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Flight Deals from Toronto to Chicago O Hare Airport from $120

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Stops

  • Nonstop
    from $161
  • Up to 1 stop
    $160
  • Up to 2 stops
    $170

Airlines

  • Air Canada
    $160
  • American Airlines
    $194
  • Delta Air Lines
    $291
  • United Airlines
    $197
  • Virgin Atlantic
    $290

Cabin Class

  • Economy
    $160

Departure Airports

  • Toronto Hamilton Airport
    $222
  • Toronto Island Airport
    $160
  • Toronto Kitchener Waterloo Airport
    $254
  • Toronto Pearson Airport
    $161

Arrival Airports

  • Chicago O Hare Airport
    $160

Layover Airports

  • Charlotte Douglas International Airport
    $280
  • Detroit Metropolitan Airport
    $290
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $290
  • Montreal Trudeau Airport
    $160
  • Nashville International Airport
    $204
  • New York LaGuardia Airport
    $228
  • Newark Liberty Airport
    $291
  • Ottawa Macdonald-Cartier International Airport
    $170
  • Philadelphia International Airport
    $282
  • Reagan Washington National Airport
    $237
  • Toronto Pearson Airport
    $201
  • Washington Dulles Airport
    $213

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On average save $240 per traveler
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

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

06/02/25

YYZ
55m
Direct

06/02/25

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

05/23/25

YYZ
55m
Direct

05/23/25

ORD
Air Canada Logo
Air Canada

06/06/25

ORD
2h 42m
Direct

06/06/25

YYZ
$161
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
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

05/26/25

YYZ
55m
Direct

05/26/25

ORD
United Airlines Logo
United Airlines

06/02/25

ORD
2h 42m
Direct

06/02/25

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

05/31/25

YYZ
59m
Direct

05/31/25

ORD
United Airlines Logo
United Airlines

06/13/25

ORD
2h 44m
Direct

06/13/25

YYZ
$197
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
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
Air Canada Logo
Air Canada

05/12/25

YHM
4h 16m
YYZ

05/12/25

ORD
Air Canada Logo
Air Canada

05/27/25

ORD
2h 52m
Direct

05/27/25

YHM
$222
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
4h 39m
LGA

05/28/25

ORD
United Airlines Logo
United Airlines

05/29/25

ORD
2h 59m
Direct

05/29/25

YYZ
$228
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

05/29/25

YYZ
5h 55m
DCA

05/29/25

ORD
United Airlines Logo
United Airlines

05/29/25

ORD
6h 21m
YOW

05/29/25

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

05/15/25

YKF
5h 45m
YYZ

05/15/25

ORD
Air Canada Logo
Air Canada

05/28/25

ORD
2h 40m
Direct

05/28/25

YKF
$254
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

YYZ
55m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/12/25

ORD
6h 4m
LGA

06/12/25

YYZ
$254
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
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
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
United Airlines Logo
United Airlines

06/07/25

YYZ
4h 3m
IAD

06/07/25

ORD
United Airlines Logo
United Airlines

06/11/25

ORD
7h 47m
EWR

06/11/25

YYZ
$302
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

Top Deals on flights from Toronto to Chicago O Hare Airport

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

Dec 3

YTZ
3h 28m
YOW

Dec 3

ORD

as low as

$120

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

Jun 14

YYZ
55m
Direct

Jun 14

ORD

as low as

$122

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
6h 23m
IAD

Jul 30

ORD

as low as

$138

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

Delta Air Lines Logo
Delta Air Lines

Jun 11

YYZ
6h 25m
DTW

Jun 11

ORD

as low as

$155

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

Air Canada Logo
Air Canada

Jul 12

YKF
3h 34m
YYZ

Jul 12

ORD

as low as

$157

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

United Airlines Logo
United Airlines

Aug 18

YYZ
54m
Direct

Aug 18

ORD

as low as

$157

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

Air Canada Logo
Air Canada

Jul 13

YHM
4h 9m
YYZ

Jul 13

ORD

as low as

$157

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

Delta Air Lines Logo
Delta Air Lines

May 31

YYZ
8h 18m
MSP

May 31

ORD

as low as

$158

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

Air Canada Logo
Air Canada

Jun 28

YTZ
11h 21m
YOW
EWR

Jun 28

ORD

as low as

$164

Frequently Asked Questions

What is the typical flight duration from Toronto to Chicago O Hare Airport?
The typical flight duration from Toronto to Chicago O Hare Airport usually ranges between 1.5 to 2.5 hours. This timeframe depends on factors such as flight path, weather conditions, and operational efficiency. Although this is a relatively short international journey, it is always a good idea to allow extra time for check-in and security procedures, given the cross-border requirement between Toronto and Chicago O Hare Airport. Planning ahead and confirming flight details can help ensure a smooth travel experience.
Are there any direct flights from Toronto to Chicago O Hare Airport?
Yes, there are direct flights from Toronto to Chicago O Hare Airport available on several days of the week. Many airlines offer non-stop services that facilitate a quick transition between the two cities, allowing travelers to bypass layovers. It is advisable to research and book early to secure the most convenient times and potentially better fares. Direct flights typically offer a smoother travel experience from Toronto to Chicago, minimizing layover times and ensuring a more efficient journey overall.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
Transportation options from Chicago O Hare Airport to downtown Chicago are diverse and cater to various budgets. Travelers can opt for the CTA Blue Line train, which generally takes between 30 to 45 minutes and costs around $5 to $10. Alternatively, rideshare services like Uber or Lyft offer door-to-door convenience with fares ranging from $30 to $60 depending on the time of day and traffic conditions. Taxis and shuttle services are also available for those seeking direct transportation without the need to navigate public transit systems.
What are the must-see attractions in Chicago for travelers arriving from Toronto?
For travelers flying from Toronto, Chicago offers a rich blend of architectural marvels and cultural landmarks. Must-see attractions include Millennium Park, with its iconic Cloud Gate sculpture; Willis Tower’s Skydeck for panoramic views; and Navy Pier for entertainment and dining. Additionally, the Art Institute of Chicago presents world-class exhibits. Each destination provides a unique insight into the city’s vibrant history and culture, making them essential stops to maximize your visit while exploring the urban charm and scenic lakeside settings.
What are the best dining options in Chicago for visitors from Toronto?
Chicago is renowned for its culinary diversity, offering an array of dining experiences suitable for visitors from Toronto. Iconic spots include deep-dish pizza establishments like Lou Malnati’s and Giordano’s, as well as upscale eateries in the West Loop offering modern American cuisine with price ranges typically between $15 to $50 per dish. For a more eclectic experience, consider trying local gourmet food markets or neighborhood bistros. These venues not only deliver superb food quality but also give a taste of the city’s distinct gastronomic scene.
Are there any cultural festivals in Chicago that travelers from Toronto should not miss?
Yes, Chicago hosts several cultural festivals throughout the year that offer a taste of its rich heritage and arts scene, making them a must for travelers from Toronto. Key events include the Chicago Blues Festival, which celebrates musical traditions, and the Taste of Chicago, a food festival showcasing local cuisine. Other seasonal events like the Chicago Air and Water Show also offer family-friendly entertainment. Checking local event calendars for updated dates and ticket ranges, typically from free to moderate costs, will help you plan your visit around these unique experiences.
What are the best family-friendly activities in Chicago for travelers from Toronto?
Chicago offers numerous family-friendly activities that ensure an enjoyable experience for visitors from Toronto. Families can explore attractions such as the Shedd Aquarium, which provides interactive exhibits, and the Field Museum of Natural History, where children can learn about prehistoric life. Other fun options include exploring Lincoln Park Zoo, riding on the Navy Pier Ferris wheel, or enjoying the scenic Millennium Park events. These attractions generally have admission fees ranging from free to moderate prices, and they provide both educational and entertaining opportunities for all ages.
What are the most affordable accommodation options in Chicago for visitors from Toronto?
Visitors from Toronto can find several affordable accommodations in Chicago, ranging from budget hotels to well-rated hostels. Options in areas with good transit access, such as near the Loop or in neighborhoods like River North, typically offer rates between $100 to $200 per night. Consider booking in advance to secure discounted rates or exploring vacation rental platforms. These accommodations not only provide the essentials but also allow convenient access to transportation, dining, and major attractions, ensuring a comfortable stay while exploring Chicago on a budget.
What safety tips should travelers from Toronto keep in mind when visiting Chicago?
Travelers from Toronto heading to Chicago should prioritize personal safety by staying aware of their surroundings, especially in crowded urban areas. Always secure valuable items since pickpocketing can occur in busy spots like tourist attractions or transit hubs. Utilize reputable transportation options and plan your routes in advance. It is also advisable to review local news or advisories regarding areas to avoid, particularly at night. Additionally, keep emergency contacts handy and consider travel insurance. Following these actionable guidelines can help ensure a secure and enjoyable visit.
What unique souvenirs should travelers from Toronto look for in Chicago?
Travelers from Toronto visiting Chicago should consider picking up unique souvenirs that capture the spirit of the Windy City. Popular items include Chicago-themed memorabilia such as vintage postcards, local sports team apparel, or items featuring iconic landmarks like the Cloud Gate. Additionally, artisanal crafts, local artwork, and gourmet food items like Chicago-style popcorn or local sauces provide a taste of the city’s creative culture. Prices for souvenirs can vary from $10 to $50, making them a thoughtful reminder of the vibrant experiences and diverse neighborhoods visited during the trip.
Is there a specific time of year when Chicago is best visited by travelers from Toronto?
Travelers from Toronto might find that the best time to visit Chicago is during the spring (April to June) or early fall (September to October). During these seasons, the weather is typically mild, ideal for exploring outdoor attractions and enjoying festivals. These periods offer fewer crowds compared to the busy summer months and winter holiday season, allowing for a more relaxed travel experience. When planning your visit, consider potential cost variations in accommodations and flights, which often range lower outside peak travel periods.
What are the customs requirements for travelers flying from Toronto to Chicago O Hare Airport?
Travelers flying from Toronto to Chicago O Hare Airport must adhere to U.S. customs and immigration requirements. You will need a valid passport, and possibly an Electronic System for Travel Authorization (ESTA) if you are eligible under the Visa Waiver Program. Customs declarations must be accurately completed upon entry. It is advisable to review the latest guidelines prior to departure as policies can change. Ensuring that all documents are current and in order will help simplify the process when transitioning from Toronto to Chicago, so planning ahead is crucial.
Are there any special services available at Chicago O Hare Airport for travelers with special needs?
Yes, Chicago O Hare Airport offers a range of special services for travelers with special needs to ensure a comfortable journey from Toronto. These services include wheelchair assistance, accessible restrooms, and dedicated customer service counters. Additionally, the airport is equipped with facilities such as braille signage and hearing-impaired assistance. It is recommended to notify your airline in advance to arrange any specific accommodations and to receive detailed guidance on service locations. This preparation can help ensure that your transit through Chicago O Hare Airport is smooth and supportive.
What are the top outdoor activities in Chicago for visitors from Toronto?
Chicago offers plenty of engaging outdoor activities that appeal to visitors coming from Toronto. Enjoy a riverwalk tour along the Chicago River to admire the city’s renowned architecture, or bike along the scenic Lakefront Trail. Parks like Grant Park and Millennium Park provide a relaxed setting for picnics and cultural events. For a water perspective, consider taking a boat tour on Lake Michigan. These activities are available year-round, though duration and costs typically range from $10 to $40, depending on the service provided, ensuring an active experience while exploring urban nature.
What are the best tips for first-time travelers flying from Toronto to Chicago?
For first-time travelers flying from Toronto to Chicago, it is essential to plan ahead for a smooth experience. Research flight options and budget extra time for international security and customs procedures. Familiarize yourself with local transportation options, such as the CTA Blue Line or rideshares from Chicago O Hare Airport to major attractions. Also, check weather forecasts and local events to plan your itinerary wisely. It is advisable to secure all travel documents, including passports and any required visas, and consider travel insurance for added peace of mind. Preparation is key for an enjoyable trip.