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Flights to Chicago Midway

C$ 155 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 2/6. 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
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
4:05 p.m. - 10:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 223Porter Airlines
Thu, 9 Apr - Sun, 12 Apr
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
4:05 p.m. - 10:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 224Porter Airlines
Tue, 21 Apr - Fri, 24 Apr
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
4:05 p.m. - 10:45 p.m.
MDW
-
YUL
5h 40m
1 stop
C$ 227Porter Airlines
Mon, 13 Apr - Fri, 17 Apr
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m
1 stop
C$ 229Porter Airlines
Wed, 1 Apr - Mon, 6 Apr
Air Transat Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 270Air Transat
Tue, 5 May - Tue, 26 May
Delta Logo
6:20 a.m. - 8:53 a.m.
YYZ
-
MDW
3h 33m
1 stop
Delta Logo
9:27 a.m. - 3:20 p.m.
MDW
-
YYZ
4h 53m
1 stop
C$ 307Delta
Tue, 7 Apr - Thu, 16 Apr
Delta Logo
12:15 p.m. - 5:54 p.m.
YYZ
-
MDW
6h 39m
1 stop
Delta Logo
9:27 a.m. - 5:21 p.m.
MDW
-
YYZ
6h 54m
1 stop
C$ 308Delta
Thu, 9 Apr - Mon, 13 Apr
Multiple Airlines Logo
3:20 p.m. - 1:00 p.m.
YYZ
-
MDW
22h 40m
1 stop
Multiple Airlines Logo
7:30 a.m. - 7:35 p.m.
MDW
-
YYZ
11h 05m
1 stop
C$ 344Multiple Airlines
Sun, 19 Apr - Mon, 27 Apr
Multiple Airlines Logo
3:30 p.m. - 1:00 p.m.
YOW
-
MDW
22h 30m
2 stops
Multiple Airlines Logo
7:30 a.m. - 5:40 p.m.
MDW
-
YOW
9h 10m
1 stop
C$ 385Multiple Airlines
Fri, 1 May - Tue, 5 May
KLM Logo
7:25 a.m. - 5:54 p.m.
YVR
-
MDW
8h 29m
2 stops
KLM Logo
9:30 a.m. - 8:55 p.m.
MDW
-
YVR
13h 25m
2 stops
C$ 524KLM
Mon, 30 Mar - Sun, 5 Apr

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 26 February 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

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 9/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Sun 12/4

4:05 p.m.-10:45 p.m.

1 stop5h 40m

C$ 223

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 21/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Fri 24/4

4:05 p.m.-10:45 p.m.

1 stop5h 40m

C$ 224

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 13/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Fri 17/4

4:05 p.m.-10:45 p.m.

1 stop5h 40m

C$ 227

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 1/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 6/4

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 229

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/5

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

Nonstop1h 50m

Chicago Midway

Tue 26/5

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

Nonstop1h 40m

C$ 270

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 7/4

6:20 a.m.-8:53 a.m.

1 stop3h 33m

Chicago Midway

Thu 16/4

9:27 a.m.-3:20 p.m.

1 stop4h 53m

C$ 307

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 9/4

12:15 p.m.-5:54 p.m.

1 stop6h 39m

Chicago Midway

Mon 13/4

9:27 a.m.-5:21 p.m.

1 stop6h 54m

C$ 308

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 19/4

3:20 p.m.-1:00 p.m.

1 stop22h 40m

Chicago Midway

Mon 27/4

7:30 a.m.-7:35 p.m.

1 stop11h 05m

C$ 344

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 1/5

3:30 p.m.-1:00 p.m.

2 stops22h 30m

Chicago Midway

Tue 5/5

7:30 a.m.-5:40 p.m.

1 stop9h 10m

C$ 385

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 30/3

7:25 a.m.-5:54 p.m.

2 stops8h 29m

Chicago Midway

Sun 5/4

9:30 a.m.-8:55 p.m.

2 stops13h 25m

C$ 524

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 Monday when prices can be found for as low as C$ 267. 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$ 301.

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$ 235. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Canada during the month January is also very affordable. Most momondo users find prices during this month for around C$ 263.

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$ 279. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 663.

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$ 293 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTSeptember58% more expensiveIt costs about C$ 621 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 AIRPORTJuly350% 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$ 155

Best Round-Trip Price

C$ 223

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$ 155 (Montreal Pierre Elliott Trudeau Intl to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 223 (Montreal Pierre Elliott Trudeau Intl 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 Monday. 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$ 1,080 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 Las Vegas found flights 86% 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 February 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
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$ 172