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Grab Cheap Flight Tickets to Chicago

Chicago, located on the shores of freshwater Lake Michigan, is the most populous city in the state of Illinois, and the third most populous city in the United States. Chicago is well known for its vibrant art scene, food, distinctive cultural attractions, endless shopping opportunities, exciting architecture, its memorable skyline, museums, parks, and beautiful beaches. The city pulls tourists from across the world who look for cheap flights to Chicago to explore its various attractions. Chicago has contribution in sports too with the Chicago Bears in American football, the Chicago White Sox and Cubs in baseball, and the Chicago Bulls in basketball.

Chicago is known by various nicknames, including - the Windy City, the City of Big Shoulders, the Second City, and the City that Works. The city is also known as the United States Railroad Capital, with over 1,300 trains carrying freight and passengers arriving and departing the city each day. Chicago is an international centre for finance, culture, commerce, industry, technology, telecommunications, and transportation. The city also offers wealth of not-to-be-missed attractions, and can also be explored on foot along the Lakefront Trail or the new Riverwalk,

Top Attractions in Chicago

Here're top attractions worth booking flights to Chicago. These include -

  • Navy Pier
  • 360 Chicago
  • Lincoln Park
  • Millennium Park
  • Buckingham Fountain
  • Willis Tower SkyDeck
  • Art Institute of Chicago
  • Museum of Science and Industry
  • Field Museum of Natural History
  • Michigan Avenue and the Magnificent Mile

Famous Festivals and Events in Chicago

Chicago celebrates plenty of festivals and events year around. Some of these include -

  • Chicago Chinese New Year Parade (End January.
  • Chicago Underground Film Festival (June).
  • Chicago St Patrick’s Day Parade (Mid-March).
  • Taste of Chicago (July).
  • Chicago Air & Water Show (Mid-August).
  • Chicago Jazz Festival (Late August/ Early September).
  • Chicago Marathon (Mid October).
  • Chicago International Film Festival (Mid October).
  • Magnificent Mile Lights Festival (Mid November).
  • Aquatic Experience (Mid November).

Tourists who are planning to attend any of these festivals are suggested to book Chicago flights in advance to avoid paying more at the last minute, as air fares tend to rise for the last-minute flights.

Interesting Facts about Chicago

  • Spray paint was invented in Chicago.
  • Over 52 million people visit Chicago annually.
  • The entire Chicago shoreline (28 miles) along Lake Michigan is man-made.
  • Chicago became the first city in the world to construct a blood bank in 1939.
  • Having a collection of approximately 2 million books, Chicago's Harold Washington Library, is the largest public library in the world.

Share your Travel Experience

Once you’ve visited the city, do share with us your experience through CheapOair.ca review section. Your tips and recommendation will be of immense help for other travelers. Have a happy trip!

FAQs for Booking Canada to Chicago Flight Tickets

Which is the best time to visit Chicago?

Chicago experiences blustery winters and sweltering summers. The most recommended time for booking flight tickets is in the late spring, early summer, and early fall. The best months to visit are May, June, September, and October. For those looking for Chicago flight deals, the most appropriate time to visit is in the winter months, especially in January, and February. During this time, you can enjoy great discounts in luxury hotels, and can get cheap flights. Late November and early December also see dips in pricing for hotels. Keep in mind that winters in Chicago are incredibly cold, so do carry plenty of layers, if you plan a visit during winters.

What are the tricks to get cheap flights to Chicago?

To get cheap flights, use the following tricks -

  • Book early morning or late-night flights.
  • Book your flights in budget airlines to save big.
  • Try traveling during low tourist season to save on tickets.
  • Book your flights well in advance to enjoy discounts on Chicago flight tickets.
  • Join the airline mailing lists. It will ensure, you receive a mail when seat sales happen and when new routes are announced.

What is the cheapest month to fly to Chicago?

The cheapest months to fly to Chicago are January and February. And the months of April and December are the next best options to score cheap flights.

What airlines fly into Chicago?

Some of the airlines that fly to Chicago from Canada are

  • Delta Airlines
  • United Airlines
  • Air Canada
  • Aer Lingus
  • American Airlines

Does Southwest Airlines fly to Chicago?

Yes, Southwest Airlines flies to Chicago.

Which airlines offers cheap flights to Chicago from Toronto?

Numerous airlines offer cheap Chicago plane tickets to Chicago from Toronto including American Airlines, Porter Airlines, and Air Canada.

Which airlines offer cheap flights to Chicago from Hamilton?

The airlines that offer cheap flights to Chicago from Hamilton include -

  • Westjet
  • Air Canada
  • American Airlines

Chicago Travel Resources