MDW
Find cheap flights to Chicago Midway Airport from C$ 177
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 8/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
Return
1 adult
Economy
Sat 28/10
Sat 4/11
In the last 7 days travellers have searched 44,168,898 times on KAYAK, and here is why:
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These are the airlines KAYAK users have selected most often for flights to Chicago
...and more
These are the airlines KAYAK users have selected most often for flights to Chicago
How much is the cheapest flight to Midway?
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.Good to know
When to book flights to Midway
Are your dates flexible? Find out the best times to travel to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.
Average price per month
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each departure date.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
Top tips for finding cheap flights to Chicago Midway Airport
- Looking for cheap airfare to Chicago Midway Airport? 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Toronto Island C$ 215 one-way - C$ 294 round-trip
- Book at least 2 weeks before departure in order to get a below-average price.
- High season is considered to be March, April and May. The cheapest month to fly from Canada is January.
- Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.
FAQs - booking Chicago Midway Airport flights
How long is the flight to Chicago Midway Airport?
Flights from Toronto 1h 45m What is the cheapest flight to Chicago Midway Airport?
In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Toronto, at C$ 239 one-way and C$ 422 round-trip. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as C$ 347 in the last 3 days.
How far is Chicago Midway Airport from central Chicago?
The distance between Chicago Midway Airport and downtown Chicago is 14 km.
How much is a flight to Chicago?
On average, a flight to Chicago costs C$ 382. The cheapest price found on KAYAK in the last 2 weeks cost C$ 196 and departed from Toronto Island Airport.
What is the cheapest month to fly to Chicago?
The cheapest month for flights to Chicago is January. On the other hand, the most expensive months are October and November.
Which airlines have a flexible cancellation policy for flights to Chicago due to COVID-19?
Porter Airlines has waived its change and cancellation fees on flights to Chicago. Confirm policy on booking site.
How does KAYAK find such low prices on flights to Chicago Midway Airport?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago Midway Airport?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport is likely to change within 7 days, so travellers know whether to wait or book now.
What is the Hacker Fare option on flights to Chicago Midway Airport?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago Midway Airport?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.
Top 4 airlines flying to Midway
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years.
7.8
Endeavor AirlinesOverall score based on 57 reviews
71entertainment
77comfort
83crew
77food
81boarding
80overall
Airline reviews
Pros: "seat space was great and I was lucky enough to have medium size passenger next to me :-)"
Cons: "Can't really think of anything . . . my expectations were exceeded"
Pros: "seat space was great and I was lucky enough to have medium size passenger next to me :-)"
Cons: "Can't really think of anything . . . my expectations were exceeded"
Cons: "The aircraft was old and in need of some work. Nice crew and smooth flight. Just aging equipment."
Pros: "Free open seats"
Cons: "Opd plane. USB ports only in Comfort Plus and above"
Pros: "Preflight announcement on smart bags. Beverage servive god. Snack could be more than 2 cookies."
Cons: "2 flights need more than 2 cookies."
Pros: "Staff was great and service friendly. The flight attendants were truly exceptional."
Pros: "Good flight. Nice staff."
Cons: "Old plane with obviously dated cabin, questionable cleanliness, smaller than average seats. Short flight without beverage service (understandably so)"
Cons: "SeAts too close to each other. The girl next to me kept hitting me with her elbow the whole time."
Cons: "I missed my outbound flight from Chicago to Dallas, and although I called to inform Delta, my return trip was cancelled and i did not find out until the day of my return to Chicago. When I called Delta to figure out what was going on, I was put on hold for two and a half hours. I'm not giving the flight a bad review, since I never got on the plane, but I'm disappointed with the accuracy and care for customers that I've experienced with Delta service. Delta was the first company I've ever flown with when I first started travelling when I was twelve years old, and it is unfortunate that I will probably never book with Delta again."
Pros: "I've done many flights this distance, and just take for granted that there will be entertainment. There wasn't."
Pros: "Unfortunately there were unavoidable delays due to weather but the staff gave regular updates and were very honest. Also, they brought out food and drinks for people bc they knew people wouldn't feel comfortable leaving the gate in case of changes. Staff handled the whole situation very well."
Cons: "Announcements are delivered with too much speed and lack connection with passengers."
Pros: "On time, fast flight."
Cons: "There were some very obnoxious other passengers and the flight crew only reminded them once about using headphones for watching videos, but after that the flight attendants were very aware of the situation and ignoring it. Tough as as a passenger sitting close by for 4 hours."
Pros: "Didn’t make my flight"
Cons: "If the app didn’t send me a message saying my flight had been delayed when it was in fact on time."
Cons: "Our trip got completely rerouted - we are still in Edmonton and expected to be with family in Regina a couple of hours ago. :((("
Pros: "We were a little cramped in, but overall it was nice."
Cons: "Not much. It was a quick flight overall."
Pros: "Could not tap opinion on previous page. Good trip. Good service. Good legroom which was covered."
Cons: "Food prices."
Cons: "After checking in 24 hours prior and receiving my boarding passes when we got to the airport we found out our seats were changed and only one of them was confirmed if not for one empty seat on the plane we would have had to stay behind this is unacceptable That we were not informed of these changes"
Pros: "Good crew."
Cons: "My tv screen was not working. I did not have anything to watch my entire 6 hours flight from Toronto to San Jose California. My connecting flight/airline was changed on the day of my flight. Not really a problem as the time was the same."
Pros: "We left late and after a six and a half hour flight with a 5 hour layover we were not impressed. The plane was a Boeing 737-600 and the rows were close together. The first plane was a Boeing 37-800 with a lot more legroom. WestJet should take these things into consideration when scheduling their flights."
Cons: "Didn't like leaving late, I don't care the reason. Rows close together."
Pros: "Kayak and the WestJet app are a great combination. Overall the trip was excellent. No food (just a light snack from Toornto to Montreal) and no entertainment, but the flight was pleasant."
Cons: "No food, no usb for charging."
Pros: "The crew is always friendly at Porter. The free wine is awesome."
Cons: "There’s no entertainment."
Pros: "Nothing"
Cons: "Porter declined re-booking the flight due to weather conditions and forced us to purchase new tickets. Reservations made through anything other than Porter are treated poorly, service can be declined due to overbooking."
Pros: "Efficient check in. Liked the shuttle bus service from subway to airport."
Cons: "As expected this is a commuter flight so very stripped down in terms of amenities. Tight plane seating and those overhead bins just barely accommodate the carry on."
Pros: "The crew was very attentive and the seats are comfortable. The waiting time is horrible...they are always late!"
Cons: "I like landing at Billy Bishop, it is very convenient and not too crowed but lately the common lounge has gotten so crowed that you can only seat on the floor. The flights are usually 2 hrs delayed sometimes 3 or 4 hrs delayed! so never plan on having a connecting flight on the other side of your tr"
Pros: "The crew was helpful and everything was on time."
Cons: "The ride was a bit rough at the end if the flight."
Pros: "Flight was fine"
Cons: "So many delays which missed our connection. Very costly. It’s the next day and I’m still not to Montreal!"
Pros: "The crew is lovely"
Cons: "Porters flights out of Toronto have been significantly delayed every time I’ve flown"
Pros: "First time in 10 flights in 3 months flying with Porter in time - what a miracle!"
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"
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."
Everything was efficient and comfortable. The food was typical airline fair, and steamed into oblivion. Service was prompt and friendly
I had to cancel flight because of an injury so this whole trip that I supposed to go on was poor.
my flight got late due to weather so they gave me another direct air india flight.
Pros: "The crew was nice."
Cons: "Everything is too cramped. The sound on the entertainment unit is terrible."
Cons: "Put on Turkish air landed 12 hrs late lggage still missing"
Pros: "Nothing"
Cons: "This was probably the worst handled flight I have been on; there was first a slight delay, then a longer delay, then a much longer delay, all of which one could find out only after checking online; there were no announcements about the delay until after the scheduled time of departure; then there was another announcement that there was a mechanical problem and we'll be apprised of the situation at 7pm (the flight was scheduled at 6:25). The person at the counter disappeared. At 7:30, the gate changed to a different flight altogether--still no announcement, still no person at the gate. When a different person finally appeared and I asked her what happened to the Pittsburgh flight, she said, it's here, it'll be departing at this precise gate shortly. At that exact time, the PA system had an announcement that the flight to Pittsburgh is now scheduled at gate 86 at 7.01 (yes, 7:01, even though it was already after 7:30). When we went to gate 86, there, of course, was another flight there. After waiting some more, the woman at the first counter now appeared at gate 86 and said the flight was to be at gate 88. Until the very end when we boarded, gate 88 continued to say the flight was to Columbus. Absolutely abysmal customer service. (Even the boarding was handled badly, but at that time we didn't even care.) I am never recommending Air Canada."
Cons: "I never got on that flight because the flight from Montreal to Toronto was delayed so I would have missed the connection. The flight from Montreal was late. I showed up a the airport three times before I got on a plane. Air Canada asked me to check in online but the system didn't work. Because of the storm, Air Canada couldn't even place me on hold so I had to go to the airport earlier in the day. When I complained about not being able to check in online, they asked gaslighted me and kept repeating that their system was "a great product" and that there was no way it didn't work. One person finally told me that it was because I had a pet in cabin. I could have saved a lot of frustration if someone had told me that. I also think that for a flight that left late and caused me to change plans and leave on a different day with another delayed flight because of the luggage conveyor belt that didn't work - which paralyzed an entire airport - they could have offered us a complimentary meal on the plane."
Cons: "Very cramped space. Once boarded on air Canada rouge we were told we should have loaded an app while in the airport so we could watch movies etc on our own devices. Too late once you're on the plane!!!! Now an 8 hour flight without ANY entertainment. Would not fly Rouge again."
Pros: "1st time on Air Canada and we were overall impressed, this was a fast an easy flight across the board. Love the free inflight entertainment too!"
Cons: "Food availability was restricted because it was only a 3hr flight despite it being during dinner time. Still what was there was enough, I had cheese and crackers and Granola balls and it was filling enough."
Pros: "Seats were nice to recline and the in flight tv is much nicer than tablets etc. The in flight safety video is good and quick easy"
Cons: "Seriously? No free snacks? It's ridiculous that you want us to purchase snacks. Something small should be complimentary. Staff was in ok moods but a little edgy. The air was too cold."
Book Cheap Chicago Plane Tickets
Recent round-trip flight deals
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
20/10Fri
2 stopsMultiple Airlines
15h 49mYYC-MDW
21/10Sat
1 stopMultiple Airlines
12h 31mMDW-YYC
C$ 312
20/10Fri
2 stopsMultiple Airlines
15h 49mYYC-MDW
21/10Sat
1 stopMultiple Airlines
12h 31mMDW-YYC
C$ 323
29/11Wed
2 stopsMultiple Airlines
12h 11mYYZ-MDW
4/12Mon
1 stopMultiple Airlines
7h 16mMDW-YYZ
C$ 330
1/11Wed
directPorter Airlines
1h 50mYTZ-MDW
2/11Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 347
19/10Thu
directPorter Airlines
1h 47mYTZ-MDW
24/10Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 349
27/10Fri
directPorter Airlines
1h 47mYTZ-MDW
3/11Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 351
25/10Wed
1 stopPorter Airlines
4h 52mYUL-MDW
1/11Wed
1 stopPorter Airlines
3h 55mMDW-YUL
C$ 355
7/11Tue
1 stopDelta
7h 47mYUL-MDW
13/11Mon
1 stopDelta
5h 54mMDW-YUL
C$ 416
19/10Thu
1 stopDelta
7h 34mYYZ-MDW
24/10Tue
1 stopDelta
4h 30mMDW-YYZ
C$ 428
22/10Sun
1 stopDelta
3h 26mYYZ-MDW
25/10Wed
1 stopDelta
5h 20mMDW-YYZ
C$ 430
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Recent one-way flight deals
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
8/11Wed
2 stopsMultiple Airlines
17h 00mYYZ-MDW
C$ 177
29/10Sun
2 stopsMultiple Airlines
42h 53mYVR-MDW
C$ 180
10/11Fri
1 stopPorter Airlines
4h 50mYUL-MDW
C$ 196
25/10Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 197
25/10Wed
1 stopAeromexico
8h 36mYYC-MDW
C$ 203
29/10Sun
1 stopDelta
8h 36mYYC-MDW
C$ 226
8/11Wed
1 stopDelta
4h 11mYYZ-MDW
C$ 251
9/11Thu
1 stopWestJet
5h 58mYUL-MDW
C$ 301
11/11Sat
1 stopWestJet
13h 17mYUL-MDW
C$ 314
11/10Wed
1 stopAeromexico
6h 11mYYZ-MDW
C$ 334
Search by stops
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Search by price
Recent domestic flight deals
28/10Sat
directDelta
1h 38mMSP-MDW
31/10Tue
directDelta
1h 40mMDW-MSP
C$ 214
31/10Tue
directDelta
1h 43mMSP-MDW
1/11Wed
directDelta
1h 40mMDW-MSP
C$ 220
16/11Thu
multi-stopDelta
3h 45mDCA-MDW
28/11Tue
multi-stopDelta
3h 50mMDW-DCA
C$ 226
24/10Tue
multi-stopFrontier
19h 41mSEA-MDW
30/10Mon
multi-stopFrontier
25h 44mMDW-SEA
C$ 227
21/10Sat
directDelta
1h 36mMSP-MDW
25/10Wed
directDelta
1h 37mMDW-MSP
C$ 227
23/10Mon
multi-stopFrontier
14h 47mSEA-MDW
29/10Sun
multi-stopFrontier
20h 32mMDW-SEA
C$ 254
24/10Tue
directSouthwest
2h 35mBOS-MDW
26/10Thu
directSouthwest
2h 10mMDW-BOS
C$ 292
25/1Thu
multi-stopFrontier
11h 36mSEA-MDW
28/1Sun
multi-stopFrontier
9h 58mMDW-SEA
C$ 295
24/10Tue
multi-stopSouthwest
7h 50mBOS-MDW
26/10Thu
directSouthwest
2h 10mMDW-BOS
C$ 305
24/10Tue
multi-stopSouthwest
10h 00mBOS-MDW
26/10Thu
directSouthwest
2h 10mMDW-BOS
C$ 312
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Last minute flights to Midway
Last minute flight, train and bus deals
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
29/9Fri
directPorter Airlines
1h 47mYTZ-MDW
10/11Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 518
29/9Fri
directPorter Airlines
1h 47mYTZ-MDW
26/10Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 532
29/9Fri
directPorter Airlines
1h 47mYTZ-MDW
24/10Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 538
1/10Sun
multi-stopMultiple Airlines
21h 25mYUL-MDW
5/10Thu
multi-stopMultiple Airlines
15h 40mMDW-YUL
C$ 564
30/9Sat
multi-stopMultiple Airlines
47h 02mYVR-MDW
4/10Wed
multi-stopMultiple Airlines
14h 57mMDW-YVR
C$ 566
29/9Fri
multi-stopDelta
6h 20mYYC-MDW
4/10Wed
multi-stopDelta
8h 31mMDW-YYC
C$ 685
29/9Fri
multi-stopDelta
6h 17mYYZ-MDW
10/11Fri
multi-stopDelta
5h 46mMDW-YYZ
C$ 707
2/10Mon
multi-stopAeromexico
6h 17mYYZ-MDW
6/10Fri
multi-stopAeromexico
8h 02mMDW-YYZ
C$ 741
2/10Mon
multi-stopWestJet
23h 37mYYZ-MDW
4/10Wed
multi-stopWestJet
10h 49mMDW-YYZ
C$ 751
3/10Tue
multi-stopWestJet
5h 18mYYZ-MDW
5/10Thu
multi-stopWestJet
5h 10mMDW-YYZ
C$ 766
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Flights to Chicago Midway Airport
Destination:
Chicago Midway Airport (MDW)United States
Return flight deals:
Chicago Midway Airport - Canada
Cabin classes:
Browse origins:
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Popular routes
The most searched flights to Chicago Midway Airport by KAYAK users.