Find flights
Deals

C$ 177+ Cheap flights from Chicago Midway Airport

MDW — YYZ
30 Oct — 6 Nov1
1 adult
1 adult, Economy, 0 bags

Find flights from Midway within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Wed 11/11

5:00 a.m.-8:05 a.m.

Nonstop2h 05m

New York LaGuardia

Wed 31/12

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

Nonstop0h 00m

C$ 197

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Mon 9/11

7:15 p.m.-10:20 p.m.

Nonstop2h 05m

New York LaGuardia

Wed 31/12

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

Nonstop0h 00m

C$ 197

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Mon 23/11

7:15 p.m.-10:20 p.m.

Nonstop2h 05m

New York LaGuardia

Wed 31/12

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

Nonstop0h 00m

C$ 197

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Thu 3/12

5:00 a.m.-8:05 a.m.

Nonstop2h 05m

New York LaGuardia

Wed 31/12

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

Nonstop0h 00m

C$ 197

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Sat 14/11

9:15 a.m.-12:15 p.m.

Nonstop2h 00m

New York LaGuardia

Wed 31/12

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

Nonstop0h 00m

C$ 197

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Wed 4/11

5:00 a.m.-8:05 a.m.

Nonstop2h 05m

New York LaGuardia

Wed 31/12

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

Nonstop0h 00m

C$ 197

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Thu 26/11

10:40 a.m.-1:05 p.m.

Nonstop2h 25m

Dallas Love Field

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 197

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Wed 21/10

12:00 p.m.-2:15 p.m.

Nonstop2h 15m

Dallas Love Field

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 197

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Mon 26/10

5:15 a.m.-7:30 a.m.

Nonstop2h 15m

Dallas Love Field

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 197

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Mon 19/10

5:15 a.m.-7:30 a.m.

Nonstop2h 15m

Dallas Love Field

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 197

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/9

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Estimated round-trip price

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago Midway Airport?

Currently, July is the cheapest month in which you can book a flight from Chicago Midway Airport (average of C$ 234). Flying from Chicago Midway Airport in February will prove the most costly (average of C$ 955). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago Midway Airport?

From Chicago Midway Airport you can expect to find greater availability for the following destinations: Detroit (170 flights per day), Atlanta (131 flights per day) and Minneapolis (84 flights per day).

Toronto
Toronto
From C$ 113
Dallas/Fort Worth
Dallas/Fort Worth
From C$ 66
Detroit
Detroit
From C$ 1,259
New York
New York
From C$ 137

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Dallas/Fort Worth, with prices starting at C$ 66. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From C$ 66
Toronto
Toronto
From C$ 113
New York
New York
From C$ 137
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 141

Browse thousands of different options on Cheapflights for your next trip

Alternate flight departure points to Midway

Flights from St. Louis
Flights from O'Hare Intl
Flights from Evansville
Flights from Belleville
Flights from Bloomington
Flights from Peoria
Flights from Champaign
Flights from Moline
Flights from Dubuque
Flights from Springfield

Related info for your journey

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    This month, the top selected destinations from Chicago Midway Airport are Atlanta, Las Vegas, Dallas/Fort Worth Airport. Throughout the year, Atlanta, Orlando Airport, Las Vegas are some of the top choices made by users flying from Chicago Midway Airport.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as C$ 66 to Dallas/Fort Worth Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for C$ 627 to fly from Chicago Midway Airport.

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

    At the present moment the cheapest month to fly from Chicago Midway Airport is currently July; with February being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    Check out the cheapest flights from Chicago Midway Airport to embark to:
    Travel from Chicago to Toronto from C$ 453 round trip
    Travel from Chicago to Montreal from C$ 489 round trip
    Travel from Chicago to Calgary from C$ 489 round trip
    Travel from Chicago to Vancouver from C$ 677 round trip

  • How does Cheapflights help users find flights from Midway?

    Deals for flights from Midway are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

  • Why should you use Cheapflights to find cheap flight tickets from Midway?

    Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Midway with no change fees?

    Yes! Cheapflights helps users easily find flights from Midway with no change fees.

  • Can Cheapflights notify me if prices for flights from Midway become cheaper?

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

See more FAQs

Fly with Cheapflights

How does Cheapflights help users find flights from Midway?

Deals for flights from Midway are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Midway?

Cheapflights helps you find that perfect flight from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway with no change fees?

Yes! Cheapflights helps users easily find flights from Midway with no change fees.

Can Cheapflights notify me if prices for flights from Midway become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.