a garden and fitness center.
Spacious Downtown 3br With Free Parking - Chicago
9.8 164 reviews

Spacious Downtown 3br With Free Parking

apartment, Chicago
This three-bedroom Chicago apartment rental is situated in the Fulton Market District, offering easy access to numerous restaurants and public transportation.
The 3-bedroom, 2-bathroom unit sleeps up to 10 guests and features a fully equipped kitchen, in-unit laundry, free parking, and a private outdoor porch with city views; nearby attractions include the many restaurants of Fulton Market.

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

The Woodsman's Gallery At Ohc - Chicago
9.8 628 reviews

The Woodsman's Gallery At Ohc

apartment, Chicago
This apartment is located in the River West neighborhood, just a short distance from popular areas like Wicker Park and Logan Square, and a mile and a half from the lakefront and the Magnificent Mile. The apartment has earned excellent ratings for its cleanliness, location, and overall experience.
This loft offers 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy the unique art gallery experience, modern design, multiple balconies, music room, and relaxing amenities, including a steam shower and soaking tub.
Chicago Suite 1br/1ba (3709-g2) - Chicago
9.5 54 reviews

Chicago Suite 1br/1ba (3709-g2)

apartment, Chicago
This one-bedroom apartment is located in a middle-class family neighborhood in Chicago, just a short bus ride from the Blue Line train station, providing easy access to various parts of the city. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is perfect for couples or two singles, with the option to accommodate up to four guests for short-term stays. Amenities include a full kitchen, air conditioning, a Jacuzzi, parking options, and a responsive host.
Spacious 7br Near The 606 Trail *Sleeps Up To 18* - Chicago
9.4 73 reviews

Spacious 7br Near The 606 Trail *Sleeps Up To 18*

apartment, Chicago
This Logan Square apartment rental is conveniently located near the 606 Trail and within walking distance of Logan Square's shops and restaurants.
This three-unit property boasts seven bedrooms, three bathrooms, and can comfortably accommodate up to 16 guests, featuring three kitchens, a two-car garage, on-site laundry, and a private garden.
Blueground | Loop, Dog Run, Nr Chicago Riverwalk - Chicago
8.4 17 reviews

Blueground | Loop, Dog Run, Nr Chicago Riverwalk

apartment, Chicago
This two-bedroom apartment is located in Chicago's Loop district, a short walk from Millennium Park and the Art Institute. This apartment has received very good ratings for location, cleanliness, and overall experience.
The apartment is modern and stylishly furnished with a fully equipped kitchen. Enjoy amenities like a swimming pool, a lounge, a BBQ area, and a doorman, along with in-apartment laundry and premium features like a wireless speaker and smart TV.

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.

Chic Stay In River North: Luxury Suites, Top Amenities, Near Arts & Nightlife! - Chicago
10 1 review

Chic Stay In River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!

apartment, Chicago
This Level River North apartment rental offers a prime River North location, minutes from the Magnificent Mile and the Loop, providing easy access to Chicago's renowned attractions like the Art Institute and Lincoln Park Zoo.
The 720-square-foot one-bedroom unit sleeps four guests and features a fully equipped kitchen with a dishwasher, in-suite laundry, a balcony, and access to a swimming pool and sauna; nearby water activities are also available.
7 Mi To Downtown: Luxe Chicago Condo - Chicago
8.0 1 review

7 Mi To Downtown: Luxe Chicago Condo

apartment, Chicago
This Washington Park condo, less than a mile from both the Green and Red Line 'L' train stations and a mile from the DuSable Museum of African American History, offers easy access to downtown Chicago and other attractions.
This 1,190-square-foot, three-bedroom apartment sleeps seven and includes a fully equipped kitchen, in-unit laundry, balcony, parking, and modern amenities like a smart TV and keyless entry.
Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop - Chicago
8.5 100 reviews

Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop

apartment, Chicago
This apartment is in the heart of Chicago, just a short walk from popular attractions like the CIBC Theatre, Willis Tower, and DePaul University. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The rental features a modern kitchen with a dishwasher, a comfortable living area, and a private bathroom. It can accommodate up to 5 guests and offers amenities like a swimming pool, jacuzzi, terrace, and free Wi-Fi.
High-floor 2brs With City & Lake Views - Chicago
No reviews

High-floor 2brs With City & Lake Views

apartment, Chicago
This four-bedroom, four-bathroom condo is situated in Chicago's South Loop, a 5-minute walk from Grant Park and a 10-minute walk to the Art Institute.
This family-friendly residence offers a guest capacity of 10 and includes amenities such as a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, terrace/balcony, fitness center, and parking, with access to over 80,000 sq ft of resort-style building amenities including a Sky Deck and Observation Lounge.

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.

Cozy Chicago Smoke Ok 3br Suite | Near Mccormick - Chicago
No reviews

Cozy Chicago Smoke Ok 3br Suite | Near Mccormick

apartment, Chicago
This 3-bedroom, 2-bathroom apartment in Chicago's South Loop offers prime access, situated on South State Street, a 10-12 minute walk from McCormick Place and a short drive to Soldier Field and the Museum Campus.
The "State Suite" accommodates up to 6 guests, featuring a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, and a 4K Roku HDTV, with optional secure parking available for an additional fee.
Prime Lakeview Apt: Walk To Wrigley Field - Chicago
10 448 reviews

Prime Lakeview Apt: Walk To Wrigley Field

apartment, Chicago
This two-bedroom, one-bathroom apartment is located in Lakeview, a popular Chicago neighborhood, within a five-minute walk of the Red Line "L" station and several bus lines. The apartment offers a garden, parking, and a kitchen equipped with a refrigerator, microwave, and dishwasher, and can accommodate up to four guests.
Zoo Holiday Retreat - Chicago
9.9 14 reviews

Zoo Holiday Retreat

apartment, Brookfield
This Brookfield, Illinois apartment is conveniently located near the Brookfield Zoo and less than a mile from the Burlington Northern Santa Fe train station, offering easy access to downtown Chicago.
This four-bedroom, two-bathroom dwelling comfortably sleeps eight guests, boasting a full kitchen, air conditioning, parking, and internet access; enjoy nearby restaurants and taverns in downtown Brookfield.
Spacious 3br Condo W/ Skyline Views Near Mccormick - Chicago
9.6 113 reviews

Spacious 3br Condo W/ Skyline Views Near Mccormick

apartment, Chicago
This three-bedroom Chicago apartment boasts a prime Michigan Avenue location, a 9-minute walk from McCormick Place and a short Uber ride from the Museum Campus and Soldier Field.
The 3-bedroom suite sleeps up to 8 guests, features a fully equipped kitchen, in-unit laundry, a fitness center, and parking (for an extra $30/day), plus 4K Roku HDTVs in every room and a 65" Smart HDTV in the living room.

Best Chicago vacation rentals with parking

Cozy 3br Chicago Garden Apartment Near Loyola & Downtown - Chicago
9.0 5 reviews

Cozy 3br Chicago Garden Apartment Near Loyola & Downtown

apartment, Chicago
Lincoln Park Living - Suite 2 - Chicago
8.4 22 reviews

Lincoln Park Living - Suite 2

house, Chicago
Brand New Luxury Space + Roof Deck! - Chicago
9.9 67 reviews

Brand New Luxury Space + Roof Deck!

apartment, Chicago
4br Near Downtown W/rooftop Lounge - Chicago
No reviews

4br Near Downtown W/rooftop Lounge

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.

Sentral Michigan Avenue - Chicago
8.9 3355 reviews

Sentral Michigan Avenue

hotel, 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.

Downtown Park #11 - Mich Ave Ph | Gym+rooftop - Chicago
9.4 8 reviews

Downtown Park #11 - Mich Ave Ph | Gym+rooftop

apartment, Chicago
Sleeps 4  New Modern 1br  Private Workspace - Chicago
10 1 review

Sleeps 4 New Modern 1br Private Workspace

apartment, Chicago
Modern Condo  Safe Chicago Stay Near Ohare - Chicago
10 9 reviews

Modern Condo Safe Chicago Stay Near Ohare

apartment, Chicago
Bronzeville Home! Downtown + Mccormick + U Of C - Chicago
9.8 56 reviews

Bronzeville Home! Downtown + Mccormick + U Of C

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.

Luxury Designer Penthouse 3803 | Pool | Gold Coast - Chicago
10 8 reviews

Luxury Designer Penthouse 3803 | Pool | Gold Coast

apartment, Chicago
The Parkside Perch (Fitness Center  Lounge) - Chicago
9.9 15 reviews

The Parkside Perch (Fitness Center Lounge)

apartment, Chicago
Level - Studio In Fulton Market With Full Kitchen - Chicago
10 2 reviews

Level - Studio In Fulton Market With Full Kitchen

apartment, Chicago
Modern Lux Apt, Fastwi-fi, Pool, Huge Gym, Kingbed - Chicago
10 21 reviews

Modern Lux Apt, Fastwi-fi, Pool, Huge Gym, Kingbed

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.

The Aerial Oasis (Indoor Pool  Fitness Center) - Chicago
9.7 90 reviews

The Aerial Oasis (Indoor Pool Fitness Center)

apartment, Chicago
River West 3br Penthouse Duo: Skyline Comfort - Chicago
No reviews

River West 3br Penthouse Duo: Skyline Comfort

apartment, Chicago
Stylish 2br With Skyline Views Near Riverwalk - Chicago
No reviews

Stylish 2br With Skyline Views Near Riverwalk

apartment, Chicago
Modern 2br In The Loop + Panoramic City Views - Chicago
No reviews

Modern 2br In The Loop + Panoramic City Views

apartment, Chicago
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