Toronto, ON YTO to Chicago, IL CHI flight with United

Fri, Oct 30
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Porter Airlines
Jazz Aviation
Air Canada
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The cheapest and fastest flights from Toronto, ON to Chicago, IL

Showing times, prices and bookable tickets for Oct 30

Cheapest price on Oct 30

$361

Average ticket price on Oct 30

$455

Fastest journey on Oct 30

2 h

Average journey duration on Oct 30

2 h 2 m

Flights on Oct 30

56

Distance

702 km

Cheap tickets

The best way to find a cheap flight ticket from Toronto, ON to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from Toronto, ON to Chicago, IL will cost around $455 if you buy it on the day, but the cheapest tickets can be found for only $361.

Fast flights

On Fri, Oct 30, we found 56 flights from Toronto, ON to Chicago, IL, including 20 direct services.

On Fri, Oct 30 the direct flights cover the 702 km distance in an average of 2 h 2 m but if you time it right, some flights will get you there in just 2 h .

On Fri, Oct 30 the longest flights will take 2 h 3 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

  • envoy airAA3610
    0 transfers
  • envoy airAA3608
    0 transfers
  • skywest airlinesAA6488
    0 transfers
  • envoy airAA3524
    0 transfers
  • envoy airAA3606
    0 transfers

Journey information

Overview: Toronto, ON to Chicago, IL flight

CanadaCanada
USAUSA
Icon of flight

Flights from Toronto, ON to Chicago, IL depart on average 58 times per day, taking around 3h 35m. Cheap flight tickets for this journey start at $121 but you can travel from only $54 by bus.

There are 19 flights per day. The earliest flight runs at 00:30, the last at 23:20. The fastest flight covers the 436 miles (702 km) distance in 1h 40m. June is the cheapest month to fly.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $54

Plan this route

Journey facts

  • Distance436 miles (702 km)
  • Average flight duration3h 35m
  • Cheapest ticket price$121
  • Flights per day58
  • Direct flights19
  • Fastest flight1h 40m
  • First flight12:30 AM
  • Last flight11:20 PM
  • Cheapest MonthJun
  • Cheapest DaySun
  • High SeasonOct - Dec
  • Low SeasonJan - Mar
  • Busiest DaySun
  • Least Busy DaySat
  • Best time to book28 days

Understand & plan this route

Explore this journey

Book with confidence

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $54

Frequently asked questions about your Toronto, ON to Chicago, IL trip

Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Toronto, ON to Chicago, IL.

Cheap plane tickets from Toronto, ON to Chicago, IL can start from as little as $121 when you book in advance. The average flight ticket price for Toronto, ON to Chicago, IL is $396 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The earliest flight from Toronto, ON to Chicago, IL leaves at 12:30 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Toronto, ON to Chicago, IL leaves at 11:20 PM.
Yes, there are 19 direct flights a day from Toronto, ON to Chicago, IL with Porter Airlines, Jazz Aviation, Air Canada, United, Republic Airlines, skywest airlines. Schedules can vary on holidays or weekends with fewer direct flights.

Live departures

Toronto, ON to Chicago, IL flight times

The table below shows live departures for Toronto, ON to Chicago, IL flights for today, Thursday, October 29. You can also manually refresh the results below to see updated flight journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
WestJetWS6340 · WS70859:40 AM Toronto
4h30
1:10 PM O'Hare International Airport1 transfer
WestJetWS6340 · WS70599:40 AM Toronto
4h07
12:47 PM Midway International Airport1 transfer
UnitedUA3629 · UA233110:00 AM Toronto
5h38
2:38 PM O'Hare International Airport1 transfer
UnitedUA3424 · UA205310:30 AM Toronto
5h44
3:14 PM O'Hare International Airport1 transfer
UnitedUA45010:53 AM Toronto
2h04
11:57 AM O'Hare International Airport0 transfersDirect
psa airlinesAA5668+American AirlinesAA163711:09 AM Toronto
7h08
5:17 PM O'Hare International Airport1 transfer
psa airlinesAA5668+American AirlinesAA35911:09 AM Toronto
6h06
4:15 PM O'Hare International Airport1 transfer
psa airlinesAA5668+American AirlinesAA113511:09 AM Toronto
9h57
8:06 PM O'Hare International Airport1 transfer
psa airlinesAA5668+American AirlinesAA118911:09 AM Toronto
8h25
6:34 PM O'Hare International Airport1 transfer
skywest airlinesAA648811:40 AM Toronto
2h05
12:45 PM O'Hare International Airport0 transfersDirect
psa airlinesAA5020+American AirlinesAA242311:47 AM Toronto
5h18
4:05 PM O'Hare International Airport1 transfer
UnitedUA869412:00 PM Toronto
2h13
1:13 PM O'Hare International Airport0 transfersDirect
UnitedUA861612:05 PM Toronto Island
2h15
1:20 PM O'Hare International Airport0 transfersDirect
WestJetWS6343 · WS742112:10 PM Toronto
5h22
4:32 PM O'Hare International Airport1 transfer
psa airlinesAA5525+American AirlinesAA47012:40 PM Toronto
5h53
5:33 PM O'Hare International Airport1 transfer
WestJetWS8416 · WS819112:49 PM Toronto
4h51
4:40 PM O'Hare International Airport1 transfer
UnitedUA3649 · UA225912:55 PM Toronto
5h24
5:19 PM O'Hare International Airport1 transfer
envoy airAA36061:15 PM Toronto
2h05
2:20 PM O'Hare International Airport0 transfersDirect
UnitedUA8670 · UA24972:15 PM Toronto
5h39
6:54 PM O'Hare International Airport1 transfer
psa airlinesAA5324+American AirlinesAA11892:24 PM Toronto
5h10
6:34 PM O'Hare International Airport1 transfer
psa airlinesAA5324+American AirlinesAA11352:24 PM Toronto
6h42
8:06 PM O'Hare International Airport1 transfer
psa airlinesAA5324+American AirlinesAA4882:24 PM Toronto
8h36
10:00 PM O'Hare International Airport1 transfer
WestJetWS7387 · WS70562:26 PM Toronto
4h34
6:00 PM Midway International Airport1 transfer
UnitedUA83072:35 PM Toronto
2h03
3:38 PM O'Hare International Airport0 transfersDirect
Air CanadaAC5072:35 PM Toronto
2h03
3:38 PM O'Hare International Airport0 transfersDirect
UnitedUA8450 · UA36592:40 PM Toronto
4h49
6:29 PM O'Hare International Airport1 transfer
UnitedUA3637 · UA24972:45 PM Toronto
5h09
6:54 PM O'Hare International Airport1 transfer
envoy airAA36083:14 PM Toronto
2h00
4:14 PM O'Hare International Airport0 transfersDirect
UnitedUA35003:35 PM Toronto
2h09
4:44 PM O'Hare International Airport0 transfersDirect
American AirlinesAA1876 · AA24883:47 PM Toronto
5h04
7:51 PM O'Hare International Airport1 transfer
UnitedUA82874:30 PM Toronto
2h13
5:43 PM O'Hare International Airport0 transfersDirect
UnitedUA8548 · UA52514:40 PM Toronto
6h04
9:44 PM O'Hare International Airport1 transfer
psa airlinesAA5667+Republic AirlinesAA45165:29 PM Toronto
7h07
11:36 PM O'Hare International Airport1 transfer
psa airlinesAA5667+American AirlinesAA4885:29 PM Toronto
5h31
10:00 PM O'Hare International Airport1 transfer
psa airlinesAA5030+American AirlinesAA8155:51 PM Toronto
6h09
11:00 PM O'Hare International Airport1 transfer
UnitedUA22435:55 PM Toronto
2h10
7:05 PM O'Hare International Airport0 transfersDirect
piedmont airlinesAA5886+American AirlinesAA4906:00 PM Toronto
5h30
10:30 PM O'Hare International Airport1 transfer
envoy airAA36106:25 PM Toronto
2h05
7:30 PM O'Hare International Airport0 transfersDirect
Air CanadaAC5116:55 PM Toronto
2h03
7:58 PM O'Hare International Airport0 transfersDirect
UnitedUA82936:55 PM Toronto
2h03
7:58 PM O'Hare International Airport0 transfersDirect
psa airlinesAA5045+American AirlinesAA6277:24 PM Toronto
5h44
12:08 AM O'Hare International Airport1 transfer
UnitedUA57047:26 PM Toronto
2h22
8:48 PM O'Hare International Airport0 transfersDirect
Friday, October 30
American AirlinesAA1746 · AA25346:00 AM Toronto
6h05
11:05 AM O'Hare International Airport1 transfer
WestJetWS6342 · WS70896:00 AM Toronto
5h29
10:29 AM O'Hare International Airport1 transfer
WestJetWS6342 · WS70536:00 AM Toronto
4h32
9:32 AM Midway International Airport1 transfer
American AirlinesAA1047+piedmont airlinesAA58876:15 AM Toronto
5h50
11:05 AM O'Hare International Airport1 transfer
American AirlinesAA865+piedmont airlinesAA58876:15 AM Toronto
7h03
12:18 PM O'Hare International Airport1 transfer
Air CanadaAC480+Jazz AviationAC84776:20 AM Toronto
5h47
11:07 AM O'Hare International Airport1 transfer
WestJetWS5409 · WS82046:30 AM Toronto
6h10
11:40 AM O'Hare International Airport1 transfer
UnitedUA15406:45 AM Toronto
2h09
7:54 AM O'Hare International Airport0 transfersDirect
Air CanadaAC400+Jazz AviationAC84777:00 AM Toronto
5h07
11:07 AM O'Hare International Airport1 transfer
Republic AirlinesAA4542+American AirlinesAA18147:15 AM Toronto
5h38
11:53 AM O'Hare International Airport1 transfer
Republic AirlinesAA4542+American AirlinesAA15347:15 AM Toronto
9h54
4:09 PM O'Hare International Airport1 transfer
envoy airAA35247:29 AM Toronto
2h10
8:39 AM O'Hare International Airport0 transfersDirect
psa airlinesAA5192+American AirlinesAA8658:00 AM Toronto
5h18
12:18 PM O'Hare International Airport1 transfer
UnitedUA85338:20 AM Toronto
2h03
9:23 AM O'Hare International Airport0 transfersDirect
Air CanadaAC5018:20 AM Toronto
2h03
9:23 AM O'Hare International Airport0 transfersDirect
UnitedUA7638:35 AM Toronto
2h09
9:44 AM O'Hare International Airport0 transfersDirect

This is the last flight of the day.

Find all the dates and times for this journey

Why should you book Toronto, ON to Chicago, IL flights with Omio?

Porter Airlines as well as Jazz Aviation, Air Canada, United, Republic Airlines and more offer flights services from Toronto, ON to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Toronto, ON to Chicago, IL.

Why book with Omio vs Porter Airlines?

  • Compare with other providers: On Omio, you can not only buy tickets for Porter Airlines, but also compare tickets for the likes of Jazz Aviation, Air Canada, United or Republic Airlines to find the best option for your trip from Toronto, ON to Chicago, IL.
  • Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
  • Compare all your options: Omio allows you to compare Porter Airlines with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Toronto, ON to Chicago, IL.

Why book with Omio over Skyscanner, Edreams or Kayak?

  • Compare with other providers: On Omio, you can also compare tickets for the likes of Jazz Aviation, Air Canada, United or Republic Airlines to find the best option for your trip from Toronto, ON to Chicago, IL.
  • Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Toronto, ON to Chicago, IL.

Airlines

Airlines from Toronto, ON to Chicago, IL

Flights from Toronto, ON to Chicago, IL with United, American Airlines, and WestJet. Flights with a stop available on this route with United, American Airlines, and WestJet. Use the details below to compare onboard facilities.

United

About
United Airlines, established in 1926, is a major U.S. airline headquartered in Chicago, Illinois. Operating an extensive domestic and international network, United serves more destinations than any other airline, connecting travelers across six continents. The airline's eight hubs include Chicago–O'Hare, Denver, Houston–Intercontinental, Los Angeles, Newark, San Francisco, Washington–Dulles, and Guam. As a founding member of the Star Alliance, United offers a comprehensive range of services, including regional flights through United Express, catering to both leisure and business travelers. The airline is committed to sustainability, investing in sustainable aviation fuel and innovative technologies to reduce its environmental impact.
Luggage & cancellation policy
Average United Duration
1h 40m
Cheapest United Price
$121
United frequency
23 a day
Luggage included
Carry-on baggage allowance is 7kg total (2 pieces max. ) for both Choice and Flex fares on United Airlines and Virgin Australia flights.
Additional luggage
Excess baggage fees apply for additional checked luggage beyond the standard allowance.
Luggage storage
Both airlines provide checked baggage services for storing luggage during flights.
Cancellation Policy
Cancellation fees apply per person, per booking, with specific fees for different fare types.
Refund
Not applicable to flights; however, full refunds are available if flights are canceled by the airline.
Pregnant on board
Pregnant passengers are permitted to travel, with specific guidelines and medical certificates required after a certain gestational period.
Unaccompagned minor
Unaccompanied minors are permitted to travel, with specific age restrictions and services provided.
Amenities on board the airplane
Wifi
Food sold onboard
Meals and snacks are included on international flights operated by United Airlines and Virgin Australia.
Seat reservation
Seat selection may incur additional fees, depending on the fare type and airline.
Toilets
USB plugs
Accessibility
United Airlines and Virgin Australia offer services to and within Australia, providing accessible travel options for passengers with mobility needs.
Bikes
Both airlines permit bicycles onboard, with specific guidelines and fees.
Pets
United Airlines and Virgin Australia allow pets onboard, subject to specific policies and fees.
Learn more about United

Jazz Aviation

About
Jazz Aviation LP, commonly known as Jazz, is a Canadian regional airline and a wholly owned subsidiary of Chorus Aviation. It primarily operates as Air Canada Express, providing regional and charter services across Canada and the United States. Jazz is Canada's largest regional carrier and plays a crucial role in Air Canada's network, carrying a significant portion of its daily passengers and offering nearly half of its transborder departures. With its main base in Halifax, Jazz serves 79 destinations and operates a fleet of Bombardier aircraft. Beyond passenger flights, Jazz also offers charter services and provides maintenance, repair, and overhaul (MRO) services through Jazz Technical Services.
Luggage & cancellation policy
Average Jazz Aviation Duration
1h 55m
Cheapest Jazz Aviation Price
$121
Jazz Aviation frequency
7 a day
Luggage included
One carry-on bag and one personal item are allowed onboard, with no weight restrictions for carry-on but it must be light enough to store in overhead lockers and not exceed 55cm x 23cm x 40cm (21.5 x 9 x 15.5).
Additional luggage
Additional bags can be added for an extra fee, with a weight limit of 23kg/50lb and a maximum size of 158 cm/62 in (length + width + height).
Refund
If Air Canada Jazz is responsible for the delay, EU regulations state that passengers are owed up to €600 per person when delayed by 3 hours or more.
Pregnant on board
Being pregnant on board is allowed, and Air Canada provides useful tips for a seamless travel experience for pregnant travelers.
Unaccompagned minor
The Unaccompanied Minor service is mandatory for children aged 8 to 11 who are travelling alone on non-stop Air Canada Express flights operated by Jazz.
Amenities on board the airplane
Wifi
Food sold onboard
A meal or hot snack is included with flights offering Air Canada Bistro service for unaccompanied minors, and complimentary non-alcoholic beverages are included.
Seat reservation
A fee may apply if you decide to change the free standard seat assignment provided, or if you select Preferred Seats.
Toilets
USB plugs
Accessibility
Jazz Aviation refers all feedback on accessibility matters for Air Canada Express passengers to Air Canada.

American Airlines

About
American Airlines is one of the largest airlines in the world, connecting travelers to hundreds of destinations across the United States, Latin America, Europe, Asia, and beyond. Operating from major hubs such as Dallas/Fort Worth, Miami, and Charlotte, American offers a wide range of travel options. Passengers can choose from Economy with affordable fares, Premium Economy with extra space, or Business and First Class featuring flat-bed seats, premium dining, and lounge access. With a modern fleet and membership in the oneworld alliance, American Airlines combines global reach with comfort and reliability.
Luggage & cancellation policy
Average American Airlines Duration
4h 0m
Cheapest American Airlines Price
$145
American Airlines frequency
17 a day
Luggage included
1 carry-on bag (22 x 14 x 9 inches) and 1 personal item (18 x 14 x 8 inches) included in most fares
Additional luggage
Checked bags fees vary by route. First checked bag typically $30, second $40 on domestic flights
Cancellation Policy
Basic Economy tickets cannot be changed or refunded. Other fares allow changes with fee, refunds subject to fare rules.
Pregnant on board
Passengers can fly up to 36 weeks for single pregnancies, 32 weeks for multiple pregnancies. Medical certificate required within 7 days of departure if within 4 weeks of due date.
Unaccompagned minor
Children ages 5-14 can travel alone using American Airlines Unaccompanied Minor Service. Service fee is $150 each way.
Amenities on board the airplane
Wifi
Food sold onboard
USB plugs
Accessibility
American Airlines provides wheelchair assistance and special services for passengers with disabilities. Assistance must be requested at least 48 hours before departure.
Pets
Small dogs and cats allowed in cabin for $125 fee. Must be in approved carrier under seat. Service animals allowed.
Learn more about American Airlines

skywest airlines

About
SkyWest Airlines is a major North American regional airline headquartered in St. George, Utah. It operates flights for larger carriers such as Alaska Airlines (as Alaska SkyWest), American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express). SkyWest is the largest regional airline in North America by fleet size, passengers carried, and destinations served. The airline connects passengers to over 250 destinations across the United States, Canada, and Mexico, primarily linking smaller airports to major airline hubs. SkyWest's fleet consists of regional jets, including the Bombardier CRJ series and Embraer 175 aircraft.
Luggage & cancellation policy
Average skywest airlines Duration
1h 55m
Cheapest skywest airlines Price
$147
skywest airlines frequency
1 a day
Luggage included
One carry-on bag and one personal item are allowed for free.
Additional luggage
Additional luggage can be purchased, and fees apply for excess, oversized, or overweight baggage.
Cancellation Policy
If canceled within 24 hours of purchase, a full refund is possible, provided the departure is at least 7 days away; after 24 hours, fees range from $100 to $500.
Refund
If SkyWest Airlines cancels a flight, passengers are eligible for a full refund.
Pregnant on board
Being pregnant on board is allowed, but specific policies may depend on the partner airline.
Unaccompagned minor
Children aged 5-14 can travel alone using the unaccompanied minor service, which includes airport escort and supervision.
Amenities on board the airplane
Seat reservation
Toilets
Accessibility
SkyWest Airlines complies with all provisions of the Air Carrier Access Act and accommodates customers with special needs.
Bikes
Bicycles can be checked in but may incur additional fees and must be properly packed.
Pets
Small pets like cats and dogs are allowed in the cabin for a fee, with restrictions on pet and carrier size.

Air Canada

About
Air Canada is Canada's largest airline and flag carrier, headquartered in Saint-Laurent, Quebec. Founded in 1937 as Trans-Canada Air Lines, it was renamed Air Canada in 1964 and fully privatized in 1989. As a founding member of Star Alliance, Air Canada provides scheduled passenger and cargo services to over 220 destinations across six continents. The airline operates a diverse fleet, including Airbus A320 family aircraft, Boeing 737 MAX, Boeing 777, and Boeing 787 Dreamliner for both short and long-haul routes. Air Canada also offers leisure travel packages through its subsidiary, Air Canada Vacations.
Luggage & cancellation policy
Average Air Canada Duration
1h 54m
Cheapest Air Canada Price
$121
Air Canada frequency
4 a day
Luggage included
Economy Basic includes personal item (under seat), Economy Standard/Flex/Latitude/Premium Economy/Business include carry-on bag + personal item
Additional luggage
Checked baggage fees vary by route and fare type, starting at $30-$70 for first bag
Cancellation Policy
Refundable fares allow full refund, non-refundable fares may receive future travel credit minus cancellation fee.
Pregnant on board
Pregnant passengers can travel up to 36 weeks without medical certificate. After 36 weeks, medical clearance required
Unaccompagned minor
Unaccompanied Minor Service available for children aged 8-11 (mandatory) and 12-17 (optional). Service fee applies.
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Air Canada provides wheelchair assistance and special services for passengers with disabilities, including mobility aids and service animals.
Pets
Pets allowed in cabin and cargo hold, restrictions apply based on aircraft type and route
Learn more about Air Canada

psa airlines

About
PSA Airlines is an American regional airline and a wholly-owned subsidiary of the American Airlines Group, operating exclusively on behalf of American Airlines under the American Eagle brand. Headquartered in Charlotte, North Carolina, PSA Airlines operates over 800 daily flights to nearly 100 destinations across the United States. The airline maintains an all-jet fleet consisting of Bombardier CRJ700 and CRJ900 regional aircraft. With a team of over 5,000 employees, PSA Airlines plays a significant role in connecting smaller cities to major hubs within American Airlines' network.
Luggage & cancellation policy
Average psa airlines Duration
4h 27m
Cheapest psa airlines Price
$145
psa airlines frequency
2 a day
Luggage included
One carry-on bag and one personal item are allowed.
Additional luggage
Additional luggage can be checked for a fee, with weight limits up to 32kg (70lbs) for a single piece.
Cancellation Policy
PSA Airlines' cancellation policy depends on the timeframe of cancellation and ticket flexibility, with some flexible ticket options offering easier cancellations.
Refund
Passengers are entitled to a refund if the airline cancels a flight and they choose not to travel.
Amenities on board the airplane
Food sold onboard
Non-alcoholic beverages are complimentary in Economy Class, while alcoholic drinks and snack boxes can be purchased.
Seat reservation
Seat selection for standard seating is typically included, but preferred or Main Cabin Extra seats may require an additional fee.
Accessibility
Wheelchair assistance is available and should be requested at least 24 hours prior to flight departure.
Bikes
Bicycles can be carried as checked baggage if handlebars are turned sideways, pedals are removed, tires are deflated, and the bike is packed in a case or durable cardboard box.

Porter Airlines

About
Porter Airlines is a Canadian airline headquartered at Billy Bishop Toronto City Airport, known for its focus on convenience and customer service. Established in 2006, it has grown to be the third-largest airline in Canada. Porter operates scheduled flights across North America, utilizing a fleet of De Havilland Canada DHC-8-400 turboprops and Embraer 195-E2 jet aircraft. A key feature of Porter Airlines is its "Flying Refined" brand, emphasizing a premium travel experience with amenities like complimentary beer, wine, and snacks, as well as free Wi-Fi on its E195-E2 jets. They also offer a unique two-by-two seating configuration, ensuring no middle seats on their flights. Porter's main hubs include Toronto–Billy Bishop, Toronto–Pearson, and Ottawa Macdonald-Cartier airports.
Luggage & cancellation policy
Average Porter Airlines Duration
1h 50m
Cheapest Porter Airlines Price
$130
Porter Airlines frequency
2 a day
Luggage included
Basic fare includes personal item (17 x 33 x 43 cm) and standard carry-on bag (23 x 40 x 55 cm)
Additional luggage
Checked baggage can be purchased, max 23kg per piece
Cancellation Policy
Basic fares non-refundable, flexible fares allow changes/cancellations with fee, Freedom fares fully refundable.
Pregnant on board
Pregnant passengers can travel up to 36 weeks without medical certificate. After 36 weeks, medical clearance required.
Unaccompagned minor
Children aged 8-11 can travel as unaccompanied minors. Service fee applies. Must be booked through contact center.
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Porter Airlines provides wheelchair assistance and special services for passengers with disabilities. Service must be arranged 48 hours before departure.

Sun Country Airlines

Luggage & cancellation policy
Average Sun Country Airlines Duration
3h 49m
Cheapest Sun Country Airlines Price
$261
Sun Country Airlines frequency
1 a day
Luggage included
One personal item (17 x 13 x 9 inches) included
Additional luggage
Checked bags available for purchase, fees vary by route
Cancellation Policy
Refunds available within 24 hours of booking, after that fees apply based on fare type
Pregnant on board
Pregnant passengers can travel up to 36 weeks (32 weeks for multiple pregnancies). Medical certificate required after 28 weeks
Unaccompagned minor
Unaccompanied minor service available for children 5-14 years old, fee applies, must be booked in advance
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Wheelchair assistance available with 48-hour advance notice

Republic Airlines

About
Republic Airways is a major regional airline in the United States, operating as a subsidiary of Republic Airways Holdings. It provides scheduled passenger service for American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express) using a fleet of Embraer 170 and 175 regional jets. Headquartered in Indianapolis, Indiana, Republic Airways operates over 900 daily flights to more than 80 cities across the U.S. and Canada. The company is known for its large fleet of Embraer E-Jets and its state-of-the-art training facilities. In April 2025, Republic Airways Holdings announced its acquisition of Mesa Air Group, which is expected to create the second-largest regional carrier in the U.S.
Luggage & cancellation policy
Average Republic Airlines Duration
1h 55m
Cheapest Republic Airlines Price
$147
Republic Airlines frequency
7 a day
Luggage included
One carry-on bag (24 x 16 x 10) and one personal item
Additional luggage
Checked bags for a fee
Cancellation Policy
Tickets are non-refundable but may be cancelled for future flight credit minus applicable fees
Pregnant on board
Passengers can fly up to the end of their 36th week for single pregnancies and the end of their 32nd week for multiple pregnancies
Unaccompagned minor
Unaccompanied minor service is available for children ages 5-14. Must be booked directly with Republic Airlines
Amenities on board the airplane
USB plugs
Accessibility
Republic Airlines offers assistance for passengers with reduced mobility, including wheelchair services and priority boarding. Passengers are advised to request these services in advance to ensure availability and proper arrangements.

WestJet

Luggage & cancellation policy
Average WestJet Duration
2h 33m
Cheapest WestJet Price
$178
WestJet frequency
6 a day

Companies, tickets, and onboard amenities between Toronto, ON and Chicago, IL

Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.

When taking a flight from Toronto, ON to Chicago, IL, you can count on Porter Airlines, Jazz Aviation, Air Canada, United, Republic Airlines, American Airlines, WestJet, skywest airlines, psa airlines, Sun Country Airlines for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service between Toronto, ON and Chicago, IL and compare the amenities they offer before buying a plane ticket.
For international flights we recommend to arrive 2.5 to 3 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.

Complete guide to Chicago, IL

Things to do in Chicago, IL

Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.

  • Must visit

Art Institute of Chicago

World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.

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  • Must visit

Field Museum

Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.

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  • Must visit

Museum of Science and Industry

Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.

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US dollar ($)

Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.

Average meal costs

Budget
$10-18 for fast food or casual takeout.
Mid-range
$20-40 per person for a restaurant meal.
Fine dining
$75+ per person for upscale restaurants.
Coffee
$3-6 for coffee or cappuccino.

Tipping culture

Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.

Plan your visit to Chicago, IL

Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Chicago, IL.

The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.

FAQs: Toronto, ON to Chicago, IL Flight

Find answers to the most common questions about traveling from Toronto, ON to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

FAQs
It's helpful to compare your options as there are 3 ways to travel between Toronto, ON and Chicago, IL including taking a train, bus, and flight.

popular airports

Popular airports from Toronto, ON to Chicago, IL

Most Toronto, ON to Chicago, IL flights use the Toronto to O'Hare International Airport airport pair, with some services landing at Midway International Airport. Use this guide to compare Toronto, ON and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.

Departure airports in Toronto
Arrival airports in Chicago

Which Toronto, ON airport do flights to Chicago, IL leave from?

Flights from Toronto, ON to Chicago, IL depart from Toronto. The airport is 3 miles (5 km) from Toronto, ON city centre at 6301 Silver Dart Dr, Mississauga, ON L5P 1B2, Cada.
Toronto (YYZ)6301 Silver Dart Dr, Mississauga, ON L5P 1B2, CadaWifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rental
City-centre transport

Getting to Toronto from Toronto city centre

Toronto is 4 km from Toronto city centre. Public transport options include:

UP Express train, Union Station, 25 km

Toronto airport facilities and services

Toronto has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.

Food and drink

Food options include: Various restaurants are available, including fast food and sit-down options like Tim Hortons and Mill Street Brewery, located in both terminals.

Wi-Fi and ATMs

Free Wi-Fi available throughout the airport. ATMs are located throughout the airport, offering various currencies.

Luggage and lost property

Lost and found is available at the station.

Parking, taxis and toilets

Available at Toronto: Parking, Taxis, WC.

Bike and car services

Available at Toronto: Car Rental.

Accessibility

Accessibility facilities are available at Toronto: Elevators, ramps, assistance.

Shops, hotels and contact

Nearby hotels include Hotels such as the Sheraton Gateway Hotel are directly connected to terminal 3..

More about Toronto
Toronto Island (YTZ)2 Eireann Quay, Toronto, ON M5V 1A1, CadaWifiShoppingParkingDiningATMTaxisAccessibilityWCLoungeLost and Found OfficeCar Rental
City-centre transport

Getting to Toronto Island from Toronto city centre

Toronto Island is 7 km from Toronto city centre. Public transport options include:

Billy Bishop Airport Shuttle, Union Station, 3 km

Toronto Island airport facilities and services

Toronto Island has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Lounge, Lost and Found Office, and Car Rental.

Food and drink

Food options include: There are a few dining options, including a café and a bar, located in the terminal.

Wi-Fi and ATMs

Free Wi-Fi available throughout the airport. ATMs are located in the terminal, near the entrance and baggage claim area.

Luggage and lost property

Lost and found is available at the station.

Parking, taxis and toilets

Available at Toronto Island: Parking, Taxis, WC.

Bike and car services

Available at Toronto Island: Car Rental.

Accessibility

Accessibility facilities are available at Toronto Island.

More about Toronto Island

Airports for flights from Toronto, ON to Chicago, IL

See which airports are used for flights between Toronto, ON and Chicago, IL, including airport details.

Flights from Toronto, ON to Chicago, IL generally leave from Toronto and arrive in O'Hare International Airport.Toronto is 3 miles (5 km) away from Toronto, ON city centre and O'Hare International Airport is 2 miles (4 km) from Chicago, IL city centre.

Most popular flights to and from Chicago, IL and Toronto, ON

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Flights New York, NY - Chicago, IL
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