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How Much Does it Cost To Fly To Chicago?

Prices starting at C$174 for one-way flights and C$297 for round trip flights were available in the last 7 days. Prices and availability are subject to change. Additional terms apply.

Flights To Chicago

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.

Transportation from Chicago Airports

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.

Hotels Near ORD and MDW

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 Palmer House Hilton: This hotel bills itself as hip and historic, and one step inside the lobby lets you know the description is spot on. Opulent ceilings and marble accents remind you of an era when dinner was always a formal affair, while the rooms are adorned in bright furniture and clean modern lines.
  • Wyndham Grand Chicago Riverfront: From the cocktails served fireside at Hoyt’s Patio to in-room massages, this downtown hotel is designed to pamper. Get a room with a view and overlook the Windy City from the moment you wake up, and let the concierge help you book excursions to Chicago attractions.
  • Hyatt Regency Chicago: This four-diamond hotel is connected to the Illinois Center downtown, right in the heart of the city. You’ll be just a short and leisurely walk from the Magnificent Mile and Grant Park.
  • Congress Plaza Hotel: Legendary hotels are just your style, so this Grant Park hotel has your name on it. Enjoy a view of Lake Michigan from your room, and revel in the property’s storied history, which dates back to 1893.

Things to Do in Chicago

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.

How to find cheap flights

What is the best day to buy a plane ticket?

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.

What are the cheapest days to fly?

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.

How far in advance can you book a flight?

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.

How can I save money on airline tickets?

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.

Most Frequently Booked Hotels

Flight Review

Feb 27, 2020

power on all planes would be nice - it is rare that it is not there

Feb 3, 2020

All good

Jan 20, 2020

Baggage delayed

Dec 28, 2019

Flight was perfect thanks

Nov 23, 2019

TV screen not functional

Nov 14, 2019

It would be very helpful if the airline crew would remind passengers to put smaller luggage and backpacks under their seat to leave more space in overheads for larger things. I watched quite a few people have issues with their luggage due to others with small things in the overhead and nothing under their seat. Also, would really appreciate maybe a reminder to passengers of the person behind them when reclining their seat.. there should be an education on that or just remove the feature, sitting with the person in fronts seat back in your face isn't fun.

Nov 10, 2019

Seat power did not work, otherwise flight was fine.

Nov 9, 2019

Baggage took forever upon arrival. I know that is Pearson and not united so I didn’t let it impact my score but T1 is the worst for baggage times

Nov 7, 2019

Staff very friendly and knowledgeable!!

Aug 18, 2019

A little more seat room would be better

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.