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Cheap flights from Ottawa to Chicago from $165

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 9/14. 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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Cheap round-trip flights

Porter Airlines Logo
11:00 am - 4:24 pmYOW-MDW
6h 24m1 stop
Porter Airlines Logo
9:35 am - 5:14 pmMDW-YOW
6h 39m1 stop
$289Porter Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Porter Airlines Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Porter Airlines Logo
9:35 am - 5:14 pmMDW-YOW
6h 39m1 stop
$292Porter Airlines
Find Deal
Wed, Sep 3 - Sun, Sep 7
Porter Airlines Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Porter Airlines Logo
9:35 am - 4:34 pmMDW-YOW
5h 59m1 stop
$309Porter Airlines
Find Deal
Tue, Sep 2 - Thu, Sep 11
Porter Airlines Logo
11:00 am - 4:24 pmYOW-MDW
6h 24m1 stop
Porter Airlines Logo
9:35 am - 4:34 pmMDW-YOW
5h 59m1 stop
$311Porter Airlines
Find Deal
Fri, Sep 19 - Mon, Sep 22
Logo
5:55 am - 4:24 pmYOW-MDW
11h 29m1 stop
Logo
9:35 am - 12:22 amMDW-YOW
13h 47m1 stop
$355
Find Deal
Thu, Aug 28 - Thu, Sep 4
Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Logo
9:35 am - 7:34 pmMDW-YOW
8h 59m1 stop
$455
Find Deal
Wed, Sep 3 - Sun, Sep 7
WestJet Logo
5:55 am - 5:37 pmYOW-MDW
12h 42m2 stops
WestJet Logo
9:15 am - 12:22 amMDW-YOW
14h 07m2 stops
$468WestJet
Find Deal
Wed, Sep 3 - Sun, Sep 7
WestJet Logo
5:55 am - 9:36 pmYOW-MDW
16h 41m2 stops
WestJet Logo
12:43 pm - 12:22 amMDW-YOW
10h 39m2 stops
$521WestJet
Find Deal
Fri, Sep 19 - Mon, Sep 22
Delta Logo
5:55 am - 12:28 pmYOW-MDW
7h 33m2 stops
Delta Logo
9:31 am - 12:22 amMDW-YOW
13h 51m2 stops
$718Delta
Find Deal
Wed, Sep 3 - Sun, Sep 7
Delta Logo
5:55 am - 6:35 pmYOW-MDW
13h 40m2 stops
Delta Logo
9:35 am - 12:22 amMDW-YOW
13h 47m2 stops
$770Delta
Find Deal
Fri, Sep 19 - Mon, Sep 22

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
Sep 4
YOW11:00 amOttawa
6h 24m
1 stop
MDW4:24 pmChicago Midway
Sep 7
MDW9:35 amChicago Midway
6h 39m
1 stop
YOW5:14 pmOttawa
$289
Find similar
Porter Airlines
Sep 3
YOW1:25 pmOttawa
3h 59m
1 stop
MDW4:24 pmChicago Midway
Sep 7
MDW9:35 amChicago Midway
6h 39m
1 stop
YOW5:14 pmOttawa
$292
Find similar
Porter Airlines
Sep 2
YOW1:25 pmOttawa
3h 59m
1 stop
MDW4:24 pmChicago Midway
Sep 11
MDW9:35 amChicago Midway
5h 59m
1 stop
YOW4:34 pmOttawa
$309
Find similar

Delta flights from Ottawa to Chicago Midway Airport

Our best Delta deals on Ottawa to Chicago Midway Airport flight tickets
Delta
Sep 3
YOW5:55 amOttawa
7h 33m
2 stops
MDW12:28 pmChicago Midway
Sep 7
MDW9:31 amChicago Midway
13h 51m
2 stops
YOW12:22 amOttawa
$718
Find similar
Delta
Sep 19
YOW5:55 amOttawa
13h 40m
2 stops
MDW6:35 pmChicago Midway
Sep 22
MDW9:35 amChicago Midway
13h 47m
2 stops
YOW12:22 amOttawa
$770
Find similar
Delta
Aug 18
YOW5:55 amOttawa
13h 42m
2 stops
MDW6:37 pmChicago Midway
Aug 20
MDW12:43 pmChicago Midway
10h 39m
2 stops
YOW12:22 amOttawa
$862
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 July 31, 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

Thu 9/4

11:00 am-4:24 pm

1 stop6h 24m

Chicago Midway

Sun 9/7

9:35 am-5:14 pm

1 stop6h 39m

$289

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 9/3

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Sun 9/7

9:35 am-5:14 pm

1 stop6h 39m

$292

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 9/2

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Thu 9/11

9:35 am-4:34 pm

1 stop5h 59m

$309

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/19

11:00 am-4:24 pm

1 stop6h 24m

Chicago Midway

Mon 9/22

9:35 am-4:34 pm

1 stop5h 59m

$311

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 8/28

5:55 am-4:24 pm

1 stop11h 29m

Chicago Midway

Thu 9/4

9:35 am-12:22 am

1 stop13h 47m

$355

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 9/3

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Sun 9/7

9:35 am-7:34 pm

1 stop8h 59m

$455

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 9/3

5:55 am-5:37 pm

2 stops12h 42m

Chicago Midway

Sun 9/7

9:15 am-12:22 am

2 stops14h 07m

$468

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/19

5:55 am-9:36 pm

2 stops16h 41m

Chicago Midway

Mon 9/22

12:43 pm-12:22 am

2 stops10h 39m

$521

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 9/3

5:55 am-12:28 pm

2 stops7h 33m

Chicago Midway

Sun 9/7

9:31 am-12:22 am

2 stops13h 51m

$718

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/19

5:55 am-6:35 pm

2 stops13h 40m

Chicago Midway

Mon 9/22

9:35 am-12:22 am

2 stops13h 47m

$770

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 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 February is also very affordable. Most momondo users find prices during this month for around $322.

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

Best Price Found

$165

Fastest flight time

3h 50m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Ottawa in the past 72 hours is $165. The best round-trip flight deal from Ottawa to Chicago Midway Airport found on momondo in the last 72 hours is $289.
The fastest flight from Ottawa to Chicago Midway Airport takes 3h 50m
There are no direct flights from Ottawa to Chicago Midway Airport. Popular non-direct route for this connection is Ottawa Airport - 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 3h 50m, 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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