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$185+ Cheap flights from Ottawa (YOW) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Ottawa to Midway

Cheapest flights from Ottawa to Midway
Explore the most affordable flight options available from Ottawa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/64:20 pm
YOW
-
MDW
2 stops17h 23m
Multiple Airlines
Tue 2/1011:05 am
MDW
-
YOW
1 stop12h 34m
Multiple Airlines
Deal found 1/19$377
This Trip.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:45 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Sun 3/224:15 pm
MDW
-
YOW
1 stop5h 14m
Porter Airlines
Deal found 1/20$391
This Trip.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:50 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Thu 2/2611:05 am
MDW
-
YOW
1 stop3h 39m
Porter Airlines
Deal found 1/20$392
This Mytrip deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:00 am
YOW
-
MDW
1 stop4h 05m
Porter Airlines
Wed 3/1111:00 am
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 1/19$396
This Justfly.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:50 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Sun 2/224:15 pm
MDW
-
YOW
1 stop3h 39m
Porter Airlines
Deal found 1/19$397
This FlightHub deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:55 am
YOW
-
MDW
2 stops7h 35m
WestJet
Mon 5/111:00 pm
MDW
-
YOW
2 stops27h 35m
WestJet
Deal found 1/19$400
This Kiwi.com deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:50 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Tue 2/2411:05 am
MDW
-
YOW
1 stop27h 39m
Porter Airlines
Deal found 1/19$412
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:45 am
YOW
-
MDW
1 stop4h 20m
Multiple Airlines
Tue 3/177:30 am
MDW
-
YOW
1 stop8h 55m
Multiple Airlines
Deal found 1/20$418
This FlightHub deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:35 pm
YOW
-
MDW
2 stops28h 54m
WestJet
Mon 5/46:34 pm
MDW
-
YOW
2 stops22h 01m
WestJet
Deal found 1/20$424
This FlightHub deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:40 am
YOW
-
MDW
2 stops13h 14m
WestJet
Sat 4/251:10 pm
MDW
-
YOW
2 stops27h 25m
WestJet
Deal found 1/20$426

Find flight deals from Ottawa to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Ottawa (YOW) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$377
(Kiwi.com)

One-way from

$185
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$825
Provider with most accurate pricing for Ottawa-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Ottawa-Chicago Midway flights.
Search Deals
From Ottawa to Chicago Midway
Search Deals
One-way flight from Ottawa to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Ottawa to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 20, 2026.
Use the filters below to find and compare flights from Ottawa to Chicago Midway Airport that are best for you.

Fly from

Ottawa

Fly to

Midway

Route

Depart

Return

Price

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 2/6

4:20 pm-8:43 am

2 stops17h 23m

Chicago Midway

Tue 2/10

11:05 am-12:39 am

1 stop12h 34m

$377

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/16

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Fri 3/20

11:00 am-5:29 pm

1 stop5h 29m

$392

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 3/4

7:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Wed 3/11

11:00 am-5:29 pm

1 stop5h 29m

$396

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 2/19

6:50 am-10:10 am

1 stop4h 20m

Chicago Midway

Sun 2/22

4:15 pm-8:54 pm

1 stop3h 39m

$397

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 5/8

5:55 am-12:30 pm

2 stops7h 35m

Chicago Midway

Mon 5/11

1:00 pm-5:35 pm

2 stops27h 35m

$400

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 2/20

6:50 am-10:10 am

1 stop4h 20m

Chicago Midway

Tue 2/24

11:05 am-3:44 pm

1 stop27h 39m

$412

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 5/1

6:35 pm-10:29 pm

2 stops28h 54m

Chicago Midway

Mon 5/4

6:34 pm-5:35 pm

2 stops22h 01m

$424

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 4/20

5:40 am-5:54 pm

2 stops13h 14m

Chicago Midway

Sat 4/25

1:10 pm-5:35 pm

2 stops27h 25m

$426

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 2/14

8:40 am-11:55 am

1 stop4h 15m

Chicago Midway

Sat 2/21

12:50 pm-5:39 pm

1 stop3h 49m

$427

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 2/22

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Fri 2/27

11:05 am-6:09 pm

1 stop6h 04m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 19 results
1
2
  • Most accurate provider: When it comes to deals on Ottawa-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Ottawa-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Ottawa-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Ottawa-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Ottawa-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Ottawa to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Ottawa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Ottawa to Chicago Midway Airport

What is the cheapest month to book a flight from Ottawa to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Ottawa to Chicago Midway Airport (average of $131). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of $490). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Ottawa to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Ottawa to Chicago Midway?

    Located just 6.6 mi from the city center, Ottawa is the airport most travelers will use when flying to Chicago Midway from Ottawa. Booking flights from Ottawa (YOW) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • How long is the flight from Ottawa to Chicago Midway Airport?

    Airlines like Porter Airlines fly from Ottawa to Chicago Midway Airport in about 4h 15m. The time it takes to get you to your destination can typically vary by up to . The distance from Ottawa to Chicago Midway Airport is about 651 mi.

  • Can I find deals for flights from Ottawa to Midway that include hotel bookings?

    Yes. In addition to deals on Ottawa to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Ottawa to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Ottawa to Midway.

  • Can I find deals for business class flights from Ottawa to Midway?

    Yes. Cheapflights offers flight deals from Ottawa to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Ottawa to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Ottawa to Chicago Midway Airport (average of $131). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of $490). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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