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Flights to Chicago Midway

C$ 275 Cheap flights to Chicago Midway Airport

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.
Delta Logo
6:10 a.m. - 9:16 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 06m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:59 p.m. - 10:59 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 00m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Fri, 8 Jan - Sun, 10 Jan
Delta Logo
2:25 p.m. - 6:01 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 36m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:37 a.m. - 5:20 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 43m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Mon, 7 Dec - Mon, 14 Dec
Delta Logo
6:00 a.m. - 9:37 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Thu, 3 Dec - Sun, 6 Dec
Delta Logo
9:45 a.m. - 1:01 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 16m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:33 a.m. - 4:04 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
5h 31m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Sun, 7 Feb - Sat, 13 Feb
Delta Logo
12:15 p.m. - 6:01 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Fri, 4 Dec - Mon, 7 Dec
Delta Logo
12:15 p.m. - 6:01 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
6h 46m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Fri, 4 Dec - Sun, 6 Dec
Delta Logo
9:45 a.m. - 1:01 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 16m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 26m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Tue, 1 Dec - Fri, 4 Dec
Delta Logo
9:45 a.m. - 1:17 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 32m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:59 p.m. - 7:14 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 15m1 stop Detroit Metropolitan Wayne County
C$ 468Delta
Fri, 8 Jan - Mon, 11 Jan
Delta Logo
6:00 a.m. - 9:37 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:41 p.m. - 11:07 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
8h 26m1 stop Detroit Metropolitan Wayne County
C$ 469Delta
Thu, 3 Dec - Sun, 6 Dec
Delta Logo
6:00 a.m. - 9:37 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 a.m. - 5:33 p.m.MDW  Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl
10h 33m1 stop Atlanta Hartsfield-Jackson
C$ 482Delta
Fri, 4 Dec - Sun, 13 Dec

momondo Fare Finder

 
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

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 8/1

6:10 a.m.-9:16 a.m.

1 stop4h 06m

Chicago Midway

Sun 10/1

1:59 p.m.-10:59 p.m.

1 stop8h 00m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 7/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

Chicago Midway

Mon 14/12

9:37 a.m.-5:20 p.m.

1 stop6h 43m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 3/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Sun 6/12

1:41 p.m.-11:07 p.m.

1 stop8h 26m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 7/2

9:45 a.m.-1:01 p.m.

1 stop4h 16m

Chicago Midway

Sat 13/2

9:33 a.m.-4:04 p.m.

1 stop5h 31m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 4/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Mon 7/12

6:41 p.m.-11:07 p.m.

1 stop3h 26m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 4/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Sun 6/12

1:41 p.m.-11:07 p.m.

1 stop8h 26m

C$ 468
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 1/12

9:45 a.m.-1:01 p.m.

1 stop4h 16m

Chicago Midway

Fri 4/12

6:41 p.m.-11:07 p.m.

1 stop3h 26m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 8/1

9:45 a.m.-1:17 p.m.

1 stop4h 32m

Chicago Midway

Mon 11/1

1:59 p.m.-7:14 p.m.

1 stop4h 15m

C$ 468

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 3/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Sun 6/12

1:41 p.m.-11:07 p.m.

1 stop8h 26m

C$ 469

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 4/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Sun 13/12

6:00 a.m.-5:33 p.m.

1 stop10h 33m

C$ 482

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 Thursday when prices can be found for as low as C$ 324. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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$ 388.

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$ 288. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Canada during the month December is also very affordable. Most momondo users find prices during this month for around C$ 312.

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$ 336. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the afternoon when prices are around C$ 385.

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

Cheap Chicago Midway Airport flight deals and tips

Summary info about Chicago Midway Airport flight prices, duration and airlines

Best One-Way Price

C$ 275

Best Round-Trip Price

C$ 468

Fastest flight time

8h 01m
The best one-way flight price to Chicago from Canada in the last 5 days is C$ 275 (Toronto Pearson Intl to Chicago Midway).
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The best round-trip flight price to Chicago from Canada in the last 5 days is C$ 468 (Toronto Pearson Intl to Chicago Midway).
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The fastest flight to Chicago from Canada takes 8h 01m (Toronto Pearson Intl 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 Thursday. Try to avoid departing on a Monday, 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. Afternoon 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$ 1,041 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 82% 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 1 as of November 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
Benton Harbor
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.

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Find better results for your trip to Chicago Midway Airport MDW

Popular Flights to Chicago Midway Airport

Flights from Toronto Island to MDWfrom C$ 207