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Cheap flights from Ottawa to Chicago Midway Airport from C$ 329

YOW — MDW
19 Nov — 26 Nov1
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

Sat 14/115:30 a.m. -
3 stops19h 17m
Tue 17/116:08 a.m. -
3 stops14h 54m
Deal found 16/10C$ 853
Sun 22/113:30 p.m. -
2 stops17h 44m
Mon 30/118:42 p.m. -
1 stop19h 03m
Deal found 15/10C$ 884
Mon 2/118:00 a.m. -
2 stops10h 47m
Wed 4/116:42 p.m. -
2 stops18h 50m
Deal found 15/10C$ 960
Mon 2/117:05 a.m. -
3 stops29h 17m
Thu 5/116:42 p.m. -
3 stops27h 52m
Deal found 19/10C$ 989
Sun 1/118:00 a.m. -
2 stops10h 47m
Wed 4/116:42 p.m. -
2 stops21h 03m
Deal found 16/10C$ 1,076
Thu 26/117:05 a.m. -
2 stops26h 07m
Sun 29/118:42 p.m. -
2 stops25h 58m
Deal found 16/10C$ 1,092
Sat 21/118:55 p.m. -
2 stops23h 52m
Mon 30/118:42 p.m. -
1 stop19h 03m
Deal found 15/10C$ 1,113

Find flight deals from Ottawa to Midway

Round-trip from

C$ 853

One-way from

C$ 329

Popular in

January

Cheapest in

February

Average price

C$ 1,142
14/11-17/11
  • 14/11-17/11
  • 6 total stops
  • 34h 11m total
  • Ottawa to Chicago
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2/12-31/12
  • 2/12-31/12
  • 2 total stops
  • 25h 52m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 8% potential price rise
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Cheapest flight prices on average. 4% potential price decrease (C$ 52 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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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

Wed 2/12

3:15 p.m.-4:07 p.m.

2 stops25h 52m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 329

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 4/12

3:15 p.m.-11:33 a.m.

2 stops21h 18m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 368

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 10/11

7:05 a.m.-11:47 p.m.

2 stops17h 42m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 375

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 20/11

5:30 a.m.-1:45 p.m.

3 stops33h 15m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 419

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 10/1

3:25 p.m.-4:26 p.m.

2 stops26h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 425

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 30/11

7:05 a.m.-11:33 a.m.

2 stops29h 28m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 429

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 16/1

10:35 a.m.-7:42 p.m.

2 stops34h 07m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 458
Quickest round-trip

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 15/3

12:40 p.m.-4:40 p.m.

1 stop5h 00m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 472

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 21/1

9:05 a.m.-11:46 p.m.

2 stops15h 41m

Chicago Midway

Sun 24/1

8:47 p.m.-4:44 p.m.

1 stop18h 57m

C$ 960

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 14/1

8:40 a.m.-7:42 p.m.

2 stops12h 02m

Chicago Midway

Sun 17/1

8:47 p.m.-4:44 p.m.

1 stop18h 57m

C$ 1,024

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/10

Showing 1-10 of 19 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.

  • 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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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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