Latest deals
Insights
When to book
FAQs
Price Alerts
Flights to Chicago Midway

C$ 175 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 8/6. 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

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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$ 277Porter Airlines
Fri, 3 Jul - Mon, 6 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$ 279Porter Airlines
Thu, 16 Jul - Sun, 19 Jul
Porter Airlines Logo
8:45 a.m. - 9:35 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 280Porter Airlines
Fri, 12 Jun - Sun, 14 Jun
Porter Airlines Logo
8:45 a.m. - 9:35 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 281Porter Airlines
Sat, 13 Jun - Sun, 14 Jun
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 361Delta
Thu, 25 Jun - Mon, 29 Jun
Delta Logo
7:45 a.m. - 9:45 p.m.
YYC
-
MDW
13h 00m
2 stops
Delta Logo
1:00 p.m. - 8:54 p.m.
MDW
-
YYC
8h 54m
2 stops
C$ 363Delta
Tue, 27 Oct - Sat, 31 Oct
WestJet Logo
6:05 a.m. - 12:39 p.m.
YYZ
-
MDW
7h 34m
1 stop
WestJet Logo
9:35 a.m. - 5:25 p.m.
MDW
-
YYZ
6h 50m
1 stop
C$ 368WestJet
Sat, 26 Sep - Tue, 29 Sep
WestJet Logo
12:14 p.m. - 6:36 p.m.
YYZ
-
MDW
7h 22m
1 stop
WestJet Logo
1:31 p.m. - 11:07 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 371WestJet
Tue, 16 Jun - Fri, 19 Jun
Multiple Airlines Logo
11:00 p.m. - 9:35 a.m.
YHZ
-
MDW
12h 35m
1 stop
Multiple Airlines Logo
10:15 a.m. - 12:24 p.m.
MDW
-
YHZ
24h 09m
1 stop
C$ 554Multiple Airlines
Sat, 13 Jun - Tue, 16 Jun
Multiple Airlines Logo
11:00 p.m. - 9:35 a.m.
YHZ
-
MDW
12h 35m
1 stop
Multiple Airlines Logo
10:15 a.m. - 2:10 p.m.
MDW
-
YHZ
25h 55m
1 stop
C$ 561Multiple Airlines
Sat, 13 Jun - Mon, 15 Jun

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 30 May 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

Fri 3/7

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

Nonstop1h 50m

Chicago Midway

Mon 6/7

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

Nonstop1h 40m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/7

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

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

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

Nonstop1h 40m

C$ 280

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 13/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

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

Nonstop1h 40m

C$ 281

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 25/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Mon 29/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 361

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 27/10

7:45 a.m.-9:45 p.m.

2 stops13h 00m

Chicago Midway

Sat 31/10

1:00 p.m.-8:54 p.m.

2 stops8h 54m

C$ 363

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 26/9

6:05 a.m.-12:39 p.m.

1 stop7h 34m

Chicago Midway

Tue 29/9

9:35 a.m.-5:25 p.m.

1 stop6h 50m

C$ 368

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 16/6

12:14 p.m.-6:36 p.m.

1 stop7h 22m

Chicago Midway

Fri 19/6

1:31 p.m.-11:07 p.m.

1 stop8h 36m

C$ 371

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 13/6

11:00 p.m.-9:35 a.m.

1 stop12h 35m

Chicago Midway

Tue 16/6

10:15 a.m.-12:24 p.m.

1 stop24h 09m

C$ 554

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 13/6

11:00 p.m.-9:35 a.m.

1 stop12h 35m

Chicago Midway

Mon 15/6

10:15 a.m.-2:10 p.m.

1 stop25h 55m

C$ 561

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Friday when prices can be found for as low as C$ 293. 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$ 320.

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

In general, June 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$ 110. If you are unable to visit Chicago Midway Airport during the month of June, then departing from Canada during the month August is also very affordable. Most momondo users find prices during this month for around C$ 113.

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$ 295. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 668.

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 AIRPORTDecember21% cheaperFlying from Toronto Pearson Intl Airport to Chicago Midway Airport costs on average just C$ 295 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTApril100% more expensiveIt costs about C$ 742 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 AIRPORTJuly300% 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$ 175

Best Round-Trip Price

C$ 277

Fastest flight time

1h 50m

Popular in

November
The best one-way flight price to Chicago from Canada in the last 5 days is C$ 175 (Toronto Island to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 277 (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 27% 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$ 854 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 78% 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 May 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 29/6
Mon 6/7
By creating a price alert you accept our terms of use and privacy policy.

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$ 177