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Cheap flights from Ottawa to Chicago from C$ 242

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ottawa to Chicago departing on 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Ottawa to Chicago

Cheap round-trip flights

Logo
4:25 p.m. - 10:21 a.m.YOW-MDW
18h 56m1 stop
Logo
8:05 a.m. - 5:20 p.m.MDW-YOW
32h 15m2 stops
C$ 471
Find Deal
Fri, 3 Oct - Wed, 15 Oct
Logo
1:25 p.m. - 4:24 p.m.YOW-MDW
3h 59m1 stop
Logo
9:35 a.m. - 12:22 a.m.MDW-YOW
13h 47m1 stop
C$ 473
Find Deal
Wed, 1 Oct - Sat, 11 Oct
Logo
9:30 a.m. - 10:20 p.m.YOW-MDW
13h 50m1 stop
Logo
11:00 a.m. - 7:54 p.m.MDW-YOW
7h 54m1 stop
C$ 507
Find Deal
Fri, 7 Nov - Mon, 10 Nov
Logo
5:40 a.m. - 3:20 p.m.YOW-MDW
10h 40m1 stop
Logo
11:00 a.m. - 12:42 a.m.MDW-YOW
12h 42m1 stop
C$ 526
Find Deal
Tue, 2 Dec - Thu, 4 Dec
Porter Airlines Logo
9:35 a.m. - 4:24 p.m.YOW-MDW
7h 49m1 stop
Porter Airlines Logo
9:35 a.m. - 4:34 p.m.MDW-YOW
5h 59m1 stop
C$ 532Porter Airlines
Find Deal
Thu, 9 Oct - Sun, 12 Oct
Logo
5:40 a.m. - 3:20 p.m.YOW-MDW
10h 40m1 stop
Logo
2:15 p.m. - 9:24 a.m.MDW-YOW
18h 09m2 stops
C$ 541
Find Deal
Tue, 2 Dec - Thu, 4 Dec
WestJet Logo
5:40 a.m. - 9:40 a.m.YOW-MDW
29h 00m2 stops
WestJet Logo
10:47 a.m. - 12:42 a.m.MDW-YOW
12h 55m2 stops
C$ 584WestJet
Find Deal
Fri, 7 Nov - Mon, 10 Nov
WestJet Logo
5:40 a.m. - 9:54 a.m.YOW-MDW
29h 14m2 stops
WestJet Logo
10:49 a.m. - 12:42 a.m.MDW-YOW
12h 53m2 stops
C$ 603WestJet
Find Deal
Mon, 1 Dec - Wed, 3 Dec
Porter Airlines Logo
12:10 p.m. - 3:20 p.m.YOW-MDW
4h 10m1 stop
Porter Airlines Logo
4:15 p.m. - 10:29 p.m.MDW-YOW
5h 14m1 stop
C$ 645Porter Airlines
Find Deal
Mon, 10 Nov - Sun, 16 Nov
Delta Logo
5:55 a.m. - 6:35 p.m.YOW-MDW
13h 40m2 stops
Delta Logo
9:35 a.m. - 12:22 a.m.MDW-YOW
13h 47m2 stops
C$ 1,554Delta
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Thu, 2 Oct - Mon, 6 Oct

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
9 Oct
YOW9:35 a.m.Ottawa
7h 49m
1 stop
MDW4:24 p.m.Chicago Midway
12 Oct
MDW9:35 a.m.Chicago Midway
5h 59m
1 stop
YOW4:34 p.m.Ottawa
C$ 532
Find similar
Porter Airlines
10 Nov
YOW12:10 p.m.Ottawa
4h 10m
1 stop
MDW3:20 p.m.Chicago Midway
16 Nov
MDW4:15 p.m.Chicago Midway
5h 14m
1 stop
YOW10:29 p.m.Ottawa
C$ 645
Find similar
Porter Airlines
8 Jan
YOW6:50 a.m.Ottawa
4h 15m
1 stop
MDW10:05 a.m.Chicago Midway
11 Jan
MDW4:15 p.m.Chicago Midway
5h 14m
1 stop
YOW10:29 p.m.Ottawa
C$ 669
Find similar

WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
7 Nov
YOW5:40 a.m.Ottawa
29h 00m
2 stops
MDW9:40 a.m.Chicago Midway
10 Nov
MDW10:47 a.m.Chicago Midway
12h 55m
2 stops
YOW12:42 a.m.Ottawa
C$ 584
Find similar
WestJet
1 Dec
YOW5:40 a.m.Ottawa
29h 14m
2 stops
MDW9:54 a.m.Chicago Midway
3 Dec
MDW10:49 a.m.Chicago Midway
12h 53m
2 stops
YOW12:42 a.m.Ottawa
C$ 603
Find similar
WestJet
3 Oct
YOW5:55 a.m.Ottawa
32h 08m
2 stops
MDW1:03 p.m.Chicago Midway
15 Oct
MDW12:48 p.m.Chicago Midway
10h 34m
2 stops
YOW12:22 a.m.Ottawa
C$ 652
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Ottawa to Chicago Midway Airport 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, momondo users made 96,600 searches. Data last updated 15 September 2025.
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

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/10

4:25 p.m.-10:21 a.m.

1 stop18h 56m

Chicago Midway

Wed 15/10

8:05 a.m.-5:20 p.m.

2 stops32h 15m

C$ 471

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 1/10

1:25 p.m.-4:24 p.m.

1 stop3h 59m

Chicago Midway

Sat 11/10

9:35 a.m.-12:22 a.m.

1 stop13h 47m

C$ 473

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/11

9:30 a.m.-10:20 p.m.

1 stop13h 50m

Chicago Midway

Mon 10/11

11:00 a.m.-7:54 p.m.

1 stop7h 54m

C$ 507

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 2/12

5:40 a.m.-3:20 p.m.

1 stop10h 40m

Chicago Midway

Thu 4/12

11:00 a.m.-12:42 a.m.

1 stop12h 42m

C$ 526

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 9/10

9:35 a.m.-4:24 p.m.

1 stop7h 49m

Chicago Midway

Sun 12/10

9:35 a.m.-4:34 p.m.

1 stop5h 59m

C$ 532

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 2/12

5:40 a.m.-3:20 p.m.

1 stop10h 40m

Chicago Midway

Thu 4/12

2:15 p.m.-9:24 a.m.

2 stops18h 09m

C$ 541

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/11

5:40 a.m.-9:40 a.m.

2 stops29h 00m

Chicago Midway

Mon 10/11

10:47 a.m.-12:42 a.m.

2 stops12h 55m

C$ 584

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 1/12

5:40 a.m.-9:54 a.m.

2 stops29h 14m

Chicago Midway

Wed 3/12

10:49 a.m.-12:42 a.m.

2 stops12h 53m

C$ 603

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 10/11

12:10 p.m.-3:20 p.m.

1 stop4h 10m

Chicago Midway

Sun 16/11

4:15 p.m.-10:29 p.m.

1 stop5h 14m

C$ 645

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 2/10

5:55 a.m.-6:35 p.m.

2 stops13h 40m

Chicago Midway

Mon 6/10

9:35 a.m.-12:22 a.m.

2 stops13h 47m

C$ 1,554

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Ottawa to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

In general, December is the cheapest month to fly from Ottawa to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 418. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Ottawa during the month July is also very affordable. Most momondo users find prices during this month for around C$ 440.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Sunday when prices can be found for as low as C$ 491. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Ottawa because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 700.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Ottawa to Chicago Midway Airport during this time can be as low as C$ 476. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 572.

When to book flights from Ottawa to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Ottawa to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Ottawa to Chicago Midway Airport (YOW to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Ottawa to Chicago Midway Airport

Direct flights

None
There are no direct flights from Ottawa to Chicago Midway Airport. There are no popular flight routes from Ottawa to Chicago Midway Airport.
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  • How far is Ottawa to Chicago Midway by plane?

    There are 1048.7 km between Ottawa and Chicago Midway. Flights usually cover this in 3h 59m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Ottawa Airport to Chicago Midway Airport?

    Prices for flights from Ottawa Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Ottawa Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Ottawa Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Ottawa Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Ottawa to Chicago Midway Airport?

Best airlines flying from Ottawa to Chicago Midway Airport

Compare and see reviews for airlines that fly from Ottawa to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 372Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ottawa to Chicago?

It is quick and easy to find Ottawa to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Ottawa to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Ottawa on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Ottawa to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Ottawa.

I’m not ready to book a flight from Ottawa to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Ottawa. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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