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.

Stylish 1br With Laundry In-unit - Chicago
9.6 74 reviews

Stylish 1br With Laundry In-unit

apartment, Chicago
This Chicago apartment rental is conveniently located near public transportation, offering easy access to the city's attractions.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, and air conditioning.
Secluded 2br Apt In Chinatown By Mccormick/dwtn - Chicago
9.7 200 reviews

Secluded 2br Apt In Chinatown By Mccormick/dwtn

apartment, Chicago
This apartment is located in the heart of Chicago's Chinatown neighborhood, steps away from McCormick Place and public transportation. It has received excellent ratings for its location, cleanliness, and user experience. The apartment has two bedrooms, one bathroom, and can accommodate up to seven guests. It features a fully equipped kitchen, free parking, Wi-Fi internet, and a smart TV.
In addition to its convenient location and amenities, this apartment also offers a unique interior with a modern touch. It is surrounded by a variety of Asian cuisine options, bubble tea shops, and other local culinary delights.
Chic Studio In The Heart Of The Gold Coast - Chicago
9.2 10 reviews

Chic Studio In The Heart Of The Gold Coast

apartment, Chicago
This modern studio is located in Chicago's Gold Coast, a 14-minute walk from the Art Institute of Chicago and a 5-9 minute walk from Oak Street Beach.
This pet-friendly studio features a queen bed, a kitchenette with a mini fridge, and reliable Wi-Fi, accommodating up to two guests.
The Modern Retreat: 1br|near City|free Parking - Chicago
9.2 62 reviews

The Modern Retreat: 1br|near City|free Parking

apartment, Chicago
This one-bedroom Chicago apartment rental is located blocks from the Loop, offering easy access to attractions like Millennium Park (3 miles), Chinatown (2 miles), and McCormick Place (3 miles).
The unit features a fully equipped kitchen, in-unit laundry, fast Wi-Fi, and accommodates up to three guests with a plush velvet sofa bed; enjoy nearby beaches and explore Chicago's many museums and sporting venues.

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

Walkers Paradise! Prime Logan Square 5 Bedrms/2ba - Chicago
9.6 82 reviews

Walkers Paradise! Prime Logan Square 5 Bedrms/2ba

apartment, Chicago
This Logan Square apartment rental offers easy access to the Blue Line, providing quick commutes to downtown Chicago, O'Hare International Airport, and Rosemont.
The five-bedroom, two-bathroom unit sleeps up to 14 guests comfortably, featuring two living rooms with smart TVs, a fully equipped kitchen, and complimentary coffee; nearby attractions include numerous bars, restaurants, and shops.
Costa Lota  Vintage 1br Near Wrigley - Chicago
9.9 151 reviews

Costa Lota Vintage 1br Near Wrigley

apartment, Chicago
This ground-floor apartment in Wrigleyville is a 12-minute walk from the Southport Corridor, near Wrigley Field, Boystown, and offers easy access to the Brown Line 'L' train and Lakefront Trail.
The one-bedroom, one-bathroom unit sleeps two guests and includes a full kitchen with fridge, freezer, microwave, and dishwasher, air conditioning, free street parking (restrictions apply), and a free membership to The Metropolitan co-working space in the Willis Tower.
Modern 1br Retreat *Rooftop + Gym + Wifi - Chicago
No reviews

Modern 1br Retreat *Rooftop + Gym + Wifi

apartment, Chicago
This one-bedroom condo in Chicago offers convenient access to McCormick Place, just 5 minutes away, and is a 10-15 minute drive from The Loop, with nearby attractions including the Museum Campus and Soldier Field.
This pet-friendly unit accommodates up to 4 guests with a queen bed and a trundle sofa, featuring a full kitchen, complimentary Wi-Fi, and access to a fitness center and rooftop lounge with grills.
15 Mins Dt Humboldtpark Gem Sleeps 8 Freepark - Chicago
10 1 review

15 Mins Dt Humboldtpark Gem Sleeps 8 Freepark

apartment, Chicago
This Humboldt Park apartment is located 2.8 miles from the United Center and within 4 miles of downtown Chicago attractions including the Museum of Contemporary Art, Water Tower Chicago, and 360 Chicago.
This 1000 square foot rental offers 2 bedrooms, 1 bathroom, and accommodates up to 8 guests with complimentary Wi-Fi, air conditioning, a full kitchen, and free parking.

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.

Charming 2br Hideaway Flw District-theater/games/laundry/office/private Backyard - Chicago
10 3 reviews

Charming 2br Hideaway Flw District-theater/games/laundry/office/private Backyard

apartment, Oak Park
This Oak Park coach house is located in a quiet residential neighborhood, a short walk from local shops and restaurants, and approximately 9 miles from downtown Chicago's Art Institute and Chicago Theatre.
This 1190 sq ft detached coach house sleeps up to 4 guests and features a private theater room, game room, a fenced backyard, and free parking for two vehicles.
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.
1 #31 - 4 Bedroom Condo - Mccormick Place, Wintrust Arena, Chinatown - Chicago
9.5 98 reviews

1 #31 - 4 Bedroom Condo - Mccormick Place, Wintrust Arena, Chinatown

apartment, Chicago
This newly renovated apartment is located in Chicago's Chinatown, just minutes from Downtown, McCormick Place, and the South Loop. This apartment has received excellent ratings for location, cleanliness, and user experience.
This spacious dwelling has four bedrooms, two bathrooms, two kitchens, two dining rooms, and two living rooms. Guests can enjoy a private terrace, a garden, a spa, and parking, along with access to the internet, air conditioning, and a fully equipped kitchen.
Luxe 1br: Unmatched Views & Location - Chicago
No reviews

Luxe 1br: Unmatched Views & Location

apartment, Chicago
This River West condo offers panoramic city views and puts you 5 minutes from Fulton Market and 10 minutes from Old Town, with easy access to Logan Square.
This 1-bedroom, 1-bathroom unit accommodates up to 3 guests and features a fully-equipped kitchen, air conditioning, a swimming pool, jacuzzi, fitness center, and co-working spaces.

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.

New! O'hare Cozy Home /Patio/ Free Prk/king Bed - Chicago
9.6 10 reviews

New! O'hare Cozy Home /Patio/ Free Prk/king Bed

apartment, Chicago
This family-friendly apartment in Chicago is situated in a comfortable neighborhood, 10 minutes from O'Hare Airport and the Rosemont Entertainment District, with convenient transit links to downtown Chicago via the Edison Park Metra station or Harlem Blue Line, and just steps from a Walgreens.
This 3-bedroom, 1-bathroom dwelling accommodates up to 6 guests and features a fully stocked kitchen, a private patio, and dedicated workspace with 600 Mbps Wi-Fi, offering a split-level layout for distinct living, kitchen/dining, and sleeping areas.
Spacious 3-bedroom Apartment In Awesome Chicago With Ac, Wifi - Chicago
10 1 review

Spacious 3-bedroom Apartment In Awesome Chicago With Ac, Wifi

apartment, Chicago
This 3-bedroom, 1-bathroom Washington Park apartment is a 6-minute drive from Lake Michigan and a 2-minute drive from State Street, with the Garfield 'L' station a 14-minute walk away.
This 1600 square foot residence offers a private terrace with outdoor furniture and a fire pit, accommodating up to 3 guests with amenities including Wi-Fi, air conditioning, a full kitchen, and in-unit laundry.
Livn West Loop Chicago 2 Br City View - Chicago
9.4 11 reviews

Livn West Loop Chicago 2 Br City View

apartment, Chicago
This downtown Chicago condo is an 8-minute walk from Skydeck Ledge and a 14-minute walk from State Street, with Clinton Station and Ogilvie Transportation Center within a 7-minute walk.
This 650-square-foot apartment offers 2 bedrooms, 1 bathroom, a full kitchen with an ice dispenser, air conditioning, free Wi-Fi, and an in-unit washer and dryer, accommodating up to 4 guests.
3br/2ba Dual-level W/ King Bed, Tvs & Washer/dryer - Chicago
9.9 67 reviews

3br/2ba Dual-level W/ King Bed, Tvs & Washer/dryer

apartment, Chicago
This spacious Jefferson Park duplex is conveniently located near O'Hare International Airport, Chicago Premium Outlets, and Allstate Arena, all within a 15-minute drive.
The three-bedroom, two-bathroom apartment sleeps six guests and features two living areas, a wet bar, a fully equipped kitchen with a waffle maker, and a shared backyard, plus laundry facilities and high-speed internet.

Best Chicago vacation rentals with parking

Bookman's Retreat Hundreds Of Good Books. 1 Guitar - Chicago
9.7 61 reviews

Bookman's Retreat Hundreds Of Good Books. 1 Guitar

apartment, Chicago
The Roscoe Village Guesthouse - Chicago
9.8 133 reviews

The Roscoe Village Guesthouse

apartment, Chicago
Vibrant & Chic Apt On Quiet St In Andersonville - Chicago
10 232 reviews

Vibrant & Chic Apt On Quiet St In Andersonville

apartment, Chicago
Bohemian Lodge #3 ( Clean & Affordable Travel) - Chicago
9.7 991 reviews

Bohemian Lodge #3 ( Clean & Affordable Travel)

resort, 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.

Skyline 2br In South Loop With Optional Parking & Gym Access Near Museum Campus And Mccormick Place - Chicago
9.7 3 reviews

Skyline 2br In South Loop With Optional Parking & Gym Access Near Museum Campus And Mccormick Place

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.

2bd/1 Ba With Summer Patio In Quiet Roscoe Village - Chicago
9.9 173 reviews

2bd/1 Ba With Summer Patio In Quiet Roscoe Village

apartment, Chicago
Kng+qn 2bdrm/1parking Space /18 Min Ohare/alstate - Chicago
9.9 186 reviews

Kng+qn 2bdrm/1parking Space /18 Min Ohare/alstate

apartment, Melrose Park
Charming 2br Apartment With Skyline View, Optional Parking & Gym Access Near Mccormick Place, Lakefront And Soldier Field - Chicago
10 1 review

Charming 2br Apartment With Skyline View, Optional Parking & Gym Access Near Mccormick Place, Lakefront And Soldier Field

apartment, Chicago
Suite - Queen Bed Non-smoking - Chicago
9.3 49 reviews

Suite - Queen Bed Non-smoking

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.

 - Chicago
No reviews

apartment, Chicago
Level Chicago - Old Town - Chicago
9.3 1130 reviews

Level Chicago - Old Town

hotel, Chicago
Chicago Cityview Chic -  Gold Coast/river North - Chicago
10 1 review

Chicago Cityview Chic - Gold Coast/river North

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

Explore Fulton Market + Retreat In Modern Comfort

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.

Entire House In Lakeview With Yard And Garage - Chicago
9.7 110 reviews

Entire House In Lakeview With Yard And Garage

house, Chicago
Top Of River West: Luxe Penthouse For Groups - Chicago
No reviews

Top Of River West: Luxe Penthouse For Groups

apartment, Chicago
Checkerboard Studio, Private Outdoor Hot Tub, Yard - Chicago
9.7 535 reviews

Checkerboard Studio, Private Outdoor Hot Tub, Yard

apartment, Chicago
Home Away From Home: 
Chicago Old Irving - Chicago
10 5 reviews

Home Away From Home: Chicago Old Irving

apartment, Chicago
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