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Cheap flights from Ottawa to Chicago from $106

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 12/5. 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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Porter Airlines Logo
7:00 am - 10:05 amYOW-MDW
4h 05m1 stop
Porter Airlines Logo
11:00 am - 5:29 pmMDW-YOW
5h 29m1 stop
$190Porter Airlines
Find Deal
Mon, Jan 19 - Tue, Jan 20
Porter Airlines Logo
7:00 am - 10:05 amYOW-MDW
4h 05m1 stop
Porter Airlines Logo
11:00 am - 5:29 pmMDW-YOW
5h 29m1 stop
$229Porter Airlines
Find Deal
Mon, Jan 19 - Tue, Jan 20
Porter Airlines Logo
7:00 am - 10:05 amYOW-MDW
4h 05m1 stop
Porter Airlines Logo
11:00 am - 5:29 pmMDW-YOW
5h 29m1 stop
$240Porter Airlines
Find Deal
Wed, Jan 28 - Tue, Feb 3
Porter Airlines Logo
7:00 am - 10:05 amYOW-MDW
4h 05m1 stop
Porter Airlines Logo
4:15 pm - 10:29 pmMDW-YOW
5h 14m1 stop
$245Porter Airlines
Find Deal
Tue, Feb 17 - Sun, Feb 22
Porter Airlines Logo
6:50 am - 10:05 amYOW-MDW
4h 15m1 stop
Porter Airlines Logo
4:15 pm - 8:54 pmMDW-YOW
3h 39m1 stop
$257Porter Airlines
Find Deal
Fri, Dec 5 - Fri, Dec 5
Porter Airlines Logo
6:50 am - 10:05 amYOW-MDW
4h 15m1 stop
Porter Airlines Logo
11:00 am - 5:29 pmMDW-YOW
5h 29m1 stop
$287Porter Airlines
Find Deal
Thu, Feb 26 - Mon, Mar 2
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
$311Porter Airlines
Find Deal
Thu, Mar 19 - Mon, Mar 23
Porter Airlines Logo
6:50 am - 10:05 amYOW-MDW
4h 15m1 stop
Porter Airlines Logo
4:15 pm - 8:54 pmMDW-YOW
3h 39m1 stop
$313Porter Airlines
Find Deal
Wed, Dec 10 - Thu, Dec 18
Multiple Airlines Logo
3:55 pm - 11:55 pmYOW-MDW
9h 00m1 stop
Multiple Airlines Logo
6:26 pm - 11:29 amMDW-YOW
16h 03m2 stops
$331Multiple Airlines
Find Deal
Tue, Nov 11 - Thu, Nov 13
Multiple Airlines Logo
6:50 am - 10:05 amYOW-MDW
4h 15m1 stop
Multiple Airlines Logo
11:00 am - 8:54 pmMDW-YOW
8h 54m1 stop
$332Multiple Airlines
Find Deal
Thu, Feb 26 - Mon, Mar 2

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
Jan 19
YOW7:00 amOttawa
4h 05m
1 stop
MDW10:05 amChicago Midway
Jan 20
MDW11:00 amChicago Midway
5h 29m
1 stop
YOW5:29 pmOttawa
$190
Find similar
Porter Airlines
Jan 19
YOW7:00 amOttawa
4h 05m
1 stop
MDW10:05 amChicago Midway
Jan 20
MDW11:00 amChicago Midway
5h 29m
1 stop
YOW5:29 pmOttawa
$229
Find similar
Porter Airlines
Jan 28
YOW7:00 amOttawa
4h 05m
1 stop
MDW10:05 amChicago Midway
Feb 3
MDW11:00 amChicago Midway
5h 29m
1 stop
YOW5:29 pmOttawa
$240
Find similar

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 50m
2 stops
MDW10:30 amChicago Midway
Nov 10
MDW10:47 amChicago Midway
12h 55m
2 stops
YOW12:42 amOttawa
$746
Find similar
WestJet
Nov 3
YOW7:15 pmOttawa
15h 30m
2 stops
MDW9:45 amChicago Midway
Nov 6
MDW10:40 amChicago Midway
13h 02m
2 stops
YOW12:42 amOttawa
$774
Find similar
WestJet
Nov 3
YOW7:15 pmOttawa
15h 30m
2 stops
MDW9:45 amChicago Midway
Nov 6
MDW10:40 amChicago Midway
13h 02m
2 stops
YOW12:42 amOttawa
$819
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 832,500 searches. Data last updated October 30, 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

Mon 1/19

7:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Tue 1/20

11:00 am-5:29 pm

1 stop5h 29m

$190

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 1/19

7:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Tue 1/20

11:00 am-5:29 pm

1 stop5h 29m

$229

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 1/28

7:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Tue 2/3

11:00 am-5:29 pm

1 stop5h 29m

$240

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 2/17

7:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Sun 2/22

4:15 pm-10:29 pm

1 stop5h 14m

$245

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 12/5

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Fri 12/5

4:15 pm-8:54 pm

1 stop3h 39m

$257

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 2/26

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 3/2

11:00 am-5:29 pm

1 stop5h 29m

$287

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/19

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Mon 3/23

4:15 pm-10:29 pm

1 stop5h 14m

$311

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 12/10

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Thu 12/18

4:15 pm-8:54 pm

1 stop3h 39m

$313

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 11/11

3:55 pm-11:55 pm

1 stop9h 00m

Chicago Midway

Thu 11/13

6:26 pm-11:29 am

2 stops16h 03m

$331

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 2/26

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 3/2

11:00 am-8:54 pm

1 stop8h 54m

$332

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?

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.
Search flight deals

  • 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 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 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
Portage
Lansing
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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