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Flights to Chicago Midway

C$ 193 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 28/7. 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
1 adult, Economy, 0 bags

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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
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Sat, 25 Jul - Sat, 1 Aug
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:15 p.m. - 5:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 299Porter Airlines
Thu, 20 Aug - Mon, 24 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 301Porter Airlines
Thu, 23 Jul - Mon, 27 Jul
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 302Porter Airlines
Tue, 21 Jul - Tue, 28 Jul
Delta Logo
6:10 a.m. - 12:38 p.m.
YYZ
-
MDW
7h 28m
1 stop
Delta Logo
9:24 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 00m
1 stop
C$ 342Delta
Mon, 27 Jul - Wed, 5 Aug
Delta Logo
12:09 p.m. - 6:25 p.m.
YYZ
-
MDW
7h 16m
1 stop
Delta Logo
9:19 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 05m
1 stop
C$ 353Delta
Wed, 22 Jul - Sat, 25 Jul
WestJet Logo
12:13 p.m. - 6:38 p.m.
YYZ
-
MDW
7h 25m
1 stop
WestJet Logo
9:34 a.m. - 5:25 p.m.
MDW
-
YYZ
6h 51m
1 stop
C$ 376WestJet
Fri, 18 Sep - Mon, 21 Sep
Multiple Airlines Logo
12:20 a.m. - 10:55 a.m.
YYC
-
MDW
9h 35m
1 stop
Multiple Airlines Logo
6:05 a.m. - 11:00 a.m.
MDW
-
YYC
29h 55m
1 stop
C$ 526Multiple Airlines
Thu, 20 Aug - Sun, 23 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:15 p.m. - 12:20 a.m.
MDW
-
YOW
8h 05m
1 stop
C$ 577Multiple Airlines
Mon, 17 Aug - Fri, 21 Aug
WestJet Logo
10:45 a.m. - 12:39 p.m.
YWG
-
MDW
25h 54m
2 stops
WestJet Logo
1:25 p.m. - 12:55 a.m.
MDW
-
YWG
11h 30m
2 stops
C$ 777WestJet
Sat, 8 Aug - Wed, 12 Aug

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 9 July 2026.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 25/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Sat 1/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 298

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 20/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 24/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 299

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 23/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Mon 27/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 301

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 21/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Tue 28/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 302

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 27/7

6:10 a.m.-12:38 p.m.

1 stop7h 28m

Chicago Midway

Wed 5/8

9:24 a.m.-5:24 p.m.

1 stop7h 00m

C$ 342

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 22/7

12:09 p.m.-6:25 p.m.

1 stop7h 16m

Chicago Midway

Sat 25/7

9:19 a.m.-5:24 p.m.

1 stop7h 05m

C$ 353

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 18/9

12:13 p.m.-6:38 p.m.

1 stop7h 25m

Chicago Midway

Mon 21/9

9:34 a.m.-5:25 p.m.

1 stop6h 51m

C$ 376

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/8

12:20 a.m.-10:55 a.m.

1 stop9h 35m

Chicago Midway

Sun 23/8

6:05 a.m.-11:00 a.m.

1 stop29h 55m

C$ 526

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 17/8

6:25 p.m.-9:45 a.m.

1 stop16h 20m

Chicago Midway

Fri 21/8

3:15 p.m.-12:20 a.m.

1 stop8h 05m

C$ 577

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 8/8

10:45 a.m.-12:39 p.m.

2 stops25h 54m

Chicago Midway

Wed 12/8

1:25 p.m.-12:55 a.m.

2 stops11h 30m

C$ 777

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 Airport flights?

There are 2 cabin classes available to choose from on Canada to Chicago Midway Airport 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$ 311. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday 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$ 358.

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

In general, August 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$ 116. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Canada during the month February is also very affordable. Most momondo users find prices during this month for around C$ 162.

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$ 331. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 687.

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 AIRPORTDecember26% cheaperFlying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 303 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTApril87% more expensiveIt costs about C$ 763 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 AIRPORTJuly500% more users visitedMore momondo users searched in flights to Chicago Midway Airport from Toronto Pearson Intl Airport in July 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$ 193

Best Round-Trip Price

C$ 298

Fastest flight time

1h 50m
The best one-way flight price to Chicago from Canada in the last 5 days is C$ 193 (Toronto Island to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 298 (Toronto Island to Chicago Midway).
Search Deals
The fastest flight to Chicago from Canada takes 1h 50m (Toronto Island to Chicago Midway).
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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 Wednesday. Try to avoid departing on a Saturday, 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$ 1,057 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 New York found flights 74% 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.

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 July 2026.

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
Merrillville
Hammond
Munster

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$ 181