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Flights to Chicago Midway

C$ 172 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 29/12. 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

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Find the cheapest flights from Canada to Chicago Midway Airport

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 252Porter Airlines
Find Deal
Tue, 2 Dec - Fri, 5 Dec
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 256Porter Airlines
Find Deal
Mon, 22 Dec - Mon, 5 Jan
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 266Porter Airlines
Find Deal
Tue, 23 Dec - Tue, 6 Jan
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 269Porter Airlines
Find Deal
Sat, 20 Dec - Mon, 5 Jan
Delta Logo
10:05 a.m. - 12:48 p.m.YYZ-MDW
3h 43m1 stop
Delta Logo
6:30 p.m. - 10:41 p.m.MDW-YYZ
3h 11m1 stop
C$ 283Delta
Find Deal
Thu, 8 Jan - Sun, 11 Jan
Delta Logo
10:05 a.m. - 12:48 p.m.YYZ-MDW
3h 43m1 stop
Delta Logo
1:28 p.m. - 10:41 p.m.MDW-YYZ
8h 13m1 stop
C$ 295Delta
Find Deal
Thu, 8 Jan - Sun, 11 Jan
Multiple Airlines Logo
8:55 a.m. - 11:25 p.m.YYC-MDW
13h 30m1 stop
Multiple Airlines Logo
3:02 p.m. - 9:45 p.m.MDW-YYC
31h 43m1 stop
C$ 314Multiple Airlines
Find Deal
Thu, 26 Feb - Sun, 1 Mar
Multiple Airlines Logo
7:30 a.m. - 10:19 p.m.YWG-MDW
14h 49m1 stop
Multiple Airlines Logo
6:10 a.m. - 12:41 a.m.MDW-YWG
18h 31m2 stops
C$ 319Multiple Airlines
Find Deal
Fri, 16 Jan - Mon, 19 Jan
WestJet Logo
6:35 a.m. - 4:16 p.m.YWG-MDW
9h 41m1 stop
WestJet Logo
2:00 p.m. - 11:33 p.m.MDW-YWG
9h 33m1 stop
C$ 595WestJet
Find Deal
Sat, 7 Mar - Sat, 14 Mar
WestJet Logo
5:00 p.m. - 5:29 p.m.YVR-MDW
22h 29m2 stops
WestJet Logo
9:50 a.m. - 9:15 p.m.MDW-YVR
13h 25m2 stops
C$ 658WestJet
Find Deal
Tue, 20 Jan - Sun, 25 Jan

momondo Fare Finder

 
Locate flights to Chicago Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 96,600 searches and data was last updated on 21 November 2025.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 2/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Fri 5/12

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 22/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 5/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 23/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Tue 6/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 20/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 5/1

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 269

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 8/1

10:05 a.m.-12:48 p.m.

1 stop3h 43m

Chicago Midway

Sun 11/1

6:30 p.m.-10:41 p.m.

1 stop3h 11m

C$ 283

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 8/1

10:05 a.m.-12:48 p.m.

1 stop3h 43m

Chicago Midway

Sun 11/1

1:28 p.m.-10:41 p.m.

1 stop8h 13m

C$ 295

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

8:55 a.m.-11:25 p.m.

1 stop13h 30m

Chicago Midway

Sun 1/3

3:02 p.m.-9:45 p.m.

1 stop31h 43m

C$ 314

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Fri 16/1

7:30 a.m.-10:19 p.m.

1 stop14h 49m

Chicago Midway

Mon 19/1

6:10 a.m.-12:41 a.m.

2 stops18h 31m

C$ 319

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 7/3

6:35 a.m.-4:16 p.m.

1 stop9h 41m

Chicago Midway

Sat 14/3

2:00 p.m.-11:33 p.m.

1 stop9h 33m

C$ 595

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 20/1

5:00 p.m.-5:29 p.m.

2 stops22h 29m

Chicago Midway

Sun 25/1

9:50 a.m.-9:15 p.m.

2 stops13h 25m

C$ 658

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 is only 1 cabin class 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 Friday when prices can be found for as low as C$ 304. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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$ 331.

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

In general, September 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$ 242. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Canada during the month October is also very affordable. Most momondo users find prices during this month for around C$ 283.

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$ 312. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 682.

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

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 AIRPORTNovember32% cheaperFlying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 305 in November
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTSeptember78% more expensiveIt costs about C$ 795 for flights to Chicago Midway Airport from Toronto Pearson Intl Airport in September
MOST POPULAR MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTJune700% more users visitedMore momondo users searched in flights to Chicago Midway Airport from Toronto Pearson Intl Airport in June 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$ 170

Best Round-Trip Price

C$ 253

Fastest flight time

1h 50m

Popular in

November
The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 170 (Calgary to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 253 (Toronto Island to Chicago Midway).
Search Deals
The fastest flight to Chicago from Canada takes 1h 50m (Toronto Island to Chicago Midway).
Search Deals
November has the highest demand for flights to Chicago, with a 17% 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, September is the cheapest month on average.

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 Friday. Try to avoid departing on a Sunday, 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. Evening 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) or Chicago Greater Rockford Airport (126 km from Chicago city centre).

Is there a cheaper alternative to flying into Chicago?

You can find deals at Chicago O'Hare Intl Airport for C$ 1,119 on average, but that price can change based on your departure airport. To save money, try momondo’s Airport-to-Airport Pricing Tool.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Orlando found flights 87% 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.

Which airlines fly to Chicago Midway Airport?

Porter Airlines, Air Transat and WestJet are the top three most popular airlines that fly to Chicago Midway Airport according to our data. Porter Airlines is the first choice among our users, with 94% of people opting to fly with this airline when travelling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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 4 as of November 2025.

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.

Travelling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Munster
Hammond
Merrillville

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

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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$ 128