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

C$ 158 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 22/3. 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
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 227Porter Airlines
Thu, 16 Apr - Sun, 19 Apr
Porter Airlines Logo
8:55 a.m. - 11:50 a.m.
YUL
-
MDW
3h 55m
1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.
MDW
-
YUL
5h 30m
1 stop
C$ 230Porter Airlines
Sat, 18 Apr - Mon, 20 Apr
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 233Porter Airlines
Thu, 16 Apr - Sun, 19 Apr
Air Transat Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 275Air Transat
Fri, 6 Mar - Sun, 8 Mar
Delta Logo
6:30 a.m. - 1:25 p.m.
YYC
-
MDW
5h 55m
1 stop
Delta Logo
2:05 p.m. - 8:45 p.m.
MDW
-
YYC
7h 40m
1 stop
C$ 315Delta
Tue, 31 Mar - Tue, 7 Apr
Delta Logo
12:29 p.m. - 5:56 p.m.
YYZ
-
MDW
6h 27m
1 stop
Delta Logo
6:36 p.m. - 10:59 p.m.
MDW
-
YYZ
3h 23m
1 stop
C$ 329Delta
Sat, 23 May - Sun, 31 May
Multiple Airlines Logo
11:00 p.m. - 10:24 p.m.
YVR
-
MDW
21h 24m
1 stop
Multiple Airlines Logo
6:05 a.m. - 11:12 a.m.
MDW
-
YVR
31h 07m
1 stop
C$ 347Multiple Airlines
Fri, 6 Mar - Wed, 11 Mar
Multiple Airlines Logo
8:55 a.m. - 10:29 p.m.
YYC
-
MDW
12h 34m
1 stop
Multiple Airlines Logo
6:00 a.m. - 11:43 a.m.
MDW
-
YYC
30h 43m
1 stop
C$ 365Multiple Airlines
Thu, 26 Feb - Mon, 2 Mar
WestJet Logo
9:45 a.m. - 12:30 p.m.
YYZ
-
MDW
3h 45m
1 stop
WestJet Logo
5:59 p.m. - 10:57 p.m.
MDW
-
YYZ
3h 58m
1 stop
C$ 381WestJet
Wed, 8 Jul - Fri, 10 Jul
WestJet Logo
5:55 a.m. - 6:14 p.m.
YOW
-
MDW
13h 19m
2 stops
WestJet Logo
6:36 p.m. - 5:35 p.m.
MDW
-
YOW
21h 59m
2 stops
C$ 558WestJet
Wed, 3 Jun - Sat, 6 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 15 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 16/4

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 19/4

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 227

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 18/4

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Mon 20/4

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 230

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/4

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 19/4

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 233

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/3

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

Nonstop1h 50m

Chicago Midway

Sun 8/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 275

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 31/3

6:30 a.m.-1:25 p.m.

1 stop5h 55m

Chicago Midway

Tue 7/4

2:05 p.m.-8:45 p.m.

1 stop7h 40m

C$ 314

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 23/5

12:29 p.m.-5:56 p.m.

1 stop6h 27m

Chicago Midway

Sun 31/5

6:36 p.m.-10:59 p.m.

1 stop3h 23m

C$ 329

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 6/3

11:00 p.m.-10:24 p.m.

1 stop21h 24m

Chicago Midway

Wed 11/3

6:05 a.m.-11:12 a.m.

1 stop31h 07m

C$ 347

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/2

8:55 a.m.-10:29 p.m.

1 stop12h 34m

Chicago Midway

Mon 2/3

6:00 a.m.-11:43 a.m.

1 stop30h 43m

C$ 365

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 8/7

9:45 a.m.-12:30 p.m.

1 stop3h 45m

Chicago Midway

Fri 10/7

5:59 p.m.-10:57 p.m.

1 stop3h 58m

C$ 381

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 3/6

5:55 a.m.-6:14 p.m.

2 stops13h 19m

Chicago Midway

Sat 6/6

6:36 p.m.-5:35 p.m.

2 stops21h 59m

C$ 558

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 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$ 266. 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$ 293.

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$ 234. 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$ 261.

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$ 278. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 660.

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$ 291 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTSeptember58% more expensiveIt costs about C$ 618 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$ 158

Best Round-Trip Price

C$ 227

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$ 158 (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$ 227 (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 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 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$ 1,084 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 Los Angeles found flights 87% 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

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
Tue 17/3
Tue 24/3
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$ 161