Can I fly direct from Toronto to Chicago?

Yes, direct flights from Toronto to Chicago are available. Approximately 47.5% of all flights on this route historically have been direct. For flights that include stopovers, travelers typically encounter a median of 2 stops. This indicates a significant portion of available options are non-stop, offering convenience for many travelers.

How many hours is the flight from Toronto to Chicago?

A direct flight from Toronto to Chicago typically takes about 2 hours and 0 minutes. This route covers a distance of 696 kilometers. Flights with one stopover, however, have a significantly longer median duration, averaging around 6 hours and 27 minutes. Travelers prioritizing speed should look for direct flight options.

How often do Toronto to Chicago flight prices drop?

Historically, flight prices for the Toronto to Chicago route are classified as frequent in terms of price drops. This suggests that travelers can often find opportunities for price reductions. Monitoring this route across the trailing quarter may reveal various instances of price adjustments, indicating a dynamic pricing environment.

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 today

476 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 12, 2026.)

Today’s best flight deals from Toronto to Chicago

Explore current cheapest deals departing from Toronto to Chicago

2026-11-12 – 2026-11-16
YTO - Chicago
42% AI deal score
CA$313
CA$386
Round trip
2026-11-23 – 2026-11-26
YTO - Chicago
42% AI deal score
CA$310
CA$386
Round trip
2026-11-07 – 2026-11-09
YTO - Chicago
42% AI deal score
CA$314
CA$386
Round trip
2026-12-04 – 2026-12-06
YTO - Chicago
44% AI deal score
CA$359
CA$386
Round trip
2026-11-13 – 2026-11-16
YTO - Chicago
42% AI deal score
CA$289
CA$394
Round trip
2026-11-12 – 2026-11-17
YTO - Chicago
42% AI deal score
CA$288
CA$394
Round trip
2026-12-02 – 2026-12-07
YTO - Chicago
43% AI deal score
CA$315
CA$394
Round trip
2026-11-14 – 2026-11-16
YTO - Chicago
42% AI deal score
CA$290
CA$394
Round trip
2026-11-04 – 2026-11-08
YTO - Chicago
43% AI deal score
CA$291
CA$397
Round trip
2026-12-15 – 2026-12-16
YTO - Chicago
43% AI deal score
CA$329
CA$400
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$418 - CA$628

Prices are currently within the regular range for flights from Toronto to Chicago.

The regular price range for flights from Toronto to Chicago is CAD 418 to CAD 628. The current lowest deal is CAD 420 with Porter Airlines for travel from Oct 28-Nov 5.

now CA$420

Low CA$418

High CA$628

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

Porter Airlines

Last-minute flights going from Toronto to Chicago

Sat, Oct 10

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (ORD)

United Airlines

CA$1,135

CA$623

One-way

Sat, Oct 10

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (MDW)

Deutsche Luft Hansa

CA$1,040

CA$723

One-way

Sat, Oct 10

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (MDW)

Deutsche Luft Hansa

CA$1,033

CA$784

One-way

Sat, Oct 10

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (MDW)

Deutsche Luft Hansa

CA$940

CA$834

One-way

Sun, Oct 11

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (ORD)

Porter Airlines

CA$799

CA$677

One-way

Mon, Oct 12

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (ORD)

Porter Airlines

CA$764

CA$677

One-way

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

3 nights

Oct 10 - Oct 13

CA$1,009 → CA$666

34%

4 nights

Oct 19 - Oct 23

CA$792 → CA$490

38%

1 night

Oct 28 - Oct 29

CA$699 → CA$413

41%

1 night

Oct 29 - Oct 30

CA$679 → CA$413

39%

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 at $420.

📅 Best time to fly

November offers the lowest median price

Historically, November is the cheapest month to fly, with a median price of $179.

⏱️ Flight duration

Direct flights average 2h 0m

Direct flights from Toronto to Chicago typically take 2 hours. Connecting flights average 15h 19m.

✈️ Airlines & availability

Mixed availability of direct flights

About 47.5% of recent flights are direct. Connecting flights typically have 2 stopovers.

🏆 Airline highlight

Air Canada and Porter Airlines offer direct routes

Air Canada and Porter Airlines both offer direct flights from Toronto to Chicago.

🎯 Booking tip

Deals are frequent on this route

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

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

$720

Save $722

Air Canada

Business Class

From YYZ

Elite

Oct 20

Chicago, United States

78% AI deal score

$1,497

$754

Save $743

Air Canada

Business Class

From YTZ

Elite

Nov 08

Chicago, United States

78% AI deal score

$746

$416

Save $330

Porter 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 be higher for very last-minute bookings, with flights purchased 0-6 days out averaging $662. Planning ahead by at least two weeks can lead to more favorable pricing, based on data from the trailing 90 days.

Based on historical data from the trailing 90 days, a good price for a flight from Toronto to Chicago is typically $223 or less. The median price for this route has been around $342. Prices can vary, with 75% of observed fares being $567 or less. Aiming for a price below the $223 threshold generally indicates a favorable deal.

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 competitive prices, with a median of $238. These months typically present better value compared to the annual median price of $342, based on data from the trailing 270 days.

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

How much is a round trip from Toronto to Chicago

Regular price: CA$418 - CA$628

Prices are currently within the regular range for flights from Toronto to Chicago.

The regular price range for flights from Toronto to Chicago is CAD 418 to CAD 628. The current lowest deal is CAD 420 with Porter Airlines for travel from Oct 28-Nov 5.

now CA$420

Low CA$418

High CA$628

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