Cheap flights from Lester B. Pearson Intl to Chicago Midway

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How to find the cheapest flight from
Lester B. Pearson Intl (YYZ) to Chicago Midway (MDW)

YYZ - MDW
Price
C$ 266 - C$ 616
MDW
Temperature
1 - 29 °C
MDW
Rainfall
17 - 109 mm

Popular in

August

High demand for flights, 42% potential price rise

Cheapest in

April

Best time to find cheap flights, 25% potential price drop

Round-trip from

C$ 266

From Lester B. Pearson Intl to Chicago Midway

One-way from

C$ 241

One-way flight from Lester B. Pearson Intl to Chicago Midway

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Lester B. Pearson Intl to Chicago Midway?

Tuesday is generally a great day to depart. Flying on this day could help you save up to 71%.

How far in advance should I book a flight from Lester B. Pearson Intl to Chicago Midway?

Travellers have found it’s best to book a flight 34 days in advance to save up to 86% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 34 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Lester B. Pearson Intl to Chicago Midway 1-2 weeks in advance for as low as C$ 440, or C$ 596 for flights within the next 24 hours.

What is the cheapest month to fly from Lester B. Pearson Intl to Chicago Midway?

April can be a great time to fly to Chicago Midway from Lester B. Pearson Intl with a flight ticket averaging about C$ 320. Cheapflights users have found deals in the month of April for as cheap as C$ 242. The most expensive prices can be found in the month of January.

When is the cheapest time to fly from Lester B. Pearson Intl to Chicago Midway (YYZ - MDW)?

It’s optimal to fly from Lester B. Pearson Intl to Chicago Midway at noon. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the afternoon.

Cheap flights from Lester B. Pearson Intl to Chicago Midway in January, February 2021

The best prices found for YYZ to MDW flights for January, February
17 Feb - 24 Feb
C$ 388pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl
22 Jan - 5 Feb
C$ 420pp
YYZ
Toronto Pearson Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl
22 Jan - 5 Feb
C$ 432pp
YYZ
Toronto Pearson Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl

Lester B. Pearson Intl to Chicago Midway 2021 flight deals

Cheap flights to Chicago Midway from Lester B. Pearson Intl found for this year
15 May - 23 May
C$ 377pp
YYZ
Toronto Pearson Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YYZ
Toronto Pearson Intl
17 Feb - 24 Feb
C$ 388pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl
14 Apr - 23 Apr
C$ 389pp
YYZ
Toronto Pearson Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YYZ
Toronto Pearson Intl

Last minute flights from Lester B. Pearson Intl to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Lester B. Pearson Intl, departing today and this week
29 Jan - 2 Feb
C$ 469pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YYZ
Toronto Pearson Intl
30 Jan - 10 Feb
C$ 682pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl
29 Jan - 1 Feb
C$ 718pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl

One-way flights to Chicago Midway from Lester B. Pearson Intl

The cheapest one-way flights from Lester B. Pearson Intl to Chicago Midway
3:30 a.m. - 7:59 a.m.
Aeromexico
1 stop
5h 29m
YYZ - MDW
Aeromexico
C$ 241
Gate1.ca
2:30 a.m. - 11:23 a.m.
Delta
1 stop
9h 53m
YYZ - MDW
Delta
C$ 496
Delta
1:20 a.m. - 5:48 a.m.
Multiple Airlines
3 stops
29h 28m
YYZ - MDW
Multiple Airlines
C$ 1,594
Kiwi.com

Related info for your journey

Useful info, stats and facts about Lester B. Pearson Intl to Chicago Midway flights.

Flight FAQs

From Lester B. Pearson Intl to Chicago Midway

Can I find flights from Lester B. Pearson Intl to Chicago Midway for under C$ 380 on Cheapflights?

Yes, there are multiple flights from Lester B. Pearson Intl to Chicago Midway for under C$ 380. The cheapest flight booked recently is on Delta for just C$ 377, but on average you can expect to pay C$ 531.

What safety measures are being taken by airlines flying from Toronto Pearson Intl to Chicago Midway to control the spread of COVID-19?

New policies can now be found on Delta to help keep travellers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Toronto Pearson Intl to Chicago Midway. Policies will vary by airline.

Which airlines flying from Toronto Pearson Intl to Chicago Midway have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Toronto Pearson Intl to Chicago Midway that may be offering flexible cancellation policies are Delta, Air Canada, and Porter Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Are there direct flights from Lester B. Pearson Intl to Chicago Midway for under C$ 380 on Cheapflights?

There are no direct flights from Lester B. Pearson Intl to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Lester B. Pearson Intl to Chicago Midway for under C$ 507?

There are currently 6+ open flights from Lester B. Pearson Intl to Chicago Midway within the next 7 days for less than C$ 507.

Does it rain more in Lester B. Pearson Intl or Chicago Midway?

When travelling, it's generally smart to pack in preparation for rain or any other conditions that may arise. The rainfall in Lester B. Pearson Intl is roughly greater than that of Chicago Midway. You can assume this to be the case over the next 20 days.

Is Lester B. Pearson Intl weather warmer or cooler than Chicago Midway?

Expect the weather to be around 29 °C on average in July. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Chicago Midway is generally hotter than in Lester B. Pearson Intl.

How long is the flight from Lester B. Pearson Intl to Chicago Midway?

For as low as C$ 390, Delta can have you in Chicago Midway from Lester B. Pearson Intl in 3h 59m. Both multi-stop and direct flights can be found to your destination and back.

What are the cheapest airlines to flying from Lester B. Pearson Intl to Chicago Midway round-trip?

According to our current data, Delta (C$ 377), and WestJet (C$ 565) offers the cheapest pricing from Lester B. Pearson Intl to Chicago Midway.

What are the cheapest airlines to fly from Lester B. Pearson Intl to Chicago Midway one-way?

The cheapest airlines for a one-way flight from Lester B. Pearson Intl to Chicago Midway are Delta (C$ 225), Aeromexico (C$ 241), and WestJet (C$ 486).

Alternative routes for Lester B. Pearson Intl to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Lester B. Pearson Intl to Chicago Midway
Today's exchange rate
C$ 1 = $0.79
Average temperature for January in Chicago Midway
1.0 °C
Avg rainfall for January in Chicago Midway
17.0 mm

Airports servicing Toronto

Airports servicing Chicago

Top 4 airlines flying from Lester B. Pearson Intl to Chicago Midway

The chart below displays the airlines Cheapflights users travelling from Lester B. Pearson Intl to Chicago Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Air Canada
C$ 221 C$ 300 No cancel fee 67%
Search Air Canada flights
Porter Airlines
C$ 202 C$ 311 No cancel fee 52%
Search Porter Airlines flights
WestJet
C$ 210 C$ 384 No cancel fee 60%
Search WestJet flights
Delta
C$ 209 C$ 433 No cancel fee N/A
Search Delta flights
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