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Flight Deals from Toronto Pearson Airport to Chicago O Hare Airport from $121

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Stops

  • Nonstop
    from $161
  • Up to 1 stop
    $166
  • Up to 2 stops
    $248

Airlines

  • Air Canada
    $161
  • American Airlines
    $194
  • Delta Air Lines
    $291
  • United Airlines
    $197
  • Virgin Atlantic
    $290
  • WestJet
    $309

Cabin Class

  • Economy
    $161

Departure Airports

  • Toronto Pearson Airport
    $161

Arrival Airports

  • Chicago O Hare Airport
    $161

Layover Airports

  • Charlotte Douglas International Airport
    $280
  • Detroit Metropolitan Airport
    $290
  • Hartsfield Jackson Atlanta International Airport
    $309
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $290
  • Montreal Trudeau Airport
    $166
  • Nashville International Airport
    $204
  • New York LaGuardia Airport
    $254
  • Newark Liberty Airport
    $228
  • Ottawa Macdonald-Cartier International Airport
    $218
  • Philadelphia International Airport
    $282
  • Reagan Washington National Airport
    $237
  • Toronto Pearson Airport
    $235
  • Washington Dulles Airport
    $213

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On average save $240 per traveler
Air Canada Logo
Air Canada

05/19/25

YYZ
1h 6m
Direct

05/19/25

ORD
Air Canada Logo
Air Canada

06/02/25

ORD
2h 42m
Direct

06/02/25

YYZ
$161
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/26/25

YYZ
55m
Direct

05/26/25

ORD
Air Canada Logo
Air Canada

06/10/25

ORD
2h 59m
Direct

06/10/25

YYZ
$161
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/29/25

YYZ
5h 9m
YUL

05/29/25

ORD
Air Canada Logo
Air Canada

06/12/25

ORD
2h 44m
Direct

06/12/25

YYZ
$166
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/04/25

YYZ
3h 37m
YUL

06/04/25

ORD
Air Canada Logo
Air Canada

06/06/25

ORD
2h 42m
Direct

06/06/25

YYZ
$166
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

YYZ
55m
Direct

05/24/25

ORD
American Airlines Logo
American Airlines

05/26/25

ORD
2h 40m
Direct

05/26/25

YYZ
$194
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/03/25

YYZ
1h 5m
Direct

06/03/25

ORD
United Airlines Logo
United Airlines

06/05/25

ORD
2h 42m
Direct

06/05/25

YYZ
$197
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/29/25

YYZ
55m
Direct

05/29/25

ORD
United Airlines Logo
United Airlines

06/12/25

ORD
2h 44m
Direct

06/12/25

YYZ
$197
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/29/25

YYZ
59m
Direct

05/29/25

ORD
United Airlines Logo
United Airlines

05/29/25

ORD
6h 4m
BNA

05/29/25

YYZ
$204
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/14/25

YYZ
55m
Direct

05/14/25

ORD
United Airlines Logo
United Airlines

05/14/25

ORD
7h 29m
BNA

05/14/25

YYZ
$204
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/19/25

YYZ
3h 56m
IAD

05/19/25

ORD
United Airlines Logo
United Airlines

06/02/25

ORD
2h 54m
Direct

06/02/25

YYZ
$213
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/03/25

YYZ
4h 15m
IAD

06/03/25

ORD
United Airlines Logo
United Airlines

06/05/25

ORD
6h 21m
YOW

06/05/25

YYZ
$218
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/05/25

YYZ
55m
Direct

06/05/25

ORD
American Airlines Logo
American Airlines

06/13/25

ORD
3h
Direct

06/13/25

YYZ
$222
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/28/25

YYZ
1h 5m
Direct

05/28/25

ORD
United Airlines Logo
United Airlines

05/29/25

ORD
6h 46m
EWR

05/29/25

YYZ
$228
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/09/25

YYZ
3h 37m
YUL

06/09/25

ORD
Air Canada Logo
Air Canada

06/10/25

ORD
7h 30m
YYZ

06/10/25

YYZ
$235
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

YYZ
59m
Direct

05/25/25

ORD
United Airlines Logo
United Airlines

05/31/25

ORD
6h 21m
YOW

05/31/25

YYZ
$235
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

YYZ
4h 42m
DCA

05/24/25

ORD
American Airlines Logo
American Airlines

05/26/25

ORD
2h 40m
Direct

05/26/25

YYZ
$237
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/08/25

YYZ
5h 55m
DCA

06/08/25

ORD
United Airlines Logo
United Airlines

06/11/25

ORD
2h 42m
Direct

06/11/25

YYZ
$245
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/28/25

YYZ
3h 37m
YUL

05/28/25

ORD
Air Canada Logo
Air Canada

05/30/25

ORD
9h 57m
YUL
YOW

05/30/25

YYZ
$248
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/28/25

YYZ
55m
Direct

05/28/25

ORD
American Airlines Logo
American Airlines

06/03/25

ORD
8h 16m
LGA

06/03/25

YYZ
$254
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/15/25

YYZ
4h 56m
LGA

05/15/25

ORD
United Airlines Logo
United Airlines

05/15/25

ORD
2h 46m
Direct

05/15/25

YYZ
$254
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/02/25

YYZ
3h 35m
YUL

06/02/25

ORD
Air Canada Logo
Air Canada

06/04/25

ORD
9h 57m
YUL
YOW

06/04/25

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

05/23/25

YYZ
55m
Direct

05/23/25

ORD
American Airlines Logo
American Airlines

05/26/25

ORD
6h 5m
CLT

05/26/25

YYZ
$280
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

YYZ
6h 53m
PHL

05/29/25

ORD
American Airlines Logo
American Airlines

06/12/25

ORD
6h 4m
LGA

06/12/25

YYZ
$282
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/22/25

YYZ
55m
Direct

05/22/25

ORD
American Airlines Logo
American Airlines

05/26/25

ORD
15h 25m
CLT

05/26/25

YYZ
$287
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

YYZ
55m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

06/08/25

ORD
5h 21m
PHL

06/08/25

YYZ
$287
Free cancellation within 83 hours of booking
Virgin Atlantic Logo
Virgin Atlantic

05/22/25

YYZ
2h 16m
DTW

05/22/25

ORD
Virgin Atlantic Logo
Virgin Atlantic

05/26/25

ORD
5h 16m
MSP

05/26/25

YYZ
$290
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

YYZ
4h 7m
IAD

05/24/25

ORD
United Airlines Logo
United Airlines

05/28/25

ORD
6h 46m
EWR

05/28/25

YYZ
$291
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/26/25

YYZ
3h 21m
DTW

05/26/25

ORD
Delta Air Lines Logo
Delta Air Lines

06/09/25

ORD
5h 42m
MSP

06/09/25

YYZ
$291
Free cancellation within 83 hours of booking
Virgin Atlantic Logo
Virgin Atlantic

05/15/25

YYZ
6h 22m
DTW

05/15/25

ORD
Virgin Atlantic Logo
Virgin Atlantic

05/18/25

ORD
5h 16m
MSP

05/18/25

YYZ
$307
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/05/25

YYZ
5h 17m
MSP

06/05/25

ORD
WestJet Logo
WestJet

06/05/25

ORD
8h 26m
ATL

06/05/25

YYZ
$309
Free cancellation within 83 hours of booking

Top Deals on flights from Toronto Pearson Airport to Chicago O Hare Airport

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

Air Canada Logo
Air Canada

Sep 13

YYZ
54m
Direct

Sep 13

ORD

as low as

$121

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

American Airlines Logo
American Airlines

Dec 3

YYZ
1h 15m
Direct

Dec 3

ORD

as low as

$122

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

Air Canada Logo
Air Canada

Jun 1

YYZ
3h 37m
YUL

Jun 1

ORD

as low as

$128

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

Air Canada Logo
Air Canada

Jun 11

YYZ
7h 32m
YOW
YUL

Jun 11

ORD

as low as

$132

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

Air Canada Logo
Air Canada

Jul 30

YYZ
3h 43m
IAD

Jul 30

ORD

as low as

$138

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

Delta Air Lines Logo
Delta Air Lines

Jun 4

YYZ
2h 47m
DTW

Jun 4

ORD

as low as

$155

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

United Airlines Logo
United Airlines

Aug 12

YYZ
54m
Direct

Aug 12

ORD

as low as

$157

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

Delta Air Lines Logo
Delta Air Lines

Jun 21

YYZ
3h 45m
MSP

Jun 21

ORD

as low as

$158

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

American Airlines Logo
American Airlines

Jun 25

YYZ
7h 11m
LGA

Jun 25

ORD

as low as

$166

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

Air Canada Logo
Air Canada

Aug 11

YYZ
6h 7m
EWR

Aug 11

ORD

as low as

$166

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

American Airlines Logo
American Airlines

Sep 1

YYZ
4h 23m
CLT

Sep 1

ORD

as low as

$166

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

American Airlines Logo
American Airlines

May 29

YYZ
6h 53m
PHL

May 29

ORD

as low as

$166

Frequently Asked Questions

What is the typical flight duration from Toronto Pearson Airport to Chicago O Hare Airport?
The typical direct flight between Toronto Pearson Airport and Chicago O Hare Airport takes between 1.5 to 2.5 hours, depending on factors such as weather and air traffic control. While connecting flights might extend the journey, direct options provide the quickest route. Travelers should consider checking the flight schedules in advance since departure times and durations can vary. Also, keep an eye on potential delays during peak travel periods, and plan accordingly to ensure a smooth transition upon arrival.
Are there any direct flights from Toronto Pearson Airport to Chicago O Hare Airport?
Yes, several airlines offer direct flights between Toronto Pearson Airport and Chicago O Hare Airport. These non-stop services typically fly multiple times a day, ensuring convenient travel options. Direct flights are ideal for minimizing travel time and avoiding the hassles associated with layovers. Scheduling and frequency may vary seasonally, so it is recommended that travelers verify the current flight listings and book in advance to secure the best travel dates and rates. Being proactive can enhance overall travel comfort.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago for travelers arriving from Toronto?
Travelers can choose a range of transportation options from Chicago O Hare Airport to downtown Chicago. The Blue Line train is a popular option, costing between $5 to $10 and offering frequent service. Alternatively, taxis and rideshare services such as Uber or Lyft provide door-to-door convenience, with fares typically ranging from $30 to $50 depending on traffic. Shuttle buses and private transfers are also available. Each choice offers different benefits, so consider your budget, travel time, and convenience when planning your commute.
What are the must-see attractions in Chicago for travelers arriving from Toronto?
Travelers should not miss iconic Chicago attractions that blend culture, architecture, and entertainment. Notable landmarks include Millennium Park, home to the famous Cloud Gate sculpture, the Art Institute of Chicago with its vast collections, and the Willis Tower Skydeck for panoramic views. Navy Pier offers family fun with rides and dining options. A stroll along the Chicago Riverwalk can also provide unique insights into the city’s history. Each site offers a distinct experience that enriches any visit with memorable urban adventures.
Which local dishes should travelers from Toronto try when visiting Chicago?
Visitors should sample Chicago’s signature culinary delights such as the deep dish pizza, renowned for its thick, hearty crust and copious toppings. The Chicago-style hot dog, served with mustard, relish, onions, and pickles on a poppy seed bun, is another must-try. Additionally, the Italian beef sandwich and Garrett Popcorn offer unique local flavors that capture the city's diverse food culture. For an authentic experience, explore local diners and well-known eateries offering these dishes at prices ranging between $8 to $20 per meal.
Are there any family-friendly activities in Chicago for visitors from Toronto?
Yes, Chicago boasts a wide variety of family-friendly activities. Highlights include interactive museums like the Field Museum and the Shedd Aquarium, offering educational exhibits and hands-on experiences. The Lincoln Park Zoo provides free admission and engaging animal encounters, while Navy Pier features rides, games, and live performances for all ages. Additionally, local parks and riverfront walks offer leisurely activities. With options spanning indoor and outdoor attractions, families can enjoy a balanced itinerary that caters to both younger visitors and adults.
What are the best budget-friendly hotels in Chicago for travelers from Toronto?
Budget-conscious travelers have several hotel options in Chicago that offer comfort without straining budgets. Popular choices include chains like Holiday Inn Express and Hampton Inn, with prices generally ranging from $100 to $200 per night. Neighborhood guesthouses or boutique hotels outside the central downtown area can also provide cost-effective accommodations, while still offering convenient access to public transit. When booking, search for deals during off-peak seasons, and consider packages that include breakfast or transit passes. Always compare reviews and rates to ensure the best value.
What cultural tips should travelers from Toronto be aware of when visiting Chicago?
Travelers should embrace Chicago’s diverse cultural scene by recognizing local customs and etiquette. Tipping is standard practice, usually around 15-20% in restaurants and for services. The city’s vibrant mix of neighborhoods means that residents may have distinct cultural expressions, so being respectful and observant is advised. Chicagoans appreciate punctuality and direct communication. Additionally, learning about local history and art can enhance your experience, particularly when visiting museums or cultural festivals. Familiarizing yourself with local transit and event schedules can make your visit smoother.
What are the top shopping areas in Chicago for travelers from Toronto looking for souvenirs?
Chicago offers a variety of shopping districts that cater to diverse tastes. The Magnificent Mile is famed for its upscale retailers and flagship stores, while State Street provides a mix of popular brands and department stores. Neighborhoods like Wicker Park and Bucktown host boutique shops and vintage stores, ideal for unique finds. Visitors can explore local artisan markets for handcrafted souvenirs that capture Chicago’s spirit. Prices can range from $10 for small trinkets to over $100 for quality items. Comparing options across these areas can help secure the best deals.
Is there a specific time of year when Chicago is best visited by travelers from Toronto?
The optimal time to visit is during the spring and early fall when the weather is most temperate, ranging between 55°F to 75°F. This period not only eases outdoor exploration but also means lighter crowds at popular attractions. While summer is lively with festivals and outdoor activities, it can also be more crowded and warm, and winters are cold with potential snowfall. Therefore, planning your trip between May and early October typically yields the best conditions for sightseeing and enjoying the city’s numerous attractions.
What health and safety precautions should travelers from Toronto consider when visiting Chicago?
When visiting Chicago, it is important to ensure you have comprehensive travel insurance that covers medical emergencies along with any unexpected incidents. Keep personal belongings secure and be vigilant in crowded areas such as transit hubs and tourist destinations. Follow local advisories regarding public health issues, such as seasonal flu or COVID-19 updates, and maintain good hygiene practices. Using reputable transport options and avoiding poorly lit or isolated areas at night enhances personal security. Finally, carry copies of travel documents and emergency contact information for added safety.
Are there any seasonal events in Chicago that travelers from Toronto should not miss?
Yes, seasonal events in Chicago add to the unique travel experience. In the summer, events like the Taste of Chicago and the Chicago Air and Water Show provide a fantastic culinary and entertainment mix. During the fall, various street festivals offer cultural insights and local crafts. In winter, the Christkindlmarket and holiday light displays create a festive atmosphere. Additionally, music and food festivals occur throughout the year, each with varying dates and admission costs. Checking the event calendar in advance can help travelers plan their visit around these vibrant local celebrations.
What are the best seating options for families traveling from Toronto to Chicago?
For families traveling by air, selecting seating that offers extra space and convenience is essential. Many airlines provide options such as bulkhead or exit-row seats for additional legroom. It is advisable to book seats near the front of the aircraft, as these areas simplify boarding and disembarkation, which can be especially helpful when traveling with young children. Some carriers offer pre-assigned seating specifically for families or allow you to reserve seats together at check-in. Requesting assistance at the counter can also help secure favorable seating arrangements tailored to your needs.
What unique airport amenities can travelers expect at Chicago O Hare Airport?
Chicago O Hare Airport offers a diverse range of amenities designed to enhance the traveler experience. Passengers can enjoy complimentary Wi-Fi, a variety of dining options from quick snacks to sit-down meals, and several retail outlets for shopping. Unique features include art installations that reflect the city’s rich culture, comfortable lounges, and family-friendly areas with play zones. Additionally, charging stations and designated quiet areas for relaxation are available. These services typically range from free offerings to premium lounge access options, priced between $30 to $100. Always check current listings before your travel day.
What are the customs requirements for travelers flying from Toronto to Chicago?
Travelers must prepare all necessary documentation before arriving at Chicago O Hare Airport. This includes a valid passport, and for non-U.S. citizens, a visa or an approved ESTA may be required. Customs regulations also necessitate declaring high-value items and certain foods or agricultural products. The customs process typically lasts between 15 to 45 minutes depending on travel volume. It is recommended to review the most current U.S. customs guidelines and complete any applicable forms in advance to ensure a smooth entry experience. Keeping copies of travel itineraries and related documents is also beneficial.