Find Cheap Flights from Chicago to Windsor (CHI - YQG)

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Wed 11/22
Wed 11/29
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When looking for a cheap flight, consider that 25% of our users selected a flight on this route for $303 or less.

FAQs for Booking Chicago to Windsor Flights

How long does a flight from Chicago to Windsor take?
An average nonstop flight takes 4h 28m, covering a distance of 241 miles.
Which airlines provide the cheapest flights from Chicago to Windsor?
In the past 3 days, the cheapest round-trip tickets were found on Air Canada ($402)
Do I need a passport to fly between Chicago and Windsor?
Yes.

Book cheap flights from Chicago to Windsor (round-trip)

Airports
Origin
Chicago
$402
only
$402
Destination
Windsor
$402
only
$402
Thu, Jan 18
ORD
YQG
4h 28m
Sun, Jan 21
YQG
ORD
5h 47m
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19842 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
FRA
YYZ
Excellent 10.0

Movie selection was great! Thank you for having a vegetarian food option.

ORD
YYZ
Mediocre 2.0

Nothing

Flight delay led us to miss our connecting flight. Air Canada then lost our luggage for 6 days on our honeymoon!

BOS
YYZ
Excellent 9.3

T

The waiting area at the Boston airport is poor. It is very small, rundown and with limited access to refreshments. It's ok but certainly not a selling point.

YLW
YYZ
Okay 4.0

Seats were uncomfortable and tight. Leg room is not existent.

YOW
YYC
Poor 0.0

MIGHT give me a refund, and not WILL give me a refund

Service personnel at Air Canada were very helpful and re-booked me several times and when none of those flights left, they said they would refer me to refund department.

Fri, Dec 29
ORD
YQG
5h 48m
Sat, Jan 6
YQG
ORD
4h 47m
Trip: 9 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19842 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YYC
YUL
Good 6.3

I almost missed my connection. No one cared. Staff in airport were downright cranky - all due to late incoming aircraft and yet more de-icing... why ever don't they allow time for that in November!!!

YYZ
BOG
Okay 4.3

Very cold plane

FRA
YYZ
Excellent 10.0

Movie selection was great! Thank you for having a vegetarian food option.

LHR
YVR
Okay 5.6

They have good entertainment system and library

The plane delayed for almost 90m due to a mechanical issue. Of course, we missed our connection in Vancouver. Upon arriving in Vancouver, there was no help at all or guidance. Customer support desk was manned by one agent even in the presence of long queues.

YLW
YYZ
Okay 4.0

Seats were uncomfortable and tight. Leg room is not existent.

Mon, Dec 4
ORD
YQG
4h 38m
Mon, Dec 11
YQG
ORD
5h 02m
Trip: 8 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19842 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YVR
YYZ
Mediocre 2.0

I like that they are Canadian

I don't like how unhelpful they are, their food, their staff, the way they treat clients etc. Seriously my least favourite company to fly with. I'd rather pay extra and fly WestJet anyday!

BOS
YYZ
Excellent 8.0

New system with Canadian customs was fantastic. Went through really quickly.

LHR
YVR
Okay 5.6

They have good entertainment system and library

The plane delayed for almost 90m due to a mechanical issue. Of course, we missed our connection in Vancouver. Upon arriving in Vancouver, there was no help at all or guidance. Customer support desk was manned by one agent even in the presence of long queues.

EWR
YVR
Excellent 8.3

Flight attendants were courteous

We have to buy our own food

YOW
YYC
Poor 0.0

MIGHT give me a refund, and not WILL give me a refund

Service personnel at Air Canada were very helpful and re-booked me several times and when none of those flights left, they said they would refer me to refund department.

Sat, Dec 2
ORD
YQG
6h 03m
Sun, Dec 3
YQG
ORD
7h 25m
Trip: 2 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19842 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
ORD
YYZ
Mediocre 2.0

Nothing

Flight delay led us to miss our connecting flight. Air Canada then lost our luggage for 6 days on our honeymoon!

BOS
YYZ
Excellent 9.3

T

The waiting area at the Boston airport is poor. It is very small, rundown and with limited access to refreshments. It's ok but certainly not a selling point.

YVR
YYZ
Mediocre 2.0

I like that they are Canadian

I don't like how unhelpful they are, their food, their staff, the way they treat clients etc. Seriously my least favourite company to fly with. I'd rather pay extra and fly WestJet anyday!

YLW
YYZ
Okay 4.0

Seats were uncomfortable and tight. Leg room is not existent.

HND
YYZ
Okay 4.4

Lowest fare

Online checkin failed, airport kiosk couldn't handle how names are written on Japanese passports (it's English) and had to wait 2 hours on the line to check in because they were down to 1 agent toward the end. Made it to the gate just as boarding started. Very limited entertainment options for modern day airlines. Uncomfortable seating.

Thu, Nov 23
ORD
YQG
5h 43m
Fri, Dec 1
YQG
ORD
4h 47m
Trip: 9 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 19842 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.4
YLW
YYZ
Okay 4.0

Seats were uncomfortable and tight. Leg room is not existent.

ORD
YYZ
Mediocre 2.0

Nothing

Flight delay led us to miss our connecting flight. Air Canada then lost our luggage for 6 days on our honeymoon!

YVR
YYZ
Mediocre 2.0

I like that they are Canadian

I don't like how unhelpful they are, their food, their staff, the way they treat clients etc. Seriously my least favourite company to fly with. I'd rather pay extra and fly WestJet anyday!

EWR
YVR
Excellent 8.3

Flight attendants were courteous

We have to buy our own food

YYC
YUL
Good 6.3

I almost missed my connection. No one cared. Staff in airport were downright cranky - all due to late incoming aircraft and yet more de-icing... why ever don't they allow time for that in November!!!

*
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