MDW

C$ 139 Find Cheap Flights to Chicago

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 12/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 250
Overall average: C$ 372
Porter Airlines
Fri 1/5Mon 4/5
YUL - MDW • 1 stop
Cheapest direct flights
C$ 257
Typical prices: C$ 258-C$ 309
Multiple Airlines
Thu 12/3Thu 19/3
YTZ - MDW • Direct
Top routes
YUL
-
MDW
Cheapest
YTZ
-
MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 23% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Fri, 1 May - Mon, 4 May
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 250Porter Airlines
Thu, 4 Jun - Sun, 7 Jun
Porter Airlines Logo
6:30 a.m. - 9:40 a.m.
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 a.m. - 5:15 p.m.
MDW
-
YUL
5h 50m
1 stop
C$ 254Porter Airlines
Thu, 12 Mar - Thu, 19 Mar
Multiple Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 257Multiple Airlines
Fri, 22 May - Sun, 24 May
Air Transat Logo
4:00 p.m. - 4:50 p.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 261Air Transat
Thu, 12 Mar - Thu, 19 Mar
Multiple Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 268Multiple Airlines
Thu, 19 Feb - Mon, 23 Feb
Air Transat Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 276Air Transat
Tue, 17 Feb - Sat, 21 Feb
Delta Logo
12:30 p.m. - 10:33 p.m.
YUL
-
MDW
11h 03m
1 stop
Delta Logo
1:28 p.m. - 11:10 p.m.
MDW
-
YUL
8h 42m
1 stop
C$ 294Delta
Tue, 17 Feb - Tue, 24 Feb
Delta Logo
12:11 p.m. - 5:37 p.m.
YYZ
-
MDW
6h 26m
1 stop
Delta Logo
9:50 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 09m
1 stop
C$ 308Delta
Fri, 20 Mar - Fri, 27 Mar
WestJet Logo
6:20 a.m. - 8:53 a.m.
YYZ
-
MDW
3h 33m
1 stop
WestJet Logo
2:05 p.m. - 11:06 p.m.
MDW
-
YYZ
8h 01m
1 stop
C$ 323WestJet
Mon, 2 Mar - Fri, 6 Mar
WestJet Logo
12:11 p.m. - 5:37 p.m.
YYZ
-
MDW
6h 26m
1 stop
WestJet Logo
1:49 p.m. - 11:11 p.m.
MDW
-
YYZ
8h 22m
1 stop
C$ 324WestJet
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 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montreal, at C$ 139 one-way and C$ 250 round-trip. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as C$ 257 in the last 3 days.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago Midway Airport is September, where tickets cost C$ 210 on average for one-way flights. On the other hand, the most expensive months are January and October, where the average cost of tickets from Canada is C$ 757 and C$ 738 respectively. For return trips, the best month to travel is September with an average price of C$ 235.

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$ 187 one-way - C$ 262 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low seasonJanuary
Cheapest flightC$ 139
Best time to beat the crowds but there is an average 44% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Montreal 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 3 days, the cheapest flight deal to Chicago was found on the route from Montreal, at C$ 139 one-way and C$ 250 round-trip. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as C$ 257 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$ 280. The cheapest price found on KAYAK in the last 2 weeks cost C$ 141 and departed from Toronto Island Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Monday where tickets can be as cheap as C$ 266. On the other hand, the most expensive day to fly is Wednesday, where prices are C$ 292 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago Midway Airport is generally in the morning, when flights cost C$ 279 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$ 662.

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$ 225
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 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. 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 412 reviews
7.9Comfort
8.6Crew
7.5Food
6.9Entertainment
8.2Boarding
Airline reviews

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

6.0 GoodBeat, Jan 2026
YUL - YVR
Read more Porter Airlines reviews

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

Much roomer than air Canada! Great flight for the price. No complaints

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

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

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

The Turkish was good . I had a problem with air Transat terrible experience for me

I did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

Very good. A lot better experience then I expected for an economy flight.

It was very good but no tv but the experience was great

Thank you for making my first experience very enjoyable. You made it all very pleasant

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

The flight crew were very good, polite, and professional. Unfortunately, the rest of the experience left much to be desired. The food was extremely bland—almost tasteless. We chose the non vegetarian .The lasagna was just plain pasta with a tiny garnish and no seasoning. It felt like eating starch only, The bigger issue was with luggage and space. We boarded with three tickets, and while the seats in front of us were nearly empty, all the overhead compartments had already been filled by passengers boarding to the back. This left us and many others with no overhead storage for our carry-ons. Our bags couldn’t fit well under the seats either, which meant we lost the little legroom we had. The result was a horrible, cramped experience—sore knees, no space to stretch, and no way to rest or sleep comfortably. According to the crew this was a rather normal thing. It is obviously normal that people board with handbag and carry on but they should be only allowed to use their overhead compartment and under their seat not the way it is managed that all the spaces in the front of the plane being occupied by the people sitting way back in the plane.

Nice complete meal included and great services. Plus the plane was very clean.

Travelling to a place near Midway?

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

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago