How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Toronto , which takes 1h 55m , Montreal , which takes 2h 40m, Calgary , which takes 3h 31m, and Vancouver , which takes 4h 09m.

What is the cheapest flight to Chicago Midway Airport?

In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto , at $332 return . The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $475 in the last 5 days.

How far is Chicago Midway Airport from central Chicago?

You’ll need to travel 9 miles to reach the Chicago city center from Chicago Midway Airport.

How much is a flight to Chicago?

On average, a flight to Chicago costs $346. The cheapest price found on KAYAK in the last 2 weeks cost $199 and departed from Toronto Island Airport.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $229. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $349 on average.

How does KAYAK find such low prices on flights to Chicago Midway Airport?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights to Chicago Midway Airport?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

What is the cheapest time of day to fly to Chicago Midway Airport?

The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon , when round-trip flights cost $274 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $290.

How many direct flights to Chicago Midway Airport are there each day?

There are around 229 direct flights from within Canada to Chicago Midway Airport every day. Most flights depart in the morning, with 41% of flights departing in the morning.

How many direct flights to Chicago Midway Airport are there each week?

Each week there are around 1,597 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Sunday, with 17% of flights taking off on this day.

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Toronto Island Airport $214 round-trip.

$195 CHEAP FLIGHTS from Canada to Chicago Midway (MDW)

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Flight Deals

Cheap Flights from Canada to Midway

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Canada to Midway

Thu, Dec 3 - Sun, Dec 6

6:00 am - 9:37 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

1:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

8h 26m1 stop Detroit Metropolitan Wayne County

$332Delta

Sat, Dec 5 - Mon, Dec 7

6:00 am - 9:37 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

6:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 26m1 stop Detroit Metropolitan Wayne County

$332Delta

Fri, Dec 11 - Sun, Dec 13

9:45 am - 1:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 16m1 stop Detroit Metropolitan Wayne County

9:37 am - 5:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

$332Delta

Sun, Dec 6 - Sun, Dec 13

12:15 pm - 6:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

6h 46m1 stop Detroit Metropolitan Wayne County

9:37 am - 5:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

6h 43m1 stop Detroit Metropolitan Wayne County

$332Delta

Tue, Dec 1 - Wed, Dec 2

6:00 am - 1:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

8h 01m1 stop Detroit Metropolitan Wayne County

1:41 pm - 11:07 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

8h 26m1 stop Detroit Metropolitan Wayne County

$332Delta

Sat, Feb 27 - Sat, Mar 6

7:45 am - 2:25 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

7h 40m1 stop Detroit Metropolitan Wayne County

9:33 am - 4:04 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

5h 31m1 stop Detroit Metropolitan Wayne County

$332Delta

Wed, Dec 16 - Thu, Jan 7

6:00 am - 1:01 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

8h 01m1 stop Detroit Metropolitan Wayne County

9:38 am - 7:14 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

8h 36m1 stop Detroit Metropolitan Wayne County

$332Delta

Thu, Dec 3 - Sun, Dec 6

6:00 am - 9:37 amYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

6:41 pm - 11:33 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

3h 52m1 stop Detroit Metropolitan Wayne County

$335KLM

Thu, Dec 3 - Mon, Dec 7

7:00 am - 4:16 pmYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

10h 16m1 stop Atlanta Hartsfield-Jackson

5:30 pm - 11:41 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 11m1 stop Minneapolis St Paul

$342Delta

Thu, Dec 3 - Sat, Dec 5

6:00 am - 9:37 amYUL Montreal Pierre Elliott Trudeau Intl-MDW Chicago Midway

4h 37m1 stop Detroit Metropolitan Wayne County

5:30 pm - 11:41 pmMDW Chicago Midway-YUL Montreal Pierre Elliott Trudeau Intl

5h 11m1 stop Minneapolis St Paul

$344Delta

Recent last minute flight deals from Canada to Midway

Thu, Nov 12 - Sat, Nov 14

8:45 am - 4:39 pmYYC Calgary-MDW Chicago Midway

7h 54m1 stop Minneapolis St Paul

12:30 pm - 12:19 amMDW Chicago Midway-YYC Calgary

11h 49m2 stops Minneapolis St Paul Salt Lake City

$468Delta

Tue, Nov 10 - Thu, Nov 12

8:45 am - 10:54 pmYYC Calgary-MDW Chicago Midway

14h 09m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

9:30 am - 9:58 pmMDW Chicago Midway-YYC Calgary

12h 28m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul

$468Delta

Tue, Nov 10 - Thu, Nov 12

8:45 am - 10:54 pmYYC Calgary-MDW Chicago Midway

14h 09m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

12:30 pm - 9:58 pmMDW Chicago Midway-YYC Calgary

9h 28m1 stop Minneapolis St Paul

$468Delta

Tue, Nov 10 - Thu, Nov 12

8:45 am - 10:54 pmYYC Calgary-MDW Chicago Midway

14h 09m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson

10:34 am - 12:17 amMDW Chicago Midway-YYC Calgary

13h 43m2 stops Minneapolis St Paul Salt Lake City

$471Delta

Tue, Nov 10 - Tue, Nov 17

6:00 am - 9:46 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

9:30 am - 1:30 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 00m1 stop Detroit Metropolitan Wayne County

$496Delta

Tue, Nov 10 - Wed, Nov 18

9:45 am - 12:51 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 06m1 stop Detroit Metropolitan Wayne County

1:31 pm - 10:57 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

8h 26m1 stop Detroit Metropolitan Wayne County

$496Delta

Wed, Nov 11 - Tue, Nov 17

6:00 am - 9:46 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

9:30 am - 1:30 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 00m1 stop Detroit Metropolitan Wayne County

$496Delta

Wed, Nov 11 - Wed, Nov 18

6:00 am - 9:46 amYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 46m1 stop Detroit Metropolitan Wayne County

9:30 am - 1:30 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 00m1 stop Detroit Metropolitan Wayne County

$496Delta

Tue, Nov 10 - Sat, Nov 21

2:20 pm - 6:04 pmYYZ Toronto Pearson Intl-MDW Chicago Midway

4h 44m1 stop Detroit Metropolitan Wayne County

6:44 pm - 10:57 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

3h 13m1 stop Detroit Metropolitan Wayne County

$503Delta

Tue, Nov 10 - Thu, Nov 19

6:15 am - 10:24 amYYZ Toronto Pearson Intl-MDW Chicago Midway

5h 09m1 stop Atlanta Hartsfield-Jackson

9:30 am - 5:20 pmMDW Chicago Midway-YYZ Toronto Pearson Intl

6h 50m1 stop Detroit Metropolitan Wayne County

$511Delta

Booking Insights

KAYAK's insights & trends for flights to Midway

Get data-powered insights and trends for flights to Midway to help you find the cheapest flights, the best time to fly and much more.

Prices

What is the cheapest flight to Chicago Midway Airport? These are the best round-trip prices found by users searching on KAYAK in the last 5 days.: In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto, at $332 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $475 in the last 5 days.
What is the cheapest day to fly to Chicago? The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.: Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $229. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $349 on average.
What is the cheapest time of day to fly to Chicago Midway Airport? The average price for all round-trip flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.: The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when round-trip flights cost $274 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $290.
What is a good deal for flights to Chicago Midway Airport?: If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Toronto Island Airport $214 round-trip.

Find deals

Low season	February
High season	May
Cheapest flight	$195

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 22% lower on average.

Flight from Toronto Pearson Airport to Chicago Midway Airport

What is the cheapest flight to Chicago Midway Airport?
In the last 5 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto, at $332 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $475 in the last 5 days.
How far is Chicago Midway Airport from central Chicago?
You’ll need to travel 9 miles to reach the Chicago city center from Chicago Midway Airport.
How much is a flight to Chicago?
On average, a flight to Chicago costs $346. The cheapest price found on KAYAK in the last 2 weeks cost $199 and departed from Toronto Island Airport.
How does KAYAK find such low prices on flights to Chicago Midway Airport?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights to Chicago Midway Airport?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.
How many direct flights to Chicago Midway Airport are there each week?
Each week there are around 1,597 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Sunday, with 17% of flights taking off on this day.

Looking for a cheap flight? 25% of our users found flights on this route for $247 or less one-way and $214 or less round-trip.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Merrillville

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Saint John

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$195 Find Cheap Flights from Canada to Chicago Midway Airport - Compare and Save

Cheap Flights from Canada to Midway

Recent round-trip flight deals from Canada to Midway

Recent one-way flight deals from Canada to Midway

Recent last minute flight deals from Canada to Midway

KAYAK's insights & trends for flights to Midway

What is the cheapest flight to Chicago Midway Airport?

What is the cheapest day to fly to Chicago?

What is the cheapest time of day to fly to Chicago Midway Airport?

What is a good deal for flights to Chicago Midway Airport?

How long is the flight to Chicago Midway Airport?

How many direct flights to Chicago Midway Airport are there each day?

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