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Flight Deals from Chicago Midway Airport to Toronto Island Airport from $87

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  • Nonstop
    from $169

Airlines

  • Air Transat
    $199
  • Porter Airlines
    $169

Cabin Class

  • Economy
    $169

Departure Airports

  • Chicago Midway Airport
    $169

Arrival Airports

  • Toronto Island Airport
    $169

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Porter Airlines Logo
Porter Airlines

06/05/25

MDW
2h 40m
Direct

06/05/25

YTZ
Porter Airlines Logo
Porter Airlines

06/05/25

YTZ
49m
Direct

06/05/25

MDW
$169
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/26/25

MDW
2h 42m
Direct

05/26/25

YTZ
Porter Airlines Logo
Porter Airlines

06/03/25

YTZ
50m
Direct

06/03/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/27/25

MDW
2h 42m
Direct

05/27/25

YTZ
Porter Airlines Logo
Porter Airlines

06/04/25

YTZ
50m
Direct

06/04/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/21/25

MDW
2h 42m
Direct

05/21/25

YTZ
Porter Airlines Logo
Porter Airlines

05/25/25

YTZ
50m
Direct

05/25/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/12/25

MDW
2h 40m
Direct

06/12/25

YTZ
Porter Airlines Logo
Porter Airlines

06/19/25

YTZ
50m
Direct

06/19/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/06/25

MDW
2h 40m
Direct

06/06/25

YTZ
Porter Airlines Logo
Porter Airlines

06/11/25

YTZ
50m
Direct

06/11/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/03/25

MDW
2h 42m
Direct

06/03/25

YTZ
Porter Airlines Logo
Porter Airlines

06/06/25

YTZ
50m
Direct

06/06/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/01/25

MDW
2h 42m
Direct

06/01/25

YTZ
Porter Airlines Logo
Porter Airlines

06/11/25

YTZ
50m
Direct

06/11/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/25/25

MDW
2h 42m
Direct

05/25/25

YTZ
Porter Airlines Logo
Porter Airlines

06/01/25

YTZ
50m
Direct

06/01/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/14/25

MDW
2h 42m
Direct

06/14/25

YTZ
Porter Airlines Logo
Porter Airlines

06/15/25

YTZ
50m
Direct

06/15/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/18/25

MDW
2h 42m
Direct

05/18/25

YTZ
Porter Airlines Logo
Porter Airlines

06/01/25

YTZ
50m
Direct

06/01/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/02/25

MDW
2h 42m
Direct

06/02/25

YTZ
Porter Airlines Logo
Porter Airlines

06/04/25

YTZ
49m
Direct

06/04/25

MDW
$181
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/28/25

MDW
2h 42m
Direct

05/28/25

YTZ
Porter Airlines Logo
Porter Airlines

06/01/25

YTZ
50m
Direct

06/01/25

MDW
$181
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/05/25

MDW
2h 40m
Direct

06/05/25

YTZ
Air Transat Logo
Air Transat

06/05/25

YTZ
49m
Direct

06/05/25

MDW
$199
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/01/25

MDW
2h 42m
Direct

06/01/25

YTZ
Air Transat Logo
Air Transat

06/11/25

YTZ
50m
Direct

06/11/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/02/25

MDW
2h 42m
Direct

06/02/25

YTZ
Air Transat Logo
Air Transat

06/04/25

YTZ
49m
Direct

06/04/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/14/25

MDW
2h 42m
Direct

06/14/25

YTZ
Air Transat Logo
Air Transat

06/15/25

YTZ
50m
Direct

06/15/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/12/25

MDW
2h 40m
Direct

06/12/25

YTZ
Air Transat Logo
Air Transat

06/19/25

YTZ
50m
Direct

06/19/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/27/25

MDW
2h 42m
Direct

05/27/25

YTZ
Air Transat Logo
Air Transat

06/04/25

YTZ
50m
Direct

06/04/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
Air Transat Logo
Air Transat

06/11/25

YTZ
50m
Direct

06/11/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/26/25

MDW
2h 42m
Direct

05/26/25

YTZ
Air Transat Logo
Air Transat

05/29/25

YTZ
50m
Direct

05/29/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/28/25

MDW
2h 42m
Direct

05/28/25

YTZ
Air Transat Logo
Air Transat

06/01/25

YTZ
50m
Direct

06/01/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/18/25

MDW
2h 42m
Direct

05/18/25

YTZ
Air Transat Logo
Air Transat

06/01/25

YTZ
50m
Direct

06/01/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/07/25

MDW
2h 42m
Direct

06/07/25

YTZ
Air Transat Logo
Air Transat

06/21/25

YTZ
50m
Direct

06/21/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/03/25

MDW
2h 42m
Direct

06/03/25

YTZ
Air Transat Logo
Air Transat

06/06/25

YTZ
50m
Direct

06/06/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/21/25

MDW
2h 42m
Direct

05/21/25

YTZ
Air Transat Logo
Air Transat

05/25/25

YTZ
50m
Direct

05/25/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/25/25

MDW
2h 42m
Direct

05/25/25

YTZ
Air Transat Logo
Air Transat

06/01/25

YTZ
50m
Direct

06/01/25

MDW
$211
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/06/25

MDW
2h 40m
Direct

06/06/25

YTZ
Air Transat Logo
Air Transat

06/11/25

YTZ
50m
Direct

06/11/25

MDW
$211
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
Porter Airlines Logo
Porter Airlines

06/04/25

YTZ
49m
Direct

06/04/25

MDW
$212
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/10/25

MDW
2h 42m
Direct

06/10/25

YTZ
Porter Airlines Logo
Porter Airlines

06/13/25

YTZ
50m
Direct

06/13/25

MDW
$224
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago Midway Airport to Toronto Island Airport

Chicago, US (CHI) - Toronto, CA (YTO)

 Logo

May 21

MDW
2h 42m
Direct

May 21

YTZ

as low as

$87

Chicago, US (CHI) - Toronto, CA (YTO)

Porter Airlines Logo
Porter Airlines

May 21

MDW
2h 42m
Direct

May 21

YTZ

as low as

$90

Chicago, US (CHI) - Toronto, CA (YTO)

Porter Airlines Logo
Porter Airlines

May 29

MDW
2h 42m
Direct

May 29

YTZ

as low as

$90

Chicago, US (CHI) - Toronto, CA (YTO)

Porter Airlines Logo
Porter Airlines

Jun 14

MDW
2h 42m
Direct

Jun 14

YTZ

as low as

$90

Chicago, US (CHI) - Toronto, CA (YTO)

Porter Airlines Logo
Porter Airlines

Jun 1

MDW
2h 42m
Direct

Jun 1

YTZ

as low as

$90

Chicago, US (CHI) - Toronto, CA (YTO)

Porter Airlines Logo
Porter Airlines

May 27

MDW
2h 42m
Direct

May 27

YTZ

as low as

$90

Chicago, US (CHI) - Toronto, CA (YTO)

Porter Airlines Logo
Porter Airlines

May 28

MDW
2h 42m
Direct

May 28

YTZ

as low as

$90

Chicago, US (CHI) - Toronto, CA (YTO)

Air Transat Logo
Air Transat

May 23

MDW
2h 42m
Direct

May 23

YTZ

as low as

$105

Chicago, US (CHI) - Toronto, CA (YTO)

Air Transat Logo
Air Transat

Jun 7

MDW
2h 42m
Direct

Jun 7

YTZ

as low as

$105

Chicago, US (CHI) - Toronto, CA (YTO)

Air Transat Logo
Air Transat

Jun 13

MDW
2h 42m
Direct

Jun 13

YTZ

as low as

$105

Chicago, US (CHI) - Toronto, CA (YTO)

Air Transat Logo
Air Transat

Jun 3

MDW
2h 42m
Direct

Jun 3

YTZ

as low as

$105

Chicago, US (CHI) - Toronto, CA (YTO)

Air Transat Logo
Air Transat

May 29

MDW
2h 42m
Direct

May 29

YTZ

as low as

$105

Frequently Asked Questions

What is the typical flight duration from Chicago Midway Airport to Toronto Island Airport?
Typically, the flight from Chicago Midway Airport to Toronto Island Airport lasts between 2 to 3 hours, depending on weather conditions and routing. While direct flights (if available) tend to shorten the overall journey, connecting flights could extend travel time slightly. This estimate provides a useful benchmark for planning both departure and arrival activities. It’s advisable to check specific flight itineraries and potential delays that might affect the schedule, ensuring a smoother travel experience between these two dynamic cities.
Are there any direct flights from Chicago Midway Airport to Toronto Island Airport?
Generally, there are no regularly scheduled direct flights between Chicago Midway Airport and Toronto Island Airport. Most travelers must connect through other larger hubs, such as Toronto Pearson International or another connecting airport, which may add extra travel time. It is important to confirm current flight schedules with airlines as seasonal or occasional services might occasionally offer direct routes. Planning ahead and reviewing updated flight information can help you manage layovers effectively and streamline your journey between these two cities.
What are the best transportation options from Toronto Island Airport to downtown Toronto?
Since Toronto Island Airport is located on the island, the first step is a short ferry ride to the mainland. The ferry costs generally range from $8 to $12 per person and operates frequently during peak hours. Once on the mainland, travelers can opt for ride-sharing services, local taxis, or public transit, with journey times typically ranging from 15 to 30 minutes depending on traffic and the specific downtown location. Checking the latest ferry schedules and transportation apps will provide real-time updates and streamline your transit to downtown Toronto.
What are the must-see attractions in Toronto for travelers arriving from Chicago Midway Airport?
Travelers planning to visit Toronto should prioritize iconic landmarks such as the CN Tower, Royal Ontario Museum, and a stroll along the vibrant Distillery District. These spots provide an enriching mix of architecture, history, and local art. Additionally, exploring waterfront areas and parks offers scenic views and relaxation. Detailed itineraries often recommend a blend of cultural tours and outdoor experiences. With well-organized public transit and guided tours, visitors can easily navigate and enjoy these attractions as they transition from the flight experience that began at Chicago Midway Airport.
Which local dishes should travelers from Chicago Midway Airport try when visiting Toronto?
When visiting Toronto, food enthusiasts should sample local specialities that reflect the city's multicultural influence. Notable dishes include the famous peameal bacon sandwich, butter tarts, and innovative poutine variations. Additionally, vibrant neighborhoods such as Kensington Market offer diverse street food from Caribbean jerk dishes to Asian fusion cuisine. These dining experiences typically range in price from $10 to $25 per meal, ensuring options for various budgets. Embracing these culinary delights provides an immersive flavor of Toronto’s culture after arriving from Chicago Midway Airport.
What are the best family-friendly activities in Toronto for visitors from Chicago Midway Airport?
Toronto boasts a variety of family-oriented activities suitable for visitors from Chicago Midway Airport. Highlights include the interactive displays at the Ontario Science Centre, a fun-filled day at Centre Island’s amusement parks, and the engaging exhibits at Ripley’s Aquarium. The city also features spacious parks and playgrounds where families can relax. Many attractions offer discounted family rates ranging from $15 to $40 per person. Prior planning can help you balance educational visits with leisure, ensuring an enjoyable experience that caters to both younger and older family members.
Are there any seasonal events in Toronto that travelers from Chicago Midway Airport should not miss?
Yes, Toronto hosts a number of seasonal events that are worth experiencing. During the summer months, travelers can enjoy festivals such as Caribana or outdoor movie nights, while the winter season offers events like the Toronto Christmas Market. Additionally, cultural festivals and the Toronto International Film Festival provide year-round entertainment. These events typically involve ticket prices varying between $20 and $50. Staying updated with local event calendars and booking tickets in advance can significantly enhance your visit, adding a memorable cultural dimension to your travel experience from Chicago.
What are the best budget-friendly dining options in Toronto for travelers from Chicago Midway Airport?
Toronto offers a plethora of budget-friendly dining choices that don’t compromise on quality. Neighborhoods like Kensington Market and Queen Street West feature an array of affordable cafes, food trucks, and ethnic eateries, with meal prices generally ranging from $10 to $20. These spots serve quick bites to hearty lunches in a multicultural setting. Additionally, local diners and casual bistros provide a welcoming atmosphere for travelers. Exploring these options can help you savor Toronto’s diverse culinary scene without overspending, making it a practical choice for visitors arriving from Chicago Midway Airport.
What are the customs requirements for travelers flying from Chicago Midway Airport to Toronto Island Airport?
Travelers flying from Chicago Midway Airport to Toronto Island Airport must adhere to customs and immigration requirements mandated for international travel. It is essential to carry a valid passport and any necessary visas or travel documents, which generally include an Electronic System for Travel Authorization (eTA) for eligible visitors. Customs declarations will need to be completed upon arrival, and you may be asked to provide details regarding your itinerary and any items carried. Preparing these documents ahead of time and reviewing the latest guidelines from customs authorities can ensure a smooth entry process.
Is there a specific time of year when Toronto is best visited by travelers from Chicago Midway Airport?
Many travel experts recommend visiting Toronto during late spring to early fall for optimum weather and an abundance of outdoor activities. This period features temperatures ranging from 15°C to 25°C (60°F to 77°F) and a lively calendar of festivals and events. However, winter visits can also be charming with festive markets and cultural indoor activities. Depending on your interests, choosing a season with mild weather and fewer crowds might offer a more relaxed experience when transitioning from the travel hub in Chicago Midway Airport.
What are the top shopping areas in Toronto for travelers from Chicago Midway Airport?
Toronto boasts several shopping districts that appeal to a range of tastes and budgets. The Eaton Centre is a popular destination offering a mix of high-end brands and more affordable stores, while boutique shops along Queen Street West provide a unique experience with local designers. Kensington Market features eclectic vintage finds and artisanal goods for those seeking a more alternative shopping vibe. Prices here can range broadly, allowing flexibility for various budgets. These shopping areas offer both modern retail and local charm, making them a must-visit after your journey from Chicago Midway Airport.
What unique cultural experiences can travelers from Chicago Midway Airport enjoy in Toronto?
Toronto offers a wealth of unique cultural experiences that highlight its diverse heritage. Visitors can explore art galleries in the Distillery District, indulge in lectures and performances in local theaters, or join culinary tours through multicultural neighborhoods like Kensington Market. Additionally, events at the Harbourfront Centre provide engaging performances and interactive art installations. These experiences, which often range from free community events to ticketed performances costing between $15 and $40, allow travelers to immerse themselves in the city’s distinct cultural flavor, making them a rewarding complement to your transit from Chicago Midway Airport.
What are the best car rental options in Toronto for travelers arriving from Chicago Midway Airport?
For those seeking car rental options in Toronto, established companies such as Enterprise, Avis, and Budget provide reliable service with competitive rates typically ranging from $40 to $80 per day. These companies offer convenient pick-up locations, sometimes near major transit hubs, and often include options for GPS rentals and insurance packages. It is advisable to book ahead and compare prices online, as seasonal promotions and discounts may be available. Renting a car can provide flexibility in exploring various attractions around Toronto, thus complementing your journey coming from Chicago Midway Airport.
Are there any special airport amenities at Toronto Island Airport for travelers from Chicago Midway Airport?
Toronto Island Airport is a smaller facility with limited amenities when compared to larger international hubs. While it provides basic services such as a waiting area and essential passenger support, one should not expect extensive dining or lounge facilities. Given its focus on short-haul and regional flights, services like retail shops or extensive amenities might not be available, so planning ahead is recommended. For additional comforts, some travelers consider transferring to a larger hub like Toronto Pearson International if they require more comprehensive amenities and services during transit from Chicago Midway Airport.
What health precautions should travelers from Chicago Midway Airport consider when visiting Toronto?
Travelers arriving from Chicago Midway Airport should consider a few essential health precautions when visiting Toronto. Ensuring that all routine vaccinations are up to date is important, along with checking any travel health advisories specific to the region. Due to seasonal weather changes, pack suitable clothing and be mindful of potential allergens. Additionally, it’s wise to have travel insurance that covers medical expenses, and to carry a basic first-aid kit. Stay informed through local health guidelines, as Toronto’s public health recommendations may change based on seasonal or emergent conditions.