Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 184
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
24 Sep — 1 Oct1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto Pearson Intl to Chicago are usually found in March or January, booked 84 days in advance, depart on a Friday or Saturday and return on a Friday
Cheap flight deals from Pearson Intl to Chicago
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Cheapest flights from Pearson Intl to Chicago
Explore the most affordable flight options available from Pearson Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 August 2026.
Thu 17/912:25 p.m. -
Nonstop1h 58m
Sun 20/98:40 p.m. -
Nonstop1h 46m
Deal found 23/8C$ 283
Wed 7/103:55 p.m. -
Nonstop1h 58m
Wed 14/103:45 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 285
Sat 12/98:05 a.m. -
Nonstop1h 55m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 22/8C$ 288
Thu 10/99:00 p.m. -
Nonstop2h 05m
Sun 13/99:18 p.m. -
Nonstop1h 41m
Deal found 20/8C$ 293
Mon 14/99:00 p.m. -
Nonstop2h 05m
Wed 16/92:15 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 296
Fri 2/104:00 p.m. -
1 stop5h 12m
Mon 5/102:15 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 297
Fri 11/911:00 a.m. -
Nonstop2h 00m
Sun 13/99:18 p.m. -
Nonstop1h 41m
Deal found 21/8C$ 299
Thu 10/94:00 p.m. -
1 stop5h 12m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 20/8C$ 300
Sat 12/912:08 p.m. -
1 stop5h 49m
Tue 29/99:29 a.m. -
1 stop4h 46m
Deal found 22/8C$ 330
Thu 17/96:00 a.m. -
1 stop4h 07m
Wed 23/99:29 a.m. -
1 stop6h 51m
Deal found 24/8C$ 340
Sat 12/96:00 a.m. -
1 stop4h 07m
Sun 13/99:29 a.m. -
1 stop6h 51m
Deal found 22/8C$ 342
Wed 7/1012:10 p.m. -
1 stop6h 50m
Tue 13/109:29 a.m. -
1 stop6h 50m
Deal found 24/8C$ 360
Best flights from Pearson Intl to Chicago
Discover carefully curated flight deals from Pearson Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 25 August 2026.
Mon 14/99:00 p.m. -
Nonstop2h 05m
Mon 21/99:18 p.m. -
Nonstop1h 41m
Deal found 21/8C$ 293
Sat 12/97:00 p.m. -
1 stop6h 28m
Tue 15/93:40 p.m. -
1 stop6h 38m
Deal found 20/8C$ 326
Fri 18/912:08 p.m. -
1 stop7h 18m
Mon 21/98:55 a.m. -
1 stop7h 25m
Deal found 20/8C$ 340
Tue 22/97:00 a.m. -
Nonstop2h 00m
Sun 27/95:53 p.m. -
Nonstop1h 51m
Deal found 24/8C$ 332
Thu 17/910:15 a.m. -
Nonstop2h 06m
Sun 20/98:40 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 333
Mon 21/912:08 p.m. -
1 stop7h 25m
Sat 26/96:40 p.m. -
1 stop3h 19m
Deal found 24/8C$ 340
Mon 21/99:00 p.m. -
Nonstop2h 05m
Thu 24/99:55 a.m. -
Nonstop1h 45m
Deal found 21/8C$ 335
Sat 12/912:08 p.m. -
1 stop5h 49m
Tue 15/99:29 a.m. -
1 stop6h 51m
Deal found 20/8C$ 340
Sun 20/96:00 a.m. -
1 stop7h 39m
Mon 28/99:29 a.m. -
1 stop6h 51m
Deal found 24/8C$ 340
Wed 30/97:00 a.m. -
Nonstop2h 00m
Sun 4/109:20 p.m. -
Nonstop1h 39m
Deal found 21/8C$ 398
Thu 24/92:24 p.m. -
1 stop7h 06m
Sun 27/97:05 a.m. -
1 stop7h 10m
Deal found 21/8C$ 342
Thu 24/912:08 p.m. -
1 stop7h 25m
Sun 27/99:29 a.m. -
1 stop3h 05m
Deal found 24/8C$ 342
Thu 10/911:00 a.m. -
Nonstop2h 00m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 20/8C$ 420
Thu 10/95:15 p.m. -
Nonstop2h 03m
Sat 19/99:18 p.m. -
Nonstop1h 41m
Deal found 23/8C$ 431
Wed 7/1012:10 p.m. -
1 stop6h 50m
Wed 14/109:29 a.m. -
1 stop6h 50m
Deal found 24/8C$ 387
Wed 9/99:45 a.m. -
1 stop8h 12m
Tue 29/99:29 a.m. -
1 stop4h 46m
Deal found 22/8C$ 419
Sun 6/96:10 a.m. -
1 stop4h 07m
Wed 16/99:29 a.m. -
1 stop6h 51m
Deal found 22/8C$ 440
Thu 10/912:08 p.m. -
1 stop5h 49m
Wed 23/99:29 a.m. -
1 stop6h 51m
Deal found 22/8C$ 440
Thu 10/126:00 a.m. -
1 stop4h 37m
Mon 14/129:37 a.m. -
1 stop6h 43m
Deal found 24/8C$ 454
Sun 11/106:00 a.m. -
1 stop4h 17m
Mon 12/109:29 a.m. -
1 stop6h 50m
Deal found 24/8C$ 458
Sat 3/106:00 a.m. -
1 stop4h 07m
Tue 6/109:29 a.m. -
1 stop3h 07m
Deal found 20/8C$ 473
Sat 3/106:00 a.m. -
1 stop7h 39m
Mon 5/109:29 a.m. -
1 stop6h 51m
Deal found 20/8C$ 494
Direct flights from Pearson Intl to Chicago
Explore direct flight options from Pearson Intl to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 25 August 2026.
Thu 17/912:25 p.m. -
Nonstop1h 58m
Sun 20/98:40 p.m. -
Nonstop1h 46m
Deal found 23/8C$ 283
Wed 7/103:55 p.m. -
Nonstop1h 58m
Wed 14/103:45 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 285
Sat 12/98:05 a.m. -
Nonstop1h 55m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 22/8C$ 288
Thu 17/96:50 p.m. -
Nonstop1h 58m
Mon 21/99:30 a.m. -
Nonstop1h 45m
Deal found 23/8C$ 289
Thu 10/97:00 a.m. -
Nonstop2h 00m
Tue 15/95:53 p.m. -
Nonstop1h 51m
Deal found 20/8C$ 293
Mon 14/99:00 p.m. -
Nonstop2h 05m
Wed 16/92:15 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 296
Thu 17/911:00 a.m. -
Nonstop2h 00m
Sun 20/99:18 p.m. -
Nonstop1h 41m
Deal found 23/8C$ 297
Fri 11/911:00 a.m. -
Nonstop2h 00m
Sun 13/99:18 p.m. -
Nonstop1h 41m
Deal found 21/8C$ 299
Last-minute flights from Pearson Intl to Chicago
Discover last-minute flight deals from Pearson Intl to Chicago. Data last updated 25 August 2026 and is based on user searches.
Thu 10/99:00 p.m. -
Nonstop2h 05m
Sun 13/99:18 p.m. -
Nonstop1h 41m
Deal found 20/8C$ 293
Thu 10/94:00 p.m. -
1 stop5h 12m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 20/8C$ 300
Fri 11/96:50 p.m. -
Nonstop1h 58m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 21/8C$ 285
Fri 11/911:00 a.m. -
Nonstop2h 00m
Sun 13/99:18 p.m. -
Nonstop1h 41m
Deal found 21/8C$ 299
Sat 12/98:05 a.m. -
Nonstop1h 55m
Sun 13/98:40 p.m. -
Nonstop1h 46m
Deal found 22/8C$ 288
Sat 12/912:08 p.m. -
1 stop5h 49m
Tue 29/99:29 a.m. -
1 stop4h 46m
Deal found 22/8C$ 330
Sat 12/96:00 a.m. -
1 stop4h 07m
Sun 13/99:29 a.m. -
1 stop6h 51m
Deal found 22/8C$ 342
Mon 14/99:00 p.m. -
Nonstop2h 05m
Wed 16/92:15 p.m. -
Nonstop1h 46m
Deal found 24/8C$ 296
Thu 17/912:25 p.m. -
Nonstop1h 58m
Sun 20/98:40 p.m. -
Nonstop1h 46m
Deal found 23/8C$ 283
Thu 17/96:50 p.m. -
Nonstop1h 58m
Mon 21/99:30 a.m. -
Nonstop1h 45m
Deal found 23/8C$ 289
Thu 17/911:00 a.m. -
Nonstop2h 00m
Sun 20/99:18 p.m. -
Nonstop1h 41m
Deal found 23/8C$ 297
Thu 17/96:00 a.m. -
1 stop4h 07m
Thu 24/99:29 a.m. -
1 stop3h 05m
Deal found 20/8C$ 340
One-way flights from Pearson Intl to Chicago
Search for one-way flight options from Pearson Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated 25 August 2026.
Sat 19/98:50 a.m. -
Nonstop2h 03m
Deal found 21/8C$ 184
Sat 19/99:00 a.m. -
1 stop6h 52m
Deal found 21/8C$ 185
Mon 21/97:40 a.m. -
Nonstop1h 55m
Deal found 23/8C$ 188
Tue 29/98:05 a.m. -
Nonstop1h 55m
Deal found 24/8C$ 191
Sat 12/912:25 p.m. -
Nonstop1h 58m
Deal found 21/8C$ 192
Sat 26/96:50 p.m. -
Nonstop1h 58m
Deal found 23/8C$ 198
Mon 5/1012:25 p.m. -
Nonstop1h 58m
Deal found 24/8C$ 200
Tue 22/910:15 a.m. -
Nonstop2h 06m
Deal found 23/8C$ 203
Fri 18/99:45 a.m. -
1 stop7h 28m
Deal found 21/8C$ 205
Fri 25/92:24 p.m. -
1 stop5h 09m
Deal found 24/8C$ 212
Mon 5/1012:08 p.m. -
1 stop7h 25m
Deal found 24/8C$ 220
Wed 14/102:26 p.m. -
1 stop4h 34m
Deal found 24/8C$ 221
Find flight deals from Pearson Intl to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Pearson Intl (YYZ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 25 August 2026.
Customize your flight search to find flights from Pearson Intl to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated 25 August 2026.
Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest round-trip
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Mon 14/9
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Mon 21/9
9:18 p.m.-11:59 p.m.
Nonstop1h 41m
C$ 293
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Sat 12/9
7:00 p.m.-12:28 a.m.
1 stop6h 28m
Chicago O'Hare Intl
Tue 15/9
3:40 p.m.-11:18 p.m.
1 stop6h 38m
C$ 326
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Tue 22/9
7:00 a.m.-8:00 a.m.
Nonstop2h 00m
Chicago O'Hare Intl
Sun 27/9
5:53 p.m.-8:44 p.m.
Nonstop1h 51m
C$ 332
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 17/9
10:15 a.m.-11:21 a.m.
Nonstop2h 06m
Chicago O'Hare Intl
Sun 20/9
8:40 p.m.-11:26 p.m.
Nonstop1h 46m
C$ 333
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Mon 21/9
9:00 p.m.-10:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Thu 24/9
9:55 a.m.-12:40 p.m.
Nonstop1h 45m
C$ 335
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Fri 18/9
12:08 p.m.-6:26 p.m.
1 stop7h 18m
Chicago O'Hare Intl
Mon 21/9
8:55 a.m.-5:20 p.m.
1 stop7h 25m
C$ 340
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Mon 21/9
12:08 p.m.-6:33 p.m.
1 stop7h 25m
Chicago Midway
Sat 26/9
6:40 p.m.-10:59 p.m.
1 stop3h 19m
C$ 340
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sat 12/9
12:08 p.m.-4:57 p.m.
1 stop5h 49m
Chicago Midway
Tue 15/9
9:29 a.m.-5:20 p.m.
1 stop6h 51m
C$ 340
TorontoChicago
YYZ Toronto Pearson Intl - MDW Chicago Midway
YYZMDW
Toronto Pearson Intl
Sun 20/9
6:00 a.m.-12:39 p.m.
1 stop7h 39m
Chicago Midway
Mon 28/9
9:29 a.m.-5:20 p.m.
1 stop6h 51m
C$ 340
TorontoChicago
YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl
YYZORD
Toronto Pearson Intl
Thu 24/9
2:24 p.m.-8:30 p.m.
1 stop7h 06m
Chicago O'Hare Intl
Sun 27/9
7:05 a.m.-3:15 p.m.
1 stop7h 10m
C$ 342
Flights are sorted by cheapest round-trip flights first.
Deals found on 24/8
Showing 1-10 of 42 resultsSorted by cheapest first
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5
Best time to book a flight from Pearson Intl to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Pearson Intl with our price prediction graph.
YYZ-CHI
YYZ-ORD
YYZ-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Toronto Pearson Intl Airport to Chicago
YYZ-CHI
YYZ-ORD
YYZ-MDW
What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?
Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 343). Flying from Toronto Pearson Intl Airport to Chicago in August is currently the most expensive (average of C$ 462). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YYZ to CHI?
Find hourly flight availability from Pearson Intl to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 25 August 2026.
It’s optimal to fly from Toronto Pearson Intl Airport to Chicago in the evening. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Toronto Pearson Intl Airport to Chicago
Explore weekly flight availability from Pearson Intl to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 25 August 2026.
The most flights from YYZ to CHI are scheduled on a Friday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (63 on average).
How much does it cost to fly round-trip from Toronto Pearson Intl Airport to Chicago?
Airfare is below average for this route at the moment.
Toronto Pearson Intl Airport to Chicago flights typically cost between C$ 327 and C$ 523 in September.The cheapest round-trip price found within the last 5 days was C$ 283 on Air Canada (17 Sep-20 Sep).
How often are flights from Toronto to Chicago delayed?
About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.
What is the most punctual flight time for Toronto to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Toronto to Chicago flights?
Over the past year, United Airlines has had the lowest number of delays on this route, with just 8% of flights being delayed.
How far ahead should I book a flight from Toronto Pearson Intl Airport to Chicago?
Booking 83 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto Pearson Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Toronto Pearson Intl Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Pearson Intl to Chicago. Price data was last updated on 22 August 2026.
Travelers seeking maximum savings on their Toronto Pearson Intl Airport to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 25 August 2026.
Read reviews from past customers who have flown Porter Airlines,United Airlines, andWestJet
from Toronto Pearson Intl Airport to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
My first flight with an all female flight crew who were the best ever.
Related info for your journey
Find useful and relevant information for your journey from Pearson Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
How long is the flight from Toronto Pearson Intl Airport to Chicago?
Airlines like United Airlines and Delta fly from Toronto Pearson Intl Airport to Chicago in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 5h 20m. The distance between Toronto Pearson Intl Airport and Chicago is about 702 km. This flight may include one or multiple stops.
What are the cheapest airlines flying from Toronto Pearson Intl Airport to Chicago round-trip?
Currently priced at C$ 245, Porter Airlines will fly you from Toronto Pearson Intl Airport to Chicago and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Air Canada - these airlines can fly you to your destination from C$ 260 and C$ 285, respectively. Users have found that Porter Airlines is 37% cheaper than the other options available to this destination.
What are the cheapest airlines to fly from Toronto Pearson Intl Airport to Chicago one-way?
One-way options have recently been found by users for as low as C$ 156 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 162 and American Airlines from C$ 165 one-way.
What are the most reliable airlines from Toronto Pearson Intl Airport to Chicago?
Before booking your flight to Chicago from Toronto Pearson Intl Airport, check out the most reliable airlines to get you to your destination on time: Egyptair (88%), Japan Airlines (82%), ANA( 76%).
What are the cheapest flights from Toronto Pearson Intl Airport to Chicago?
On average you can expect to pay C$ 1,432 for a flight from Toronto Pearson Intl Airport to Chicago. The cheapest flight overall is C$ 248 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 296.
Can I find deals for business class flights from Pearson Intl to Chicago?
Yes. Cheapflights offers flight deals from Pearson Intl to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Toronto Pearson Intl Airport to Chicago?
Currently, January is the cheapest month in which you can book a flight from Toronto Pearson Intl Airport to Chicago (average of C$ 343). Flying from Toronto Pearson Intl Airport to Chicago in August is currently the most expensive (average of C$ 462). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Browse thousands of different options on Cheapflights for your next trip
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Fly from Pearson Intl to Chicago on these airlines
Choose from the following airlines for your flight from Pearson Intl to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 25 August 2026.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 25 August 2026.
Browse through other flights departing from Pearson Intl. Flights are based on user searches made on Cheapflights and were last updated on 25 August 2026.
Top 5 airlines flying from Pearson Intl to Chicago
Discover the top 5 airlines that operate flights from Pearson Intl to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated 25 August 2026.
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Pearson Intl to Chicago?
Cheapflights makes it easy to find Pearson Intl to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Pearson Intl to Chicago?
Cheapflights simply makes it quick and affordable to book flights from Pearson Intl to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Pearson Intl to Chicago with no change fees?
Certainly. Search results for flights to Chicago from Pearson Intl shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Pearson Intl to Chicago become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!
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