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Cheap flights from Ottawa to Chicago from C$ 182

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 28/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.YOW-MDW
4h 05m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 265Porter Airlines
Find Deal
lun., 19 janv. - mar., 20 janv.
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.YOW-MDW
4h 05m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 320Porter Airlines
Find Deal
lun., 19 janv. - mar., 20 janv.
Porter Airlines Logo
12:10 p.m. - 3:20 p.m.YOW-MDW
4h 10m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 387Porter Airlines
Find Deal
lun., 15 déc. - ven., 16 janv.
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.YOW-MDW
4h 15m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 401Porter Airlines
Find Deal
jeu., 26 févr. - lun., 2 mars
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$ 434Porter Airlines
Find Deal
jeu., 19 mars - lun., 23 mars
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.YOW-MDW
4h 15m1 stop
Porter Airlines Logo
4:15 p.m. - 8:54 p.m.MDW-YOW
3h 39m1 stop
C$ 437Porter Airlines
Find Deal
mer., 10 déc. - jeu., 18 déc.
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.YOW-MDW
4h 15m1 stop
Porter Airlines Logo
12:45 p.m. - 5:29 p.m.MDW-YOW
3h 44m1 stop
C$ 440Porter Airlines
Find Deal
mar., 2 déc. - sam., 6 déc.
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.YOW-MDW
4h 15m1 stop
Porter Airlines Logo
12:45 p.m. - 5:29 p.m.MDW-YOW
3h 44m1 stop
C$ 443Porter Airlines
Find Deal
lun., 1 déc. - sam., 6 déc.
Multiple Airlines Logo
6:50 a.m. - 10:05 a.m.YOW-MDW
4h 15m1 stop
Multiple Airlines Logo
11:00 a.m. - 8:54 p.m.MDW-YOW
8h 54m1 stop
C$ 464Multiple Airlines
Find Deal
jeu., 26 févr. - lun., 2 mars
Multiple Airlines Logo
6:50 a.m. - 1:01 p.m.YOW-MDW
7h 11m2 stops
Multiple Airlines Logo
11:00 a.m. - 12:42 a.m.MDW-YOW
12h 42m1 stop
C$ 486Multiple Airlines
Find Deal
jeu., 4 déc. - lun., 8 déc.

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
19 Jan
YOW7:00 a.m.Ottawa
4h 05m
1 stop
MDW10:05 a.m.Chicago Midway
20 Jan
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 265
Find similar
Porter Airlines
19 Jan
YOW7:00 a.m.Ottawa
4h 05m
1 stop
MDW10:05 a.m.Chicago Midway
20 Jan
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 320
Find similar
Porter Airlines
15 Dec
YOW12:10 p.m.Ottawa
4h 10m
1 stop
MDW3:20 p.m.Chicago Midway
16 Jan
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 387
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 50m
2 stops
MDW10:30 a.m.Chicago Midway
10 Nov
MDW10:47 a.m.Chicago Midway
12h 55m
2 stops
YOW12:42 a.m.Ottawa
C$ 1,042
Find similar
WestJet
3 Nov
YOW7:15 p.m.Ottawa
15h 30m
2 stops
MDW9:45 a.m.Chicago Midway
6 Nov
MDW10:40 a.m.Chicago Midway
13h 02m
2 stops
YOW12:42 a.m.Ottawa
C$ 1,081
Find similar
WestJet
3 Nov
YOW7:15 p.m.Ottawa
15h 30m
2 stops
MDW9:45 a.m.Chicago Midway
6 Nov
MDW10:40 a.m.Chicago Midway
13h 02m
2 stops
YOW12:42 a.m.Ottawa
C$ 1,144
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 30 octobre 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

lun. 19/1

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

mar. 20/1

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 265

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

lun. 19/1

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

mar. 20/1

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 320

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

lun. 15/12

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

1 stop4h 10m

Chicago Midway

ven. 16/1

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 387

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

jeu. 26/2

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

lun. 2/3

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 401

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

jeu. 19/3

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

1 stop4h 10m

Chicago Midway

lun. 23/3

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

1 stop5h 14m

C$ 434

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

mer. 10/12

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

jeu. 18/12

4:15 p.m.-8:54 p.m.

1 stop3h 39m

C$ 437

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

mar. 2/12

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

sam. 6/12

12:45 p.m.-5:29 p.m.

1 stop3h 44m

C$ 440

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

lun. 1/12

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

sam. 6/12

12:45 p.m.-5:29 p.m.

1 stop3h 44m

C$ 443

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

jeu. 26/2

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

lun. 2/3

11:00 a.m.-8:54 p.m.

1 stop8h 54m

C$ 464

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

jeu. 4/12

6:50 a.m.-1:01 p.m.

2 stops7h 11m

Chicago Midway

lun. 8/12

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

1 stop12h 42m

C$ 486

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 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$ 495. 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$ 706.

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$ 481. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 577.

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 4h 05m, 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$ 375Free CancellationRating
8.0
384 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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