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.

Blueground | W. Loop, Pool, In Heart Of Greektown - Chicago
9.5 4 reviews

Blueground | W. Loop, Pool, In Heart Of Greektown

apartment, Chicago
This one-bedroom apartment is in Chicago's West Loop, a trendy neighborhood with restaurants, bars, and art galleries, all within walking distance. The apartment has excellent ratings for location, cleanliness, and user experience.
The apartment has a comfortable bedroom, a fully equipped kitchen, and a modern bathroom. You'll enjoy amenities such as a swimming pool, a fitness center, and a laundry facility.
Livn Millennium Park Downtown Chicago Superior 1br - Chicago
9.4 14 reviews

Livn Millennium Park Downtown Chicago Superior 1br

apartment, Chicago
This downtown Chicago condo offers a prime location, just a 6-minute walk from Millennium Station and 0.4 miles from the city center, placing you 600 yards from DePaul University and near attractions like Cloud Gate – The Bean.
This 450 square foot studio apartment accommodates up to three guests, featuring a full kitchen with a microwave and dishwasher, air conditioning, free WiFi, and an in-unit washer for convenience.
Luxury 2br Apartment In Downtown Chicago - Chicago
9.9 48 reviews

Luxury 2br Apartment In Downtown Chicago

apartment, Chicago
This River West Chicago apartment boasts a prime location, a 5-minute walk from multiple CTA train lines and a 9-minute drive from downtown, placing you near top restaurants like Avec and Piccolo Sogno.
The two-bedroom, two-bathroom unit sleeps four, offering in-unit laundry, Gigabit Wi-Fi, smart home technology, and building amenities including a rooftop deck, fitness center, and secure package lockers; a high chair and crib are available upon request.
The Drake - Designer Highrise Condo W/ Gym, Pool - Chicago
10 5 reviews

The Drake - Designer Highrise Condo W/ Gym, Pool

apartment, Chicago
This downtown Chicago condo is centrally located, within a 5–15 minute walk or drive of Michigan Avenue, Navy Pier, Millennium Park, and several beaches.
The one-bedroom unit sleeps three, features a fully equipped kitchen with dishwasher, in-unit laundry, two Smart TVs, a dedicated workspace, and access to a swimming pool, fitness center, and parking (fee applies).

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

Wrigleyville Oasis 1 Minute Walk To Wrigley Field - Chicago
9.9 56 reviews

Wrigleyville Oasis 1 Minute Walk To Wrigley Field

apartment, Chicago
This Wrigleyville apartment rental is a half block from Wrigley Field, under five minutes from the main Wrigleyville area, and a 15-minute walk from Lake Michigan and downtown Chicago.
The two-bedroom, one-bathroom unit sleeps six guests comfortably and features a full kitchen, in-apartment entertainment (Netflix, Hulu Live, Disney+, Prime on a 50" TV), complimentary street parking for one car, and a coffee and tea bar with breakfast items.
6br Apt  Workspace  Near Lakefront + Red Line - Chicago
No reviews

6br Apt Workspace Near Lakefront + Red Line

apartment, Chicago
This spacious 6-bedroom apartment offers convenient access to Chicago's lakefront, situated near Lake Michigan beaches and the Red Line station for easy city exploration.
Accommodating up to 12 guests, this family-friendly rental features individual air conditioning in each room, a fully equipped kitchen, and includes a Pack 'n Play and High Chair, with coin-operated laundry available in the basement.
️ Great Apt, 3 Miles West Of Wrigley Field ️ - Chicago
10 124 reviews

️ Great Apt, 3 Miles West Of Wrigley Field ️

apartment, Chicago
This spacious Chicago apartment, ideal for families or groups, is conveniently located in Chicagoland near two Metra stations and the Blue Line, offering easy access to various Chicago neighborhoods and attractions.
The 1800-square-foot rental boasts three bedrooms, one bathroom, and sleeps six, featuring a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, and parking.
Logan Square Lookout - Chicago
9.7 633 reviews

Logan Square Lookout

apartment, Chicago
This Logan Square apartment is conveniently located just a short walk from the Blue Line train station, making it easy to explore all that Chicago has to offer. The neighborhood is known for its lively atmosphere, with plenty of restaurants, bars, and shops to discover. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom apartment comfortably accommodates up to four guests. The apartment features a well-equipped kitchen, a private backyard, on-site laundry facilities, and free street parking with a permit.

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.

Spacious 2br South Loop With Skyline View, Optional Parking And Gym Access Near Mccormick Place And - Chicago
No reviews

Spacious 2br South Loop With Skyline View, Optional Parking And Gym Access Near Mccormick Place And

apartment, Chicago
Apartment. You will be in Chicago.
Facilities and services include an elevator, a dish washer and a washing machine. This apartment in Chicago also has a gym!
Blueground River North Pool Gym Nr Mile Chi-1143 - Chicago
No reviews

Blueground River North Pool Gym Nr Mile Chi-1143

apartment, Chicago
This River North condo is located 0.3 miles from Ohio Street Beach and 0.7 miles from Millennium Park, offering proximity to Water Tower Chicago and the Art Institute of Chicago.
This 1040 square foot, two-bedroom, two-bathroom residence accommodates up to 7 guests and features a private balcony, an indoor swimming pool, a fitness center, and paid on-site parking.
Chicago - Pilsen Studio Apartment - Unit B - Chicago
8.9 8 reviews

Chicago - Pilsen Studio Apartment - Unit B

studio, Chicago
This Pilsen studio apartment is located 2.4 miles from the United Center and 3.7 miles from Guaranteed Rate Field, offering easy access to Chicago's major attractions.
This one-bedroom apartment, sleeping up to three guests, features a kitchenette, private terrace, garden access, free Wi-Fi, and parking.
Brilliant Downtown Chicago 3-bedroom Condominium - Chicago
9.8 257 reviews

Brilliant Downtown Chicago 3-bedroom Condominium

apartment, Chicago
This apartment is located in downtown Chicago, just steps from the Godfrey Hotel and the Magnificent Mile, offering easy access to the city's best shopping, dining, and entertainment. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a pleasant and comfortable stay. This spacious dwelling offers 1600 square feet of living space, comfortably accommodating up to eight guests with three bedrooms and two bathrooms. The apartment includes a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, smart home features, a private garden, and parking options, making it ideal for families and groups seeking a convenient and comfortable home base for exploring Chicago.

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.

Daquietplacetorelax/5bdrm/15min Downtown/8mmidway. - Chicago
9.6 158 reviews

Daquietplacetorelax/5bdrm/15min Downtown/8mmidway.

apartment, Chicago
This apartment is located in the quiet Brighton Park neighborhood, just minutes from downtown Chicago and major attractions like Chinatown, McCormick Place, and Soldier Field. It has excellent user and location ratings, and is very clean.
It is a spacious and comfortable apartment that can accommodate up to 16 people in five bedrooms. It has a fully equipped kitchen, a private back patio, and modern amenities like keyless locks, a safety box, Wi-Fi, and four smart TVs. It also has private garage parking available for a special rate.
Luxéry Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena - Chicago
8.6 169 reviews

Luxéry Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena

apartment, Chicago
This apartment is located in Chicago's South Loop neighborhood, just a short distance from McCormick Place and Wintrust Arena, making it ideal for travelers attending events at these venues. The apartment has received very good user ratings, excellent location ratings, and excellent cleanliness ratings.
The apartment offers a comfortable and convenient stay with modern amenities like air conditioning, a kitchen, and a terrace or balcony. You can enjoy the on-site fitness center, parking, and easy access to public transportation, making it easy to explore all that Chicago has to offer.
The Loyola Garden Flat: Huge 2br Near Lake - Chicago
9.9 147 reviews

The Loyola Garden Flat: Huge 2br Near Lake

apartment, Chicago
This East Rogers Park apartment rental is conveniently located a few blocks from the Loyola Red Line 'L' station, offering easy access to Wrigleyville in 15 minutes and downtown Chicago in 18 minutes.
The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchenette with a dishwasher, private garden access, and family-friendly amenities like a pack 'n play and high chair available upon request.
Lincoln Park Light-filled Loft - Chicago
9.9 330 reviews

Lincoln Park Light-filled Loft

apartment, Chicago
This studio apartment is located in Lincoln Park, a neighborhood with parks, restaurants, and shops, within walking distance of the Lincoln Park Zoo and a short drive from the Magnificent Mile. The studio has excellent user, location, and cleanliness ratings.
This apartment is a converted storefront with a spacious open-concept living area, a two-level layout, and a floor area of 800 square feet, comfortably accommodating up to four guests. The studio has a fully equipped kitchen, a comfortable queen-sized bed, a garden, parking, and internet access, making it perfect for travelers who want to enjoy the city and have a comfortable place to relax.

Best Chicago vacation rentals with parking

Wicker Park/bucktown Condo With Large Balcony - Chicago
9.8 125 reviews

Wicker Park/bucktown Condo With Large Balcony

apartment, Chicago
Home Near Wrigley With A Garage. - Chicago
9.8 131 reviews

Home Near Wrigley With A Garage.

apartment, Chicago
Modern 2 Bdrm Apt Near O'hare-downtown. King Bed. - Chicago
9.7 148 reviews

Modern 2 Bdrm Apt Near O'hare-downtown. King Bed.

apartment, Chicago
Chatham Beauty - Chicago
9.2 59 reviews

Chatham Beauty

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.

Colorful & Peaceful Boho-chic Unit In Logan Square - Chicago
9.9 235 reviews

Colorful & Peaceful Boho-chic Unit In Logan Square

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.

California Cottage/4br Prime Location Logan Square - Chicago
9.7 132 reviews

California Cottage/4br Prime Location Logan Square

apartment, Chicago
Big Family Escape, W/parking, Love Pets - Chicago
9.6 186 reviews

Big Family Escape, W/parking, Love Pets

apartment, Oak Park
13 Mins Dt | 4 Mins Lake | Artistic Loft Rooftop - Chicago
9.8 59 reviews

13 Mins Dt | 4 Mins Lake | Artistic Loft Rooftop

apartment, Chicago
Logan Sq 4br Duplex  Garage  Sleeps 8 - Chicago
10 1 review

Logan Sq 4br Duplex Garage Sleeps 8

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.

Level Two Bedroom Suite | Fulton Market - Chicago
9.7 42 reviews

Level Two Bedroom Suite | Fulton Market

apartment, Chicago
River North 1br W Pool Fitness 1 Block To L Chi-1039 - Chicago
No reviews

River North 1br W Pool Fitness 1 Block To L Chi-1039

apartment, Chicago
West Loop 2br With Skyline Views + Prime Location - Chicago
10 5 reviews

West Loop 2br With Skyline Views + Prime Location

apartment, Chicago
The Waldorf® Highrise W/ City Views, Gym, King Bed - Chicago
No reviews

The Waldorf® Highrise W/ City Views, Gym, King Bed

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.

Sweet Home Chicago - Chicago
10 3 reviews

Sweet Home Chicago

apartment, Chicago
1br In Luxury Building W/ Rooftop Pool - Chicago
No reviews

1br In Luxury Building W/ Rooftop Pool

resort, Chicago
Fully Furnished Gold Coast Luxury Condo With Sunset View Ideal For 30+ Day Stays - Chicago
No reviews

Fully Furnished Gold Coast Luxury Condo With Sunset View Ideal For 30+ Day Stays

apartment, Chicago
Casa Brookfield - 5 Bedroom- Hot Tub Retreat - Chicago
10 1 review

Casa Brookfield - 5 Bedroom- Hot Tub Retreat

house, Brookfield
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