C$ 120 Cheap flights to Chicago
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 29/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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What is the cheapest month to fly to Chicago?
The month of May is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 333.
What is the absolute cheapest flight to Chicago?
Users booking trips to Chicago from Los Angeles found flights 64% cheaper than the average price of flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.
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What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 678. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,266. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the evening is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 561. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,443 per ticket.
Cheapest flights to Chicago
Find the cheapest flights to Chicago from your nearest city or airport
| CHEAPEST MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT | May | 13% cheaper | Flying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 345 in May |
| MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT | December | 18% more expensive | It costs about C$ 466 for flights to Chicago from Toronto Pearson Intl Airport in December |
| MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORT | July | 232% more users visited | More momondo users searched in flights to Chicago from Toronto Pearson Intl Airport in July than any other month |
Cheap Chicago flight deals and tips
Summary info about Chicago flight prices, duration and airlines
Best One-Way Price | C$ 120 |
|---|---|
Best Round-Trip Price | C$ 177 |
Fastest flight time | 1h 49m |
Popular in | November |
Frequently asked questions about flying to Chicago
When is it best to fly to Chicago to go sightseeing?
The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seem like the best times of year to plan your visit.
How far in advance should I book a flight to Chicago?
The best time to book a flight to Chicago from Canada is 52 days out, which is when prices tend to be around C$ 363. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as C$ 261.
Is there an alternative airport near Chicago?
Those flying to Chicago could potentially find better pricing at Chicago Midway Airport (14 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre) depending on the month and departure airport.
Is there a cheaper alternative to flying into Chicago?
Chicago Midway Airport has an average price of C$ 388 per person and is typically the cheapest airport to fly into when visiting Chicago. This average price does vary based on departure city. Try momondo’s Airport-to-Airport Pricing Tool to find the cheapest flight.
Are there flights to Downtown?
Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Downtown (14.3 km away).
What’s the closest airport to Magnificent Mile?
The closest airport to Magnificent Mile is Chicago Midway, 15.7 km away.
When did momondo last update prices for flights to Chicago?
Prices for flights to Chicago are updated daily.
How many operators does momondo search for flights to Chicago?
As of July 2025, there are 9 operators available to choose from for flights to Chicago.
How old do you have to be to fly to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
Travelling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal to Chicago?
It is quick and easy to find flights to Chicago on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago. Filter by price, airline, airport, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.
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Popular Flights to Chicago
Popular routes according to searches in the past day on momondo
Cheapest flight routes to Chicago
These routes have the cheapest flights to Chicago found by momondo users in Canada
| Departing | Destination | Best Time | Best Price |
|---|---|---|---|
| Toronto | Chicago | 1h 49m | C$ 177 |
| Montreal | Chicago | 4h 14m | C$ 187 |
| Calgary | Chicago | 3h 25m | C$ 306 |
| Edmonton | Chicago | 3h 24m | C$ 310 |
| Vancouver | Chicago | 4h 03m | C$ 374 |
| Winnipeg | Chicago | 6h 21m | C$ 375 |
| Sudbury | Chicago | 6h 19m | C$ 397 |
| Comox | Chicago | 6h 49m | C$ 403 |
| Saskatoon | Chicago | 7h 48m | C$ 420 |
| Ottawa | Chicago | 3h 59m | C$ 427 |
| Victoria | Chicago | 6h 58m | C$ 457 |
| Québec City | Chicago | 2h 46m | C$ 466 |
| Kelowna | Chicago | 7h 12m | C$ 505 |
| Regina | Chicago | 8h 01m | C$ 506 |
| Halifax | Chicago | 3h 45m | C$ 526 |
| Hamilton | Chicago | 11h 44m | C$ 532 |