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Flights to Chicago Midway

C$ 160 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 21/4. 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
10:35 a.m. - 2:35 p.m.
YUL
-
MDW
5h 00m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 246Porter Airlines
Fri, 1 May - Sun, 3 May
Porter Airlines Logo
9:50 a.m. - 3:20 p.m.
YUL
-
MDW
6h 30m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.
MDW
-
YUL
5h 45m
1 stop
C$ 247Porter Airlines
Sun, 19 Apr - Thu, 23 Apr
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
3:20 p.m. - 10:10 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 250Porter Airlines
Fri, 8 May - Sun, 10 May
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$ 251Porter Airlines
Wed, 15 Apr - Tue, 21 Apr
Delta Logo
6:10 a.m. - 8:47 a.m.
YYZ
-
MDW
3h 37m
1 stop
Delta Logo
6:38 p.m. - 10:56 p.m.
MDW
-
YYZ
3h 18m
1 stop
C$ 349Delta
Fri, 17 Apr - Sun, 19 Apr
Delta Logo
6:30 a.m. - 5:54 p.m.
YYC
-
MDW
10h 24m
2 stops
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
C$ 350Delta
Tue, 7 Apr - Tue, 14 Apr
Multiple Airlines Logo
11:35 a.m. - 12:10 p.m.
YHZ
-
MDW
26h 35m
1 stop
Multiple Airlines Logo
4:05 p.m. - 11:54 p.m.
MDW
-
YHZ
29h 49m
2 stops
C$ 494Multiple Airlines
Fri, 10 Apr - Fri, 17 Apr
Multiple Airlines Logo
11:35 a.m. - 12:10 p.m.
YHZ
-
MDW
26h 35m
1 stop
Multiple Airlines Logo
11:00 a.m. - 12:35 p.m.
MDW
-
YHZ
23h 35m
2 stops
C$ 500Multiple Airlines
Fri, 10 Apr - Wed, 15 Apr
WestJet Logo
5:20 p.m. - 6:40 p.m.
YWG
-
MDW
25h 20m
1 stop
WestJet Logo
7:16 p.m. - 10:56 a.m.
MDW
-
YWG
15h 40m
1 stop
C$ 649WestJet
Tue, 7 Apr - Tue, 14 Apr
WestJet Logo
5:00 a.m. - 5:54 p.m.
YWG
-
MDW
12h 54m
2 stops
WestJet Logo
7:16 p.m. - 10:56 a.m.
MDW
-
YWG
15h 40m
1 stop
C$ 654WestJet
Tue, 7 Apr - Tue, 14 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 11 March 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

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 1/5

10:35 a.m.-2:35 p.m.

1 stop5h 00m

Chicago Midway

Sun 3/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 246

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 19/4

9:50 a.m.-3:20 p.m.

1 stop6h 30m

Chicago Midway

Thu 23/4

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

1 stop5h 45m

C$ 247

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 8/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Sun 10/5

3:20 p.m.-10:10 p.m.

1 stop5h 50m

C$ 250

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/4

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

1 stop4h 25m

Chicago Midway

Tue 21/4

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

1 stop4h 30m

C$ 251
Quickest round-trip

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 17/4

6:10 a.m.-8:47 a.m.

1 stop3h 37m

Chicago Midway

Sun 19/4

6:38 p.m.-10:56 p.m.

1 stop3h 18m

C$ 349

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 7/4

6:30 a.m.-5:54 p.m.

2 stops10h 24m

Chicago Midway

Tue 14/4

9:27 a.m.-8:40 p.m.

2 stops12h 13m

C$ 350

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 10/4

11:35 a.m.-12:10 p.m.

1 stop26h 35m

Chicago Midway

Fri 17/4

4:05 p.m.-11:54 p.m.

2 stops29h 49m

C$ 494

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 10/4

11:35 a.m.-12:10 p.m.

1 stop26h 35m

Chicago Midway

Wed 15/4

11:00 a.m.-12:35 p.m.

2 stops23h 35m

C$ 500

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 7/4

5:20 p.m.-6:40 p.m.

1 stop25h 20m

Chicago Midway

Tue 14/4

7:16 p.m.-10:56 a.m.

1 stop15h 40m

C$ 649

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 7/4

5:00 a.m.-5:54 p.m.

2 stops12h 54m

Chicago Midway

Tue 14/4

7:16 p.m.-10:56 a.m.

1 stop15h 40m

C$ 654

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$ 265. 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$ 298.

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$ 277. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 658.

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$ 291 in December
MOST EXPENSIVE MONTH TO FLY TO CHICAGO MIDWAY AIRPORT FROM TORONTO PEARSON INTL AIRPORTSeptember69% more expensiveIt costs about C$ 616 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 AIRPORTJuly800% 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$ 160

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$ 160 (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$ 246 (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 21% 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$ 976 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 84% 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 March 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
Munster
Hammond

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$ 165