Can I fly direct from Toronto to Chicago?

Yes, direct flights from Toronto to Chicago are available. Historically, approximately 47.5% of the flights on this route have been direct. For flights that include stopovers, travelers typically experience a median of 2 stopovers. This data is based on observations over a 90-day period.

How many hours is the flight from Toronto to Chicago?

The typical direct flight from Toronto to Chicago has a median duration of 2 hours and 0 minutes. For flights with one stop, the median travel time increases to 6 hours and 27 minutes. The approximate air distance between the two cities is 696 kilometers. These durations provide a general expectation for travel time on this route.

How often do Toronto to Chicago flight prices drop?

Historically, flight prices for the Toronto to Chicago route tend to drop frequently. This route is classified as one where price fluctuations are common, offering travelers regular opportunities to find deals. This pattern of frequent price drops has been observed over a 30-day period.

Flights From Toronto

To Chicago

Cheap Flights from Toronto to Chicago

Browse current best options from Toronto. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Toronto

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 2 days ago

461 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Toronto to Chicago

Explore current cheapest deals departing from Toronto to Chicago

2026-09-26 – 2026-09-27
YTO - Chicago
74% AI deal score
CA$377
CA$258
Round trip
2026-10-22 – 2026-10-29
YTO - Chicago
77% AI deal score
CA$458
CA$258
Round trip
2026-10-11 – 2026-10-17
YTO - Chicago
77% AI deal score
CA$457
CA$258
Round trip
2026-10-24 – 2026-10-31
YTO - Chicago
77% AI deal score
CA$457
CA$258
Round trip
2026-10-01 – 2026-10-05
YTO - Chicago
79% AI deal score
CA$503
CA$258
Round trip
2026-10-11 – 2026-10-14
YTO - Chicago
78% AI deal score
CA$479
CA$258
Round trip
2026-10-12 – 2026-10-15
YTO - Chicago
78% AI deal score
CA$479
CA$258
Round trip
2026-10-19 – 2026-10-21
YTO - Chicago
78% AI deal score
CA$478
CA$258
Round trip
2026-10-02 – 2026-10-04
YTO - Chicago
79% AI deal score
CA$501
CA$258
Round trip
2026-10-01 – 2026-10-03
YTO - Chicago
79% AI deal score
CA$505
CA$258
Round trip

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

For cheap flights from Toronto to Chicago, fares typically range from $223–$567, with a median of $342. Right now, current fares are significantly above the typical level for this route. Only 8% of recent fares were classified as a good price, indicating that finding a deal requires careful timing.

When is the cheapest time to fly from Toronto to Chicago? The most affordable month to fly is typically November, with a median fare of $179. Other inexpensive options include April, with a median fare of $225, and February, where the median fare is $238.

How long is the flight from Toronto to Chicago? A typical journey takes 2h 0m. Given that a meaningful share of itineraries are non-stop, the median time for connecting flights is considerably longer at 15h 19m, while non-stop flights average 2h 0m.

This route covers a distance of 696 kilometers, classifying it as a short-haul journey. For flights from Toronto to Chicago, a meaningful share are non-stop, while the remaining itineraries typically include 2 connections. New deals appear almost daily for this route, so setting up a price alert can be beneficial.

How much is a round trip from Toronto to Chicago

Regular price: CA$342 - CA$651

Prices are currently below the regular range.

The regular price range for flights from Toronto to Chicago is CAD 342 to CAD 651. The current lowest deal is CAD 257 with Porter Airlines for travel from Oct 10-Oct 17.

now CA$257

Low CA$342

High CA$651

The cheapest time to fly from Toronto to Chicago

The cheapest month to fly from YTO to CHI is December, with a median price of $140. The most expensive month is July, with a median price of $512. Prices are generally lower from February to December.

December

Cheapest

Flights from CA$140

July

Most Expensive

Flights from CA$512

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Toronto to Chicago

Air Canada

Porter Airlines

Last-minute flights going from Toronto to Chicago

Thu, Sep 24

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (ORD)

Air Canada

CA$599

CA$269

One-way

Sat, Sep 26

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$377

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$503

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$505

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$505

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$504

CA$260

One-way

Biggest price drops on these dates for flights from Toronto to Chicago

5 nights

Feb 25 - Mar 2

CA$1,313 → CA$449

66%

4 nights

Feb 25 - Mar 1

CA$1,308 → CA$449

66%

5 nights

Feb 24 - Mar 1

CA$1,303 → CA$449

66%

6 nights

Feb 25 - Mar 3

CA$1,297 → CA$449

65%

Popular Airports to fly from Toronto to Chicago

Toronto - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Toronto to Chicago are above the typical level for this route.

📅 Best time to fly

November, April, and February are historically cheapest

Historically, the cheapest months to fly are November ($179), April ($225), and February ($238).

⏱️ Flight duration

Direct flights average 2h 0m

Direct flights from Toronto to Chicago typically take 2h 0m, while connecting flights average 15h 19m.

✈️ Airlines & availability

Direct flights are available from 2 airlines

Direct flights are available from Air Canada and Porter Airlines, with a 47.5% share of recent deals.

🏆 Airline highlight

Porter Airlines has a recent deal for $257

Porter Airlines offered a recent deal for $257 from Billy Bishop Toronto City to Chicago Midway International.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Toronto to Chicago appear frequently, with good prices available 8% of the time.

Toronto main airports to depart from

Billy Bishop Toronto City (YTZ)

Cheapest

Billy Bishop Toronto City Airport is a convenient option for flights from Toronto to Chicago, with prices from 242 CAD.

📍 ~3 km from Toronto city center (reachable by car, ferry, or public transport).

💸 Flights from ~CA$242

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights from Toronto to Chicago.

📍 ~14 km from Chicago city center (reachable by car)

💸 Flights from ~CA$248

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by rail or car)

💸 Flights from ~CA$565

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Toronto to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From YYZ

Elite

Oct 10

Chicago, United States

81% AI deal score

$1,409

$638

Save $771

United Airlines

Business Class

From YTZ

Elite

Oct 01

Chicago, United States

81% AI deal score

$2,132

$650

Save $1,482

Air Canada

Business Class

From YTZ

Elite

Nov 30

Chicago, United States

81% AI deal score

$859

$403

Save $456

Porter Airlines

Business Class

From YTZ

Elite

Nov 26

Chicago, United States

81% AI deal score

$849

$403

Save $446

Porter Airlines

Business Class

From YYZ

Elite

Oct 12

Chicago, United States

80% AI deal score

$1,366

$638

Save $728

United Airlines

Business Class

From YTZ

Elite

Oct 15

Chicago, United States

80% AI deal score

$2,055

$651

Save $1,404

Air Canada

Business Class

From YTZ

Elite

Nov 26

Chicago, United States

80% AI deal score

$826

$403

Save $423

Porter Airlines

Business Class

From YTZ

Elite

Nov 28

Chicago, United States

80% AI deal score

$833

$403

Save $430

Porter Airlines

Business Class

From YTZ

Elite

Nov 25

Chicago, United States

80% AI deal score

$830

$403

Save $427

Porter Airlines

Business Class

From YTZ

Elite

Nov 25

Chicago, United States

80% AI deal score

$838

$403

Save $435

Porter Airlines

Business Class

From YTZ

Elite

Nov 11

Chicago, United States

80% AI deal score

$800

$403

Save $397

Porter Airlines

Business Class

From YTZ

Elite

Nov 06

Chicago, United States

80% AI deal score

$813

$403

Save $410

Porter Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Toronto to Chicago is typically 14-27 days before departure. During this period, the average price observed was $294. Prices tend to increase significantly for bookings made closer to the travel date, with flights booked 0-6 days out averaging $662. Conversely, booking too far in advance, such as 60+ days out, also shows higher average prices, around $415.

Across the trailing quarter, a good price for a flight from Toronto to Chicago is considered to be $223 or less. The median price for this route historically stands at $342. Prices can go higher, with 75% of observed prices being $567 or less. This threshold is based on data collected over a 90-day period.

Historically, the cheapest months to fly from Toronto to Chicago include November, with a median price of $179, and April, with a median price of $225. February also tends to offer more affordable options, with a median price of $238. The annual median price for this route is $342, indicating these months offer notable savings compared to the yearly average.

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

How much is a round trip from Toronto to Chicago

Regular price: CA$342 - CA$651

Prices are currently below the regular range.

The regular price range for flights from Toronto to Chicago is CAD 342 to CAD 651. The current lowest deal is CAD 257 with Porter Airlines for travel from Oct 10-Oct 17.

now CA$257

Low CA$342

High CA$651

The cheapest time to fly from Toronto to Chicago

December

Cheapest

Flights from CA$140

July

Most Expensive

Flights from CA$512

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Toronto to Chicago

Air Canada

Porter Airlines

Last-minute flights going from Toronto to Chicago

Thu, Sep 24

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (ORD)

Air Canada

CA$599

CA$269

One-way

Sat, Sep 26

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$377

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$503

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$505

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$505

CA$258

One-way

Thu, Oct 1

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$504

CA$260

One-way

Biggest price drops on these dates for flights from Toronto to Chicago

5 nights

Feb 25 - Mar 2

CA$1,313 → CA$449

66%

4 nights

Feb 25 - Mar 1

CA$1,308 → CA$449

66%

5 nights

Feb 24 - Mar 1

CA$1,303 → CA$449

66%

6 nights

Feb 25 - Mar 3

CA$1,297 → CA$449

65%

Popular Airports to fly from Toronto to Chicago

Toronto - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Toronto to Chicago are above the typical level for this route.

📅 Best time to fly

November, April, and February are historically cheapest

Historically, the cheapest months to fly are November ($179), April ($225), and February ($238).

⏱️ Flight duration

Direct flights average 2h 0m

Direct flights from Toronto to Chicago typically take 2h 0m, while connecting flights average 15h 19m.

✈️ Airlines & availability

Direct flights are available from 2 airlines

Direct flights are available from Air Canada and Porter Airlines, with a 47.5% share of recent deals.

🏆 Airline highlight

Porter Airlines has a recent deal for $257

Porter Airlines offered a recent deal for $257 from Billy Bishop Toronto City to Chicago Midway International.

🎯 Booking tip

Deals appear frequently on this route

Deals for flights from Toronto to Chicago appear frequently, with good prices available 8% of the time.

Toronto main airports to depart from

Billy Bishop Toronto City (YTZ)

Cheapest

Billy Bishop Toronto City Airport is a convenient option for flights from Toronto to Chicago, with prices from 242 CAD.

📍 ~3 km from Toronto city center (reachable by car, ferry, or public transport).

💸 Flights from ~CA$242

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights from Toronto to Chicago.

📍 ~14 km from Chicago city center (reachable by car)

💸 Flights from ~CA$248

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

Chicago, United States

80% AI deal score

$813

$403

Save $410

Porter Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Toronto to Chicago

Today’s best flight deals from Toronto to Chicago

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

How much is a round trip from Toronto to Chicago

The cheapest time to fly from Toronto to Chicago

Direct flights from Toronto to Chicago

Last-minute flights going from Toronto to Chicago

Biggest price drops on these dates for flights from Toronto to Chicago

Popular Airports to fly from Toronto to Chicago

Toronto - Chicago route insights

Recent fares are above the typical level

November, April, and February are historically cheapest

Direct flights average 2h 0m

Direct flights are available from 2 airlines

Porter Airlines has a recent deal for $257

Deals appear frequently on this route

Toronto main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 10

Oct 01

Nov 30

Nov 26

Oct 12

Oct 15

Nov 26

Nov 28

Nov 25

Nov 25

Nov 11

Nov 06

Frequently Asked Questions About Flights to Chicago

When should I buy Toronto to Chicago tickets?

How much should a flight from Toronto to Chicago cost?

When is the cheapest time of year to fly from Toronto to Chicago?

Can I fly direct from Toronto to Chicago?

How many hours is the flight from Toronto to Chicago?

How often do Toronto to Chicago flight prices drop?

Related routes

More routes from Toronto

Flights to Chicago from other cities

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

How much is a round trip from Toronto to Chicago

The cheapest time to fly from Toronto to Chicago

Direct flights from Toronto to Chicago

Last-minute flights going from Toronto to Chicago

Biggest price drops on these dates for flights from Toronto to Chicago

Popular Airports to fly from Toronto to Chicago

Toronto - Chicago route insights

Recent fares are above the typical level

November, April, and February are historically cheapest

Direct flights average 2h 0m

Direct flights are available from 2 airlines

Porter Airlines has a recent deal for $257

Deals appear frequently on this route

Toronto main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Oct 10

Oct 01

Nov 30

Nov 26

Oct 12

Oct 15

Nov 26

Nov 28

Nov 25

Nov 25

Nov 11

Nov 06

Frequently Asked Questions About Flights to Chicago

When should I buy Toronto to Chicago tickets?

How much should a flight from Toronto to Chicago cost?

When is the cheapest time of year to fly from Toronto to Chicago?