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Cheap flights from Ottawa to Chicago Midway Airport from C$ 317

YOW — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Ottawa to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Ottawa to Midway

Thu 15/1010:40 a.m. -
1 stop4h 55m
Mon 19/103:20 p.m. -
1 stop3h 42m
Deal found 16/9C$ 590
Fri 16/105:55 p.m. -
1 stop18h 05m
Wed 21/1011:45 a.m. -
1 stop7h 17m
Deal found 14/9C$ 604
Sat 10/1010:40 a.m. -
1 stop4h 55m
Tue 13/103:20 p.m. -
1 stop25h 32m
Deal found 16/9C$ 611
Thu 15/105:55 p.m. -
1 stop18h 05m
Sun 18/103:20 p.m. -
1 stop25h 32m
Deal found 14/9C$ 614
Sat 10/1010:40 a.m. -
1 stop4h 55m
Sat 17/1011:45 a.m. -
1 stop6h 22m
Deal found 12/9C$ 618
Fri 16/108:00 a.m. -
1 stop4h 00m
Sun 18/103:20 p.m. -
1 stop5h 22m
Deal found 16/9C$ 633
Fri 16/108:00 a.m. -
1 stop4h 00m
Mon 19/103:20 p.m. -
1 stop3h 42m
Deal found 13/9C$ 635
Wed 21/108:00 a.m. -
1 stop4h 00m
Thu 22/103:20 p.m. -
1 stop5h 22m
Deal found 15/9C$ 637
Wed 7/108:00 a.m. -
1 stop4h 00m
Sun 11/103:20 p.m. -
1 stop3h 42m
Deal found 13/9C$ 643
Wed 14/1010:40 a.m. -
1 stop4h 55m
Wed 21/103:20 p.m. -
1 stop3h 42m
Deal found 16/9C$ 644
Sun 4/1010:40 a.m. -
1 stop4h 55m
Thu 8/103:20 p.m. -
1 stop5h 22m
Deal found 15/9C$ 724

Find flight deals from Ottawa to Midway

Round-trip from

C$ 590

One-way from

C$ 317

Popular in

January

Cheapest in

February

Average price

C$ 750
Porter Airlines
  • Porter Airlines
  • 15/10-19/10
  • 2 total stops
  • 8h 37m total
  • Ottawa to Chicago
Search Deals
13/11-31/12
  • 13/11-31/12
  • 3 total stops
  • 30h 02m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 53 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Ottawa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 3/11

7:00 a.m.-11:47 p.m.

3 stops17h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 351
Quickest round-trip

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 21/10

8:00 a.m.-11:00 a.m.

1 stop4h 00m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 370

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 8/10

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 372

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 3/10

9:15 a.m.-2:35 p.m.

1 stop6h 20m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 393

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 29/9

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 423

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 30/9

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 423

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 7/11

8:55 p.m.-5:47 p.m.

3 stops45h 52m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 449

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 23/9

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 523

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 14/10

8:55 p.m.-5:45 p.m.

3 stops21h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 586

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 16/10

5:55 p.m.-11:00 a.m.

1 stop18h 05m

Chicago Midway

Wed 21/10

11:45 a.m.-8:02 p.m.

1 stop7h 17m

C$ 604

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 20 resultsSorted by cheapest first
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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

Related info for your journey

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

    Located just 10.6 km from the city centre, Ottawa is the airport most travellers 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?

    There are many flights that can get you from Ottawa to Chicago Midway Airport in 18h 05m. Fly via Porter Airlines to get the fastest option. There are 1048 km between Ottawa and Chicago Midway Airport.

  • 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.

See more FAQs

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How does Cheapflights help users find flights from Ottawa to Midway?

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Why should you use Cheapflights to find cheap flight tickets from Ottawa to Midway?

Cheapflights simply makes it quick and affordable to book flights from Ottawa to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Ottawa to Midway with no change fees?

Certainly. Search results for flights to Midway from Ottawa shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Ottawa to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Ottawa today and book when prices fit your budget.

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