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Flight Deals from Chicago to Toronto from $87

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Stops

  • Nonstop
    from $169
  • Up to 1 stop
    $181
  • Up to 2 stops
    $202

Airlines

  • Air Canada
    $176
  • Air Transat
    $199
  • American Airlines
    $231
  • Delta Air Lines
    $301
  • Porter Airlines
    $169
  • United Airlines
    $223

Cabin Class

  • Economy
    $169

Departure Airports

  • Chicago Midway Airport
    $169
  • Chicago O Hare Airport
    $176

Arrival Airports

  • Toronto Island Airport
    $169
  • Toronto Kitchener Waterloo Airport
    $292
  • Toronto Pearson Airport
    $176

Layover Airports

  • Charlotte Douglas International Airport
    $278
  • Detroit Metropolitan Airport
    $306
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $301
  • Montreal Trudeau Airport
    $181
  • New York LaGuardia Airport
    $272
  • Newark Liberty Airport
    $205
  • Ottawa Macdonald-Cartier International Airport
    $186
  • Philadelphia International Airport
    $272
  • Reagan Washington National Airport
    $243
  • Toronto Pearson Airport
    $292
  • Washington Dulles Airport
    $202

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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
Air Canada Logo
Air Canada

06/12/25

ORD
2h 54m
Direct

06/12/25

YYZ
Air Canada Logo
Air Canada

06/12/25

YYZ
1h 5m
Direct

06/12/25

ORD
$176
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/13/25

ORD
2h 42m
Direct

06/13/25

YYZ
Air Canada Logo
Air Canada

06/16/25

YYZ
55m
Direct

06/16/25

ORD
$180
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

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
Air Canada Logo
Air Canada

06/03/25

ORD
2h 44m
Direct

06/03/25

YYZ
Air Canada Logo
Air Canada

06/18/25

YYZ
3h 6m
YOW

06/18/25

ORD
$186
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

ORD
2h 44m
Direct

05/27/25

YYZ
Air Canada Logo
Air Canada

06/20/25

YYZ
3h 59m
YUL

06/20/25

ORD
$186
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 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
2h 44m
Direct

06/10/25

YYZ
Air Canada Logo
Air Canada

06/16/25

YYZ
7h 10m
YOW
IAD

06/16/25

ORD
$202
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/28/25

ORD
2h 40m
Direct

05/28/25

YYZ
Air Canada Logo
Air Canada

06/11/25

YYZ
7h 10m
YOW
IAD

06/11/25

ORD
$202
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/30/25

ORD
7h 47m
EWR

05/30/25

YYZ
Air Canada Logo
Air Canada

05/30/25

YYZ
1h
Direct

05/30/25

ORD
$205
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

06/12/25

YTZ
50m
Direct

06/12/25

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

06/12/25

ORD
2h 54m
Direct

06/12/25

YYZ
United Airlines Logo
United Airlines

06/12/25

YYZ
1h 5m
Direct

06/12/25

ORD
$223
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/12/25

ORD
2h 40m
Direct

06/12/25

YYZ
American Airlines Logo
American Airlines

06/17/25

YYZ
55m
Direct

06/17/25

ORD
$231
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

ORD
2h 40m
Direct

05/25/25

YYZ
American Airlines Logo
American Airlines

05/26/25

YYZ
55m
Direct

05/26/25

ORD
$231
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/12/25

ORD
2h 44m
Direct

06/12/25

YYZ
United Airlines Logo
United Airlines

06/14/25

YYZ
3h 6m
YOW

06/14/25

ORD
$234
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/14/25

ORD
7h 13m
DCA

06/14/25

YYZ
United Airlines Logo
United Airlines

06/15/25

YYZ
3h 59m
YUL

06/15/25

ORD
$243
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/29/25

ORD
6h 46m
EWR

05/29/25

YYZ
United Airlines Logo
United Airlines

05/30/25

YYZ
3h 59m
YUL

05/30/25

ORD
$243
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/07/25

ORD
5h 21m
PHL

06/07/25

YYZ
American Airlines Logo
American Airlines

06/07/25

YYZ
55m
Direct

06/07/25

ORD
$272
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

ORD
5h 53m
LGA

05/29/25

YYZ
American Airlines Logo
American Airlines

05/29/25

YYZ
55m
Direct

05/29/25

ORD
$272
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/08/25

ORD
6h 20m
CLT

06/08/25

YYZ
American Airlines Logo
American Airlines

06/16/25

YYZ
55m
Direct

06/16/25

ORD
$278
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/09/25

ORD
5h 43m
DCA

06/09/25

YYZ
American Airlines Logo
American Airlines

06/15/25

YYZ
55m
Direct

06/15/25

ORD
$278
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/11/25

ORD
7h 19m
LGA

06/11/25

YYZ
American Airlines Logo
American Airlines

06/14/25

YYZ
55m
Direct

06/14/25

ORD
$278
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

ORD
6h 5m
CLT

05/25/25

YYZ
American Airlines Logo
American Airlines

05/26/25

YYZ
55m
Direct

05/26/25

ORD
$278
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/14/25

ORD
5h 21m
PHL

06/14/25

YYZ
American Airlines Logo
American Airlines

06/17/25

YYZ
1h
Direct

06/17/25

ORD
$278
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/09/25

ORD
5h 7m
YYZ

06/09/25

YKF
Air Canada Logo
Air Canada

06/13/25

YKF
7h 10m
YOW
IAD

06/13/25

ORD
$292
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/12/25

ORD
5h 55m
MSP

06/12/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/17/25

YYZ
5h 33m
MSP

06/17/25

ORD
$301
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/14/25

ORD
5h 55m
DTW

06/14/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/17/25

YYZ
4h 56m
DTW

06/17/25

ORD
$306
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/24/25

ORD
7h 31m
MSP

05/24/25

YYZ
Delta Air Lines Logo
Delta Air Lines

05/27/25

YYZ
5h 17m
MSP

05/27/25

ORD
$306
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago to Toronto

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)

American Airlines Logo
American Airlines

Jun 12

ORD
2h 40m
Direct

Jun 12

YYZ

as low as

$90

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

Air Canada Logo
Air Canada

May 30

ORD
2h 42m
Direct

May 30

YYZ

as low as

$90

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)

Air Canada Logo
Air Canada

May 29

ORD
6h 10m
YUL

May 29

YTZ

as low as

$95

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

Air Canada Logo
Air Canada

May 24

ORD
6h 51m
YOW

May 24

YYZ

as low as

$95

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

Air Canada Logo
Air Canada

May 25

ORD
5h 27m
IAD

May 25

YYZ

as low as

$100

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

Air Canada Logo
Air Canada

Jun 11

ORD
7h 47m
EWR

Jun 11

YYZ

as low as

$100

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

Air Transat Logo
Air Transat

May 29

MDW
2h 42m
Direct

May 29

YTZ

as low as

$105

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

Delta Air Lines Logo
Delta Air Lines

Jun 3

MDW
7h 59m
DTW

Jun 3

YYZ

as low as

$122

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

Delta Air Lines Logo
Delta Air Lines

Jun 4

MDW
9h 19m
MSP

Jun 4

YYZ

as low as

$122

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

Delta Air Lines Logo
Delta Air Lines

Jun 11

ORD
6h 49m
LGA

Jun 11

YYZ

as low as

$122

Frequently Asked Questions

What is the typical flight duration from Chicago to Toronto?
The flight from Chicago to Toronto typically lasts between 1.5 to 2.5 hours, depending on weather conditions, air traffic, and the specific flight path. This non-stop travel time is based on an average distance of roughly 500 miles. It is wise to check your flight status before departure and allow extra time in case of delays. Both cities offer efficient airport services, and planning ahead can help ensure a smooth check-in and boarding process for your convenient travel experience.
Are there any direct flights from Chicago to Toronto?
Yes, direct flights from Chicago to Toronto are available and are quite popular among travelers. This route is serviced by several major airlines that offer non-stop flights, typically taking between 1.5 to 2.5 hours. Booking early could secure better prices, which generally range from $150 to $350 CAD depending on timing and season. Direct flights simplify the travel experience by reducing transit time and potential delays, making it an attractive option for those looking for a straightforward journey between both cities.
What are the best transportation options from Toronto Pearson International Airport to downtown Toronto for travelers arriving from Chicago?
Transport options from Toronto Pearson International Airport to downtown Toronto include the UP Express train, taxis, and ride-sharing services. The UP Express is a popular choice, running every 15 minutes and taking between 25 to 30 minutes, costing around $25 to $35 CAD. Taxis and rideshares provide door-to-door service, though fares can range from $50 to $70 CAD depending on traffic conditions. Evaluating these options based on convenience, budget, and schedule ensures a seamless transition from the airport to the urban center.
What are the must-see attractions in Toronto for travelers coming from Chicago?
Visitors from Chicago should explore several must-see attractions in Toronto. Highlights include the iconic CN Tower, the expansive Royal Ontario Museum, and the historic Distillery District. Walking tours around Kensington Market offer a chance to experience local street art and vibrant cafes. For a scenic escape, the Toronto Islands provide breathtaking views of the skyline. Each attraction offers a unique glimpse into Toronto's culture and history. It is advisable to plan visits during weekdays when crowd sizes are smaller, ensuring a more intimate and relaxed experience.
Which local dishes should travelers from Chicago try when visiting Toronto?
Travelers arriving in Toronto from Chicago should indulge in the local culinary diversity. Traditional dishes like peameal bacon sandwiches, poutine with unique Canadian twists, and butter tarts are a must-try. The multicultural fabric of the city means authentic Caribbean, Middle Eastern, and Asian cuisines are widely available in neighborhoods such as Queen West and Kensington Market. Prices for these dishes generally range from $10 to $25 CAD. Sampling these foods not only satisfies the palate but also offers a deep dive into the city's dynamic food scene.
What are the best family-friendly activities in Toronto for visitors from Chicago?
Families visiting Toronto have access to a variety of kid-friendly activities that deliver both fun and educational experiences. The Ontario Science Centre features interactive exhibits, and the Toronto Zoo offers engaging animal encounters with entry fees typically between $15 and $30 per person. Outdoor adventures can be found on Centre Island, and High Park provides sprawling natural spaces perfect for leisurely walks and picnics. Museums and local art galleries often host special exhibits for children. Balancing activities that entertain both adults and younger visitors ensures a memorable family vacation.
Are there any seasonal events in Toronto that travelers from Chicago should not miss?
Yes, Toronto hosts several seasonal events that are worth planning around when traveling from Chicago. The Toronto International Film Festival in the fall attracts film enthusiasts, while the Winter Festival offers a magical seasonal atmosphere with unique ice sculptures and holiday markets. Additionally, summer brings outdoor concerts, street festivals, and cultural events that celebrate the city's diverse population. Ticket prices can vary from free entry to around $100 CAD. Checking event calendars beforehand and booking tickets early can help maximize your experience during your visit.
What are the customs requirements for travelers flying from Chicago to Toronto?
Travelers flying from Chicago to Toronto must meet customs requirements that include having a valid passport and, if necessary, the appropriate visas. It is important to review the Canada Border Services Agency guidelines before departure. Be prepared to declare any high-value items, large sums of cash, or goods purchased abroad. Allow extra time in the terminal for security screenings and processing your documentation. Being informed about the detailed customs process by consulting official resources before departure can help ensure a smooth and efficient transition when entering Toronto.
What are the most affordable dining options in Toronto for travelers from Chicago?
The affordable dining scene in Toronto caters to a diverse palate and budget. Budget-friendly options include street food markets, casual diners, and ethnic eateries, particularly in areas like Kensington Market. Meals typically range from $10 to $20 CAD, allowing visitors to sample various cuisines without overspending. Additionally, many local cafes and fast-casual restaurants offer daily specials and discounts on weekdays. Exploring different neighborhoods can uncover hidden gems that provide an authentic taste of Toronto at a modest cost, ensuring that travelers from Chicago can enjoy quality meals while managing their travel budget.
What are the best shopping areas in Toronto for souvenirs for visitors from Chicago?
For a memorable shopping experience, visitors should explore areas like the Distillery District, Queen Street West, and Kensington Market. These neighborhoods offer a variety of artisanal boutiques, independent shops, and markets filled with local crafts and souvenirs. Prices typically range from $10 for small trinkets to over $100 CAD for higher-end items. Each area has its own unique vibe, reflecting both modern trends and historical charm. Spending a few hours wandering these districts can lead to finding unique mementos that capture the essence of the vibrant local culture.
Is there a specific time of year when Toronto is best visited by travelers from Chicago?
Toronto is delightful throughout the year, though summer is often considered the best time to visit for those coming from Chicago. The warm weather, bustling outdoor festivals, and vibrant street life create an appealing atmosphere during late June to early September. For visitors seeking milder weather and fewer tourists, spring and fall provide a quieter yet equally enjoyable experience. Each season offers different attractions and events, so consider your interests when planning your itinerary. This strategic seasonal choice ensures you experience the city’s charm at its peak while managing crowds and pricing.
What are the health and safety tips for travelers from Chicago visiting Toronto?
Prioritizing health and safety in Toronto involves staying aware of your surroundings and securing personal belongings. It is advisable to have travel insurance and to know the locations of nearby medical facilities before arriving. Use official transportation services and remain updated on local advisories, especially during inclement weather. Additionally, maintain good hygiene practices and check in on local news for any unexpected public health updates. Familiarizing yourself with emergency contact numbers and local services can further enhance your security, ensuring your stay in Toronto is both safe and enjoyable.
What unique cultural experiences can travelers from Chicago expect in Toronto?
Travelers from Chicago can expect a wealth of unique cultural experiences in Toronto. The city’s vibrant arts scene is showcased in its numerous galleries, theaters, and community festivals. Neighborhoods such as Greektown and Little Italy immerse visitors in authentic cultural traditions and culinary experiences. You may explore indigenous art exhibits, attend live street performances, or participate in local food festivals. Engaging with these diverse aspects of urban life not only enriches the travel experience but also provides a deep dive into the modern multicultural identity that defines Toronto.
What are the best car rental options in Toronto for travelers arriving from Chicago?
Upon arriving in Toronto, visitors can choose from several reliable car rental services located at Toronto Pearson International Airport. Major companies like Hertz, Avis, and Enterprise provide a range of vehicles, with daily rates generally between $40 and $100 CAD. Booking in advance can secure special discounts and ensure availability during peak travel seasons. Additional features such as GPS navigation, insurance coverage, and flexible rental durations can also be arranged. This allows visitors the freedom to explore not only the urban landscape but also the wider region at a pace suited to their itinerary.
Are there any airport amenities in Toronto for travelers arriving from Chicago with special needs?
Toronto Pearson International Airport is well-equipped to assist travelers with special needs. The airport offers a range of amenities including accessible check-in counters, dedicated shuttle services, and personalized assistance to help navigate the terminals. Facilities such as extended seating, tactile signage, and low-level service desks are available to ensure comfort and convenience. If you require additional support, it is advisable to notify your airline in advance. Using these specialized services can help streamline processes like security screening and boarding, ensuring a stress-free travel experience from departure to arrival.