🇺🇸 United States of America
Explore the Windy City - Chicago

Chicago - Vacation Briefing

Chicago is a vibrant city located in the heart of the Midwest. Known for its stunning architecture, delicious food, and thriving arts and culture scene, this city is a must-visit destination for travelers. Get a panoramic view of the city from the Willis Tower's Skydeck or take a stroll along the Navy Pier. Enjoy the view of Lake Michigan and take a riverboat architecture tour, or enjoy some of the best deep-dish pizza in the world.

Popular Sights in Chicago

Things to do during your Chicago vacation

Welcome to Chicago! This bustling city offers a wide range of activities for visitors of all interests. From stunning architectural marvels to vibrant cultural experiences, there is something for everyone to enjoy. Explore the diverse neighborhoods, indulge in the local cuisine, and immerse yourself in the rich history and arts scene. Whether you're a nature enthusiast, a history buff, or a foodie, Chicago has it all!

  • Millennium Park: A must-visit attraction featuring the iconic Cloud Gate sculpture and stunning outdoor art installations.
  • Art Institute of Chicago: One of the oldest and largest art museums in the United States, showcasing a vast collection of artworks.
  • Navy Pier: A well-known landmark offering stunning views of Lake Michigan, amusement rides, dining, and entertainment options.
  • Shedd Aquarium: Explore underwater worlds at this popular aquarium, home to a diverse range of aquatic species.
  • Field Museum: Discover fascinating exhibits on natural history, including the famous T. rex skeleton, Sue.
  • Chicago Riverwalk: Take a stroll along the picturesque Chicago River, dotted with cafes, restaurants, and scenic views.
  • Magnificent Mile: A shopper's paradise, this bustling avenue is lined with luxury boutiques, department stores, and renowned dining establishments.
  • Wrigley Field: Experience Chicago's rich sports culture at the historic Wrigley Field, the home of the Chicago Cubs baseball team.
  • Lincoln Park Zoo: Visit this free zoo, home to a wide variety of animals and beautifully landscaped gardens.
  • Architecture River Cruise: Embark on a scenic boat tour along the Chicago River to admire the city's stunning architecture.

Why you should visit Chicago


Chicago is a vibrant city with a lot to offer, but it does have its drawbacks.


While Chicago has seen a decrease in crime rates in recent years, certain areas can still be dangerous. It's important to stay alert and be cautious, especially at night.


Chicago is known for its rich culture and history. It boasts world-class museums, such as the Art Institute of Chicago, and iconic architectural landmarks, like the Willis Tower. The city also offers a diverse range of cuisines.


Chicago has a bustling nightlife scene with numerous bars, clubs, and live music venues. There are plenty of options for entertainment and socializing.


While Chicago may not be known for extreme adventures, it offers a variety of activities like boating on Lake Michigan, bike tours, and exploring its vibrant neighborhoods.


While Chicago has beautiful parks and waterfront areas, it may not be the most relaxing destination due to its bustling atmosphere and traffic.

Best time to visit Chicago

Chicago experiences four distinct seasons, each offering its own unique charm. To enjoy pleasant temperatures and vibrant festivals, plan your visit between May and September. For a winter wonderland experience and fewer crowds, visit from December to February.

cold, but less crowded
-8°C - -1°C
cool, fewer tourists
-6°C - 2°C
mild weather, emerging spring
-2°C - 7°C
comfortable temperatures
4°C - 14°C
pleasant weather, festivals
10°C - 20°C
warm temperatures, lively atmosphere
16°C - 26°C
sunny, least crowded
19°C - 29°C
warm weather, cultural events
18°C - 27°C
mild temperatures, fewer crowds
14°C - 23°C
crisp autumn, fall foliage
8°C - 17°C
chilly but less tourists
2°C - 10°C
winter wonderland, holiday spirit
-4°C - 3°C
December offers a winter wonderland experience and a festive holiday spirit. Enjoy ice-skating, holiday markets, and the city's iconic Christmas decorations.

A guide To your first day of Chicago vacation


  • Start your day by taking a walk along the beautiful Lake Michigan shoreline.
  • Visit Millennium Park and marvel at the famous Cloud Gate sculpture, also known as 'The Bean'.


  • Explore the iconic Navy Pier and enjoy its various attractions, including the Ferris wheel and boat tours.
  • Indulge in some deep-dish pizza at one of Chicago's renowned pizzerias.


  • Take a scenic architectural boat tour along the Chicago River to admire the stunning city skyline.
  • Catch a spectacular live performance at one of Chicago's many theaters or jazz clubs.


  • Experience the vibrant nightlife of Chicago by visiting its lively bars and clubs.
  • Enjoy a delicious late-night snack at one of the city's famous hot dog stands.

How to get to Chicago

By Plane

Chicago O'Hare International Airport (ORD) is one of the busiest airports in the world, with excellent global connections. It offers numerous nonstop flights to major cities worldwide, making it highly convenient for international travelers. Midway International Airport (MDW) is another popular option, known for its convenient location and shorter security lines.

By other means

Chicago's public transport system is well-developed, with the 'L' train being a popular option for getting around the city and to the airports. The 'L' connects major attractions and neighborhoods, and both airports have convenient train connections to downtown. Buses and taxis are also readily available, providing additional options for local and suburban travel.

Tips for Booking Your Trip

Planning a trip can get tricky, right? Don't worry, we've got some solid advice to make your life easier. Here's how you can find flights and accommodations without a hitch.

Flights: How to Score the Best Deal

First things first, check out Google Flights. Their price calendar and nearby airport options are really useful. Found a good deal? Great, but hang on a sec—make sure you compare it with prices on Kayak, Skyscanner, Momondo, and Kiwi. A little research can go a long way.

Accommodation: Find Your Ideal Spot

For places to stay, start by scanning and Airbnb to get an idea of what's out there. Then, level up your search by looking at Hostelworld and Agoda. Oh, and a quick tip: the hotel's own website might have some special offers, so give that a look too.

Ready to make some moves? The links you need are right below. Happy booking!



Video Reviews of Chicago

Best for travelers who are ...

Travelers looking to explore a bustling and culturally rich city

How long to stay in Chicago?

Plan to stay for at least 3-4 days to experience the highlights of the city, or longer if you want to explore the city's many neighborhoods and cultural offerings.

Similar destination to Chicago, United States of America

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