Can I fly direct from Toronto to Chicago?

Yes, direct flights are available for the Toronto to Chicago route. Historically, approximately 47.5% of the flights on this route have been direct. For journeys that include stopovers, travelers typically experience a median of 2 stops. This indicates that while direct options are common, connecting flights also make up a significant portion of the available routes.

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. This route covers a distance of approximately 696 kilometers. For flights that include one stop, the median travel time increases significantly to 6 hours and 27 minutes. Travelers should consider these durations when planning their journey between the two cities.

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 travelers may often find opportunities to secure more favorable fares. The consistent price fluctuations suggest that monitoring prices over time could be beneficial for those looking to find a better deal. This route is classified as one with frequent price changes.

Flights From Toronto

To Chicago

Cheap Flights from Toronto to Chicago

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Deals from

Toronto

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

Prices updated 2 days ago

405 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Toronto to Chicago

Explore current cheapest deals departing from Toronto to Chicago

2026-09-10 – 2026-09-13
YTO - Chicago
68% AI deal score
CA$317
CA$241
Round trip
2026-09-17 – 2026-09-20
YTO - Chicago
68% AI deal score
CA$316
CA$241
Round trip
2026-09-05 – 2026-09-09
YTO - Chicago
68% AI deal score
CA$317
CA$244
Round trip
2026-09-03 – 2026-09-13
YTO - Chicago
66% AI deal score
CA$285
CA$244
Round trip
2026-09-17 – 2026-09-22
YTO - Chicago
68% AI deal score
CA$313
CA$244
Round trip
2026-09-05 – 2026-09-10
YTO - Chicago
68% AI deal score
CA$314
CA$244
Round trip
2026-09-24 – 2026-09-30
YTO - Chicago
68% AI deal score
CA$318
CA$244
Round trip
2026-09-24 – 2026-09-26
YTO - Chicago
72% AI deal score
CA$327
CA$244
Round trip
2026-09-18 – 2026-09-20
YTO - Chicago
68% AI deal score
CA$317
CA$244
Round trip
2026-09-23 – 2026-09-29
YTO - Chicago
68% AI deal score
CA$316
CA$244
Round trip

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

Fares for flights from Toronto to Chicago typically range from $223–$567, with a median price of $342. Right now, fares are above the typical level. Only 8% of recent fares were classified as a good price, indicating that finding cheap flights from Toronto to Chicago may require some flexibility or advance planning.

If you are looking for the cheapest time to fly from Toronto to Chicago, consider traveling in November, when the median fare is $179. Other cost-effective months include April, with a median fare of $225, and February, where the median fare is $238.

The typical journey from Toronto to Chicago takes about 2h 0m, including connections. This route is considered short-haul, covering a distance of 696 kilometers.

For flights from Toronto to Chicago, a meaningful share are non-stop, while the rest connect once. When itineraries include connections, the median number of stopovers is 2.

How much is a round trip from Toronto to Chicago

Regular price: CA$252 - CA$593

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

The regular price range for this route is between 252 CAD and 593 CAD. The current lowest deal is 242 CAD with Porter Airlines, for travel from Sep 8 to Sep 10.

now CA$242

Low CA$252

High CA$593

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

Mon, Jul 27

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$1,078

CA$585

One-way

Tue, Jul 28

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$1,067

CA$607

One-way

Wed, Jul 29

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$1,067

CA$600

One-way

Thu, Jul 30

⌛ Last-Minute

YTZ - Chicago

Toronto (YTZ) - Chicago (MDW)

Porter Airlines

CA$1,070

CA$589

One-way

Sat, Aug 1

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (MDW)

Deutsche Luft Hansa

CA$881

CA$497

One-way

Sat, Aug 1

⌛ Last-Minute

YYZ - Chicago

Toronto (YYZ) - Chicago (ORD)

Deutsche Luft Hansa

CA$1,135

CA$576

One-way

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

3 nights

Aug 1 - Aug 4

CA$1,135 → CA$576

49%

2 nights

Aug 5 - Aug 7

CA$955 → CA$449

53%

2 nights

Jul 27 - Jul 29

CA$1,078 → CA$585

46%

1 night

Jul 30 - Jul 31

CA$1,070 → CA$589

45%

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

Fly in December for the best prices

Historically, December offers the lowest median prices at $140 for flights from Toronto to Chicago.

⏱️ Flight duration

Direct flights take 2h 0m

The typical direct flight from Toronto to Chicago takes 2h 0m, covering 696 km.

✈️ Airlines & availability

47.5% of recent flights are direct

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

🏆 Airline highlight

Porter Airlines offers a recent deal for $242

A recent deal with Porter Airlines from Toronto to Chicago was found for $242.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Toronto to Chicago are frequent, appearing within a 30-day window.

Toronto main airports to depart from

Billy Bishop Toronto City (YTZ)

Cheapest

Billy Bishop Toronto City Airport offers a convenient departure point for flights from Toronto to Chicago, with prices from 253 CAD.

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

💸 Flights from ~CA$253

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

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

📍 ~14 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~CA$253

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Milwaukee offers a major international airport with significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by car or train, requires travel across state lines into Wisconsin)

💸 Flights from ~CA$543

Business & First Class Flight Deals to Chicago

76% AI deal score

$1,046

$565

Save $481

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to purchase flights from Toronto to Chicago is typically between 14 and 27 days before departure. During this period, the average price for a ticket has been observed at approximately $294. Prices tend to increase significantly closer to the departure date, with flights booked 0-6 days out averaging around $662. Conversely, booking too far in advance, such as 60+ days out, also shows higher average prices, at about $415.

Based on historical data over the trailing 90 days, a good price for a flight from Toronto to Chicago is considered to be $223 or less. The median price for this route has been $342. Prices can go higher, with 75% of tickets costing $567 or less. Travelers aiming for a more economical trip should target prices at or below the $223 threshold.

Historically, the cheapest months to fly from Toronto to Chicago are November, April, and February. In November, the median price was $179, while April saw a median of $225, and February had a median of $238. These prices are notably lower than the annual median price of $342 for this route. Planning your trip during these months could lead to significant savings.

Toronto to Chicago: Overview

Insights for flights from Toronto to Chicago

The typical journey from Toronto to Chicago takes about 2h 0m, including connections. This route is considered short-haul, covering a distance of 696 kilometers.

For flights from Toronto to Chicago, a meaningful share are non-stop, while the rest connect once. When itineraries include connections, the median number of stopovers is 2.

How much is a round trip from Toronto to Chicago

Regular price: CA$252 - CA$593

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

The regular price range for this route is between 252 CAD and 593 CAD. The current lowest deal is 242 CAD with Porter Airlines, for travel from Sep 8 to Sep 10.

now CA$242

Low CA$252

High CA$593

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