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Business Class Flight Deals from Chicago Midway Airport to Toronto

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Departure times

Early Morning

12am - 5am

$240
337 flights
Morning

5am - 12pm

$241
583 flights
Midday

12pm - 2pm

$217
353 flights

Cheapest

Afternoon

2pm - 5pm

$244
535 flights

Highest

Evening

5pm - 9pm

$244
418 flights

Best day to fly

Best performing days by departure day

Wed is the cheapest day to fly business class, averaging $354, while Fri is the priciest at $404.

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 354

$244
31% below avg
Thu

avg 398

$244
39% below avg
Fri

avg 404

$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 nonstop flight from Chicago (MDW) to Toronto (YTO) typically takes about 1 hour 45 minutes. However, there are no nonstop flights from Midway to Toronto; you would need to connect, usually through a hub like Detroit, resulting in total travel times around 4 to 6 hours. The return flight is similar in duration.

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) daily, with five departures spread across the day at 10:25 AM, 11:00 AM, 12:45 PM, 4:15 PM, and 5:35 PM. Porter is the only airline offering nonstop service on this route.

Methodology

Are there visa requirements to travel from Chicago to Toronto?

Yes, visa requirements apply for travel from Chicago to Toronto. U.S. citizens do not need a visa for tourist visits but must present a valid U.S. passport; as of January 2025, they also need an approved Electronic Travel Authorization (eTA) if arriving by air. Canadian citizens can enter Canada freely with a valid Canadian passport. Other nationals may require a visitor visa or an eTA depending on their citizenship. For returning from Toronto to Chicago, Canadian citizens generally do not need a visa for short visits but must have an approved ESTA under the Visa Waiver Program, while U.S. citizens can re-enter with a U.S. passport. Always verify current rules before travel.

What are the ground transportation options in Toronto?

Toronto has two main airports. From Toronto Pearson (YYZ), the Union Pearson Express train reaches Union Station in twenty-five minutes and is the fastest option. The TTC operates buses to subway stations, which is cheaper but slower. Taxis and ride-share services take about thirty to forty-five minutes to downtown depending on traffic. From Billy Bishop Airport (YTZ), a free shuttle bus connects to Union Station, or you can walk via the pedestrian tunnel to the mainland. Taxis and ride-shares are also available. Car rentals are offered at both airports but driving in downtown Toronto is often congested. The UP Express is the most used choice from Pearson for its speed and reliability.

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

Based on seasonal price data, the cheapest months to fly from Chicago (MDW) to Toronto (YTO) are September, July, and August, with average fares around $281 to $295. The most expensive months are January and February, averaging $492 to $493, with May also relatively high at $470.

Methodology

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

For flights from Chicago (MDW) to Toronto (YTO), the best fares are typically found when booking 14 to 16 weeks ahead of departure, with an average price around $284. Booking around 100 days in advance can yield the lowest observed fare of about $278, while last-minute bookings (0–5 days out) can cost $500 or more.

Methodology

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

No overnight (red-eye) flights are available from Chicago Midway (MDW) to Toronto (YTO). The schedule data shows no nonstop red-eyes on this route, and no connecting itineraries with a red-eye long leg were found either.

Methodology

Which airlines usually operate this route from Chicago to Toronto?

Based on the schedule data, Porter Airlines (PD) operates nonstop flights from Chicago Midway (MDW) to Billy Bishop Toronto City Airport (YTZ) with about 26 weekly flights daily and multiple departure times. This is the only nonstop carrier shown for the MDW–YTO route; other airlines may offer connecting service through other hubs.

Methodology

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

On-time performance is generally reliable, though winter weather can cause disruptions. Early morning flights, particularly on Porter Airlines, tend to have better punctuality.

Which months have the best weather for traveling to Toronto?

May through June and September through October offer pleasant temperatures and smaller crowds compared to peak summer.

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

Bring a passport valid for the duration of your stay; U.S. citizens do not need a visa but must have an eTA if flying. Carry proof of onward or return travel, a payment method for baggage, and any required vaccination certificates.

Which airport should I use in Toronto?

Toronto Pearson is the primary international airport serving most flights from Chicago. It is about 25 km northwest of downtown and handles all major alliances. Billy Bishop Airport is on the Toronto Islands, much closer to downtown, but mainly serves regional and domestic flights, with limited U.S. service via Porter Airlines.

How do I get to Midway Intl Airport from the city center?

From downtown Chicago to Midway, the CTA Orange Line train takes about 25–30 minutes and is the most popular and cost-effective option. Rideshares and taxis take 20–35 minutes depending on traffic and are more expensive. Shuttle services are available but less common. Driving and parking are possible but generally the costliest choice.

Are there hotels or sleeping facilities at Toronto airport?

Yes. Toronto Pearson has the Sheraton Gateway Hotel in Terminal 3, accessible via a direct walkway. Terminal 1 does not have an on-site hotel, but nearby hotels like the Alt Hotel are connected by a free shuttle. There are no capsule hotels or sleeping pods.

Are there currency exchange offices, prayer rooms and Wi‑Fi at Pearson Intl Airport?

Toronto Pearson has currency exchange offices in both Terminal 1 and Terminal 3. There is a multi‑faith chapel in Terminal 1, pre‑security. Free Wi‑Fi is available throughout all terminals.

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

At Chicago Midway, wheelchair assistance and accessible restrooms are available; request help from your airline at least 48 hours before travel. Toronto Pearson offers mobility assistance, quiet spaces, and a children's play area in Terminal 1 near Gate D20; arrange services through your airline 48 hours in advance.

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

The most common aircraft on the nonstop MDW–Toronto route are the Embraer 175 and the De Havilland Canada DHC-8-400 Dash 8Q, with the Airbus A220-200, A320-100, and Canadair Regional Jet 700 also appearing regularly, while the Boeing 737-900, 737-800, and Airbus A319 show up less often; the exact aircraft can vary by day and airline. Wi-Fi and seatback entertainment are widely available on these aircraft, though the specific offerings depend on the carrier and the individual plane.

Methodology

Which airline alliances serve flights from Chicago to Toronto?

On the nonstop schedule between Chicago Midway (MDW) and Toronto (YTO), Porter Airlines (PD) is the only carrier shown, and it belongs to no major global alliance — it is an independent airline. Other alliances may serve the broader Chicago–Toronto market via connecting itineraries, but for the nonstop MDW–YTO service the sole operator is unaligned Porter.

Methodology

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

Chicago Midway has no airline-branded lounges or independent lounges like Priority Pass or Plaza Premium. The airport's only lounge is the USO Center for active-duty military. Passengers seeking lounge access should consider nearby O'Hare, where multiple airline clubs and independent lounges are available.

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

Baggage allowance on Chicago–Toronto flights depends on the airline and fare class. Basic economy tickets are restrictive and may not include a checked bag, while standard economy often includes one checked bag and a carry-on. Premium fares typically allow more. Always verify with your airline.

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

Flights from Chicago Midway to Toronto are all‑Economy, with no Premium Economy or flat‑bed Business available.

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

Same‑day changes and standby depend on the airline and fare class, with flexible and premium tickets offering the most options, while basic economy typically restricts these changes.

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