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

Restaurant/places to eat
4.1
Excellent(593 Reviews)
The Drake Hotel
Hotel
 in Chicago
4star
2 single beds
Pets allowed · Kitchen or Kitchenette · Air conditioner
Most favorited

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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Breakfast
4.1
Excellent(1,652 Reviews)
Sheraton Suites Chicago O'Hare
Hotel
 in Rosemont
4star
1 king bed
Air conditioner · Internet / Wifi · Parking
Most favorited

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 building
4.3
Excellent(650 Reviews)
Hampton Inn & Suites Rosemont Chicago O'Hare
Hotel
 in Rosemont
3star
1 king bed
Pool · Pets allowed · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our Hotel in Chicago has everything you need for a rejuvenating stay. Treat yourself to Hampton Inn & Suites Rosemont Chicago O'Hare's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

$$$$
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Property view
Skyscraper
Apartment
 in Chicago
2 guests · 1 bedroom · 1 bath
Pets allowed · Family friendly · Wheelchair accessible

Are you ready to indulge in a relaxing getaway? Our Apartment in Chicago has everything you need for a rejuvenating stay. Treat yourself to Skyscraper's exceptional amenities, such as Family friendly, Pets allowed and Wheelchair accessible.

$$$$
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Vacation rentals with air conditioning in Chicago

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Outdoor pool
4.9
Outstanding(212 Reviews)
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Apartment hotel
 in Chicago
4 guests · 2 bedrooms · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at 51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi for $292 for your next trip.

$$$$
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Facade/entrance, Property logo or sign
4.1
Excellent(5,430 Reviews)
River Hotel
Hotel
 in Chicago
4star
1 queen bed
Pets allowed · Kitchen or Kitchenette · Air conditioner

Experience vacation in Chicago with our Hotel, River Hotel. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property building
4.2
Excellent(2,130 Reviews)
Hyatt Regency Chicago
Hotel
 in Chicago
4star
1 king bed
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This inviting Hotel in Chicago can fit your needs for many types of vacations, at $104 per night.

$$$$
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Property view
4.1
Excellent(3,999 Reviews)
Club Quarters Hotel Wacker at Michigan, Chicago
Hotel
 in Chicago
4star
1 queen bed
Pets allowed · Kitchen or Kitchenette · Air conditioner

Experience vacation in Chicago with our Hotel, Club Quarters Hotel Wacker at Michigan, Chicago. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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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?

  • Air conditioner
  • Internet / Wifi
  • Kitchen or Kitchenette

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-$6,333. The average price for rentals in Chicago is $168 per night.

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