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.

What are the most popular Airbnbs in Chicago?

Among the Airbnbs in Chicago, Beautiful Corner 2 Bedroom In The Loop | Roof Deck , Kasa | Walk To Lincoln Park Zoo | Chicago and 52nd Floor Magmile Penthouse Views Fireplace Pool are the most popular ones.

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?

52nd Floor Magmile Penthouse Views Fireplace Pool , Beautiful Corner 2 Bedroom In The Loop | Roof Deck and Amazing Location | Luxury Apt | Rooftop Pool 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?

The best rentals for families and kids in Chicago are 2bd/2ba Mag Mile Masterpiece (+Rooftop) , Dtown Penthouse #2|safe Vintage 3bd +Gym & Balcony and Urban Chicago Loft - 1 Blk To Train W/ 2 Pkg Spots .

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?

The best vacation rentals or Airbnb with a jacuzzi in Chicago are Train Ride To Chicago - Welcome Home , Sun Filled Tranquil 2 Br Great Part Of Logan Sq and "Home Away From Home" - Free Street Parking .

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).

Chicago Vacation rentals & Airbnb

9.8 286 reviews

Chicago

07/08 – 07/12

$304/nighttotal: $1216 (4 )

1br South Loop Loft I Superhost + Top Rated!

1 1

apartment , Chicago

This Chicago apartment is located in the South Loop, just a short walk from Grant Park and a quick drive to McCormick Place and the Museum Campus. The area has a lively atmosphere with plenty of restaurants, bars, and shops. This property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The apartment offers a spacious layout perfect for a group of up to four guests. Enjoy modern amenities like a fully equipped kitchen, high-speed internet, a comfortable king-size bed, and a washer/dryer, all within this unique space housed in a renovated Post Office building.

9.7 212 reviews

Chicago

08/26 – 08/30

$199/nighttotal: $796 (4 )

Lovely And Cozy Suite On Southport !

1 2

apartment , Chicago

This two-bedroom Chicago apartment is conveniently located in the Southport Corridor neighborhood, less than a mile from Wrigley Field.
The unit offers a full kitchen with a fridge, microwave, and dishwasher, accommodates three guests, and includes air conditioning, a garden, and parking; nearby attractions and public transportation ensure easy access to Chicago's offerings.

9.8 151 reviews

Chicago

07/13 – 07/15

$638/nighttotal: $1276 (2 )

Spacious Downtown 3br With Free Parking

1 8

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.

9.9 177 reviews

Chicago

06/23 – 06/27

$272/nighttotal: $1088 (4 )

Custom Apartment In The Heart Of Avondale

1 2

apartment , Chicago

This two-bedroom, one-bathroom apartment rental is located in Chicago's Lakeview neighborhood, two blocks from the Belmont Blue Line station, offering easy access to downtown, Wrigley Field, and O'Hare International Airport.
The second-floor unit sleeps six with a pull-out couch, full kitchen, in-unit laundry, and amenities including Netflix, cable TV, and a private balcony; nearby attractions include shops and restaurants.

9.9 153 reviews

Chicago

09/01 – 09/05

$255/nighttotal: $1020 (4 )

Lovely Top Floor 2br/2ba, Steps From Everything!

1 2

apartment , Chicago

This two-bedroom, two-bathroom apartment rental in Chicago's Avondale neighborhood is a 7-minute walk from the CTA Blue Line and a 15-minute drive from Wrigley Field.
The unit features a fully equipped kitchen with stainless steel appliances, a private backyard Weber grill, in-unit laundry, and accommodates up to four guests with two queen beds; nearby attractions include award-winning restaurants and bars.

9.5 1340 reviews

Chicago

07/23 – 07/27

$428/nighttotal: $1712 (4 )

Kasa | Spectacular City Views | Chicago

1 2

apartment , Chicago

This one-bedroom Chicago apartment boasts a prime downtown location, steps from Oak Street Beach and a short walk from Michigan Avenue's Magnificent Mile and Millennium Park.
The 1-bathroom unit sleeps 3 guests and features a full kitchen with dishwasher, in-unit laundry, and self check-in, plus access to a fitness center, garden, and parking.

9.5 2 reviews

Chicago

09/06 – 09/13

$373/nighttotal: $2611 (7 )

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

2 7

apartment , Chicago

This family-friendly Chicago apartment rental is located approximately 1.5 miles from the Field Museum and within 2 miles of the Art Institute of Chicago and the Chicago Symphony Orchestra.
This 800-square-foot, two-bedroom, two-bathroom unit comfortably sleeps eight guests and offers amenities including a fully equipped kitchen, free Wi-Fi, on-site parking, a fitness center, and a private patio with skyline views.

9.9 100 reviews

Chicago

07/20 – 07/24

$215/nighttotal: $860 (4 )

Bustin’ A Mauve • Vintage Flat Near Wrigley

1 2

apartment , Chicago

This Wrigleyville apartment is a 4-minute walk from Wrigley Field, a 5-minute walk from the Southport Corridor, and offers easy access to the Red and Brown Line 'L' train stations.
The unit sleeps two guests, features a kitchen with a fridge, freezer, and microwave, and includes free membership to The Metropolitan co-working space in the Willis Tower.

9.6 100 reviews

Chicago

06/23 – 06/26

$171/nighttotal: $513 (3 )

Cozy Apartment In Lake View

1 2

apartment , Chicago

This Lake View studio apartment is ideally located near the Brown Line CTA, a 20-minute walk from Wrigley Field and Boystown.
The unit features a 50" Roku TV with streaming services, a fully equipped kitchen with microwave and dishwasher, a private entrance, and accommodates two guests; paid washer/dryer access is available in the building.

Chicago

08/01 – 08/08

$617/nighttotal: $4319 (7 )

Renovated 3 Bedroom Chicago Downtown Pilsen

1 10

apartment , Chicago

This renovated 3-bedroom rental unit is located in Chicago's Pilsen neighborhood, 1.9 miles from the United Center and approximately 3.5 miles from Union Station and Willis Tower.
This 1300 square foot apartment accommodates up to 16 guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a private patio, and complimentary WiFi, with a casino and cycling opportunities nearby.

9.9 352 reviews

Chicago

07/15 – 07/22

$342/nighttotal: $2394 (7 )

Perfect Spot & Spacious 2br+2ba | Mapletree Suites

2 2

apartment , Chicago

This Chicago apartment is located in the West Loop neighborhood, just two blocks from a Target store and a block away from Skinner Park, offering a convenient location for exploring the city. The apartment has excellent user, location, and cleanliness ratings.
This two-bedroom, two-bathroom apartment features a private balcony and in-unit laundry. Guests can enjoy a fully equipped kitchen, keyless entry, and on-site luggage storage.

9.7 103 reviews

Chicago

09/21 – 09/25

$339/nighttotal: $1356 (4 )

River North | Rooftop With In & Out Parking | 5

2 2

apartment , Chicago

This downtown Chicago apartment offers easy access to many attractions, including a short walk or ride to Millennium Park and the Magnificent Mile.
This 1000-square-foot, two-bedroom unit sleeps six, features a fully equipped kitchen, free parking, and access to a fitness center and rooftop patio with BBQ grill.

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.

Chicago

07/01 – 07/31

$359/nighttotal: $10770 (30 )

South Loop Chicago 2br Retreat With Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field

1 2

apartment , Chicago

This Chicago apartment is located in River North, a 5-minute walk from the Magnificent Mile and the Chicago Riverwalk.
This 900 sq ft unit features 1 bathroom, air conditioning, a full kitchen with a fridge, microwave, and dishwasher, and offers access to a fitness center and parking.

9.7 38 reviews

Chicago

07/03 – 07/05

$418/nighttotal: $836 (2 )

Bright Apt In Heart Of Chinatown

1 4

apartment , Chicago

This Chinatown Chicago apartment rental is two blocks from the Red Line, a 10-minute drive from McCormick Place and downtown, and near Ping Tom Park with water taxi access to the Magnificent Mile and West Loop.
The three-bedroom, two-bathroom unit sleeps six, features a full kitchen with dishwasher, in-unit laundry, and a Google Chromecast; nearby attractions include diverse Asian restaurants and shops.

9.9 67 reviews

Chicago

06/17 – 06/21

$880/nighttotal: $3520 (4 )

Cityline Views • Rooftop • Free Ev Garage Parking

1 8

apartment , Chicago

This two-bedroom, two-bathroom Chicago apartment boasts excellent location near the Western Blue Line, offering a quick 15-minute commute to downtown.
The 2024-built unit features a private balcony with city skyline views, free secure indoor parking (though space is tight), a fully equipped kitchen, and accommodates up to 11 guests with zero-stair access and elevator.

10 13 reviews

Chicago

06/19 – 06/21

$912/nighttotal: $1824 (2 )

Architect-designed 2br Oak Park Flat

1 2

apartment , Oak Park

This renovated 2-bedroom, 1-bathroom apartment in Oak Park is a short walk from historic cultural attractions and offers direct access to Chicago's Green Line for easy city travel.
This 1923 building unit accommodates up to 4 guests and features a full kitchen, air conditioning, and shared roof deck access, with 3 Fold Bakery located downstairs.

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

9.9 35 reviews

Chicago

10/09 – 10/13

$796/nighttotal: $3184 (4 )

Skyline Oasis: City & Lake Views

1 2

apartment , Chicago

This Chicago apartment is located in the Fulton Market District, a trendy neighborhood near the Chicago River and a short drive from Lake Michigan. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This apartment is perfect for couples or solo travelers seeking a stylish and modern accommodation in a vibrant part of the city. It features a spacious layout with a full kitchen, a dedicated work area, a king-size bed, and a balcony offering stunning city views. You can also enjoy the building's amenities like a swimming pool, jacuzzi, fitness center, and a garden.

9.9 254 reviews

Chicago

07/03 – 07/05

$1969/nighttotal: $3938 (2 )

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

4 2

apartment , Chicago

This charming basement dwelling is located just two blocks from Lake Michigan and Lincoln Park, placing you in the heart of Chicago's vibrant East Lakeview neighborhood. The apartment boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious home has four bedrooms and two bathrooms, comfortably accommodating up to 20 guests. The apartment offers a full kitchen, a private backyard, a garage, and a 85-inch HDTV, making it perfect for families or groups looking to explore all that Chicago has to offer.

9.1 1737 reviews

Chicago

06/20 – 06/27

$568/nighttotal: $3976 (7 )

The Robey, Chicago, A Member Of Design Hotels

1 2

boutique hotel , Chicago

The Robey, Chicago, A Member of Design Hotels, is located in the Wicker Park neighborhood, a short distance from the Magnificent Mile, Lincoln Park Zoo, and Wrigley Field.
This 4-star hotel features a rooftop lounge with city views, a French-American restaurant, a fitness center, and a spa, as well as in-room amenities like a flat-screen TV and a Bluetooth-enabled sound system.

Chicago

06/26 – 06/28

$244/nighttotal: $488 (2 )

Midway Hideaway - Spacious Chicago Apartment Near Midway Airport

1 2

apartment , Chicago

This 1-bedroom, 1-bathroom apartment in Chicago's Gage Park neighborhood is located 3 miles from Midway Airport and offers easy access to CTA bus routes and the Orange Line for travel to downtown attractions.
This unit accommodates up to 4 guests and features a sofa bed in the living area, a functional kitchen, shared yard space, and shared basement laundry facilities, with convenient street parking available on 56th Street.

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.
What are the most popular Airbnbs in Chicago?
Among the Airbnbs in Chicago, Beautiful Corner 2 Bedroom In The Loop | Roof Deck, Kasa | Walk To Lincoln Park Zoo | Chicago and 52nd Floor Magmile Penthouse Views Fireplace Pool are the most popular ones.
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?
52nd Floor Magmile Penthouse Views Fireplace Pool, Beautiful Corner 2 Bedroom In The Loop | Roof Deck and Amazing Location | Luxury Apt | Rooftop Pool 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?
The best rentals for families and kids in Chicago are 2bd/2ba Mag Mile Masterpiece (+Rooftop), Dtown Penthouse #2|safe Vintage 3bd +Gym & Balcony and Urban Chicago Loft - 1 Blk To Train W/ 2 Pkg Spots.
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?
The best vacation rentals or Airbnb with a jacuzzi in Chicago are Train Ride To Chicago - Welcome Home, Sun Filled Tranquil 2 Br Great Part Of Logan Sq and "Home Away From Home" - Free Street Parking.
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).

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.

9.4 48 reviews

Chicago

06/21 – 06/26

$485/nighttotal: $2425 (5 )

3br Modern Condo Near Wrigley/dwtn +Free Parking

3 5

apartment , Chicago

This apartment is located in the Lincoln Park neighborhood, just a short distance from Wrigley Field, downtown Chicago, and O'Hare Airport, offering easy access to the city's best attractions. It has received excellent user ratings, making it a popular choice for travelers.
This 4-bedroom home comfortably accommodates 7 guests, providing plenty of space for families or groups. Amenities include a fully equipped kitchen, a private study, free parking, a washer/dryer, and a jacuzzi, making it a perfect choice for a relaxing and enjoyable stay.

9.1 26 reviews

Chicago

06/22 – 06/24

$168/nighttotal: $336 (2 )

Gallery Loft Of Oak Park #1 Top Host In Il

1 2

apartment , Oak Park

The Gallery Loft of Oak Park apartment rental is conveniently located in Oak Park, Illinois, 7.1 miles from the United Center, 8.6 miles from Union Station, and 6.8 miles from Midway International Airport.
This 900-square-foot, one-bedroom, one-bathroom unit sleeps five guests and features a private terrace, garden access, on-site parking, a tennis court, and free Wi-Fi.

10 9 reviews

Chicago

09/12 – 09/15

$693/nighttotal: $2079 (3 )

Your Chicago Home Base 4br, 2ba, Sleeps 15, Ideal For Families & Groups!

4 7

apartment , Chicago

This Albany Park rental is conveniently located in Chicago, offering easy access to Lincoln Park Zoo and the Field Museum, with Michigan Avenue and Navy Pier also within reasonable travel distance.
This 3-bedroom, 2-bathroom shared apartment features a private room, granite countertops, stainless steel appliances, free parking, and accommodates up to two guests.

9.2 12 reviews

Chicago

10/09 – 10/12

$2483/nighttotal: $7449 (3 )

Luxury Designer Penthouse 3802 | Pool | Gold Coast

3 2

apartment , Chicago

This apartment is conveniently located in the heart of downtown Chicago, within walking distance of Michigan Avenue and State Street. It offers a unique blend of comfort and convenience, with a spacious layout of 1500 square feet and a guest capacity of 10.
The apartment boasts a fully equipped kitchen, air conditioning, a private terrace, access to a communal swimming pool, and an on-site fitness center. It is also close to public transportation and major tourist attractions, making it an ideal choice for travelers seeking a comfortable and well-located accommodation in Chicago.

Neighborhoods and points of interest in Chicago

Best Chicago vacation rentals with air conditioning

9.9 109 reviews

Chicago

08/10 – 08/13

$286/nighttotal: $858 (3 )

New 2 Br/1 Bth, Free Parking, Near Lake & Loyola

1 3

apartment , Chicago

This brand-new Rogers Park garden apartment is located steps from Loyola University Chicago and a short walk to Lake Michigan, offering easy Red Line access to downtown.
The two-bedroom, one-bathroom unit features a spacious open floor plan, accommodating up to six guests and including amenities such as free on-site parking, a shared patio, and kitchen essentials.

8.8 7 reviews

Chicago

07/02 – 07/06

$198/nighttotal: $792 (4 )

Sleek 1-bedroom Apt In Chicago - East Park Tower 0610 Rep

1 2

apartment , Chicago

This Hyde Park one-bedroom apartment is conveniently located near the Museum of Science and Industry and 57th Street Beach, with easy public transport access to downtown Chicago.
The 620-square-foot unit sleeps seven guests and features a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and a separate bedroom.

9.8 92 reviews

Chicago

07/22 – 07/23

$535/nightfor 1 night

Entire Home W/ 2bath 7 Beds & 2car Private Parking

1 8

apartment , Cicero

This 4-bedroom, 1-bathroom house in Cicero offers a private residential feel with easy access to Chicago's urban attractions, ideal for families and larger groups.
This accommodation features a private backyard, air conditioning, parking, and a full kitchen with a fridge, freezer, and microwave, accommodating up to 10 guests.

9.5 107 reviews

Chicago

08/13 – 08/18

$880/nighttotal: $4400 (5 )

Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio!

4 8

apartment , Chicago

This four-bedroom Chicago home is conveniently located less than 10 minutes from downtown, offering easy access to Chicago's major attractions.
The 2-bathroom house, comfortably sleeping 10 guests, features a fully equipped kitchen, private patio with Solostove and smoker, six 55" Smart TVs, a game area, and free street parking.

Vacation rentals in Chicago

Best Vacation rentals and Airbnb offers in Chicago

1br South Loop Loft I Superhost + Top Rated!

Lovely And Cozy Suite On Southport !

Spacious Downtown 3br With Free Parking

Custom Apartment In The Heart Of Avondale

Lovely Top Floor 2br/2ba, Steps From Everything!

Kasa | Spectacular City Views | Chicago

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

Bustin’ A Mauve • Vintage Flat Near Wrigley

Cozy Apartment In Lake View

Renovated 3 Bedroom Chicago Downtown Pilsen

Perfect Spot & Spacious 2br+2ba | Mapletree Suites

River North | Rooftop With In & Out Parking | 5

South Loop Chicago 2br Retreat With Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field

Bright Apt In Heart Of Chinatown

Cityline Views • Rooftop • Free Ev Garage Parking

Architect-designed 2br Oak Park Flat

The Loop

Gold Coast

Wicker Park

Lakeview

Lincoln Park

West Loop

Logan Square

Hyde Park

Pilsen

Skyline Oasis: City & Lake Views

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

The Robey, Chicago, A Member Of Design Hotels

Midway Hideaway - Spacious Chicago Apartment Near Midway Airport

3br Modern Condo Near Wrigley/dwtn +Free Parking

Gallery Loft Of Oak Park #1 Top Host In Il

Your Chicago Home Base 4br, 2ba, Sleeps 15, Ideal For Families & Groups!

Luxury Designer Penthouse 3802 | Pool | Gold Coast

New 2 Br/1 Bth, Free Parking, Near Lake & Loyola

Sleek 1-bedroom Apt In Chicago - East Park Tower 0610 Rep

Entire Home W/ 2bath 7 Beds & 2car Private Parking

Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio!