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Business Class Flight Deals from Chicago to Toronto Island Airport

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Departure times

Early Morning

12am - 5am

$240
330 flights
Morning

5am - 12pm

$241
596 flights
Midday

12pm - 2pm

$217
347 flights

Cheapest

Afternoon

2pm - 5pm

$244
526 flights

Highest

Evening

5pm - 9pm

$244
419 flights

Best day to fly

Best performing days by departure day

Wed is the cheapest day to fly business class, averaging $349, while Fri is the priciest at $405.

Sun

avg 388

$240
38% below avg
Mon

avg 403

$244
39% below avg

Highest

Tue

avg 366

$217
41% below avg

Cheapest

Wed

avg 349

$244
30% below avg
Thu

avg 399

$244
39% below avg
Fri

avg 405

$244
40% below avg
Sat

avg 366

$244
33% below avg

Top layover cities

Most popular stopover destinations

Montreal

Montreal / Pierre Elliott Trudeau International Airport (YUL)

from $217

ACUA

Detroit

Detroit Metropolitan Wayne County Airport (DTW)

from $278

WSDLUA

Washington

Washington Dulles International Airport (IAD)

from $262

UAAC

Washington

Ronald Reagan Washington National Airport (DCA)

from $348

AAUA

Charlotte

Charlotte Douglas International Airport (CLT)

from $354

AA

Toronto

Lester B. Pearson International Airport (YYZ)

from $241

AC

New York

La Guardia Airport (LGA)

from $364

AAUADL+1

Ottawa

Ottawa Macdonald-Cartier International Airport (YOW)

from $280

ACUA

Newark

Newark Liberty International Airport (EWR)

from $262

UA

Philadelphia

Philadelphia International Airport (PHL)

from $348

AA

See all cities

Price Range Distribution

Fare distribution across budget segments

Great deal:$261

Lowest price:$217

Typical price:$388

Higher end:$1,800–$2,000

Frequently Asked Questions

What is the typical flight duration from Chicago to Toronto?

A direct flight from Chicago (ORD) to Toronto (YTZ) typically takes about 1 hour 40 to 1 hour 50 minutes. Flights with a layover, often in Montreal or Ottawa, can extend total travel time to 4 to 6 hours. Return flights from Toronto to Chicago are similar in duration, usually around 1 hour 50 minutes to 2 hours. Porter Airlines offers direct service on this route with competitive flight times.

Are there any direct flights from Chicago to Toronto?

Yes, Porter Airlines (PD) flies nonstop from Chicago Midway (MDW) to Billy Bishop Toronto City Airport (YTZ) with 26 weekly flights operating daily. Departure times are spread across the day at 10:25 AM, 11:00 AM, 12:45 PM, 4:15 PM, and 5:35 PM.

Methodology

Are there visa requirements to travel from Chicago to Toronto?

Yes, there are visa and entry requirements for travel from Chicago to Toronto, as this is an international flight between the United States and Canada. U.S. citizens do not need a visa for tourist visits up to six months but must carry a valid U.S. passport. As of 2025, U.S. citizens are not required to obtain an Electronic Travel Authorization (eTA) for flights to Canada, but they must present a passport. Permanent residents of the U.S. (Green Card holders) do not need a visa or eTA but must carry their Green Card and valid passport. Citizens of other countries may need a visa or an eTA depending on their nationality. Always check current Government of Canada travel requirements before departure.

What are the ground transportation options in Toronto?

Assuming you are flying into Billy Bishop Toronto City Airport (YTZ), ground transportation to downtown Toronto is quick and convenient. A free pedestrian tunnel and a short ferry ride connect the airport to the mainland in under ten minutes. From there, a free shuttle bus runs to Union Station, or you can walk to the city center in about fifteen minutes. Taxis and ride-share services are available at the mainland terminal, offering a five-minute ride to downtown. The 509 and 510 streetcars stop nearby and provide inexpensive access to the broader city. Car rentals are available but are not recommended for downtown travel due to congestion. Most passengers use the free shuttle or walk, given the airport’s proximity to the city center. For Toronto Pearson International Airport (YYZ), the UP Express train reaches Union Station in twenty-five minutes and is the top choice, while taxis and ride-shares take longer in traffic.

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

Based on seasonal price data, the cheapest months to fly from Chicago to Toronto are September (average $281), July ($291), and August ($295), while the most expensive are February ($493) and January ($492). The low season runs from June through September, and the high season spans January, February, April, and May.

Methodology

How far in advance should I book tickets from Chicago to Toronto?

For flights from Chicago to Toronto, the best fares are typically found when booking 14 to 16 weeks in advance, with an average price around $284. The absolute cheapest prices appear about 100 days before departure, while last-minute bookings can cost over $590. For summer and holiday travel, booking even earlier—up to 20 weeks ahead—is advisable, as prices tend to rise closer to departure.

Methodology

Are overnight (red‑eye) flights available from Chicago to Toronto?

There are no red-eye (overnight) flights from Chicago to Toronto's Billy Bishop Airport (YTZ). The schedule data shows no nonstop red-eyes on this route, and no connecting itineraries with an overnight leg were found either.

Methodology

Which airlines usually operate this route from Chicago to Toronto?

Nonstop flights from Chicago to Toronto's Billy Bishop Airport (YTZ) are operated by Porter Airlines (PD), with service from Chicago Midway (MDW) to YTZ running daily on a schedule that includes multiple departure times such as 10:25, 11:00, 12:45, 16:15, and 17:35. The schedule data shows Porter as the only nonstop carrier on this route, though connecting itineraries via other hubs may also be available.

Methodology

If I need a connection, what are common layover cities between Chicago and Toronto?

Common layovers between Chicago and Toronto include Detroit, Minneapolis, and New York, which offer efficient connections and keep total travel time competitive. These hubs provide frequent flights and streamlined transfers, with the added benefit of visa‑free transit for eligible travelers.

How reliable are on‑time departures on this route from Chicago to Toronto?

On-time performance is generally good on this short-haul route, but afternoon and evening flights can be affected by air traffic congestion and weather. Early morning departures, particularly on Air Canada and United, tend to have the best on-time records. Flights from O'Hare (ORD) to Billy Bishop (YTZ) are limited, so booking the first departure of the day is advisable for reliability.

Which months have the best weather for traveling to Toronto?

May to June and September to early October offer pleasant temperatures and fewer tourists than the busy summer months.

What documents should I bring with me to the airport when flying from Chicago to Toronto?

Bring a passport valid for your stay, any required visa or eTA for Canada, proof of onward travel, payment for baggage and any required vaccination certificates.

Which airport should I use in Toronto?

Billy Bishop Airport is closest to downtown Toronto and ideal for short-haul business trips. Toronto Pearson is the main international gateway with full-service airlines and global connections.

Are there hotels or sleeping facilities at Toronto airport?

Billy Bishop Toronto City Airport (YTZ) does not have on-site hotels, capsule hotels, or sleeping pods. Several nearby hotels are a short walk or taxi ride away, such as the Radisson Admiral Hotel and the Westin Harbour Castle, but no dedicated airport shuttle is available.

Are there currency exchange offices, prayer rooms and Wi‑Fi at Toronto Island?

Billy Bishop Toronto City Airport has a currency exchange kiosk in the main terminal, a quiet room for prayer and reflection near the gates, and free Wi‑Fi throughout the terminal.

Are there accessible services or children's facilities at the Chicago and Toronto airports?

Chicago O’Hare provides wheelchair assistance and accessible facilities; request help via your airline 48 hours in advance. A children’s play area is in Terminal 2. Billy Bishop Toronto City Airport offers wheelchair assistance and barrier‑free washrooms but has no dedicated children’s play area; contact the airport or airline to arrange assistance.

What aircraft are typically used on flights from Chicago to Toronto?

Nonstop flights from Chicago to Toronto Billy Bishop (YTZ) are typically operated with Embraer 175 and De Havilland Canada DHC-8-400 Dash 8Q regional jets, though Airbus A320-family and A220-200 narrowbodies, Canadair Regional Jet 700s, and Boeing 737s also appear on the route. The exact aircraft varies by day and airline, and Wi-Fi and seatback entertainment are widely available on these flights.

Methodology

Which airline alliances serve flights from Chicago to Toronto?

The only nonstop carrier on the Chicago to Toronto (Billy Bishop) route is Porter Airlines, which is not a member of any global airline alliance. Other alliances may serve Chicago to Toronto via connections through Toronto Pearson, but no Star Alliance, oneworld, or SkyTeam carrier operates nonstop to YTZ.

Methodology

What are the best airport lounge options when departing from Chicago?

At Chicago O'Hare, the United Club in Terminals 1 and 2, the United Polaris Lounge in Terminal 1, and the American Airlines Admirals Club in Terminal 3 are available. The Delta Sky Club is in Terminal 5. Independent lounges include the Swissport Lounge in Terminal 5 and the Air France‑KLM Lounge in Terminal 5. Access typically requires business‑class tickets, elite status, or day passes.

What is the baggage allowance on this route from Chicago to Toronto?

Baggage allowance on flights from Chicago to Toronto depends on the airline and fare type. Basic economy tickets are restrictive and typically do not include a checked bag, while standard economy often includes one checked bag and a carry‑on. Premium cabins offer more generous allowances.

What cabin and seat options are typical from Chicago to Toronto?

Flights from Chicago to Toronto typically offer Economy and sometimes Premium Economy, but flat-bed Business is not common on this short route.

Are same‑day changes or standby possible on this route?

Policies differ by airline and fare; flexible and premium tickets usually allow same‑day changes or standby, while Basic Economy generally does not.

What are the cheapest days and times to fly from Chicago to Toronto?

The cheapest day to fly from Chicago to Toronto is Saturday, with an average fare of $338, while Monday is the most expensive at $382. The cheapest time of day to depart is Morning, with fares starting at $218.

Methodology

What is a good price for a flight from Chicago to Toronto?

A good price for a flight from Chicago to Toronto is anything under $246, which counts as a great deal; typically, fares range around $355, with most prices falling between $200 and $400.

Methodology

Flights to Toronto Island Airport