Bring your appetite when you travel to Chicago — not just for food, but also for design, culture, architecture, and adventure. Dive into everything the Windy City has to offer, like stand-up paddleboarding in Lake Michigan, cheering on the Chicago Cubs at Wrigley Field, exploring the city’s endless art galleries and museums, and strolling the gardens at Millennium Park. Need a shopping fix? Take a weekend getaway and browse through the luxury brands lining the Magnificent Mile and the boutiques of River North. No visit to Chicago is complete without taking an architecture cruise on the Chicago River or devouring the city’s eclectic and classic eats. A slice of deep-dish pizza, anyone? Between the trendy cocktails in Logan Square and the Centennial Wheel at Navy Pier, you’ll find what will make your Chicago vacation so much better — Chicago vacation homes and hotels that put you right in the middle of the action, like cosmopolitan hotel suites and penthouses on the Gold Coast. Prefer nature and trees over city skyscrapers? Cozy log cabin rentals await in nearby state parks.

Top vacation rentals in Chicago

Interior
4.9
Outstanding(374 Reviews)
Apartment hotel
 in Chicago
52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi
4 guests · 1 bedroom · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Chicago? Our Apartment hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Award winning views
4.9
Outstanding(260 Reviews)
Apartment hotel
 in Chicago
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
8 guests · 3 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Chicago? Our Apartment hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Property view
4.2
Excellent(969 Reviews)
Hotel
 in Chicago
3star
Hampton Inn Chicago McCormick Place
Pool · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Chicago? Look no further than our Hotel, Hampton Inn Chicago McCormick Place. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property view
4.0
Good(226 Reviews)
Apartment hotel
 in Chicago
Sonder The Plymouth
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Sonder The Plymouth, our elegant Apartment hotel in Chicago. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Vacation rentals with internet & wifi in Chicago

Beautiful space for family vacation, girls getaways
5.0
Outstanding(179 Reviews)
Condo
 in Chicago
Magic Factory Loft 2West
10 guests · 3 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Enjoy the best of Chicago in our Condo, Magic Factory Loft 2West. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Living area
4.8
Outstanding(225 Reviews)
Condo
 in Chicago
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
6 guests · 3 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Chicago with a stay at Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!, a top rated Condo with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
3.9
Good(558 Reviews)
Hotel
 in Chicago
4star
The Drake Hotel
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Chicago? Our Hotel might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$
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Property view
3.6
Good(1,097 Reviews)
Hotel
 in Chicago
3star
Best Western Grant Park Hotel
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Chicago for Hotel, for $99 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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city photo
Chicago

Chicago travel guide

Let us help you plan your perfect Chicago vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chicago, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Chicago?

  • Internet / Wifi
  • Air conditioner
  • TV

What are the top attractions in Chicago?

Chicago has plenty of top attractions, making it one of the most dynamic cities in the world. Some of these attractions include:
  • Millenium Park
  • - Chicago Riverwalk
  • - Navy Pier
  • - Lake Michigan Lakefront Trail
  • - Willis Tower
  • - 360 Chicago
  • - Michigan Avenue and Magnificent Mile
  • - Wrigley Field
  • - Lincoln Park
  • - Second City Comedy Club
  • - Cloud Gate

Is Chicago a good place for a family vacation?

Yes, Chicago is a great place for a family vacation. Your whole family will fall in love with Chicago’s unique attractions and experiences, such as:
  • Scoping out the view at the Willis Tower Skydeck
  • Riding the Centennial Wheel at Navy Pier
  • Taking a boat or kayak tour on the Chicago River
  • Catching a game at Wrigley Field
  • Exploring the Museum of Science and Industry
  • Getting lost in the Chicago Children’s Museum

When is the best time of year to visit Chicago?

The best time of year to visit Chicago is late spring between April to May and fall in September or October, when you’ll experience pleasant temperatures, fewer crowds, and some of Chicago’s most popular events — including the Hyde Park Jazz Festival, baseball home opener games, and Chicago Restaurant Week.

What is the Chicago Loop?

Exploring the Loop on foot is a can't-miss activity when visiting Chicago. Enjoy historical buildings, shopping, art galleries, and delicious food. Put the iconic Bean in Millennium Park on your list, and swing through the Theater District as well.

What is the Humboldt Park area in Chicago known for?

The Spanish Colonial architecture in Humboldt Park helps create a distinctively Latin aura. This is even more evident in the specialty shopping and cuisine.

What is the Lakeview area in Chicago known for?

Lakeview is a thriving lakefront community with a wide array of attractions. Street festivals are popular during the summer, and acres of green space offer breathtaking beauty.

What are the best neighborhoods to visit in Chicago, IL?

  • The Loop: Located in the heart of downtown Chicago and is home to iconic attractions like the Willis Tower, Millennium Park, and the Art Institute of Chicago.
  • Wicker Park: Popular among young professionals and students, with trendy bars, restaurants, and shops.
  • Lincoln Park: A vibrant and sophisticated neighborhood, with lush parks, beaches, and cultural attractions.

What are the most popular vacation rental amenities in Chicago, IL?

The most popular vacation rental amenities in Chicago, IL include:

  • High-speed Wi-Fi
  • Fully-equipped kitchens
  • Washer/Dryer
  • Air conditioning
  • Balcony/Patio Area

Having access to high-speed Wi-Fi is a must-have for many travelers who need to stay connected while away from home. Fully-equipped kitchens provide the convenience of being able to prepare meals in the comfort of your rental unit. The inclusion of a washer and dryer ensures that laundry needs can be tended to without having to leave the property. Air conditioning is essential in the summer months, and a balcony or patio area can provide a great spot for outdoor relaxation.

What are the must-visit tourist attractions in Chicago, IL?

Chicago, IL is a great city to visit and has many attractions that should not be missed. Here are four must-visit tourist attractions in Chicago:

  • The Magnificent Mile
  • The Art Institute of Chicago
  • The Willis Tower
  • Millennium Park
Visitors can explore the shops and restaurants of The Magnificent Mile, admire the artwork and architecture of The Art Institute of Chicago, take in the views from the top of The Willis Tower, and enjoy the outdoor beauty of Millennium Park. Chicago offers something for everyone, and these four attractions are a great place to start.

How can I get around in Chicago, IL?

There are a variety of ways to get around Chicago, IL:

  • By car
  • By train
  • By bike
  • By foot

You can also use ride-hailing services, such as Uber and Lyft, or take a bus or cab.

Where can I find affordable accommodation in Chicago, IL?

Chicago, IL is an exciting city to visit with a variety of affordable accommodation options. Here are some of the best:

  • Freehand Chicago – an upscale hostel with modern amenities and a great location in the heart of the city.
  • The Willows Hotel – a vibrant boutique hotel with a central location and a wealth of amenities.
  • La Quinta Inn & Suites Chicago Downtown – a budget-friendly hotel with comfortable, modern rooms and a great location.
  • The Hyatt Place Chicago/Downtown – The Hyatt Place offers great value for money and is conveniently located close to the city's main attractions.

What is the culture like in Chicago, IL?

Chicago has a rich culture, offering something for everyone. From its music and art scenes to its culinary offerings, the city has something to offer everyone. Here are a few aspects of Chicago's culture:

  • The city is known for its great music, including jazz, blues, house music and gospel.
  • It is home to a vibrant art scene, with plenty of galleries and art museums.
  • Chicago is a culinary mecca, with a variety of options for foodies.
  • The city is home to a number of cultural festivals, including food, music and art festivals.
  • Chicago is a city of sports, with teams in each of the four major professional sports.

Is Chicago, IL safe to travel to?

Chicago, IL is generally safe to travel to. Here are some tips to help you stay safe while visiting:

  • Be aware of your surroundings and avoid dark or secluded areas.
  • Be aware of pickpockets in crowded areas.
  • Avoid carrying large amounts of cash when possible.

What are the popular shopping destinations in Chicago, IL?

The following are some of the popular shopping destinations in Chicago, IL:

  • Magnificent Mile
  • State Street
  • Water Tower Place
  • Randolph Street Market

Where is Chicago, IL?

Chicago, IL is located in the northern region of the United States, in the state of Illinois. It is the most populous city in the Midwest, and the third most populous city in the US, with a population of over 2.7 million. It is also the county seat of Cook County, Illinois.

What are the top things to do in Chicago, IL?

Chicago, IL is a great city to explore, with plenty of activities to choose from. Here are the top four things to do in the city:

  • Visit Millennium Park and take a stroll through the iconic Cloud Gate sculpture
  • Explore the Art Institute of Chicago and take in the impressive collection of art and artifacts
  • Catch a show at the Chicago Theatre for a night of music and entertainment
  • Spend a day at Navy Pier, where you can ride the Ferris wheel, go on boat tours, and explore the shops and restaurants
Chicago, IL is a great city to explore, with plenty of activities to choose from. Here are the top four things to do in the city:
  • Visit Millennium Park and take a stroll through the iconic Cloud Gate sculpture
  • Explore the Art Institute of Chicago and take in the impressive collection of art and artifacts
  • Catch a show at the Chicago Theatre for a night of music and entertainment
  • Spend a day at Navy Pier, where you can ride the Ferris wheel, go on boat tours, and explore the shops and restaurants

What do I need to know before visiting Chicago, IL?

Before visiting Chicago, IL, it is important to know a few things. First, the city is known for its rich culture and diverse neighborhoods. Second, Chicago has a wide range of attractions to explore, from the iconic Cloud Gate sculpture to the Magnificent Mile. Third, the city has a wide range of transportation options, including the 'L' train system, buses, and taxis.

  • Chicago is known for its rich culture and diverse neighborhoods.
  • The city has a wide range of attractions, from the iconic Cloud Gate sculpture to the Magnificent Mile.
  • The city has a wide range of transportation options, including the 'L' train system, buses, and taxis.

What is the price range for rentals in Chicago?

Vacation rentals in Chicago have a price range between $39-$20,000. The average price for rentals in Chicago is $145 per night.

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