MDW

C$ 193 Find Cheap Flights to Chicago – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 28/7. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 296
Typical prices: C$ 250-C$ 580
Porter Airlines
Mon 17/8Mon 24/8
YTZ - MDW • Direct
Cheapest one-way flights
C$ 193
Porter Airlines
Tue 28/7
YTZ - MDW • Direct
Top routes
Cheapest
Most popular
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We hope you love your trip to Midway!
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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Midway

Mon, 17 Aug - Mon, 24 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:15 p.m. - 5:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 296Porter Airlines
Sat, 25 Jul - Sat, 1 Aug
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Thu, 20 Aug - Mon, 24 Aug
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:15 p.m. - 5:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 300Porter Airlines
Thu, 23 Jul - Mon, 27 Jul
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 301Porter Airlines
Mon, 27 Jul - Wed, 5 Aug
Delta Logo
6:10 a.m. - 12:38 p.m.
YYZ
-
MDW
7h 28m
1 stop
Delta Logo
9:24 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 00m
1 stop
C$ 342Delta
Wed, 22 Jul - Sat, 25 Jul
Delta Logo
12:09 p.m. - 6:25 p.m.
YYZ
-
MDW
7h 16m
1 stop
Delta Logo
9:19 a.m. - 5:24 p.m.
MDW
-
YYZ
7h 05m
1 stop
C$ 354Delta
Thu, 6 Aug - Thu, 13 Aug
WestJet Logo
12:14 p.m. - 6:38 p.m.
YYZ
-
MDW
7h 24m
1 stop
WestJet Logo
1:30 p.m. - 11:08 p.m.
MDW
-
YYZ
8h 38m
1 stop
C$ 376WestJet
Thu, 6 Aug - Sun, 9 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:15 p.m. - 8:04 p.m.
MDW
-
YOW
3h 49m
1 stop
C$ 547Multiple Airlines
Mon, 17 Aug - Fri, 21 Aug
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:15 p.m. - 12:20 a.m.
MDW
-
YOW
8h 05m
1 stop
C$ 578Multiple Airlines
Wed, 30 Sep - Tue, 6 Oct
WestJet Logo
6:05 a.m. - 6:24 p.m.
YVR
-
MDW
10h 19m
1 stop
WestJet Logo
12:33 p.m. - 8:38 p.m.
MDW
-
YVR
10h 05m
1 stop
C$ 618WestJet
Booking Insights

KAYAK's insights & trends for flights to Midway

Get data-powered insights and trends into flights to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Toronto, at C$ 296 round-trip. The most popular connection is from Toronto to Chicago, while KAYAK users have found round-trip deals for as low as C$ 296 in the last 5 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as C$ 311. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are C$ 359 on average.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all round-trip flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago Midway Airport is generally in the morning, when round-trip flights cost C$ 331 on average. The most expensive time of day to fly to Chicago Midway Airport is generally at night, which is peak travel time and where the average cost of a ticket is C$ 688.

What is a good deal for flights to Chicago Midway Airport?

If you’re 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 Airport C$ 296 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low seasonFebruary
Cheapest flightC$ 193
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 6% lower on average.
Flight from Toronto Island to Chicago Midway Airport

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.

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Toronto, at C$ 296 round-trip. The most popular connection is from Toronto to Chicago, while KAYAK users have found round-trip deals for as low as C$ 296 in the last 5 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$ 282. The cheapest price found on KAYAK in the last 2 weeks cost C$ 164 and departed from Toronto Island Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Toronto Island C$ 236
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline 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. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Porter AirlinesOverall score based on 442 reviews
7.5Food
7.9Comfort
6.9Entertainment
8.2Boarding
8.6Crew
Airline reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

4.0 OkayJeff, Jul 2026
YYZ - SFO
Read more Porter Airlines reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Organization and the adjusted times but the snacks could be of a bigger portion

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

All good the seats a little tight and no I pad screen

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Travelling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Munster
Hammond
Valparaiso
Benton Harbor
Schererville
Saint Joseph
Portage
Crown Point
New Buffalo
Chesterton
Porter
Monticello

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago