Best time to beat the crowds (3% less expensive on average)
Most popular time to fly (10% more expensive on average)
Flight from Toronto Pearson Airport to Chicago O'Hare Airport
When to book flights to Chicago
Estimated round-trip price
Average price per month
Flight prices as travel date approaches
Top tips for finding cheap flights to Chicago
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be February, March and April. The cheapest month to fly from Canada is June.
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The highest number of flights to Chicago have Chicago O'Hare International Airport (ORD) as the arrival airport. The airport is located about 16 miles (27 km) northwest of Chicago. Most travellers prefer landing here because of the availability of a variety of transport options, which makes it easier for them to connect to various parts within and outside Chicago.
You have better chances of getting cheaper flight deals when booking your flight to Chicago if you choose to book one that has Chicago Midway International Airport (MDW) as the arrival airport. This is because the flights that arrive at MDW have a lower demand among travellers flying to Chicago. Additionally, you will enjoy shorter queues at the security checkpoints and baggage claim area when you land at MDW as opposed to if you land at ORD.
You will make one stop or travel nonstop to Chicago, depending on the airline you book. Spirit Airlines is one of the carriers that makes one stop when flying to Chicago, with the layover airport being Hartsfield–Jackson Atlanta International Airport (ATL). However, if you book Air Canada, JetBlue, or Porter Airlines, you will enjoy direct flights to Chicago.
If you’re interested in flights to Chicago, there are three primary airports that you can fly into. While Chicago Midway International Airport is most convenient for travelers that will be staying in the city center, O'Hare International Airport services the highest number of flights. Chicago Rockford International Airport is a practical choice for individuals staying in the suburbs.
For those that would like a direct flight to Chicago, there are several airlines that you can choose from. While American and Porter Airlines are known for having affordable flights and comfortable chairs, United Airlines provides travelers with above-average legroom.
To unwind after a long day of traveling, stop by the yoga room in Chicago Midway International Airport. Located in Concourse C, this room provides travelers with complimentary mats and DVD footage of popular yoga positions. It is open 7 days a week from 6 AM to 10 PM.
Traveling with your family? Chicago Midway International Airport has a large baby care room that contains a sink, a private nursing area and change tables, making it a convenient place to tend to your child after your flight has landed.
If you would like to freshen up after a long day of traveling, purchase an access pass to either the Hilton Athletic Club, Airlines Admirals Club or United Club in O'Hare International Airport in order to access their private showers. Each of these locations provides complimentary towels and toiletries, so you will have everything you need.
FAQs - booking Chicago flights
Apart from serving Chicago, Chicago O'Hare International Airport also serves as the arrival airport for those travelling to Oak Park and Cicero. Therefore, booking a flight to Chicago is an opportunity to access these nearby cities conveniently. Car rentals at ORD provide the most convenient means of transport from the airport to Cicero and Oak Park.
You will enjoy a variety of kid-friendly perks with a number of airlines that fly to Chicago, with JetBlue ranking the highest. If you book JetBlue, you and your kids are guaranteed to travel in a much more comfortable way, with the airline popular for its spacious seats and extra legroom in all the cabins. Additionally, parents enjoy extra baggage allowance and are allowed to board the plane first before other travellers.
The Red Roof Inn is a budget-friendly choice that is a 15-minute drive from Rockford International Airport and a 6-minute drive to the Magic Waters Waterpark. The Radisson Hotel & Conference Center is a modern choice that is a 20-minute drive from the airport and an 8-minute drive from the Midway Village Museum.
The easiest and quickest way to travel from O'Hare International Airport to downtown Chicago is by either renting a car or grabbing a taxi, as the drive only takes 25 to 30 minutes in good traffic. If you prefer a more affordable option, it is also possible to use public transportation, such as the local train, which takes approximately 45 minutes.
O'Hare International Airport has a multi-faith chapel that is located inside of Terminal 1 on the Mezzanine level. Religious books, rosaries and prayer rugs are available for use, and the chapel is open to all travelers, no matter what their religious affiliation is. It is open 7 days a week during standard business hours.
O'Hare International Airport has several duty-free stores located in Terminals 1, 2 and 3. In these stores, you can find a variety of electronics, clothing, liquor, cosmetics, food products and even local souvenirs. There are also several smaller shops that sell travel essentials, such as books, snacks, headphones and basic medicine.
Chicago is served by 3 major airports. Chicago Midway Airport (14 km) is the closest to the centre of Chicago. Chicago O'Hare Airport is 26 km from the centre and Chicago Greater Rockford is 126 km away from the centre.
Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of C$ 388.
Air Canada, United Airlines and American Airlines have waived their change and cancellation fees on flights to Chicago. Confirm policies on booking site.
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.