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Flights to Chicago Midway

C$ 171 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 14/1. 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
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 246Porter Airlines
Mon, 26 Jan - Fri, 30 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$ 247Porter Airlines
Wed, 14 Jan - Fri, 16 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$ 249Porter Airlines
Fri, 20 Feb - Mon, 23 Feb
Delta Logo
6:05 a.m. - 12:46 p.m.
YYZ
-
MDW
7h 41m1 stop
Delta Logo
1:49 p.m. - 11:13 p.m.
MDW
-
YYZ
8h 24m1 stop
C$ 277Delta
Mon, 19 Jan - Wed, 21 Jan
Air Transat Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 278Air Transat
Fri, 17 Apr - Mon, 20 Apr
Delta Logo
7:45 a.m. - 12:46 p.m.
YYZ
-
MDW
6h 01m1 stop
Delta Logo
1:49 p.m. - 11:11 p.m.
MDW
-
YYZ
8h 22m1 stop
C$ 293Delta
Thu, 19 Feb - Mon, 23 Feb
Multiple Airlines Logo
12:45 a.m. - 11:45 a.m.
YEG
-
MDW
10h 00m1 stop
Multiple Airlines Logo
1:00 p.m. - 9:59 p.m.
MDW
-
YEG
33h 59m2 stops
C$ 321Multiple Airlines
Wed, 21 Jan - Mon, 26 Jan
Multiple Airlines Logo
7:35 p.m. - 11:47 a.m.
YYC
-
MDW
15h 12m1 stop
Multiple Airlines Logo
8:19 p.m. - 12:20 p.m.
MDW
-
YYC
17h 01m1 stop
C$ 331Multiple Airlines
Wed, 14 Jan - Sun, 18 Jan
WestJet Logo
6:30 a.m. - 6:40 p.m.
YYZ
-
MDW
13h 10m1 stop
WestJet Logo
7:20 p.m. - 3:59 p.m.
MDW
-
YYZ
19h 39m1 stop
C$ 355WestJet
Fri, 13 Mar - Mon, 16 Mar
WestJet Logo
6:15 a.m. - 10:32 a.m.
YXE
-
MDW
28h 17m2 stops
WestJet Logo
2:03 p.m. - 1:37 p.m.
MDW
-
YXE
24h 34m1 stop
C$ 1,153WestJet
Fri, 9 Jan - Sat, 21 Mar

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 6 December 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

Mon 26/1

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

Nonstop1h 50m

Chicago Midway

Fri 30/1

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

Nonstop1h 42m

C$ 246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 14/1

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

Nonstop1h 50m

Chicago Midway

Fri 16/1

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

Nonstop1h 42m

C$ 247

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 249

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 19/1

6:05 a.m.-12:46 p.m.

1 stop7h 41m

Chicago Midway

Wed 21/1

1:49 p.m.-11:13 p.m.

1 stop8h 24m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

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

Nonstop1h 50m

Chicago Midway

Mon 20/4

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

Nonstop1h 42m

C$ 278

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 19/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

Chicago Midway

Mon 23/2

1:49 p.m.-11:11 p.m.

1 stop8h 22m

C$ 293

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Wed 21/1

12:45 a.m.-11:45 a.m.

1 stop10h 00m

Chicago Midway

Mon 26/1

1:00 p.m.-9:59 p.m.

2 stops33h 59m

C$ 321

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 14/1

7:35 p.m.-11:47 a.m.

1 stop15h 12m

Chicago Midway

Sun 18/1

8:19 p.m.-12:20 p.m.

1 stop17h 01m

C$ 331

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 13/3

6:30 a.m.-6:40 p.m.

1 stop13h 10m

Chicago Midway

Mon 16/3

7:20 p.m.-3:59 p.m.

1 stop19h 39m

C$ 355

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Fri 9/1

6:15 a.m.-10:32 a.m.

2 stops28h 17m

Chicago Midway

Sat 21/3

2:03 p.m.-1:37 p.m.

1 stop24h 34m

C$ 1,153

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$ 291. 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$ 314.

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$ 239. 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$ 279.

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$ 299. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 674.

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 AIRPORTDecember33% cheaperFlying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 298 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTSeptember79% more expensiveIt costs about C$ 786 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$ 171

Best Round-Trip Price

C$ 246

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$ 171 (Toronto Island to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 246 (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 19% 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 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. 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$ 1,147 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 Minneapolis found flights 92% 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 3 as of December 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