$100 Cheap flight deals from Chicago (CHI) to Mississauga (YTO)
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This Weekend's Flight Deals from Chicago to Mississauga
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$466 Roundtrip, found 6 hours ago
$466
Roundtrip
found 6 hours ago
ORD
O'Hare Intl.
YYZ
Pearson Intl.
$480 Roundtrip, found 1 hour ago
$480
Roundtrip
found 1 hour ago
MDW
Midway Intl.
YYZ
Pearson Intl.
$525 Roundtrip, found 1 hour ago
$525
Roundtrip
found 1 hour ago
ORD
O'Hare Intl.
YTZ
Billy Bishop Toronto City
$526 Roundtrip, found 3 days ago
$526
Roundtrip
found 3 days ago
Airfares from $100 One Way, $232 Round Trip from Chicago to Mississauga
Prices starting at $232 for return flights and $100 for one-way flights to Mississauga were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
YYZ
Toronto
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
ORD
Chicago
YYZ
Toronto
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
MDW
Chicago
YTZ
Toronto
$244 Roundtrip, found 16 hours ago
$244
Roundtrip
found 16 hours ago
MDW
Chicago
YTZ
Toronto
$245 Roundtrip, found 16 hours ago
$245
Roundtrip
found 16 hours ago
ORD
Chicago
YKF
Kitchener
$252 Roundtrip, found 1 day ago
$252
Roundtrip
found 1 day ago
Mississauga economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Waterside Inn
8.6/10 Excellent! (1,040 reviews)
Sep 14 - Sep 19
5 night stay
Chicago (CHI) to Toronto (YYZ)
Air Canada • Coach
Toronto (YYZ) to Chicago (CHI)
Porter Airlines • Coach
Price was $931, price is now $637 per person
$637
per person
found 1 day ago
Wonderful location (close to many restaurants and the Port Credit GO station), and great apartment layout with lots of space! Will be returning! :)
Reviewed on Aug 8, 2026
4.0-star property
Hotel Riu Plaza Toronto
9.4/10 Exceptional! (4,215 reviews)
Sep 24 - Sep 28
4 night stay
Chicago (CHI) to Toronto (YYZ)
Air Canada • Non-stop • Coach
Toronto (YYZ) to Chicago (CHI)
Porter Airlines • Non-stop • Coach
Price was $1,551, price is now $977 per person
$977
per person
found 1 day ago
3.5-star property
Town Inn Suites Hotel
8.6/10 Excellent! (3,870 reviews)
Sep 14 - Sep 19
5 night stay
Chicago (CHI) to Toronto (YYZ)
Air Canada • Coach
Toronto (YYZ) to Chicago (CHI)
Porter Airlines • Coach
Price was $1,465, price is now $1,012 per person
$1,012
per person
found 1 day ago
Amazing staff most especially the people at the front desk. I gave 3 for the room cleanliness as it wasn’t thoroughly clean (that I completely understand though since it was peak time). I am the one who requested a really early check in, so i it’s understandable. Close to everything in the downtown area. Amenities are quite ok. Just the televisions that are not smart tv and has local channels only. But overall the place is highly recommended. Quiet, spacious and comfortable plus the friendly and accommodating staffs.
Reviewed on Aug 8, 2026
Mississauga first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Shaw Club Hotel
9.2/10 Wonderful! (1,010 reviews)
Sep 20 - Sep 22
2 night stay
Chicago (MDW) to Toronto (YYZ)
Delta • Non-stop roundtrip • FirstClass
Price was $860, price is now $852 per person
$852
per person
found 1 day ago
Shaw Club has become my favourite hotel in NOTL. It's a close walk to the downtown core, and really easy to get to from out of town with lots of parking. I have an EV, so the presence of multiple EV chargers is also very helpful.
Rooms are nice, especially the club rooms in the adjacent building (though there's a set of stairs that's the only way to get to those rooms that might be tricky for some with limited mobility).
Compared to other hotels in NOTL, Shaw Club is a good value, and very conveniently located. I'll happily stay again.
Reviewed on Aug 8, 2026
4.0-star property
124 on Queen Hotel & Spa
9.6/10 Exceptional! (1,101 reviews)
Sep 20 - Sep 22
2 night stay
Chicago (MDW) to Toronto (YYZ)
Delta • Non-stop roundtrip • FirstClass
Price was $1,175, price is now $1,147 per person
$1,147
per person
found 1 day ago
Our king room in the main building was comfortable and spacious. We arrived at 11 AM and asked if we could check in earlier than 4 PM. Staff were very unhelpful and told us that the cleaning staff have their own schedule that they have nothing to do with and that they could only guarantee us check in at 4 PM. This is very unlike other hotels we have stayed at that go out of their way to prepare a room ahead of time if we arrive in advance of check-in. Sure enough, our room was not ready until two minutes before 4 PM. It is a room that might take 20 minutes top to clean so I don’t know why they wouldn’t want to make a minimal effort for guests who arrive early. For this reason alone, we would not stay at this hotel again. Also, I called earlier in the day to ask about parking and was said yes, there’s parking at this address with no indication that the parking was underground, and that we needed to go upstairs to get a ticket to place in the windshield. The staff member I spoke with was incredibly lackadaisical as were all of the very young staff at this hotel.
Reviewed on Aug 8, 2026
More About Flying To Mississauga from Chicago
Route Information for Flights from Chicago to Mississauga
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | YTO |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Mississauga
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.