MDW

C$ 181 Find Cheap Flights to Chicago – Compare and Save

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Cheap Flights to Midway

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

Recent round-trip flight deals to Midway

Fri, 16 Oct - Wed, 21 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Fri, 25 Sep - Sat, 3 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Wed, 14 Oct - Mon, 19 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Fri, 16 Oct - Thu, 22 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Mon, 12 Oct - Mon, 19 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Fri, 25 Sep - Fri, 2 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Tue, 20 Oct - Sat, 24 Oct
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Thu, 15 Oct - Thu, 22 Oct
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 286Porter Airlines
Sat, 3 Oct - Mon, 5 Oct
Multiple Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Multiple Airlines Logo
11:45 a.m. - 2:25 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 306Multiple Airlines
Thu, 1 Oct - Sun, 4 Oct
Multiple Airlines Logo
10:10 a.m. - 11:00 a.m.YTZ  Toronto Island-MDW Chicago Midway
1h 50mdirect
Multiple Airlines Logo
3:20 p.m. - 6:00 p.m.MDW  Chicago Midway-YTZ Toronto Island
1h 40mdirect
C$ 308Multiple Airlines
Booking Insights

Price, demand, and travel trends for Canada to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights from Canada to Chicago Midway Airport with more confidence.

What is the cheapest flight to Chicago Midway Airport?

Toronto Island Airport to Chicago Midway Airport is the cheapest route at C$ 286 round-trip, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.

How much is a flight to Chicago Midway Airport?

A round-trip flight to Chicago Midway Airport costs C$ 376 on average, based on data over the past 12 months on KAYAK. Round-trip fares from Toronto average C$ 387, while Calgary runs a bit higher at C$ 461.

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

Monday is the cheapest day to fly to Chicago Midway Airport at C$ 368 round-trip on average over the past 12 months on KAYAK. Tuesday is the most expensive at C$ 433.

What is the cheapest month to fly to Chicago Midway Airport?

  • January is the cheapest month to fly to Chicago Midway Airport with an average price of C$ 316 round-trip.
  • August (C$ 433) and July (C$ 411) are the most expensive.
  • Based on KAYAK data over the past 12 months.

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

Night flights to Chicago Midway Airport are the cheapest at C$ 295 round-trip on average. Evening flights are the most expensive at C$ 425.

When are flights to Chicago Midway Airport the cheapest?

Flights to Chicago Midway Airport are cheapest 26 weeks before departure. Booking in this window typically costs about 64% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for flights to Chicago Midway Airport

Low season

February

Cheapest flight

C$ 181
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly (9% more expensive on average)
Flights from Toronto Island Airport 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

Your questions about flights to Chicago Midway Airport, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • What is the difference between the most popular and the most frequent airline at Chicago Midway Airport?

    Porter Airlines operates the most flights from Canada to Chicago Midway Airport at 7 per week, and for this route Porter Airlines is also the airline most often selected by KAYAK users searching for flights from Canada to Chicago Midway Airport. The two are sometimes different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80.5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

  • How far is Chicago Midway from Chicago Midway Airport city centre?

    Chicago Midway is 14.3 km from Chicago Midway Airport city centre.

  • How long are direct flights to Chicago Midway Airport from different departure cities?

    Direct flight time to Chicago Midway Airport varies depending on your departure city:
    • from Halifax: 3h 43m
    • from Québec City: 2h 55m
    • from Ottawa: 2h 19m
    • from Calgary: 3h 29m
    • from Toronto: 1h 50m

  • Where can I fly from to get the cheapest fares to Chicago Midway Airport?

    Based on fares booked in the past 5 days, the cheapest flights to Chicago Midway Airport are from:
    • Toronto, from C$ 286 round-trip

  • How many flights serve Chicago Midway Airport?

    Chicago Midway Airport receives 1 flights per day and 7 per week from across the world. Toronto has the most flights to Chicago Midway Airport, with 144 weekly flights.

  • How do I know if a flight to Chicago Midway Airport is a good deal?

    A good deal on a flight to Chicago Midway Airport is around C$ 290 round-trip. This fare is in the lowest 25% of round-trip prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • How expensive are last-minute flights to Chicago Midway Airport?

    Last-minute fares to Chicago Midway Airport – booked within 2 weeks of departure – run 56% above the average round-trip fare of C$ 376.

  • Which airlines should I consider for flights to Chicago Midway Airport?

Your guide to booking Chicago Midway Airport flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Chicago Midway Airport, aim to book around 26 weeks before you fly. That window historically saves about 64% versus last-minute pricing based on KAYAK booking data over the last 12 months.
  • For flights to Chicago Midway Airport, recent KAYAK data shows that stronger deals tend to land around C$ 290 round-trip. If you see a fare below that threshold, it's a strong deal – book before the price climbs back up.
  • If you can choose when to go, aim to travel to Chicago Midway Airport in January. Round-trip fares historically average C$ 316 that month – typically the cheapest month to travel based on the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to evening to save up to C$ 130 per round-trip. Evening flights to Chicago Midway Airport average C$ 295 compared to C$ 425 for afternoon flights. See the time-of-day chart above for the full breakdown.
  • Bag allowances vary by airline, fare type, cabin class, and route. On flights to Chicago Midway Airport, some airlines may include bags at no extra cost. For example, Porter Airlines includes a carry-on bag and a checked bag in Economy Class, while Air Transat includes a carry-on bag and a checked bag in Economy Class. Always check the fare details before booking, since bag policies can change by ticket type.
  • Once you arrive in Chicago Midway Airport, a few great places to start are Magnificent Mile, River North, and Grant Park. These are popular with first-time visitors and can give you a good feel for the area.

Reviews of the top airline flying to Midway

 
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.
8.0
Porter AirlinesOverall score based on 458 reviews
6.9Entertainment
7.6Food
8.2Boarding
8.0Comfort
8.6Crew
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

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. :)

Travelling to a place near Midway?

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

More options for your flight to Midway