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Vacation rentals in Chicago

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Chicago vacation rentals
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Best Vacation rentals and Airbnb offers 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.

Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied - Chicago
9.0 9 reviews
Chicago
07/02 – 07/06
$596/nighttotal: $2384 (4 )

Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied

3 10
apartment , Chicago
This spacious Chicago apartment rental, located in New City, offers easy access to Lake Michigan, Grant Park, the Art Institute, and the Field Museum.
The three-bedroom, three-bathroom unit sleeps 8-12 guests and boasts family-friendly amenities like a retro theater room, a dedicated kids' "Galaxy Room," and a well-equipped kitchen; nearby activities include water skiing, parasailing, sailing, and cycling.
Lovely 5bd|3br|parking |Sleeps 16|andersonville - Chicago
10 79 reviews
Chicago
07/08 – 07/13
$1095/nighttotal: $5475 (5 )

Lovely 5bd|3br|parking |Sleeps 16|andersonville

1 10
apartment , Chicago
This spacious apartment is located in Chicago's Uptown/Andersonville neighborhood, just a short walk from popular venues like Green Mill, Aragon Ballroom, and Riviera Theatre, offering easy access to both local attractions and public transportation. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 5-bedroom, 3-bathroom home comfortably accommodates up to 14 guests, making it perfect for families or groups. The apartment features a fully equipped kitchen, a dining area with an electric fireplace, a private garden, free on-site parking, and a variety of amenities for both leisure and business travelers, including high-speed internet, a workspace, and a washer and dryer.
Cozy Comfy Clean 420 Compliant Free Parking Quiet Neighborhood A Guest Favorite! - Chicago
10 125 reviews
Chicago
11/25 – 11/29
$226/nighttotal: $904 (4 )

Cozy Comfy Clean 420 Compliant Free Parking Quiet Neighborhood A Guest Favorite!

3 4
apartment , Chicago
This renovated bungalow apartment is located in Chicago's northwest corner, a short distance from Navy Pier, Michigan Avenue, and Grant Park, offering easy access to the city's top attractions. The property has received excellent guest ratings, making it a popular choice for travelers.
This comfortable home offers three bedrooms, one bathroom, and 1000 square feet of living space, comfortably accommodating up to 10 guests. Enjoy amenities such as a fully equipped kitchen, a Jacuzzi, a garden, a spa, and free street parking, along with complimentary breakfast, coffee, tea, and Wi-Fi.
Large 2-bedroom With Huge Roof Deck View Of Chicago Skyline - Chicago
8.3 6 reviews
Chicago
06/22 – 06/30
$462/nighttotal: $3696 (8 )

Large 2-bedroom With Huge Roof Deck View Of Chicago Skyline

2 2
apartment , Chicago
This two-bedroom apartment is located in Chicago's Wrigleyville neighborhood, just 2.5 miles from Wrigley Field, home of the Chicago Cubs.
The 1,350 square-foot apartment features a fully equipped kitchen, a spacious living room, two bathrooms, and a rooftop deck with stunning views of the Chicago skyline, comfortably accommodating up to seven guests.

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 parking

Midway Park - Chicago Landmark District - Chicago
10 1 review
Chicago
08/06 – 08/11
$225/nighttotal: $1125 (5 )

Midway Park - Chicago Landmark District

2 2
apartment , Chicago
This Chicago Landmark District apartment is located 5.6 miles from the United Center and within 8.2 miles of Union Station and Willis Tower.
This 1600 square foot rental features two bedrooms, accommodates up to seven guests, and includes on-site private parking, complimentary WiFi, and a fully equipped kitchen.
Large 4br/3ba Unit Near Field Museum & Mccormick Place - Chicago
Chicago
08/01 – 08/08
$938/nighttotal: $6566 (7 )

Large 4br/3ba Unit Near Field Museum & Mccormick Place

4 10
apartment , Chicago
This 4-bedroom, 3-bathroom condo is located in Chicago's South Loop, offering 10-minute access to McCormick Place and proximity to Soldier Field, Museum Campus, Grant Park, and Millennium Park.
This residence includes a fully equipped kitchen with a fridge, microwave, and dishwasher, high-speed Wi-Fi, an in-unit washer and dryer, and on-site paid parking for $40 per night.
Chic City Escape | 2br Retreat W/ Parking. - Chicago
10 181 reviews
Chicago
08/24 – 08/26
$221/nighttotal: $442 (2 )

Chic City Escape | 2br Retreat W/ Parking.

1 3
apartment , Chicago
This Wicker Park condo is a one-minute walk from Milwaukee Avenue and a five-minute walk from the Damen Blue Line station, providing easy access to public transportation and Chicago's attractions. This two-bedroom, one-bathroom apartment sleeps four, features free on-site parking, a modern interior with 11-foot ceilings, and a fully equipped kitchen including a dishwasher.
Flexhome Ukrainian Village • 2br • Convenient Walkability · Sleeps 6 - Chicago
Chicago
07/02 – 07/06
$384/nighttotal: $1536 (4 )

Flexhome Ukrainian Village • 2br • Convenient Walkability · Sleeps 6

1 5
apartment , Chicago
This 1-bedroom condo in Chicago's Ukrainian Village is 1.5 miles from the United Center and within 3.4 miles of downtown attractions such as Water Tower Chicago and Willis Tower.
This 700-square-foot apartment accommodates up to 6 guests and includes air conditioning, WiFi, and a kitchen with a fridge, microwave, and dishwasher.

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?

    52nd Floor Magmile Penthouse Views Fireplace Pool, 2bd/2ba Mag Mile Masterpiece (+Rooftop) and Kasa | Walk To Lincoln Park Zoo | Chicago are the most popular Airbnb and vacation rentals in Chicago among travelers.

  • 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.

Destinations nearby

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.

Newly Remodeled Gem | Heart Of Chicago - Chicago
9.4 6 reviews
Chicago
07/06 – 07/10
$271/nighttotal: $1084 (4 )

Newly Remodeled Gem | Heart Of Chicago

2 1
apartment , Chicago
This Humboldt Park, Chicago rental is conveniently located one mile from the Walt Disney House and 1.3 miles from Humboldt Park, offering easy access to other Chicago attractions via public transportation.
This 1300-square-foot, two-bedroom, one-bathroom apartment sleeps four and features a fully equipped kitchen, private balcony, in-unit laundry, and access to a shared garden and grills; nearby train stations provide convenient city access.
New! Heart Of East Village 2-bed 2-bath Peaceful Oasis - Chicago
Chicago
07/22 – 07/25
$541/nighttotal: $1623 (3 )

New! Heart Of East Village 2-bed 2-bath Peaceful Oasis

2 2
apartment , Chicago
This Chicago apartment is situated in the West Town neighborhood, offering proximity to Lake Michigan and Millennium Park, and is within 2 miles of the United Center.
This 1100 square foot rental features 2 bedrooms, 2 bathrooms, and accommodates up to 4 guests, with amenities including a private patio, an ensuite primary bathroom with a jacuzzi tub, and an in-unit washer and dryer.
1 Free Parking, Gym, Balcony, Sleeps 10 - Chicago
Chicago
07/03 – 07/05
$943/nighttotal: $1886 (2 )

1 Free Parking, Gym, Balcony, Sleeps 10

3 5
apartment , Chicago
This West Loop condo is a 5-minute walk from Fulton Market and within an 8-minute drive of downtown Chicago, Millennium Park, and Navy Pier.
This 1180 sqft residence accommodates up to 10 guests with 3 bedrooms, 2 bathrooms, and features include a private balcony, in-unit laundry, high-speed WiFi, and 1 garage parking space.
Chic Modern Loft Near United Center, Uic/imd & Downtown W/ Parking - Chicago
9.2 5 reviews
Chicago
01/01 – 01/31
$126/nighttotal: $3780 (30 )

Chic Modern Loft Near United Center, Uic/imd & Downtown W/ Parking

2 6
apartment , Chicago
This pet-friendly Chicago condo is situated in the Near West Side, a short drive from the United Center and Willis Tower, and a five-minute walk from the Western Subway Station.
This 1640-square-foot apartment rental boasts two bedrooms, two bathrooms, and accommodates up to ten guests, featuring a fully equipped kitchen, in-unit laundry, a terrace, and access to a garden and fitness center.

Neighborhoods and points of interest in Chicago

Best Chicago vacation rentals with air conditioning

Artistic Loft Rooftop | 13 Mins Dt | 4 Mins Lake - Chicago
10 53 reviews
Chicago
10/14 – 12/14
$154/nighttotal: $9394 (61 )

Artistic Loft Rooftop | 13 Mins Dt | 4 Mins Lake

1 1
apartment , Chicago
This Uptown Chicago apartment rental is conveniently located near Montrose Beach, a 9-minute walk from the Argyle Red Line station, offering easy access to attractions like the Aragon Ballroom and Riviera Theatre.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen with a dishwasher, in-unit laundry, a smart TV, and access to a rooftop deck with city views; a fitness center is also available on-site.
North Center - Modern, Safe, Family-friendly, Solar-powered Apartment - Chicago
9.9 304 reviews
Chicago
10/12 – 10/14
$253/nighttotal: $506 (2 )

North Center - Modern, Safe, Family-friendly, Solar-powered Apartment

2 4
apartment , Chicago
This charming 2-bedroom apartment is located just a short walk from Wrigley Field, in a safe neighborhood with easy access to public transportation, restaurants, and shops. It has received excellent ratings for location, cleanliness, and overall experience.
The 1000 square foot apartment comfortably sleeps up to 6 guests and features a modern kitchen, a private terrace, and a backyard. The apartment also offers high-speed internet, streaming services, a DVD player, and a washer and dryer, making it perfect for a relaxing and enjoyable stay in Chicago.
Serene Chic In Ravenswood Manor! 20 Mins To Grant Park Or Wrigley Field! - Chicago
Chicago
07/02 – 08/08
$123/nighttotal: $4551 (37 )

Serene Chic In Ravenswood Manor! 20 Mins To Grant Park Or Wrigley Field!

1 2
apartment , Chicago
This one-bedroom, one-bathroom apartment is located in Chicago's Ravenswood Manor/Albany Park neighborhood, offering easy access to the Brown Line just 1 block away, placing Wrigley Field and Lollapalooza under 20 minutes away.
This pet-friendly rental accommodates up to 6 guests with a Queen Air Bed, and features a chef's kitchen, private deck, free laundry, Wi-Fi, a dedicated office space, and a mini gym.
Bright New Modern 2 Bdrm + Den - Chicago
10 3 reviews
Chicago
09/01 – 10/31
$113/nighttotal: $6780 (60 )

Bright New Modern 2 Bdrm + Den

1 2
apartment , Chicago
This 3-bedroom, 2-bathroom apartment is situated in a safe Chicago neighborhood, a short walk from St. Anthony and Mt. Sinai hospitals, and close to the Illinois Medical District and Cinespace film production facility.
This residence accommodates up to 5 guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, plus an in-unit washer and dryer, and includes one reserved parking space.
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