Latest deals
Insights
When to book
FAQs
Price Alerts
Flights to Chicago Midway

C$ 189 Cheap flights to Chicago Midway Airport

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 Midway Airport departing on 16/12. 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
"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? to track prices.
Search flight deals

Find the cheapest flights from Canada to Chicago Midway Airport

Cheap round-trip flights

These are some of the best round-trip flight deals from Canada to Chicago Midway Airport that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Canada to Chicago Midway Airport.

Cheap last-minute flights

Planning a quick getaway from Canada to Chicago Midway Airport? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago Midway Airport, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago Midway Airport

Find recent round-trip train or bus tickets from Canada to Chicago Midway Airport.

All round-trip flight deals to Chicago Midway Airport

The cheapest plane tickets to Chicago Midway Airport found on KAYAK recently.
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 307Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
7:00 a.m. - 10:06 p.m.YYC-MDW
14h 06m2 stops
9:30 a.m. - 8:38 p.m.MDW-YYC
12h 08m2 stops
C$ 308Delta
Find Deal
Sat, 7 Dec - Tue, 10 Dec
6:35 a.m. - 12:46 p.m.YYC-MDW
5h 11m1 stop
1:26 p.m. - 8:53 p.m.MDW-YYC
8h 27m1 stop
C$ 309Delta
Find Deal
Wed, 8 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 312Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 365Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
6:30 a.m. - 6:32 p.m.YYZ-MDW
13h 02m1 stop
9:38 a.m. - 11:34 p.m.MDW-YYZ
12h 56m1 stop
C$ 374WestJet
Find Deal
Thu, 12 Dec - Mon, 16 Dec
6:30 a.m. - 6:11 p.m.YYZ-MDW
12h 41m1 stop
9:20 a.m. - 6:23 p.m.MDW-YYZ
8h 03m1 stop
C$ 381WestJet
Find Deal
Sat, 12 Apr - Mon, 21 Apr
11:00 p.m. - 3:33 p.m.YVR-MDW
14h 33m1 stop
7:21 p.m. - 4:29 p.m.MDW-YVR
23h 08m2 stops
C$ 386
Find Deal
Sun, 12 Jan - Thu, 16 Jan
11:00 p.m. - 5:18 p.m.YVR-MDW
16h 18m1 stop
12:57 p.m. - 11:15 a.m.MDW-YVR
24h 18m1 stop
C$ 413
Find Deal
Wed, 4 Dec - Wed, 11 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
C$ 189Porter Airlines
Find Deal
Mon, 16 Dec
7:00 a.m. - 6:32 p.m.YYC-MDW
10h 32m1 stop
C$ 190Delta
Find Deal
Sat, 7 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 190Porter Airlines
Find Deal
Thu, 19 Dec
7:30 a.m. - 7:06 p.m.YWG-MDW
11h 36m1 stop
C$ 192
Find Deal
Wed, 29 Jan
7:30 a.m. - 5:57 p.m.YWG-MDW
10h 27m1 stop
C$ 199
Find Deal
Wed, 15 Jan
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 217Air Transat
Find Deal
Tue, 17 Dec
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
C$ 228Air Transat
Find Deal
Wed, 18 Dec
6:30 a.m. - 12:46 p.m.YYZ-MDW
7h 16m1 stop
C$ 249WestJet
Find Deal
Thu, 6 Feb
6:30 a.m. - 10:36 a.m.YYZ-MDW
5h 06m1 stop
C$ 255WestJet
Find Deal
Sun, 19 Jan
7:50 a.m. - 5:54 p.m.YYZ-MDW
11h 04m1 stop
C$ 424Undisclosed Carrier
Find Deal
Sat, 30 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 538Porter Airlines
Find Deal
Fri, 22 Nov - Tue, 3 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 550Porter Airlines
Find Deal
Sun, 24 Nov - Tue, 3 Dec
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 568WestJet
Find Deal
Sun, 24 Nov - Wed, 27 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 575Air Transat
Find Deal
Mon, 25 Nov - Tue, 3 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 601Air Transat
Find Deal
Sun, 24 Nov - Tue, 3 Dec
6:00 a.m. - 12:49 p.m.YYZ-MDW
7h 49m1 stop
1:30 p.m. - 10:36 p.m.MDW-YYZ
8h 06m1 stop
C$ 619Delta
Find Deal
Mon, 25 Nov - Tue, 3 Dec
8:00 p.m. - 7:55 a.m.YYZ-MDW
12h 55m1 stop
12:43 p.m. - 7:06 p.m.MDW-YYZ
5h 23m1 stop
C$ 651
Find Deal
Sun, 24 Nov - Tue, 3 Dec
6:15 p.m. - 9:32 a.m.YYZ-MDW
16h 17m1 stop
7:17 p.m. - 1:41 p.m.MDW-YYZ
17h 24m1 stop
C$ 657WestJet
Find Deal
Fri, 22 Nov - Fri, 29 Nov
12:50 p.m. - 5:02 p.m.YUL-MDW
5h 12m1 stop
5:42 p.m. - 11:11 p.m.MDW-YUL
4h 29m1 stop
C$ 657Delta
Find Deal
Sat, 23 Nov - Sat, 30 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 697
Find Deal
Mon, 25 Nov - Sat, 30 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 307Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 312Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 314Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 319Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 332Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 335Porter Airlines
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 365Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 367Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 577
Find Deal
Sat, 21 Dec - Sun, 5 Jan

See travel insights to Chicago Midway Airport from

Flights to Chicago Midway Airport - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago Midway Airport to help you craft the best travel plan.

What cabin class options are available on Canada to Chicago Midway flights?

There are 1 cabin classes available to choose from on Canada to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Wednesday when prices can be found for as low as C$ 339. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 403.

What is the cheapest month to fly to Chicago Midway Airport?

In general, December is the cheapest month to fly from Canada to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 295. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Canada during the month March is also very affordable. Most momondo users find prices during this month for around C$ 307.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Canada to Chicago Midway Airport during this time can be as low as C$ 366. In contrast, the most expensive time of day to depart to Chicago Midway Airport is at noon when prices are around C$ 406.

What is the cheapest Canada to Chicago Midway flight route?

Fly from Toronto Island to Chicago Midway for the best Canada - Chicago Midway flight prices

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

The best time to book a flight to Chicago Midway Airport from Canada is 24 days out, which is when prices tend to be around C$ 364. Keep in mind that you might be able to find cheaper flights to Chicago Midway Airport at any time. In fact, our users found flights for as low as C$ 333 in the past 72 hours.

Cheapest flights to Chicago Midway

Find the cheapest flights to Chicago Midway from your nearest city or airport
Find Flights from Toronto Pearson Intl Airport to Chicago Midway Airport
CHEAPEST MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTFebruary32% cheaperFlying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 344 in February
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTApril25% more expensiveIt costs about C$ 636 for flights to Chicago Midway Airport from Toronto Pearson Intl Airport in April
MOST POPULAR MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTAugust750% more users visitedMore momondo users searched in flights to Chicago Midway Airport from Toronto Pearson Intl Airport in August than any other month

Cheap Chicago Midway Airport flight deals and tips

Summary info about Chicago Midway Airport flight prices, duration and airlines

Best One-Way Price

C$ 189

Best Round-Trip Price

C$ 307

Fastest flight time

1h 50m

Popular in

October
The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 189 (Toronto Island to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 307 (Toronto Island to Chicago Midway).
Search Deals
The fastest flight to Chicago from Canada takes 1h 50m (Toronto Island to Chicago Midway).
Search Deals
October has the highest demand for flights to Chicago, with a 9% price increase on average.
Search Deals

Frequently asked questions about flying to Chicago Midway Airport

What is the cheapest month to fly to Chicago Midway Airport?

In general, when booking your flight to Chicago Midway Airport, December is the cheapest month on average.

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

From most locations, to find the best deals on airfare, our data shows that users booking 24 days before flying found the cheapest flight to Chicago Midway Airport.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

On average, the cheapest flights to Chicago Midway Airport are found when departing on a Wednesday. Try to avoid departing on a Monday, as this is usually the most expensive day.

What is the cheapest time of day to fly to Chicago Midway Airport?

Generally, when visiting Chicago Midway Airport, Morning flights represent the best value. Noon flights are likely to have higher prices.

Is there an alternative airport near Chicago Midway Airport?

Finding an alternative and possibly cheaper destination airport near Chicago Midway Airport is possible. If you are planning a flight to Chicago Midway Airport, consider booking flights to Chicago O'Hare Intl Airport (26 km from Chicago city centre).

When did momondo last update prices for flights to Chicago Midway Airport?

Prices for flights to Chicago Midway Airport are updated daily.

How many operators does momondo search for flights to Chicago Midway Airport?

The number of operators available for flights to Chicago Midway Airport is 2 as of November 2024.

How old do you have to be to fly to Chicago Midway Airport?

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 Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights to Chicago. Millions of users trust and use momondo every year so you are in good company.

Can I find flights to Chicago with flexible booking policies on momondo?

All flight searches to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight to Chicago.

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 25/11
Mon 2/12
Email me momondo's favourite deals
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago Midway Airport MDW

Popular Flights to Chicago Midway Airport

Popular routes according to searches in the past day on momondo
Flights from Toronto Island to MDWfrom C$ 215

Cheapest flight routes to Chicago Midway

These routes have the cheapest flights to Chicago Midway found by momondo users in Canada
DepartingDestinationBest TimeBest Price
TorontoChicago1h 50mC$ 307
CalgaryChicago9h 02mC$ 308
HalifaxChicago5h 30mC$ 371
VancouverChicago8h 18mC$ 386
MontrealChicago4h 20mC$ 399
OttawaChicago3h 40mC$ 482
WinnipegChicago6h 01mC$ 573
EdmontonChicago6h 59mC$ 606
SaskatoonChicago5h 27mC$ 620
KelownaChicago11h 33mC$ 804
Grande PrairieChicago27h 36mC$ 826
Québec CityChicago19h 10mC$ 879
ComoxChicago27h 57mC$ 902
St. John'sChicago12h 45mC$ 913
ReginaChicago25h 46mC$ 986
Saint JohnChicago19h 50mC$ 1,200