Insights
Latest deals
Flights to Chicago

Cheap flights to Chicago from C$ 246

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 16/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
From?
To?
Mon 29/4
Mon 6/5

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customize your results
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? Create a price alert to track prices.

Chicago flight deals found on momondo

Check out some of the best fares from airports in Canada to Chicago found recently by users on momondo
WestJet
16 May
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
26 May
ORD5:55 p.m.Chicago O'Hare Intl
3h 27m
YYC8:22 p.m.Calgary
United Airlines
4 Jul.
YUL4:50 p.m.Montreal Pierre Elliott Trudeau Intl
2h 43m
ORD6:33 p.m.Chicago O'Hare Intl
7 Jul.
ORD7:21 a.m.Chicago O'Hare Intl
2h 23m
YUL10:44 a.m.Montreal Pierre Elliott Trudeau Intl
WestJet
11 Jul.
YYC12:30 p.m.Calgary
3h 27m
ORD4:57 p.m.Chicago O'Hare Intl
14 Jul.
ORD5:55 p.m.Chicago O'Hare Intl
3h 45m
YYC8:40 p.m.Calgary
United Airlines
2 Jul.
YUL1:05 p.m.Montreal Pierre Elliott Trudeau Intl
2h 35m
ORD2:40 p.m.Chicago O'Hare Intl
5 Jul.
ORD9:28 p.m.Chicago O'Hare Intl
9h 19m
1 stop
YUL7:47 a.m.Montreal Pierre Elliott Trudeau Intl
Porter Airlines
30 May
YTZ3:30 p.m.Toronto Island
1h 47m
MDW4:17 p.m.Chicago Midway
5 Jun.
MDW5:15 p.m.Chicago Midway
1h 42m
YTZ7:57 p.m.Toronto Island
Porter Airlines
21 May
YTZ3:30 p.m.Toronto Island
1h 47m
MDW4:17 p.m.Chicago Midway
26 May
MDW12:15 p.m.Chicago Midway
1h 42m
YTZ2:57 p.m.Toronto Island

Find the cheapest one-way flights to Chicago

If you're looking for one-way flights from Canada to Chicago, view some of our deals below provided by Porter Airlines, United Airlines and WestJet
WestJet
16 May
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
WestJet
26 May
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl
WestJet
17 May
YYC12:30 p.m.Calgary
3h 35m
ORD5:05 p.m.Chicago O'Hare Intl

Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

What is the cheapest month to fly to Chicago?

The month of February is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 341.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from New York found flights 66% 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.
See prices from:

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 Saturday when prices can be found for as low as C$ 402. 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 Sunday because tickets tend to average around C$ 438. 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$ 401. 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$ 425 per ticket.

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Toronto Pearson Intl and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 1h 53m on average. Another popular route from Canada to Chicago is flying from Vancouver Intl to Chicago O'Hare Intl, which will take roughly 4h 01m. Keep in mind that layovers or delays could extend your travel time.

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Canada is 26 days out, which is when prices tend to be around C$ 399.

Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
Toronto Pearson Intl Airport
Chicago Midway Airport

CHEAPEST ROUTE FROM Toronto TO Chicago

Toronto (YTO) to Chicago (CHI)

Typically, flights to Chicago from Toronto are cheaper when flying from Toronto to Chicago, which has an average price of C$ 399

CHEAPEST MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTFebruary25% cheaperFlying from Toronto Pearson Intl Airport to Chicago costs on average just C$ 350 in February
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTAugust26% more expensiveIt costs about C$ 586 for flights to Chicago from Toronto Pearson Intl Airport in August
MOST POPULAR MONTH TO FLY TO CHICAGO FROM TORONTO PEARSON INTL AIRPORTDecember160% more users visitedMore momondo users searched in flights to Chicago from Toronto Pearson Intl Airport in December than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

C$ 149

Best Round-Trip Price

C$ 246

Fastest flight time

1h 47m

Operated By

5 airlines
The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 149 (Calgary to Chicago O'Hare Intl).
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 246 (Calgary to Chicago O'Hare Intl).
The fastest flight to Chicago from Canada takes 1h 47m (Toronto Island to Chicago Midway).
There are 5 airlines operating flights to Chicago, including United Airlines, Air Canada and Delta.

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.

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) 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$ 249 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 Lincoln Park?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Lincoln Park (16.9 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?

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.


Why 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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 29/4
Mon 6/5
Email me momondo's favourite deals

Find better results for your stay in Chicago