Can I fly direct from Toronto to Chicago?

Yes, direct flights from Toronto to Chicago are available. Across the trailing quarter, approximately 47.5% of flights on this route were direct. For travelers with connecting flights, the median number of stopovers was 2.

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 involving one stop, the median travel time is considerably longer, averaging 6 hours and 27 minutes. The air distance between the two cities is approximately 696 kilometers.

How often do Toronto to Chicago flight prices drop?

Historically, flight prices for the Toronto to Chicago route have shown frequent drops. This indicates that deals and price fluctuations are common for this particular route. Travelers may find opportunities to secure lower fares due to the dynamic pricing nature observed over the trailing 30 days.

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 1 day ago

458 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 7, 2026.)

Today’s best flight deals from Toronto to Chicago

Explore current cheapest deals departing from Toronto to Chicago

2026-09-26 – 2026-09-29
YTO - Chicago
68% AI deal score
CA$321
CA$244
Round trip
2026-09-28 – 2026-09-30
YTO - Chicago
68% AI deal score
CA$319
CA$244
Round trip
2026-10-02 – 2026-10-05
YTO - Chicago
79% AI deal score
CA$476
CA$244
Round trip
2026-10-15 – 2026-10-18
YTO - Chicago
79% AI deal score
CA$472
CA$244
Round trip
2026-10-02 – 2026-10-04
YTO - Chicago
79% AI deal score
CA$478
CA$244
Round trip
2026-10-01 – 2026-10-04
YTO - Chicago
79% AI deal score
CA$478
CA$244
Round trip
2026-10-15 – 2026-10-19
YTO - Chicago
79% AI deal score
CA$472
CA$244
Round trip
2026-11-06 – 2026-11-08
YTO - Chicago
66% AI deal score
CA$291
CA$244
Round trip
2026-09-24 – 2026-09-27
YTO - Chicago
68% AI deal score
CA$328
CA$247
Round trip
2026-11-11 – 2026-11-15
YTO - Chicago
66% AI deal score
CA$292
CA$247
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$253 - CA$615

Prices are currently below the regular range.

The regular price range for flights from Toronto to Chicago is CAD 253 to CAD 615. The current lowest deal is CAD 244 with Porter Airlines for travel from Sep 26-Sep 29.

now CA$244

Low CA$253

High CA$615

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

Wed, Sep 16

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (RFD)

WestJet

CA$543

CA$322

One-way

Fri, Sep 18

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (MDW)

Deutsche Luft Hansa

CA$656

CA$397

One-way

Wed, Sep 23

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$314

CA$248

One-way

Thu, Sep 24

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$328

CA$247

One-way

Thu, Sep 24

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (RFD)

Porter Airlines

CA$561

CA$335

One-way

Sat, Sep 26

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$321

CA$244

One-way

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

2 nights

Feb 25 - Feb 27

CA$1,371 → CA$515

62%

1 night

Oct 17 - Oct 18

CA$674 → CA$319

53%

4 nights

Oct 21 - Oct 25

CA$675 → CA$322

52%

2 nights

Oct 16 - Oct 18

CA$674 → CA$322

52%

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 cheapest

Historically, November ($179), April ($225), and February ($238) offer the lowest median prices.

⏱️ Flight duration

Direct flights take 2h 0m

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

✈️ Airlines & availability

47.5% of recent flights are direct

Historically, 47.5% of flights on this route are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Porter Airlines has a recent deal for $244

Porter Airlines offered a recent deal for $244 from Toronto Billy Bishop City to Chicago Midway.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Toronto to Chicago are frequent, appearing often in 30-day windows.

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

$1,423

$639

Save $784

United Airlines

Business Class

From YYZ

Elite

Oct 15

Chicago, United States

80% AI deal score

$1,397

$637

Save $760

United Airlines

Business Class

From YYZ

Elite

Oct 02

Chicago, United States

80% AI deal score

$1,337

$637

Save $700

United Airlines

Business Class

From YYZ

Elite

Oct 01

Chicago, United States

80% AI deal score

$1,371

$637

Save $734

United Airlines

Business Class

From YYZ

Elite

Oct 01

Chicago, United States

80% AI deal score

$1,337

$637

Save $700

United Airlines

Business Class

From YYZ

Elite

Oct 03

Chicago, United States

80% AI deal score

$1,366

$637

Save $729

United Airlines

Business Class

From YTZ

Elite

Nov 21

Chicago, United States

80% AI deal score

$859

$413

Save $446

Porter Airlines

Business Class

From YTZ

Elite

Nov 21

Chicago, United States

80% AI deal score

$833

$413

Save $420

Porter Airlines

Business Class

From YTZ

Elite

Nov 20

Chicago, United States

80% AI deal score

$834

$413

Save $421

Porter Airlines

Business Class

From YTZ

Elite

Nov 21

Chicago, United States

80% AI deal score

$835

$413

Save $422

Porter Airlines

Business Class

From YYZ

Elite

Oct 03

Chicago, United States

79% AI deal score

$1,301

$634

Save $667

United Airlines

Business Class

From YYZ

Elite

Oct 21

Chicago, United States

79% AI deal score

$1,299

$637

Save $662

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Toronto to Chicago has been between 14 and 27 days prior to departure. During this period, the average price was around $294. Prices tend to increase significantly closer to the departure date, with flights booked 0-6 days out averaging $662. For those planning further ahead, booking 60+ days in advance typically saw average prices of $415.

Across the trailing quarter, a good price for a flight from Toronto to Chicago was considered to be $223 or less. The median price for this route over the same 90-day period was $342. Prices can vary, with 75% of observed fares being $567 or less.

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 offered competitive prices, with a median of $238. The annual median price for this route was $342, indicating that certain months offer significant savings.

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

How much is a round trip from Toronto to Chicago

Regular price: CA$253 - CA$615

Prices are currently below the regular range.

The regular price range for flights from Toronto to Chicago is CAD 253 to CAD 615. The current lowest deal is CAD 244 with Porter Airlines for travel from Sep 26-Sep 29.

now CA$244

Low CA$253

High CA$615

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

Wed, Sep 16

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (RFD)

WestJet

CA$543

CA$322

One-way

Fri, Sep 18

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (MDW)

Deutsche Luft Hansa

CA$656

CA$397

One-way

Wed, Sep 23

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$314

CA$248

One-way

Thu, Sep 24

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$328

CA$247

One-way

Thu, Sep 24

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (RFD)

Porter Airlines

CA$561

CA$335

One-way

Sat, Sep 26

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$321

CA$244

One-way

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

2 nights

Feb 25 - Feb 27

CA$1,371 → CA$515

62%

1 night

Oct 17 - Oct 18

CA$674 → CA$319

53%

4 nights

Oct 21 - Oct 25

CA$675 → CA$322

52%

2 nights

Oct 16 - Oct 18

CA$674 → CA$322

52%

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 cheapest

Historically, November ($179), April ($225), and February ($238) offer the lowest median prices.

⏱️ Flight duration

Direct flights take 2h 0m

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

✈️ Airlines & availability

47.5% of recent flights are direct

Historically, 47.5% of flights on this route are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

Porter Airlines has a recent deal for $244

Porter Airlines offered a recent deal for $244 from Toronto Billy Bishop City to Chicago Midway.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Toronto to Chicago are frequent, appearing often in 30-day windows.

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

79% AI deal score

$1,299

$637

Save $662

United 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 cheapest

Direct flights take 2h 0m

47.5% of recent flights are direct

Porter Airlines has a recent deal for $244

Deals are frequent 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 15

Oct 02

Oct 01

Oct 01

Oct 03

Nov 21

Nov 21

Nov 20

Nov 21

Oct 03

Oct 21

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 cheapest

Direct flights take 2h 0m

47.5% of recent flights are direct

Porter Airlines has a recent deal for $244

Deals are frequent 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 15

Oct 02

Oct 01

Oct 01

Oct 03

Nov 21

Nov 21

Nov 20

Nov 21

Oct 03

Oct 21

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?