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Cheap flights from Ottawa to Chicago from $193

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 4/29. 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
0 bags

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Find the cheapest flights from Ottawa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:00 am - 7:31 pm
YOW
-
MDW
13h 31m
2 stops
Multiple Airlines Logo
7:30 am - 1:15 pm
MDW
-
YOW
28h 45m
1 stop
$338Multiple Airlines
wt., kwi 21 - ndz., kwi 26
Multiple Airlines Logo
6:35 pm - 9:45 am
YOW
-
MDW
16h 10m
1 stop
Multiple Airlines Logo
3:20 pm - 12:20 am
MDW
-
YOW
8h 00m
1 stop
$344Multiple Airlines
czw., maj 28 - wt., cze 2
Multiple Airlines Logo
6:25 pm - 9:45 am
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:20 pm - 12:20 am
MDW
-
YOW
8h 00m
1 stop
$345Multiple Airlines
sob., maj 30 - pt., cze 5
Multiple Airlines Logo
3:55 pm - 1:00 pm
YOW
-
MDW
22h 05m
1 stop
Multiple Airlines Logo
7:30 am - 1:15 pm
MDW
-
YOW
28h 45m
1 stop
$346Multiple Airlines
wt., kwi 21 - ndz., kwi 26
Multiple Airlines Logo
6:35 pm - 9:45 am
YOW
-
MDW
16h 10m
1 stop
Multiple Airlines Logo
3:20 pm - 12:20 am
MDW
-
YOW
8h 00m
1 stop
$347Multiple Airlines
czw., maj 28 - czw., cze 4
Multiple Airlines Logo
6:25 pm - 9:45 am
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:20 pm - 12:20 am
MDW
-
YOW
8h 00m
1 stop
$348Multiple Airlines
sob., maj 30 - czw., cze 4
Multiple Airlines Logo
6:35 pm - 9:45 am
YOW
-
MDW
16h 10m
1 stop
Multiple Airlines Logo
3:20 pm - 12:20 am
MDW
-
YOW
8h 00m
1 stop
$363Multiple Airlines
czw., maj 28 - czw., cze 4
Multiple Airlines Logo
6:25 pm - 9:45 am
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:20 pm - 12:20 am
MDW
-
YOW
8h 00m
1 stop
$365Multiple Airlines
sob., maj 9 - ndz., maj 10
Multiple Airlines Logo
6:55 am - 2:35 pm
YOW
-
MDW
8h 40m
1 stop
Multiple Airlines Logo
10:30 am - 12:20 am
MDW
-
YOW
12h 50m
1 stop
$367Multiple Airlines
wt., maj 5 - pt., maj 8
Multiple Airlines Logo
3:55 pm - 1:00 pm
YOW
-
MDW
22h 05m
1 stop
Multiple Airlines Logo
7:30 am - 5:25 pm
MDW
-
YOW
8h 55m
1 stop
$372Multiple Airlines
pon., kwi 20 - pt., kwi 24

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
May 6
YOW8:00 amOttawa
7h 35m
1 stop
MDW2:35 pmChicago Midway
May 10
MDW3:20 pmChicago Midway
5h 24m
1 stop
YOW9:44 pmOttawa
$384
Porter Airlines
Apr 30
YOW6:50 amOttawa
4h 25m
1 stop
MDW10:15 amChicago Midway
May 7
MDW10:30 amChicago Midway
8h 34m
1 stop
YOW8:04 pmOttawa
$398
Porter Airlines
May 22
YOW11:00 amOttawa
23h 45m
1 stop
MDW9:45 amChicago Midway
May 29
MDW3:20 pmChicago Midway
17h 54m
1 stop
YOW10:14 amOttawa
$423

WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
Apr 24
YOW5:40 amOttawa
8h 03m
2 stops
MDW12:43 pmChicago Midway
Apr 26
MDW6:38 pmChicago Midway
28h 42m
2 stops
YOW12:20 amOttawa
$649
WestJet
Apr 20
YOW5:40 amOttawa
28h 07m
2 stops
MDW8:47 amChicago Midway
Apr 24
MDW10:41 amChicago Midway
12h 58m
2 stops
YOW12:39 amOttawa
$702
WestJet
Apr 17
YOW5:40 amOttawa
13h 18m
2 stops
MDW5:58 pmChicago Midway
Apr 20
MDW10:41 amChicago Midway
12h 58m
2 stops
YOW12:39 amOttawa
$849

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 Kwiecień 10, 2026.
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

Cheapest round-trip

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

wt. 4/21

7:00 am-7:31 pm

2 stops13h 31m

Chicago Midway

ndz. 4/26

7:30 am-1:15 pm

1 stop28h 45m

$338

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

czw. 5/28

6:35 pm-9:45 am

1 stop16h 10m

Chicago Midway

wt. 6/2

3:20 pm-12:20 am

1 stop8h 00m

$344

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

sob. 5/30

6:25 pm-9:45 am

1 stop16h 20m

Chicago Midway

pt. 6/5

3:20 pm-12:20 am

1 stop8h 00m

$345

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

wt. 4/21

3:55 pm-1:00 pm

1 stop22h 05m

Chicago Midway

ndz. 4/26

7:30 am-1:15 pm

1 stop28h 45m

$346

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

czw. 5/28

6:35 pm-9:45 am

1 stop16h 10m

Chicago Midway

czw. 6/4

3:20 pm-12:20 am

1 stop8h 00m

$347

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

sob. 5/30

6:25 pm-9:45 am

1 stop16h 20m

Chicago Midway

czw. 6/4

3:20 pm-12:20 am

1 stop8h 00m

$348

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

czw. 5/28

6:35 pm-9:45 am

1 stop16h 10m

Chicago Midway

czw. 6/4

3:20 pm-12:20 am

1 stop8h 00m

$363

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

sob. 5/9

6:25 pm-9:45 am

1 stop16h 20m

Chicago Midway

ndz. 5/10

3:20 pm-12:20 am

1 stop8h 00m

$365
Quickest round-trip

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

wt. 5/5

6:55 am-2:35 pm

1 stop8h 40m

Chicago Midway

pt. 5/8

10:30 am-12:20 am

1 stop12h 50m

$367

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

pon. 4/20

3:55 pm-1:00 pm

1 stop22h 05m

Chicago Midway

pt. 4/24

7:30 am-5:25 pm

1 stop8h 55m

$372

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 airline that flies from Ottawa to Chicago Midway?

Porter Airlines is the most popular carrier operating from Ottawa to Chicago Midway

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

Fastest flight time

4h 30m

Direct flights

None
The fastest flight from Ottawa to Chicago Midway Airport takes 4h 30m
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

Frequently asked questions about flying from Ottawa to Chicago Midway Airport

  • 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 30m, 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

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ndz. 5/10
ndz. 5/17
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