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Flight Deals from Chicago to Toronto Island Airport from $87

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Stops

  • Nonstop
    from $169
  • Up to 1 stop
    $181
  • Up to 2 stops
    $207

Airlines

  • Air Canada
    $181
  • Air Transat
    $199
  • Porter Airlines
    $169

Cabin Class

  • Economy
    $169

Departure Airports

  • Chicago Midway Airport
    $169
  • Chicago O Hare Airport
    $181

Arrival Airports

  • Toronto Island Airport
    $169

Layover Airports

  • Montreal Trudeau Airport
    $181
  • Newark Liberty Airport
    $328
  • Ottawa Macdonald-Cartier International Airport
    $192
  • Washington Dulles Airport
    $207

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On average save $240 per traveler
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

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
Air Canada Logo
Air Canada

06/07/25

ORD
6h 10m
YUL

06/07/25

YTZ
Air Canada Logo
Air Canada

06/07/25

YTZ
55m
Direct

06/07/25

ORD
$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

06/12/25

YTZ
50m
Direct

06/12/25

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

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 42m
Direct

06/12/25

YTZ
Porter Airlines Logo
Porter Airlines

06/16/25

YTZ
50m
Direct

06/16/25

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
Air Canada Logo
Air Canada

06/14/25

ORD
6h 21m
YOW

06/14/25

YTZ
Air Canada Logo
Air Canada

06/18/25

YTZ
3h 6m
YOW

06/18/25

ORD
$192
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/05/25

ORD
6h 21m
YOW

06/05/25

YTZ
Air Canada Logo
Air Canada

06/17/25

YTZ
3h 6m
YOW

06/17/25

ORD
$192
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

ORD
8h 10m
YUL

05/27/25

YTZ
Air Canada Logo
Air Canada

06/20/25

YTZ
3h 59m
YUL

06/20/25

ORD
$192
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/07/25

ORD
7h 10m
YUL

06/07/25

YTZ
Air Canada Logo
Air Canada

06/19/25

YTZ
3h 6m
YOW

06/19/25

ORD
$192
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/04/25

ORD
7h 31m
YUL

06/04/25

YTZ
Air Canada Logo
Air Canada

06/07/25

YTZ
3h 59m
YUL

06/07/25

ORD
$192
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/18/25

ORD
6h 10m
YUL

05/18/25

YTZ
Air Canada Logo
Air Canada

06/01/25

YTZ
55m
Direct

06/01/25

ORD
$193
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/06/25

ORD
7h 28m
YUL

06/06/25

YTZ
Air Canada Logo
Air Canada

06/13/25

YTZ
4h 53m
YOW

06/13/25

ORD
$198
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 Canada Logo
Air Canada

06/10/25

ORD
7h 28m
YUL

06/10/25

YTZ
Air Canada Logo
Air Canada

06/16/25

YTZ
7h 10m
YOW
IAD

06/16/25

ORD
$207
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/06/25

ORD
7h 28m
YUL

06/06/25

YTZ
Air Canada Logo
Air Canada

06/16/25

YTZ
7h 10m
YOW
IAD

06/16/25

ORD
$207
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

ORD
7h 28m
YUL

05/27/25

YTZ
Air Canada Logo
Air Canada

06/20/25

YTZ
7h 10m
YOW
IAD

06/20/25

ORD
$207
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

05/25/25

MDW
2h 42m
Direct

05/25/25

YTZ
Air Transat Logo
Air Transat

06/10/25

YTZ
50m
Direct

06/10/25

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

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

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
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 Canada Logo
Air Canada

05/24/25

ORD
6h 21m
YOW

05/24/25

YTZ
Air Canada Logo
Air Canada

06/02/25

YTZ
7h 10m
YOW
IAD

06/02/25

ORD
$250
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/05/25

ORD
6h 21m
YOW

06/05/25

YTZ
Air Canada Logo
Air Canada

06/16/25

YTZ
7h 10m
YOW
IAD

06/16/25

ORD
$250
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/30/25

ORD
7h 31m
YUL

05/30/25

YTZ
Air Canada Logo
Air Canada

06/09/25

YTZ
7h 10m
YOW
IAD

06/09/25

ORD
$250
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/14/25

ORD
6h 21m
YOW

06/14/25

YTZ
Air Canada Logo
Air Canada

06/16/25

YTZ
7h 10m
YOW
IAD

06/16/25

ORD
$250
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/31/25

ORD
11h 50m
EWR
YUL

05/31/25

YTZ
Air Canada Logo
Air Canada

06/02/25

YTZ
7h 10m
YOW
IAD

06/02/25

ORD
$328
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago 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

Jun 11

MDW
2h 42m
Direct

Jun 11

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)

Air Canada Logo
Air Canada

May 27

ORD
8h 10m
YUL

May 27

YTZ

as low as

$95

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

Air Canada Logo
Air Canada

May 28

ORD
6h 21m
YOW

May 28

YTZ

as low as

$95

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

Air Canada Logo
Air Canada

Jun 10

ORD
7h 31m
YUL

Jun 10

YTZ

as low as

$95

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

Air Canada Logo
Air Canada

Jun 12

ORD
6h 21m
YOW

Jun 12

YTZ

as low as

$95

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

Air Transat Logo
Air Transat

May 27

MDW
2h 42m
Direct

May 27

YTZ

as low as

$105

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

Air Transat Logo
Air Transat

Jun 1

MDW
2h 42m
Direct

Jun 1

YTZ

as low as

$105

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

Air Canada Logo
Air Canada

May 16

ORD
8h 40m
IAD
YUL

May 16

YTZ

as low as

$185

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

Air Canada Logo
Air Canada

Jun 4

ORD
10h 50m
EWR
YUL

Jun 4

YTZ

as low as

$198

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

Air Canada Logo
Air Canada

Jun 7

ORD
10h 50m
EWR
YUL

Jun 7

YTZ

as low as

$217

Frequently Asked Questions

What is the typical flight duration from Chicago to Toronto Island Airport?
For travelers flying from Chicago to Toronto Island Airport, the typical direct flight duration usually ranges between 1.5 to 2.5 hours. This variation depends on factors such as air traffic congestion and weather conditions. Connecting flights or layovers may extend the travel time further. It is advisable to check schedules and factor in additional time for boarding and security processes when planning your itinerary. This approach helps ensure a smooth transition from Chicago to your destination, allowing sufficient flexibility in case of delays.
Are there any direct flights from Chicago to Toronto Island Airport?
Yes, there are direct flights available from Chicago to Toronto Island Airport, though availability can vary seasonally. Direct flights offer the benefit of a shorter transit time compared to itineraries with layovers. The frequency of these non-stop services may fluctuate, so it is important for travelers from Chicago to verify flight schedules well in advance. Booking early can also secure better fares. As always, checking with your preferred airlines for the latest updates on direct route availability is highly recommended.
What are the best transportation options from Toronto Island Airport to downtown Toronto?
Upon arrival from Chicago to Toronto Island Airport, travelers can choose from several transportation options to reach downtown Toronto. Options include pre-booked shuttle services with fares ranging from CAD 40 to CAD 60, taxis offering similar pricing, or even water taxi services during warmer months for an enjoyable scenic route. Some also prefer ride-sharing apps, which can be cost-effective for groups. Checking schedules in advance and comparing prices will help ensure a smooth and hassle-free transfer during your visit.
What are the must-see attractions in Toronto for travelers arriving from Chicago?
Travelers arriving from Chicago should make time to visit several Toronto highlights. Attractions such as the CN Tower, Royal Ontario Museum, and Ripley’s Aquarium offer iconic sightseeing experiences. For a taste of local culture, exploring neighborhoods like Kensington Market and the Distillery District is worthwhile. Ticket prices for these attractions range from CAD 20 to CAD 50, and guided tours are often available. Planning your itinerary around these landmarks can provide a balanced mix of art, history, and entertainment during your stay.
Which local dishes should travelers from Chicago try when visiting Toronto?
When visiting Toronto, travelers from Chicago are encouraged to sample local delicacies such as poutine, butter tarts, and peameal bacon sandwiches. These dishes reflect the city’s diverse culinary influences and are typically available at eateries with prices ranging from CAD 10 to CAD 30 per plate. Additionally, exploring international fusion cuisines in multicultural neighborhoods can offer delightful surprises. Asking locals for recommendations or checking recent reviews can help you select authentic and popular spots to experience the true flavor of the city.
What are the best family-friendly activities in Toronto for visitors from Chicago?
Families traveling from Chicago to Toronto will find a wide variety of activities ideal for all ages. The Toronto Zoo, Ontario Science Centre, and Centre Island amusement park provide interactive and educational experiences for children. Admission fees generally range from CAD 15 to CAD 30 per person, with family packages often available at discounted rates. Outdoor activities, such as boat rides and park visits, also offer great opportunities to bond while exploring nature and urban beauty. Checking attraction websites ahead of time ensures you have updated timing and pricing details.
Are there any seasonal events in Toronto that travelers from Chicago should not miss?
Yes, seasonal events in Toronto present fantastic opportunities for visitors from Chicago to immerse themselves in local culture. During different times of the year, festivals such as the Toronto International Film Festival, Winterlicious, and various summer outdoor concerts offer unique experiences. Ticket prices for these events can range from free entrance to about CAD 50 for premium events. It is advisable to check event calendars in advance and book tickets early, as these events can get booked up quickly. This planning helps ensure you don’t miss out on Toronto’s vibrant seasonal offerings.
What are the most affordable dining options in Toronto for travelers from Chicago?
Travelers from Chicago seeking affordable dining in Toronto are in luck, as the city offers a wide range of budget-friendly options. Casual diners, street food vendors, and ethnic restaurants in areas like Chinatown and Greektown typically serve meals priced between CAD 10 to CAD 20. Additionally, food courts in major shopping areas or local cafes provide satisfying meals without breaking the bank. It is recommended that you review recent dining guides or use local apps to explore the latest offerings and enjoy authentic culinary experiences at a reasonable cost.
What are the best shopping areas in Toronto for travelers from Chicago?
Travelers coming from Chicago will enjoy exploring several diverse shopping districts in Toronto. The Eaton Centre offers a mix of international brands and local shops, while Queen Street West and Kensington Market present unique boutiques and artisanal products. Shopping prices can vary widely, typically ranging from CAD 20 to CAD 200 per item. Each area offers its own vibe, so planning your route based on the type of merchandise you’re interested in will enhance your experience. Always check for seasonal sales or local markets to discover great bargains.
What cultural etiquette should travelers from Chicago be aware of when visiting Toronto?
Travelers from Chicago visiting Toronto should observe a few cultural etiquette norms to ensure respectful interactions. Punctuality is valued, whether meeting for business or leisure, and a polite handshake or nod is a common greeting. Dining etiquette typically includes a tip of around 15-20% in restaurants, and maintaining a moderate tone in public spaces is appreciated. Being courteous, listening actively, and expressing gratitude can help bridge cultural differences. These practices ensure smooth social interactions during your visit and can create a positive impression in both casual and professional settings.
What health precautions should travelers from Chicago consider before flying to Toronto?
Travelers departing from Chicago to Toronto should consider several key health precautions before embarking on their journey. It is important to ensure vaccinations, such as the seasonal flu shot, are up-to-date. Check current travel advisories and any COVID-19 related guidelines, as these may affect your travel plans. Carry essential medications and a basic travel health kit. Purchasing travel insurance that covers health emergencies, typically ranging from $50 to $150, is advisable. Staying informed through official health channels will help maintain a safe and enjoyable travel experience.
Are there any unique airport amenities at Toronto Island Airport for travelers arriving from Chicago?
Toronto Island Airport offers several unique amenities that can enhance the travel experience for visitors arriving from Chicago. The facility features boutique retail shops, comfortable lounges, and a selection of local artisanal food outlets. Amenities such as complimentary Wi-Fi and duty-free shopping options—with prices generally ranging from CAD 5 to CAD 50—cater to various needs. Additionally, the relaxed ambiance of the terminal reflects local culture, making for a pleasant waiting experience. Travelers should check the airport’s website for the latest updates on amenities and services available at the time of travel.
What are the best seating options for families traveling from Chicago to Toronto?
Families traveling from Chicago to Toronto should consider specific seating arrangements to ensure a comfortable journey. Many airlines offer bulkhead seating or pre-assigned group seating, which typically provides extra legroom and space, ideal for managing young children. These seating options can sometimes include an additional fee ranging from $15 to $40, depending on airline policies. Booking these seats early during the reservation process is recommended. Confirming seating arrangements at check-in can further enhance comfort for all family members, making the flight experience as smooth and pleasant as possible.
What are the customs requirements for travelers flying from Chicago to Toronto?
Travelers flying from Chicago to Toronto must adhere to Canadian customs regulations. You will need a valid passport, and upon arrival, declarations for items such as cash exceeding CAD 10,000, certain food products, and other restricted goods are required. It is advisable to familiarize yourself with the latest guidelines and complete any necessary declaration forms provided onboard. Duties or taxes may apply on declared items. To avoid delays or complications at border control, ensure you understand the customs requirements well before your departure and carry any supporting documentation if needed.
Is there a specific time of year when Toronto is best visited by travelers from Chicago?
Yes, it is generally recommended that travelers from Chicago visit Toronto during the late spring to early fall months. This period, roughly from May to September, offers pleasant weather, with temperatures ranging from 15°C to 25°C, ideal for outdoor activities and sightseeing. The season also coincides with various cultural events and festivals, providing a dynamic experience. Alternatively, winter in Toronto showcases a unique charm with seasonal events but requires extra preparation for cold weather. Planning your visit based on preferred activities and climate preferences will help maximize your experience.