Find Cheap Flights from Toronto Island to Chicago Midway (YTZ - MDW)

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Toronto Island to Chicago Midway Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Chicago Midway
Flights Depart from Toronto Island
Flight Price $175
Distance 442 miles
Airlines Porter Airlines

Good to Know

Good Deal:
$234
or less round-trip within
2 months
of travel is a good deal

When to Book Flights from Toronto Island to Chicago Midway

Estimated round-trip price
Flight prices as travel date approaches
-1 day
-2 days

Top Tips for Finding a Cheap Flight

The cheapest flight from Toronto Island to Chicago Midway was found 53 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Toronto Island to Chicago Midway Flights

How long does a flight from Toronto Island to Chicago Midway take?
An average nonstop flight takes 1h 50m, covering a distance of 442 miles.
How many flights are there between Toronto Island and Chicago Midway?
There are 73 (nonstop) flights between Toronto Island and Chicago Midway per week, averaging 10 per day.
Which airlines provide the cheapest flights from Toronto Island to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines ($175)
Do I need a passport to fly between Toronto Island and Chicago Midway?
Yes.
Which airlines fly most frequently between Toronto Island and Chicago Midway?
Porter Airlines (10 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Toronto Island to Chicago Midway?
For Toronto Island to Chicago Midway, Friday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago Midway back to Toronto Island, the best deals are generally found on Friday, with Wednesday being the most expensive.

Book cheap flights from Toronto Island to Chicago Midway (round-trip)

Airports
Origin
Toronto
$175
only
$175
Destination
Chicago
$175
only
$175
Fri, Jan 18
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Tue, Jan 22
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 8.0

Cons: Delay

Wed, Jan 9
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Jan 13
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

Thu, Jan 10
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Jan 13
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

Mon, Jan 14
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Thu, Jan 17
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

Fri, Jan 18
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Jan 20
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

Fri, Jan 25
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Mon, Jan 28
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

Wed, Feb 6
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sat, Feb 9
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 10.0

Cons: Good

Thu, Feb 7
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sat, Feb 9
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

Fri, Feb 22
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Feb 24
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

Fri, Mar 1
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Mar 3
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

Wed, Mar 6
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Fri, Mar 8
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 10.0

Cons: Good

Fri, Mar 22
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Mar 24
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

Wed, Apr 10
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Apr 14
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

Fri, Mar 8
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Mar 10
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 2 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

Mon, Jan 7
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Thu, Jan 10
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

Wed, Jan 16
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sat, Jan 19
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

Wed, Jan 9
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Thu, Jan 10
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 2 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

Fri, Jan 11
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Mon, Jan 14
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

Sat, Jan 12
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Jan 13
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 2 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 10.0

Cons: Good

Tue, Jan 15
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sat, Jan 19
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 128 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

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