Cheap flights from Toronto Pearson to Chicago Midway from Can$244

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Cheap Toronto Pearson - Chicago Midway flight offers

Find cheap flight tickets and last-minute flight deals from Toronto Pearson to Chicago Midway

DELTA
Fri, 09-25 (YYZ) Toronto -> (MDW) Chicago
DELTA
Mon, 09-28 (MDW) Chicago -> (YYZ) Toronto
Price found 2 days ago
from Can$154
DELTA
Sat, 06-20 (YYZ) Toronto -> (MDW) Chicago
DELTA
Tue, 06-23 (MDW) Chicago -> (YYZ) Toronto
Price found 3 days ago
from Can$183
DELTA
Sat, 06-27 (YYZ) Toronto -> (MDW) Chicago
DELTA
Tue, 06-30 (MDW) Chicago -> (YYZ) Toronto
Price found 8 days ago
from Can$222
DELTA
Fri, 06-12 (YYZ) Toronto -> (MDW) Chicago
DELTA
Mon, 06-15 (MDW) Chicago -> (YYZ) Toronto
Price found 12 days ago
from Can$230
DELTA
Sat, 08-15 (YYZ) Toronto -> (MDW) Chicago
DELTA
Wed, 08-19 (MDW) Chicago -> (YYZ) Toronto
Price found 8 days ago
from Can$236
DELTA
Thu, 06-18 (YYZ) Toronto -> (MDW) Chicago
DELTA
Sat, 06-20 (MDW) Chicago -> (YYZ) Toronto
Price found 2 days ago
from Can$266
DELTA
Sun, 11-15 (YYZ) Toronto -> (MDW) Chicago
DELTA
Mon, 11-30 (MDW) Chicago -> (YYZ) Toronto
Price found 6 days ago
from Can$273
DELTA
Wed, 06-17 (YYZ) Toronto -> (MDW) Chicago
DELTA
Sat, 06-27 (MDW) Chicago -> (YYZ) Toronto
Price found 12 days ago
from Can$309
DELTA
Fri, 06-12 (YYZ) Toronto -> (MDW) Chicago
Price found 9 days ago
from Can$174
WestJet
Mon, 07-06 (YYZ) Toronto -> (MDW) Chicago
Price found 6 days ago
from Can$244

Info about flights from Toronto Pearson to Chicago Midway

Some useful info about flights from Toronto Pearson to Chicago Midway to help you plan your next trip

Best price last 15 days Can$244
Average flight duration 2h 41m
Cheapest month February
Average number of flights per week 1
First flight time 00:30
Last flight time 23:50
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Top airlines on the route Toronto Pearson - Chicago Midway

Airlines providing flights to Chicago Midway from Toronto Pearson

DELTA
DELTA
WestJet
WestJet

Looking for the price of a flight from Toronto Pearson to Chicago Midway?

There’s no fixed price — fares between Toronto and Chicago can vary a lot by day or time.

Can$244 is the best price recorded in the last 15 days.

It’s often useful to check whether nearby airports offer better fares. Flying during less crowded periods also increases your chances of finding good deals.

What are the airport options between Toronto and Chicago?

If both departure and destination cities offer multiple airports, comparing them can help you save time and money.

  • Airports in Toronto: Toronto has 4 airports - John C. Munro, Kitchener Lake, Lester B. Pearson, Toronto Island Airport.
  • Airports in Chicago: 3 airports serve Chicago - Midway, O'Hare, Rockford.

Some airports have different terminals for low-cost and traditional airlines — knowing in advance can save time. You can filter results to see only the airports that suit you.

Flights from Toronto - Lester B. Pearson to Chicago - Midway

Plan smarter: flights from Toronto Pearson to Chicago Midway

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to United States also checked out: Las Vegas, Los Angeles, Miami, New York City, Orlando.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.
Frequently Asked Questions

Frequently asked questions about flights from Toronto Pearson to Chicago Midway.

How much does an airline ticket from Toronto Pearson to Chicago Midway cost?

The lowest price recorded in the last 15 days for a flight from Toronto Pearson to Chicago Midway is Can$244.

How far is Toronto from Chicago?

Toronto is about 696 km from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in Toronto?

Toronto has 4 airports: John C. Munro, Kitchener Lake, Lester B. Pearson, Toronto Island Airport.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Toronto to Chicago?

The best time to book a flight from Toronto to Chicago is 1 month in advance, while the worst time is 1 week in advance.

What is the cheapest month to fly from Toronto to Chicago?

The cheapest month to fly from Toronto to Chicago is February.

What is the most expensive month to fly from Toronto to Chicago?

The most expensive month to fly from Toronto to Chicago is May.

What is the best day of the week to fly from Toronto to Chicago?

For flights from Toronto to Chicago Friday is on average the cheapest day to fly, while Friday is the most expensive day to fly.