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$156+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/26. 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.
Mon 4/2712:10 pm
YOW
-
MDW
1 stop4h 10m
Porter Airlines
Thu 4/3011:00 am
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 1/26$275
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/236:45 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Wed 3/2511:00 am
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 1/27$322
This Trip.com deal was found by Cheapflights users on 1/27. 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 2/276:50 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Sun 3/14:15 pm
MDW
-
YOW
1 stop5h 14m
Porter Airlines
Deal found 1/27$361
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/279:30 am
YOW
-
MDW
2 stops13h 49m
Multiple Airlines
Thu 4/307:30 am
MDW
-
YOW
1 stop8h 55m
Multiple Airlines
Deal found 1/27$362
This FlightHub deal was found by Cheapflights users on 1/27. 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 4/66:50 am
YOW
-
MDW
1 stop4h 15m
Porter Airlines
Fri 4/104:15 pm
MDW
-
YOW
1 stop3h 39m
Porter Airlines
Deal found 1/27$368
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/155:55 am
YOW
-
MDW
1 stop11h 55m
Multiple Airlines
Tue 5/197:30 am
MDW
-
YOW
1 stop28h 00m
Multiple Airlines
Deal found 1/28$377
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/108:40 am
YOW
-
MDW
1 stop7h 40m
Multiple Airlines
Mon 4/139:04 pm
MDW
-
YOW
1 stop19h 09m
Multiple Airlines
Deal found 1/28$379
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 5/166:25 pm
YOW
-
MDW
1 stop16h 15m
Multiple Airlines
Tue 5/1910:25 am
MDW
-
YOW
1 stop12h 55m
Multiple Airlines
Deal found 1/28$382
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/234:20 pm
YOW
-
MDW
2 stops21h 42m
Multiple Airlines
Wed 3/2511:00 am
MDW
-
YOW
1 stop5h 29m
Multiple Airlines
Deal found 1/27$397

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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(Mytrip)

One-way from

$156
(Trip.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 29, 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

Mon 4/27

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Thu 4/30

11:00 am-5:29 pm

1 stop5h 29m

$275

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/23

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Wed 3/25

11:00 am-5:29 pm

1 stop5h 29m

$322

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 4/27

9:30 am-10:19 pm

2 stops13h 49m

Chicago Midway

Thu 4/30

7:30 am-5:25 pm

1 stop8h 55m

$362

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 4/6

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Fri 4/10

4:15 pm-8:54 pm

1 stop3h 39m

$368

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 4/10

8:40 am-3:20 pm

1 stop7h 40m

Chicago Midway

Mon 4/13

9:04 pm-5:13 pm

1 stop19h 09m

$379

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 5/16

6:25 pm-9:40 am

1 stop16h 15m

Chicago Midway

Tue 5/19

10:25 am-12:20 am

1 stop12h 55m

$382

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/23

4:20 pm-1:02 pm

2 stops21h 42m

Chicago Midway

Wed 3/25

11:00 am-5:29 pm

1 stop5h 29m

$397

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 3/1

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Fri 3/6

11:00 am-6:24 pm

1 stop6h 24m

$400

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 4/4

8:40 am-11:50 am

1 stop4h 10m

Chicago Midway

Mon 4/6

4:15 pm-10:29 pm

1 stop5h 14m

$400

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 3/1

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Sat 3/7

12:45 pm-5:29 pm

1 stop3h 44m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 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 10m. 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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