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Each time you visit Chi-Town, you’ll fall in love anew. Even if you’ve stood in front of the famous metallic bean and stood along the Navy Pier, you won’t be left wanting for original ways to spend your time. As Mark Twain posited, “She is novelty, for she is never the same Chicago you saw when you passed through the last time.” The modern city on the shores of Lake Michigan is always evolving and will never fail to enchant you. Between the exciting sports culture and buildings that hearken back to a time when Frank Sinatra and Al Capone ran the scene, Chicago always impresses.
Flights to Chicago depart from tons of destinations; just sit back, start dreaming of deep-dish pizza, and before you know it you’ll be touching down in the Windy City. Book your airfare on Travelocity today, and you’ll save enough cash to afford all the famous frankfurters you want.
Chicago flights land at one of the two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Getting to downtown Chicago from ORD is a breeze when you take the Blue line train, which is part of the Chicago Transit Authority train system. From MDW, jump on the Orange line train.
If you’re not staying downtown, buses are available to most parts of the city from both airports. When a private ride is more your style, hail a taxi outside the baggage claim area. Many hotels also have shuttle buses that will take you to and from the airport. But if independence is more your style, there are many rental car companies located within the airport if you need your own wheels; book your ride when you purchase your airfare to Chicago and your vacation is set.
A savvy traveler such as yourself is sure to purchase one of our top flight deals to Chicago. Not only will you travel on one of the most affordable and convenient flights, but you’re wise enough to book a Chicago hotel befitting of your fine taste:
The Windy City is known for its pizza and beloved sports teams, but the Midwest powerhouse packs a cultural punch and can impress even seasoned world travelers. Begin your exploration with an investigation of Millennium Park, and then get a taste of Chi-Town’s creative offerings at the Art Institute of Chicago. From the observation deck of the Willis Tower, you can spot your favorite attractions and plot your route of the city. Like the savvy tourist you are, you booked cheap plane tickets to Chicago. Go ahead, buy entrance to the Lincoln Park Conservatory and Brookfield Zoo.
Use Travelocity to search through the flight options to the Windy City. Once you find one of the cheapest flights to Chicago and buy your tickets, there is nothing left to do but start dreaming of mozzarella and pack your bags. Chi-Town is waiting to welcome you with open arms and delight you with its Midwest charms.
Airfares offered on Fridays tend to be the cheapest, according to flight demand on Travelocity.ca in 2019. Purchasing your airfares on a Monday or Tuesday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Saturday. Our data shows, the start of the weekend has the highest ticket values on average, so keep this in mind if you’re browsing flight deals on a weekend.
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Tuesday are the cheapest of the week. Since weekend flights tend to be more popular, this causes the prices to rise which is why on average, airfares booked on Travelocity.ca in 2019 were most expensive for Saturday departures.
Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2019 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 1-2 weeks prior to their travel dates.
We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travellers who booked flights on Travelocity.ca in 2019 saved close to 55% when their return flights consisted of two different airlines or fare types.
*According to flight demand on Travelocity.ca from January to December 2019. Savings are subject to change and may vary depending on selections made.