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Flight Deals from Chicago Midway Airport to Toronto from $87

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Stops

  • Nonstop
    from $169
  • Up to 1 stop
    $306
  • Up to 2 stops
    $393

Airlines

  • Air Transat
    $199
  • Delta Air Lines
    $306
  • Porter Airlines
    $169
  • WestJet
    $383

Cabin Class

  • Economy
    $169

Departure Airports

  • Chicago Midway Airport
    $169

Arrival Airports

  • Toronto Island Airport
    $169
  • Toronto Pearson Airport
    $306

Layover Airports

  • Calgary International Airport
    $393
  • Detroit Metropolitan Airport
    $306
  • Edmonton Airport
    $393
  • Hartsfield Jackson Atlanta International Airport
    $383
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $307
  • New York LaGuardia Airport
    $426

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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

05/27/25

MDW
2h 42m
Direct

05/27/25

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

06/12/25

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

06/14/25

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

05/28/25

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

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

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

05/26/25

MDW
2h 42m
Direct

05/26/25

YTZ
Porter Airlines Logo
Porter Airlines

05/29/25

YTZ
50m
Direct

05/29/25

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

06/06/25

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

06/12/25

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

05/28/25

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
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

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

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

06/02/25

MDW
2h 42m
Direct

06/02/25

YTZ
Air Transat Logo
Air Transat

06/07/25

YTZ
50m
Direct

06/07/25

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

06/11/25

MDW
7h 51m
DTW

06/11/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/15/25

YYZ
6h 7m
DTW

06/15/25

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

05/31/25

MDW
7h 59m
DTW

05/31/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/04/25

YYZ
4h 15m
MSP

06/04/25

MDW
$307
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/04/25

MDW
4h 33m
DTW

06/04/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/07/25

YYZ
4h 6m
DTW

06/07/25

MDW
$307
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/30/25

MDW
4h 7m
DTW

05/30/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/01/25

YYZ
5h 58m
DTW

06/01/25

MDW
$307
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/13/25

MDW
4h 38m
DTW

06/13/25

YYZ
Delta Air Lines Logo
Delta Air Lines

06/16/25

YYZ
5h 49m
DTW

06/16/25

MDW
$312
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/16/25

MDW
4h 33m
DTW

05/16/25

YYZ
Delta Air Lines Logo
Delta Air Lines

05/25/25

YYZ
5h 58m
DTW

05/25/25

MDW
$383
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/06/25

MDW
9h 11m
MSP

06/06/25

YYZ
WestJet Logo
WestJet

06/11/25

YYZ
5h 33m
MSP

06/11/25

MDW
$383
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/15/25

MDW
4h 7m
DTW

05/15/25

YYZ
Delta Air Lines Logo
Delta Air Lines

05/28/25

YYZ
2h 39m
DTW

05/28/25

MDW
$383
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/24/25

MDW
11h 7m
ATL

05/24/25

YYZ
WestJet Logo
WestJet

05/28/25

YYZ
2h 47m
DTW

05/28/25

MDW
$383
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/05/25

MDW
9h 8m
ATL

06/05/25

YYZ
WestJet Logo
WestJet

06/07/25

YYZ
4h 15m
DTW

06/07/25

MDW
$383
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/07/25

MDW
15h 13m
MSP
YEG

06/08/25

YYZ
WestJet Logo
WestJet

06/11/25

YYZ
11h 37m
YYC
MSP

06/11/25

MDW
$393
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/29/25

MDW
9h 19m
MSP

05/29/25

YYZ
WestJet Logo
WestJet

06/01/25

YYZ
6h 22m
DTW

06/01/25

MDW
$426
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/31/25

MDW
9h 19m
MSP

05/31/25

YYZ
WestJet Logo
WestJet

06/01/25

YYZ
2h 52m
DTW

06/01/25

MDW
$426
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/07/25

MDW
11h 7m
ATL

06/07/25

YYZ
WestJet Logo
WestJet

06/11/25

YYZ
7h 54m
LGA

06/11/25

MDW
$426
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago Midway Airport 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)

Porter Airlines Logo
Porter Airlines

May 25

MDW
2h 42m
Direct

May 25

YTZ

as low as

$90

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

Porter Airlines Logo
Porter Airlines

May 30

MDW
2h 42m
Direct

May 30

YTZ

as low as

$90

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

Air Transat Logo
Air Transat

Jun 5

MDW
2h 40m
Direct

Jun 5

YTZ

as low as

$105

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

Air Transat Logo
Air Transat

Jun 4

MDW
2h 42m
Direct

Jun 4

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

May 27

MDW
9h 19m
MSP

May 27

YYZ

as low as

$122

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

Delta Air Lines Logo
Delta Air Lines

Jun 10

MDW
7h 51m
DTW

Jun 10

YYZ

as low as

$122

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

WestJet Logo
WestJet

May 29

MDW
9h 8m
ATL

May 29

YYZ

as low as

$185

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

WestJet Logo
WestJet

Jun 10

MDW
11h 14m
ATL

Jun 10

YYZ

as low as

$185

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

WestJet Logo
WestJet

Jun 7

MDW
17h 24m
ATL
YYC

Jun 8

YYZ

as low as

$190

Frequently Asked Questions

What is the typical flight duration from Chicago Midway Airport to Toronto?
The typical flight duration from Chicago Midway Airport to Toronto is generally between 1.5 to 2.5 hours on a direct flight. This estimate can vary slightly due to weather conditions and air traffic. For those planning this journey, it’s advisable to check current schedules and plan for possible minor delays. Ensuring you have extra time in your itinerary will help accommodate any unexpected changes. This information assists travelers looking to optimize their connection between these two important travel hubs.
Are there any direct flights from Chicago Midway Airport to Toronto?
Yes, there are direct flights available from Chicago Midway Airport to Toronto. Some airlines operate non-stop routes, offering a convenient option for travelers looking to minimize travel time. However, schedules can vary seasonally and by day of the week, so it pays to check current listings. Booking these flights in advance often secures competitive fares and ensures a seamless travel experience. This focused planning can really simplify your journey from Chicago to Toronto if you prefer non-stop travel.
What are the best transportation options from Toronto airport to downtown?
When arriving in Toronto, several transportation options are available to reach downtown efficiently. You can take the UP Express train service, which typically costs between $12 and $20 and takes 25 to 30 minutes. Taxis and rideshare services are also available, generally ranging from $50 to $70 depending on traffic. Additionally, airport shuttle services or local transit buses provide a more budget-friendly alternative with fares typically from $3 to $5. Each option allows travelers to move comfortably between the airport and downtown.
What are the must-see attractions in Toronto for travelers arriving from Chicago Midway Airport?
Travelers arriving from Chicago Midway Airport should definitely explore some of Toronto’s standout attractions. Iconic landmarks like the CN Tower and Royal Ontario Museum deliver both cultural insight and breathtaking views. The Distillery District offers a mix of history, boutique shopping, and unique dining experiences. Additionally, Kensington Market and the Toronto Waterfront provide diverse, vibrant settings. Each of these spots promises distinctive local flavor, ensuring that visitors enjoy an engaging and memorable itinerary upon their arrival.
Which local dishes should travelers from Chicago Midway Airport try when visiting Toronto?
Travelers visiting Toronto should immerse themselves in the city’s diverse culinary scene. Be sure to try the renowned peameal bacon sandwich and indulge in traditional treats like butter tarts. Toronto’s multicultural influences also offer inventive twists on poutine and a variety of international cuisines available in neighborhoods like Chinatown and St. Lawrence Market. Sampling these dishes not only gives a taste of local flavor but also offers insightful cultural experiences. Enjoying these meals is a great way to celebrate Toronto’s rich culinary heritage.
What are the best family-friendly activities in Toronto for visitors from Chicago Midway Airport?
Toronto boasts a wide range of family-friendly activities suited for visitors from Chicago Midway Airport. The Toronto Zoo and Ontario Science Centre offer interactive and educational exhibits that delight children and adults alike. Additional options include Ripley’s Aquarium and Centre Island, both of which provide engaging experiences amid scenic urban settings. There are also numerous parks and community centers with seasonal events. With admission fees generally ranging from $15 to $30 per person, these attractions provide fun, safe, and enriching experiences for every member of the family.
Are there any seasonal events in Toronto that travelers from Chicago Midway Airport should not miss?
Yes, Toronto hosts a variety of seasonal events that are well worth experiencing when traveling from Chicago Midway Airport. In the summer, outdoor concerts and street festivals create a vibrant atmosphere, while the Toronto International Film Festival in early September draws film enthusiasts from around the world. Winter offers charming ice skating rinks and festive markets, whereas spring and fall feature art fairs and cultural parades. Checking the event calendar ahead of your trip ensures you can participate in those activities that best match your interests.
What are the most affordable dining options in Toronto for travelers from Chicago Midway Airport?
Toronto offers several affordable dining options that suit a range of tastes and budgets. Neighborhoods such as Kensington Market, Chinatown, and St. Lawrence Market feature food stalls, casual cafes, and diners where meals usually range from $10 to $20. These spots provide a mix of local specialties and international cuisine at budget-friendly prices. Additionally, many food courts and casual eateries in shopping districts offer daily specials and set menus. This diversity ensures that travelers can enjoy high-quality meals without overspending while exploring the city's culinary scene.
What are the customs requirements for travelers flying from Chicago Midway Airport to Toronto?
Travelers flying from Chicago Midway Airport to Toronto must comply with international customs regulations. U.S. citizens typically need a valid passport or an enhanced driver’s license to cross the border, and all passengers should be prepared to complete customs declaration forms upon arrival. It is also advisable to review current regulations regarding prohibited items and duty-free allowances. Staying informed about any recent changes in border policy can help ensure a smooth passage. Checking both U.S. and Canadian customs guidelines before departure is a wise preparatory step.
What are the best shopping districts in Toronto for travelers from Chicago Midway Airport?
Toronto features several dynamic shopping districts catering to varied tastes and budgets. The Eaton Centre is a vast retail hub with both international chains and local boutiques, perfect for those seeking convenience and variety. Yorkville offers a more upscale shopping experience with designer labels and luxurious services. For a unique experience filled with vintage and eclectic finds, Kensington Market stands out as a favorite. Whether looking for high-end fashion or one-of-a-kind souvenirs, each district delivers a tailored shopping experience for travelers making their way from Chicago.
Is there a specific time of year when Toronto is best visited by travelers from Chicago Midway Airport?
Travelers often find that Toronto is best visited during the late spring to early fall months, typically from May to September. These seasons offer pleasant weather and an array of festivals, outdoor activities, and cultural events, making it ideal for exploring the city’s attractions. While winter in Toronto offers its own charm, including festive events and cozy indoor attractions, the warmer months provide a broader range of activities. Selecting your travel period based on your interests will enhance your overall experience between these two dynamic urban centers.
What are the health and safety tips for travelers from Chicago Midway Airport to Toronto?
When journeying from Chicago Midway Airport to Toronto, it's essential to prioritize your health and safety. Bring any necessary medications, ensure you have a valid travel insurance plan, and stay updated on local health advisories in both cities. It is wise to secure your belongings and avoid isolated areas, particularly at night. Furthermore, be mindful of local transportation safety by using reputable services. Checking weather forecasts and travel advisories ahead of time will help you prepare for any unforeseen circumstances, ensuring a secure and comfortable trip.
What unique airport amenities can travelers expect at Toronto airport?
Travelers arriving in Toronto can look forward to a variety of unique airport amenities designed for comfort and convenience. Toronto Pearson International Airport, for example, offers modern lounges, art exhibits, and diverse dining options that cater to different tastes. Free Wi-Fi, plentiful charging stations, and retail boutiques provide additional comfort and leisure opportunities. From quiet relaxation zones to upscale duty-free shopping, these amenities enable passengers to make the most of their time between flights, ensuring that the transition from Chicago Midway Airport is both pleasant and efficient.
What are the best car rental options in Toronto for travelers from Chicago Midway Airport?
At Toronto, several top-tier car rental companies are ready to meet a variety of traveler needs. Notable firms such as Enterprise, Avis, and Budget offer daily rental rates typically ranging from $40 to $80, depending on the type of vehicle and rental period. Many of these agencies have conveniently located counters at the airport, simplifying pick-up and drop-off processes. It is advisable to compare rental packages and include insurance options when booking to optimize your travel budget. This ensures a smooth, flexible travel experience upon arrival.
Are there any tips for first-time travelers flying from Chicago Midway Airport to Toronto?
For first-time travelers making the journey from Chicago Midway Airport to Toronto, thorough preparation is key. Confirm that all travel documents, such as your passport and any necessary visas, are current before departure. Arrive early to accommodate security procedures and familiarize yourself with the airport layout. Reviewing Toronto’s local transport, weather conditions, and cultural norms ahead of time can enhance your experience. Additionally, planning an itinerary that includes high-priority attractions and dining recommendations will help you navigate the new environment with confidence during your inaugural trip.