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Flights to Chicago Midway

C$ 191 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 17/8. 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
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$ 284Porter Airlines
Sat, 19 Sep - Sun, 20 Sep
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 285Porter Airlines
Wed, 26 Aug - Sat, 29 Aug
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 286Porter Airlines
Sat, 22 Aug - Mon, 24 Aug
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 288Porter Airlines
Thu, 6 Aug - Sun, 9 Aug
Delta Logo
6:00 a.m. - 9:07 a.m.
YYZ
-
MDW
4h 07m
1 stop
Delta Logo
5:37 p.m. - 10:59 p.m.
MDW
-
YYZ
4h 22m
1 stop
C$ 343Delta
Wed, 9 Sep - Sat, 12 Sep
Delta Logo
6:00 a.m. - 9:18 a.m.
YYZ
-
MDW
4h 18m
1 stop
Delta Logo
9:29 a.m. - 1:36 p.m.
MDW
-
YYZ
3h 07m
1 stop
C$ 361Delta
Tue, 6 Oct - Sun, 11 Oct
WestJet Logo
9:50 a.m. - 5:04 p.m.
YYZ
-
MDW
8h 14m
1 stop
WestJet Logo
9:34 a.m. - 5:25 p.m.
MDW
-
YYZ
6h 51m
1 stop
C$ 364WestJet
Tue, 1 Sep - Tue, 8 Sep
Multiple Airlines Logo
8:30 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 05m
1 stop
Multiple Airlines Logo
11:45 a.m. - 11:44 p.m.
MDW
-
YHZ
9h 59m
2 stops
C$ 483Multiple Airlines
Sat, 12 Sep - Sat, 19 Sep
Multiple Airlines Logo
6:25 p.m. - 11:00 a.m.
YOW
-
MDW
17h 35m
1 stop
Multiple Airlines Logo
3:20 p.m. - 8:05 a.m.
MDW
-
YOW
15h 45m
1 stop
C$ 507Multiple Airlines
Sun, 6 Sep - Mon, 14 Sep
WestJet Logo
6:05 a.m. - 4:44 p.m.
YVR
-
MDW
8h 39m
1 stop
WestJet Logo
12:33 p.m. - 8:38 p.m.
MDW
-
YVR
10h 05m
1 stop
C$ 629WestJet
Wed, 14 Oct - Tue, 20 Oct

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 20 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 19/9

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

Nonstop1h 50m

Chicago Midway

Sun 20/9

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

Nonstop1h 40m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 26/8

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

Nonstop1h 50m

Chicago Midway

Sat 29/8

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

Nonstop1h 40m

C$ 285

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 22/8

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

Nonstop1h 50m

Chicago Midway

Mon 24/8

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

Nonstop1h 40m

C$ 286

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/8

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

Nonstop1h 50m

Chicago Midway

Sun 9/8

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

Nonstop1h 40m

C$ 288

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 9/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Sat 12/9

5:37 p.m.-10:59 p.m.

1 stop4h 22m

C$ 343

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 6/10

6:00 a.m.-9:18 a.m.

1 stop4h 18m

Chicago Midway

Sun 11/10

9:29 a.m.-1:36 p.m.

1 stop3h 07m

C$ 361

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 1/9

9:50 a.m.-5:04 p.m.

1 stop8h 14m

Chicago Midway

Tue 8/9

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

1 stop6h 51m

C$ 364

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 12/9

8:30 a.m.-2:35 p.m.

1 stop8h 05m

Chicago Midway

Sat 19/9

11:45 a.m.-11:44 p.m.

2 stops9h 59m

C$ 483

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 6/9

6:25 p.m.-11:00 a.m.

1 stop17h 35m

Chicago Midway

Mon 14/9

3:20 p.m.-8:05 a.m.

1 stop15h 45m

C$ 507

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 14/10

6:05 a.m.-4:44 p.m.

1 stop8h 39m

Chicago Midway

Tue 20/10

12:33 p.m.-8:38 p.m.

1 stop10h 05m

C$ 629

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 is only 1 cabin class 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$ 318. 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$ 366.

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

In general, January 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$ 286. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Canada during the month September is also very affordable. Most momondo users find prices during this month for around C$ 291.

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 at noon. Flights from Canada to Chicago Midway Airport during this time can be as low as C$ 332. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 680.

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$ 300 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTApril86% more expensiveIt costs about C$ 755 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 AIRPORTJuly450% 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$ 191

Best Round-Trip Price

C$ 284

Fastest flight time

1h 50m
The best one-way flight price to Chicago from Canada in the last 5 days is C$ 191 (Toronto Island to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 284 (Toronto Island to Chicago Midway).
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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, Noon 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$ 914 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 Fort Lauderdale found flights 75% 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 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
Valparaiso
Portage

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