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Cheap flights from Ottawa to Chicago from $175

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 10/1. 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 pm - 10:21 amYOW-MDW
18h 56m1 stop
Logo
8:05 am - 5:20 pmMDW-YOW
32h 15m2 stops
$340
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Fri, Oct 3 - Wed, Oct 15
Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Logo
9:35 am - 12:22 amMDW-YOW
13h 47m1 stop
$342
Find Deal
Wed, Oct 1 - Sat, Oct 11
Logo
9:30 am - 10:20 pmYOW-MDW
13h 50m1 stop
Logo
11:00 am - 7:54 pmMDW-YOW
7h 54m1 stop
$366
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Fri, Nov 7 - Mon, Nov 10
Logo
5:40 am - 3:20 pmYOW-MDW
10h 40m1 stop
Logo
11:00 am - 12:42 amMDW-YOW
12h 42m1 stop
$380
Find Deal
Tue, Dec 2 - Thu, Dec 4
Porter Airlines Logo
9:35 am - 4:24 pmYOW-MDW
7h 49m1 stop
Porter Airlines Logo
9:35 am - 4:34 pmMDW-YOW
5h 59m1 stop
$384Porter Airlines
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Thu, Oct 9 - Sun, Oct 12
Logo
5:40 am - 3:20 pmYOW-MDW
10h 40m1 stop
Logo
2:15 pm - 9:24 amMDW-YOW
18h 09m2 stops
$391
Find Deal
Tue, Dec 2 - Thu, Dec 4
WestJet Logo
5:40 am - 9:40 amYOW-MDW
29h 00m2 stops
WestJet Logo
10:47 am - 12:42 amMDW-YOW
12h 55m2 stops
$422WestJet
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Fri, Nov 7 - Mon, Nov 10
WestJet Logo
5:40 am - 9:54 amYOW-MDW
29h 14m2 stops
WestJet Logo
10:49 am - 12:42 amMDW-YOW
12h 53m2 stops
$436WestJet
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Mon, Dec 1 - Wed, Dec 3
Porter Airlines Logo
12:10 pm - 3:20 pmYOW-MDW
4h 10m1 stop
Porter Airlines Logo
4:15 pm - 10:29 pmMDW-YOW
5h 14m1 stop
$466Porter Airlines
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Mon, Nov 10 - Sun, Nov 16
Delta Logo
5:55 am - 6:35 pmYOW-MDW
13h 40m2 stops
Delta Logo
9:35 am - 12:22 amMDW-YOW
13h 47m2 stops
$1,123Delta
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Thu, Oct 2 - Mon, Oct 6

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
Oct 9
YOW9:35 amOttawa
7h 49m
1 stop
MDW4:24 pmChicago Midway
Oct 12
MDW9:35 amChicago Midway
5h 59m
1 stop
YOW4:34 pmOttawa
$384
Find similar
Porter Airlines
Nov 10
YOW12:10 pmOttawa
4h 10m
1 stop
MDW3:20 pmChicago Midway
Nov 16
MDW4:15 pmChicago Midway
5h 14m
1 stop
YOW10:29 pmOttawa
$466
Find similar
Porter Airlines
Nov 21
YOW6:50 amOttawa
4h 15m
1 stop
MDW10:05 amChicago Midway
Nov 30
MDW4:15 pmChicago Midway
3h 39m
1 stop
YOW8:54 pmOttawa
$482
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WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
Nov 7
YOW5:40 amOttawa
29h 00m
2 stops
MDW9:40 amChicago Midway
Nov 10
MDW10:47 amChicago Midway
12h 55m
2 stops
YOW12:42 amOttawa
$422
Find similar
WestJet
Dec 1
YOW5:40 amOttawa
29h 14m
2 stops
MDW9:54 amChicago Midway
Dec 3
MDW10:49 amChicago Midway
12h 53m
2 stops
YOW12:42 amOttawa
$436
Find similar
WestJet
Oct 3
YOW5:55 amOttawa
32h 08m
2 stops
MDW1:03 pmChicago Midway
Oct 15
MDW12:48 pmChicago Midway
10h 34m
2 stops
YOW12:22 amOttawa
$471
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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 832,500 searches. Data last updated September 15, 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 10/3

4:25 pm-10:21 am

1 stop18h 56m

Chicago Midway

Wed 10/15

8:05 am-5:20 pm

2 stops32h 15m

$340

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 10/1

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Sat 10/11

9:35 am-12:22 am

1 stop13h 47m

$342

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 11/7

9:30 am-10:20 pm

1 stop13h 50m

Chicago Midway

Mon 11/10

11:00 am-7:54 pm

1 stop7h 54m

$366

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 12/2

5:40 am-3:20 pm

1 stop10h 40m

Chicago Midway

Thu 12/4

11:00 am-12:42 am

1 stop12h 42m

$380

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 10/9

9:35 am-4:24 pm

1 stop7h 49m

Chicago Midway

Sun 10/12

9:35 am-4:34 pm

1 stop5h 59m

$384

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 12/2

5:40 am-3:20 pm

1 stop10h 40m

Chicago Midway

Thu 12/4

2:15 pm-9:24 am

2 stops18h 09m

$391

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 11/7

5:40 am-9:40 am

2 stops29h 00m

Chicago Midway

Mon 11/10

10:47 am-12:42 am

2 stops12h 55m

$422

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 12/1

5:40 am-9:54 am

2 stops29h 14m

Chicago Midway

Wed 12/3

10:49 am-12:42 am

2 stops12h 53m

$436

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 11/10

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Sun 11/16

4:15 pm-10:29 pm

1 stop5h 14m

$466

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 10/2

5:55 am-6:35 pm

2 stops13h 40m

Chicago Midway

Mon 10/6

9:35 am-12:22 am

2 stops13h 47m

$1,123

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?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Ottawa, with most prices found around $302. 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 $318.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Ottawa. The lowest ticket price found for a Thursday departure recently was $278. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Ottawa because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $472.

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

Flying to Chicago Midway Airport from Ottawa in the morning is the least expensive time of day to depart. momondo users have found prices as low as $278 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $435. Of course, these prices can vary depending on the time of year and what airport you fly to.

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?

    A flight from Ottawa to Chicago Midway will travel around 651.6 mi. 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 are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Ottawa Airport to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Ottawa to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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 can track prices for Ottawa to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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