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Flight Deals from Toronto Island Airport to Chicago from $115

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Stops

  • Nonstop
    from $155
  • Up to 1 stop
    $160
  • Up to 2 stops
    $165

Airlines

  • Air Canada
    $160
  • Air Transat
    $187
  • Porter Airlines
    $155

Cabin Class

  • Economy
    $155

Departure Airports

  • Toronto Island Airport
    $155

Arrival Airports

  • Chicago Midway Airport
    $155
  • Chicago O Hare Airport
    $160

Layover Airports

  • Montreal Trudeau Airport
    $160
  • Ottawa Macdonald-Cartier International Airport
    $165
  • Toronto Pearson Airport
    $201
  • Washington Dulles Airport
    $269

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On average save $240 per traveler
Porter Airlines Logo
Porter Airlines

06/03/25

YTZ
49m
Direct

06/03/25

MDW
Porter Airlines Logo
Porter Airlines

06/06/25

MDW
2h 42m
Direct

06/06/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/04/25

YTZ
49m
Direct

06/04/25

MDW
Porter Airlines Logo
Porter Airlines

06/06/25

MDW
2h 42m
Direct

06/06/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/05/25

YTZ
50m
Direct

06/05/25

MDW
Porter Airlines Logo
Porter Airlines

06/11/25

MDW
2h 42m
Direct

06/11/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/01/25

YTZ
49m
Direct

06/01/25

MDW
Porter Airlines Logo
Porter Airlines

06/06/25

MDW
2h 42m
Direct

06/06/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

06/02/25

YTZ
50m
Direct

06/02/25

MDW
Porter Airlines Logo
Porter Airlines

06/02/25

MDW
2h 42m
Direct

06/02/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/26/25

YTZ
50m
Direct

05/26/25

MDW
Porter Airlines Logo
Porter Airlines

06/08/25

MDW
2h 42m
Direct

06/08/25

YTZ
$155
Free cancellation within 83 hours of booking
Porter Airlines Logo
Porter Airlines

05/28/25

YTZ
49m
Direct

05/28/25

MDW
Porter Airlines Logo
Porter Airlines

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
$155
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/22/25

YTZ
3h 59m
YUL

05/22/25

ORD
Air Canada Logo
Air Canada

06/09/25

ORD
2h 44m
Direct

06/09/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/26/25

YTZ
3h 59m
YUL

05/26/25

ORD
Air Canada Logo
Air Canada

06/10/25

ORD
2h 54m
Direct

06/10/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/24/25

YTZ
4h 47m
YUL

05/24/25

ORD
Air Canada Logo
Air Canada

05/30/25

ORD
2h 45m
Direct

05/30/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/03/25

YTZ
3h 59m
YUL

06/03/25

ORD
Air Canada Logo
Air Canada

06/10/25

ORD
2h 49m
Direct

06/10/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/19/25

YTZ
4h 47m
YUL

05/19/25

ORD
Air Canada Logo
Air Canada

05/27/25

ORD
2h 42m
Direct

05/27/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

YTZ
3h 59m
YUL

05/27/25

ORD
Air Canada Logo
Air Canada

06/08/25

ORD
2h 54m
Direct

06/08/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/05/25

YTZ
3h 59m
YUL

06/05/25

ORD
Air Canada Logo
Air Canada

06/13/25

ORD
2h 44m
Direct

06/13/25

YTZ
$160
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

YTZ
9h 52m
YOW
YUL

05/27/25

ORD
Air Canada Logo
Air Canada

05/28/25

ORD
2h 40m
Direct

05/28/25

YTZ
$165
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/19/25

YTZ
9h 52m
YOW
YUL

05/19/25

ORD
Air Canada Logo
Air Canada

06/11/25

ORD
2h 42m
Direct

06/11/25

YTZ
$165
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

YTZ
9h 52m
YOW
YUL

05/27/25

ORD
Air Canada Logo
Air Canada

05/28/25

ORD
8h 10m
YUL

05/28/25

YTZ
$170
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/27/25

YTZ
9h 52m
YOW
YUL

05/27/25

ORD
Air Canada Logo
Air Canada

05/28/25

ORD
8h 20m
YUL
YOW

05/28/25

YTZ
$176
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/20/25

YTZ
49m
Direct

05/20/25

MDW
Air Transat Logo
Air Transat

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/02/25

YTZ
50m
Direct

06/02/25

MDW
Air Transat Logo
Air Transat

06/02/25

MDW
2h 42m
Direct

06/02/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/27/25

YTZ
50m
Direct

05/27/25

MDW
Air Transat Logo
Air Transat

06/08/25

MDW
2h 42m
Direct

06/08/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

05/26/25

YTZ
50m
Direct

05/26/25

MDW
Air Transat Logo
Air Transat

06/04/25

MDW
2h 42m
Direct

06/04/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/05/25

YTZ
50m
Direct

06/05/25

MDW
Air Transat Logo
Air Transat

06/05/25

MDW
2h 42m
Direct

06/05/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/09/25

YTZ
49m
Direct

06/09/25

MDW
Air Transat Logo
Air Transat

06/10/25

MDW
2h 42m
Direct

06/10/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Transat Logo
Air Transat

06/01/25

YTZ
50m
Direct

06/01/25

MDW
Air Transat Logo
Air Transat

06/06/25

MDW
2h 42m
Direct

06/06/25

YTZ
$187
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/20/25

YTZ
5h 57m
YUL

05/20/25

ORD
Air Canada Logo
Air Canada

06/03/25

ORD
7h 41m
YOW

06/03/25

YTZ
$198
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/28/25

YTZ
3h 6m
YOW

05/28/25

ORD
Air Canada Logo
Air Canada

06/04/25

ORD
6h 5m
YUL

06/04/25

YTZ
$198
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/19/25

YTZ
9h 52m
YOW
YUL

05/19/25

ORD
Air Canada Logo
Air Canada

06/11/25

ORD
5h 35m
YYZ

06/11/25

YTZ
$201
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/16/25

YTZ
6h 55m
YOW
IAD

05/16/25

ORD
Air Canada Logo
Air Canada

05/30/25

ORD
2h 59m
Direct

05/30/25

YTZ
$269
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/16/25

YTZ
6h 55m
YOW
IAD

05/16/25

ORD
Air Canada Logo
Air Canada

05/28/25

ORD
7h 31m
YUL

05/28/25

YTZ
$274
Free cancellation within 83 hours of booking

Top Deals on flights from Toronto Island Airport to Chicago

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

Porter Airlines Logo
Porter Airlines

Dec 3

YTZ
50m
Direct

Dec 3

MDW

as low as

$115

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

Porter Airlines Logo
Porter Airlines

Jul 4

YTZ
50m
Direct

Jul 4

MDW

as low as

$115

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

Porter Airlines Logo
Porter Airlines

Aug 17

YTZ
50m
Direct

Aug 17

MDW

as low as

$115

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

Air Canada Logo
Air Canada

Dec 3

YTZ
3h 28m
YOW

Dec 3

ORD

as low as

$120

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

Air Canada Logo
Air Canada

Nov 24

YTZ
3h 55m
YUL

Nov 24

ORD

as low as

$120

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

Air Canada Logo
Air Canada

Aug 9

YTZ
3h 59m
YUL

Aug 9

ORD

as low as

$120

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

Air Canada Logo
Air Canada

Sep 13

YTZ
4h 46m
YUL

Sep 13

ORD

as low as

$120

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

Air Canada Logo
Air Canada

Jul 4

YTZ
3h 6m
YOW

Jul 4

ORD

as low as

$120

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

Air Canada Logo
Air Canada

Nov 13

YTZ
3h 28m
YOW

Nov 13

ORD

as low as

$121

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

Air Transat Logo
Air Transat

Oct 25

YTZ
49m
Direct

Oct 25

MDW

as low as

$132

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

Air Transat Logo
Air Transat

Jul 20

YTZ
50m
Direct

Jul 20

MDW

as low as

$132

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

Air Transat Logo
Air Transat

Oct 15

YTZ
49m
Direct

Oct 15

MDW

as low as

$132

Frequently Asked Questions

What is the typical flight duration from Toronto Island Airport to Chicago?
The typical flight duration from Toronto Island Airport to Chicago generally ranges from 1.5 to 2.5 hours on direct flights. However, if connecting flights are involved, the total travel time can increase significantly, potentially reaching up to 3 hours. Weather and air traffic conditions may also impact your schedule. It is advisable to check updated flight itineraries when booking to plan accordingly. Always factor in additional time for boarding and security checks to have a stress‐free journey between Toronto Island Airport and Chicago.
Are there any direct flights from Toronto Island Airport to Chicago?
Yes, there are direct flights available from Toronto Island Airport to Chicago, although they may be limited depending on the season and carrier schedules. Direct services typically offer a shorter overall travel time compared to connecting flights. However, the frequency can vary throughout the year, and it is best to verify current schedules before booking. Early planning might yield better fares and preferred timings. This approach ensures a smooth transition and minimizes layover stress when traveling from Toronto Island Airport to Chicago.
What are the best transportation options from Chicago airport to downtown?
From Chicago airport to downtown, the best transportation options include rideshare services like Uber and Lyft, taxis, and the CTA Blue Line train. Rideshare fares typically range between $20 to $40, while taxis are available for about $30 to $50, subject to traffic. The CTA Blue Line provides an economical option with fares generally between $5 to $10, though it might take a bit longer. Evaluating your budget, luggage, and time constraints can help decide the ideal choice for transitioning from the Chicago airport to downtown attractions.
What are the must-see attractions in Chicago for travelers arriving from Toronto Island Airport?
Chicago offers a host of must-see attractions including Millennium Park, home to the iconic Cloud Gate sculpture, the Art Institute of Chicago with its diverse collections, and Navy Pier for delightful river views and rides. Architectural river cruises and neighborhoods rich in history further enhance the experience. For travelers arriving from Toronto Island Airport, purchasing a city pass can be a smart way to save on multiple attractions while enjoying comprehensive access to cultural landmarks and scenic spots that illustrate Chicago’s unique urban charm.
Which local dishes should travelers from Toronto Island Airport try when visiting Chicago?
Travelers visiting Chicago should not miss trying the city’s signature deep-dish pizza and the famous Italian beef sandwich, both celebrated for their hearty and unique flavors. Chicago-style hot dogs, loaded with specific toppings, are also highly recommended. Many local restaurants offer these dishes at prices generally ranging from $10 to $25 per dish, allowing for a variety of budget options. Sampling these culinary delights provides a delicious insight into the city’s vibrant food culture, making it an essential part of the travel experience when journeying from Toronto Island Airport.
Are there any family-friendly activities in Chicago for visitors from Toronto Island Airport?
Yes, Chicago is known for its family-friendly attractions. Museum visits, such as to the Field Museum and the Museum of Science and Industry, offer interactive exhibits that engage children and adults alike. Outdoor spaces like Grant Park and Millennium Park feature playgrounds, open lawns, and seasonal events. Additionally, local zoos and aquariums create lasting memories for families. Admission fees generally range from $15 to $30 per person. These diverse activities ensure that travelers from Toronto Island Airport have plenty of fun and educational options during their visit to Chicago.
What are the best budget-friendly hotels in Chicago for travelers from Toronto Island Airport?
Travelers from Toronto Island Airport looking for budget-friendly accommodations in Chicago should explore options in neighborhoods such as the Loop or River North. Many budget hotels and boutique inns in these areas offer rates ranging from $80 to $150 per night while providing essential amenities like complimentary Wi-Fi and breakfast. Booking in advance, particularly during peak tourist seasons, may secure better deals. Additionally, many hotels are conveniently located near public transit lines, making it easier to explore the city and reach various attractions without exceeding your travel budget.
What cultural tips should travelers from Toronto Island Airport be aware of when visiting Chicago?
Travelers journeying from Toronto Island Airport to Chicago should embrace local customs and practices. Chicago residents appreciate punctuality and clear communication, so plan your schedule accordingly. When dining, tipping around 15-20% is customary and shows respect. Engaging with neighborhood events and local art exhibits can enhance your cultural understanding. Be mindful of the city’s diverse neighborhood identities and follow posted guidelines in museums and public spaces. Overall, understanding these cultural nuances will ensure a more respectful and enriched experience during your visit to Chicago.
What are the top shopping areas in Chicago for travelers from Toronto Island Airport?
Chicago’s top shopping venues offer a mix of upscale retail and unique local boutiques. The Magnificent Mile is renowned for its luxury department stores and designer labels, while neighborhoods like Wicker Park and Lincoln Park provide a more eclectic shopping experience with vintage stores and artisan shops. Prices vary widely, ensuring options for various budgets. Organizing your shopping route in advance can help manage time effectively. This strategic approach allows visitors from Toronto Island Airport to enjoy the diverse retail landscape that captures the dynamic spirit and style of Chicago.
Is there a specific time of year when Chicago is best visited by travelers from Toronto Island Airport?
Yes, the optimal time to visit Chicago is generally during the late spring to early fall, from May to September. During this period, the weather is pleasant and conducive to exploring outdoor attractions like parks, festivals, and river cruises. Summer offers a lively atmosphere, while early fall brings cooler weather and fewer crowds. This time frame provides travelers from Toronto Island Airport the best chance to fully enjoy the city’s vibrant festivals and outdoor events without enduring extreme temperatures, making it ideal for both sightseeing and relaxation.
What are the health and safety precautions travelers from Toronto Island Airport should take when visiting Chicago?
Travelers from Toronto Island Airport to Chicago should adhere to standard health and safety procedures. Keep up-to-date with any local health advisories or COVID-19 guidelines and maintain sanitation practices like regular hand washing and using hand sanitizers. Be vigilant in crowded areas, and secure personal belongings to avoid pickpocketing. Consider acquiring travel insurance that covers health emergencies, and always have local emergency contacts on hand. Following these proactive measures will not only provide peace of mind but also enhance your overall safety during your exploration of Chicago.
Are there any seasonal events in Chicago that travelers from Toronto Island Airport should not miss?
Yes, Chicago plays host to several notable seasonal events that are popular among travelers from Toronto Island Airport. In summer, the Chicago Air and Water Show and festivals like Taste of Chicago provide unique, large-scale public events. Fall brings various food and cultural festivals, while the winter season features festive markets and ice skating opportunities near major parks. These events often involve a mix of free and ticketed admissions, with costs ranging from minimal fees to around $20. Checking event calendars in advance can help you plan and make the most of these seasonal highlights.
What are the best rideshare options from Chicago airport to popular attractions?
For a smooth transition from Chicago airport to popular attractions, rideshare options such as Uber and Lyft remain excellent choices. Fares typically range between $20 and $40 depending on traffic and the time of day. These apps offer clear fare estimates and allow you to track your ride in real time. In addition, local taxi services are available, although they might be slightly more expensive. It’s advisable to compare wait times and cost estimates on your smartphone before booking, ensuring a cost-effective and efficient journey to explore Chicago.
What unique airport amenities can travelers expect at Chicago airport?
Chicago airport offers a variety of unique amenities designed to enhance traveler comfort. Visitors can enjoy a wide range of dining options from fast casual to sit-down restaurants offering both local and international cuisine. Complimentary Wi-Fi, charging stations, and comfortable lounges are provided to ensure a relaxed wait. Some terminals even feature retail outlets selling local souvenirs and specialty items. Additionally, dedicated family zones and quiet areas improve the overall travel experience. These facilities contribute to a seamless transition for passengers arriving from or departing to destinations like Toronto Island Airport.
What are the customs requirements for travelers flying from Toronto Island Airport to Chicago?
Travelers flying from Toronto Island Airport to Chicago must comply with U.S. customs and border protection regulations. It is essential to have valid travel documents such as a passport or an appropriate visa. Be prepared to declare any items of value and provide receipts if necessary. Familiarize yourself with the list of prohibited items to avoid issues at the checkpoint. Arriving early to allow extra time for customs processing can ease your transition. Staying updated with the most recent customs guidelines ensures a smooth entry experience when arriving in Chicago.