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Low Price Flights from Toronto to Chicago

Find Cheapest Airlines Flying from Toronto to Chicago

Choose from 2 carriers that fly from Toronto to Chicago, including Air Canada, United Airlines, Enjoy the cheapest tickets on this route with Porter Airlines.
Air Canada logo Air Canada
United Airlines logo United Airlines
Airlines are determined based on actual purchased flight tickets from Toronto to Chicago according to previous 12 months data from Trip.com.

Explore the cheapest flights from Toronto to Chicago in the next three months. Based on Trip.com's data from the latest 7 days, one-way direct flights start at AU$ 141, and round-trip direct tickets start at AU$ 229.

      • Cheapest nonstop
        YTZ 09:25
        1h 50m
        Direct
        MDW 10:15
        Toronto - Chicago | Fri, May 1 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Fri, May 8 | Porter Airlines
        AU$ 229 AU$ 267
        14% off
        14% off
        AU$ 267 AU$ 229
      • YTZ 09:25
        1h 50m
        Direct
        MDW 10:15
        Toronto - Chicago | Wed, Apr 29 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Wed, May 6 | Porter Airlines
        AU$ 229 AU$ 267
        14% off
        14% off
        AU$ 267 AU$ 229
      • YTZ 09:25
        1h 50m
        Direct
        MDW 10:15
        Toronto - Chicago | Thu, Apr 23 | Porter Airlines
        MDW 11:00
        1h 42m
        Direct
        YTZ 13:42
        Chicago - Toronto | Thu, Apr 30 | Porter Airlines
        AU$ 229 AU$ 267
        14% off
        14% off
        AU$ 267 AU$ 229
      • YTZ 09:25
        1h 50m
        Direct
        MDW 10:15
        Toronto - Chicago | Wed, Apr 22 | Porter Airlines
        MDW 12:55
        1h 42m
        Direct
        YTZ 15:37
        Chicago - Toronto | Sun, Apr 26 | Porter Airlines
        AU$ 231
        13% off
        AU$ 267 AU$ 231
      • YTZ 09:25
        1h 50m
        Direct
        MDW 10:15
        Toronto - Chicago | Thu, Apr 30 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Thu, May 7 | Porter Airlines
        AU$ 231
        13% off
        AU$ 267 AU$ 231
      • YTZ 14:30
        1h 50m
        Direct
        MDW 15:20
        Toronto - Chicago | Mon, Apr 20 | Porter Airlines
        MDW 16:05
        1h 42m
        Direct
        YTZ 18:47
        Chicago - Toronto | Sat, Apr 25 | Porter Airlines
        AU$ 231
        13% off
        AU$ 267 AU$ 231
      • YTZ 08:50
        1h 50m
        Direct
        MDW 09:40
        Toronto - Chicago | Sun, May 3 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Fri, May 8 | Porter Airlines
        AU$ 233
        13% off
        AU$ 267 AU$ 233
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Sat, May 23 | Porter Airlines
        MDW 15:20
        1h 40m
        Direct
        YTZ 18:00
        Chicago - Toronto | Wed, May 27 | Porter Airlines
        AU$ 243
        9% off
        AU$ 267 AU$ 243
      • YTZ 14:30
        1h 50m
        Direct
        MDW 15:20
        Toronto - Chicago | Mon, Apr 27 | Porter Airlines
        MDW 11:00
        1h 42m
        Direct
        YTZ 13:42
        Chicago - Toronto | Fri, May 1 | Porter Airlines
        AU$ 246
        8% off
        AU$ 267 AU$ 246
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Thu, May 28 | Porter Airlines
        MDW 10:30
        1h 40m
        Direct
        YTZ 13:10
        Chicago - Toronto | Sun, May 31 | Porter Airlines
        AU$ 248
        7% off
        AU$ 267 AU$ 248
      • YTO 13:00
        17h 25m
        1 stop
        CHI Invalid Date
        Toronto - Chicago | Tue, Apr 21 | Normal Airline
        CHI 15:00
        6h
        Direct
        YTO 16:00
        Chicago - Toronto | Thu, Apr 23 | Normal Airline
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      • Cheapest nonstop
        YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Mon, May 11 | Porter Airlines
        AU$ 141 AU$ 171
        18% off
        18% off
        AU$ 171 AU$ 141
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Mon, May 4 | Porter Airlines
        AU$ 144 AU$ 171
        16% off
        16% off
        AU$ 171 AU$ 144
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Sun, May 3 | Porter Airlines
        AU$ 144 AU$ 171
        16% off
        16% off
        AU$ 171 AU$ 144
      • YTZ 09:25
        1h 50m
        Direct
        MDW 10:15
        Toronto - Chicago | Thu, Apr 30 | Porter Airlines
        AU$ 147
        14% off
        AU$ 171 AU$ 147
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Thu, May 7 | Porter Airlines
        AU$ 151
        12% off
        AU$ 171 AU$ 151
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Sun, May 10 | Porter Airlines
        AU$ 153
        11% off
        AU$ 171 AU$ 153
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Wed, Jun 3 | Porter Airlines
        AU$ 155
        9% off
        AU$ 171 AU$ 155
      • YTZ 08:55
        1h 50m
        Direct
        MDW 09:45
        Toronto - Chicago | Sat, May 30 | Porter Airlines
        AU$ 155
        9% off
        AU$ 171 AU$ 155
      • YTZ 13:45
        1h 50m
        Direct
        MDW 14:35
        Toronto - Chicago | Fri, May 29 | Porter Airlines
        AU$ 157
        8% off
        AU$ 171 AU$ 157
      • YTZ 19:20
        1h 56m
        Direct
        ORD 20:16
        Toronto - Chicago | Fri, Jun 12 | Air Canada
        AU$ 159
        7% off
        AU$ 171 AU$ 159
      • YTO 13:00
        17h 25m
        1 stop
        CHI Invalid Date
        Toronto - Chicago | Tue, Apr 21 | Normal Airline
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Displayed flight fares from Toronto to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Toronto to Chicago Flight Details

The distance between Toronto and Chicago is approximately 701.97km. It takes around 2 hours 2 minutes on average to fly from Toronto to Chicago. Based on Trip.com's data travel demand peaks in July. The off-season for travel is September.

Cheapest one-way flight priceAU$ 141
Cheapest return ticket priceAU$ 229
Off-season for travelSeptember
Peak season for travelJuly
Flight distance701.97km
Average flight time2 hours 2 minutes
Popular airlineAir Canada
Flight statistics for the Toronto–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Trip.com Price Insights on Flights from Toronto to Chicago

What is the cheapest month for one-way flights from Toronto to Chicago?

Average price of one-way flights from Toronto to Chicago purchased by Trip.com users by month over the past 12 months.

According to Trip.com's data, the cheapest month for flights from Toronto to Chicago is June, with an average price of AU$ 232. Conversely, the most expensive month is typically October, with an average price of up to AU$ 330.

AU$ 330
AU$ 281
AU$ 232
AU$ 183
    Cheapest
  • AU$ 256
    Apr
  • AU$ 234
    May
  • AU$ 232
    Jun
  • AU$ 242
    Jul
  • AU$ 289
    Aug
  • AU$ 257
    Sep
  • AU$ 330
    Oct
  • AU$ 307
    Nov
  • AU$ 292
    Dec
  • AU$ 252
    Jan
  • AU$ 260
    Feb
  • AU$ 292
    Mar

What is the cheapest month for round-trip flights from Toronto to Chicago?

Average price of round-trip flights from Toronto to Chicago purchased by Trip.com users by month over the past 12 months.

According to historical data from Trip.com, the lowest prices for flights from Toronto to Chicago are found during September, with an average price of AU$ 319. Conversely, the highest prices are found during October, with an average price of up to AU$ 448.

AU$ 448
AU$ 384
AU$ 319
AU$ 255
    Cheapest
  • AU$ 354
    Apr
  • AU$ 354
    May
  • AU$ 341
    Jun
  • AU$ 343
    Jul
  • AU$ 367
    Aug
  • AU$ 319
    Sep
  • AU$ 448
    Oct
  • AU$ 411
    Nov
  • AU$ 409
    Dec
  • AU$ 370
    Jan
  • AU$ 353
    Feb
  • AU$ 375
    Mar

What's the cheapest day to fly from Toronto to Chicago?

Data is based on the average flight price for each day of the week from Toronto to Chicago on Trip.com over the past 12 months.

Based on Trip.com data from the past 12 months, the cheapest day to fly from Toronto to Chicago is Saturday, with average prices lower than on other days. Avoid Friday, as prices are usually highest then.

AU$ 294
AU$ 271
AU$ 247
AU$ 224
    Cheapest
  • AU$ 264
    Mon
  • AU$ 263
    Tue
  • AU$ 265
    Wed
  • AU$ 275
    Thu
  • AU$ 294
    Fri
  • AU$ 247
    Sat
  • AU$ 290
    Sun

When is the cheapest day to fly from Toronto to Chicago during ANZAC Day Holiday?

Data is based on the lowest one-way fares from Toronto to Chicago during ANZAC Day Holiday, sourced from the Trip.com database over the last 3 days.

ANZAC Day Holiday runs from Apr 25 to Apr 27. The cheapest flights from Toronto to Chicago are available on Apr 27, with fares starting at AU$ 215.

AU$ 506
AU$ 361
AU$ 215
AU$ 70
    Cheapest
  • AU$ 506
    22
    Apr
  • AU$ 445
    23
  • AU$ 357
    24
  • AU$ 358
    25
  • AU$ 322
    26
  • AU$ 215
    27
  • AU$ 321
    28

Flight FAQs

  • Which airlines offer the cheapest flights from Toronto (YTO) to Chicago (CHI)?

    Based on Trip.com data, Porter Airlines offers one-way fares as low as AU$ 141 on Cheapest nonstop routes (e.g. YTZ to MDW on Mon, May 11), while Porter Airlines offers Cheapest nonstop round-trips from AU$ 229 departing on Fri, May 1 and returning on Fri, May 8.
  • At the moment, you can catch a direct flight from Toronto to Chicago with the following airlines, including: Air Canada United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 2 hours 2 minutes to fly from Toronto (YTO) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Toronto to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 189 flight per week flying from Toronto to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA2066 (09:13)
  • To find best deals on flights from Toronto to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Mon, May 11, with one-way flights priced at just AU$ 141.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Porter Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Toronto to Chicago is September, when demand for travel is lower.
  • After crunching the numbers on our April flight calendar, it's currently cheapest to fly from Toronto to Chicago on April 22, 2026 with Porter Airlines, with prices starting at AU$ 136.
  • You can land at any one of the following hubs in Chicago, with Toronto Pearson International Airport to Chicago O'Hare International Airport (YYZ-ORD) is by far the most common option on this route: Chicago Midway International Airport (MDW) Chicago O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Toronto is 1h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Trip.com Airline Insights on Flights from Toronto toChicago

Which airlines offer the cheapest nonstop flights from Toronto to Chicago?

Data is based on the average price of all nonstop flights from Toronto to Chicago on Trip.com in the past 12 months.

Based on Trip.com data from the past 12 months, Porter Airlines offers the cheapest nonstop flights from Toronto to Chicago, with an average price of AU$ 303.

AU$ 283
AU$ 303
AU$ 324
AU$ 344
AU$ 364
Porter Airlines
AU$ 303
Porter Airlines
WestJet
AU$ 307
WestJet
United Airlines
AU$ 312
United Airlines
Air Canada
AU$ 320
Air Canada
Air Transat
AU$ 334
Air Transat
American Airlines
AU$ 364
American Airlines

Which airlines operate the most flights from Toronto to Chicago?

Data is based on the number of flights from Toronto to Chicago operated by each airline on Trip.com in the past month.

Based on Trip.com data from the past month, Air Canada operates the most flights from Toronto to Chicago, with 83 flight per week.

13
36
60
83
Air Canada
83
Air Canada
United Airlines
81
United Airlines
Air New Zealand
46
Air New Zealand
Porter Airlines
44
Porter Airlines
American Airlines
36
American Airlines
Alaska Airlines
36
Alaska Airlines

How many flights are there each day from Toronto to Chicago?

The data is based on the flight numbers for each day of the week from Toronto to Chicago within the Trip.com database over the past month.

Based on Trip.com data from the past month, the most flights from Toronto to Chicago depart on Friday, and the fewest flights depart on Tuesday.

327
283
238
194
Highest
277
Mon
238
Tue
273
Wed
239
Thu
327
Fri
286
Sat
292
Sun

More Cheap Flights & Deals on Trip.com

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

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Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, regulatory fees, etc) with all fees confirmed before payment. Fees for baggage, meals, Wi-Fi, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.