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Cheap flights from Ottawa to Chicago from $154

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 4/28. 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.
Porter Airlines Logo
6:50 am - 10:15 am
YOW
-
MDW
4h 25m
1 stop
Porter Airlines Logo
11:00 am - 4:44 pm
MDW
-
YOW
4h 44m
1 stop
$240Porter Airlines
Thu, Apr 9 - Mon, Apr 13
Porter Airlines Logo
6:45 am - 10:05 am
YOW
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 am - 5:29 pm
MDW
-
YOW
5h 29m
1 stop
$267Porter Airlines
Wed, Mar 11 - Wed, Mar 18
Porter Airlines Logo
6:45 am - 10:15 am
YOW
-
MDW
4h 30m
1 stop
Porter Airlines Logo
12:35 pm - 5:29 pm
MDW
-
YOW
3h 54m
1 stop
$293Porter Airlines
Wed, Apr 8 - Sat, Apr 11
Multiple Airlines Logo
10:35 am - 10:45 pm
YOW
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
7:30 am - 5:25 pm
MDW
-
YOW
8h 55m
1 stop
$353Multiple Airlines
Thu, Mar 19 - Thu, Mar 26
Multiple Airlines Logo
4:20 pm - 8:53 pm
YOW
-
MDW
29h 33m
1 stop
Multiple Airlines Logo
7:30 am - 5:25 pm
MDW
-
YOW
8h 55m
1 stop
$354Multiple Airlines
Thu, Mar 19 - Thu, Mar 26
Multiple Airlines Logo
7:00 am - 6:37 pm
YOW
-
MDW
12h 37m
2 stops
Multiple Airlines Logo
7:30 am - 5:40 pm
MDW
-
YOW
9h 10m
1 stop
$358Multiple Airlines
Sat, May 2 - Tue, May 5
Porter Airlines Logo
7:00 am - 10:05 am
YOW
-
MDW
4h 05m
1 stop
Porter Airlines Logo
4:15 pm - 10:29 pm
MDW
-
YOW
5h 14m
1 stop
$362Porter Airlines
Fri, Mar 6 - Sun, Mar 8
Multiple Airlines Logo
10:35 am - 10:45 pm
YOW
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
7:30 am - 12:59 pm
MDW
-
YOW
28h 29m
2 stops
$364Multiple Airlines
Thu, Mar 19 - Thu, Mar 26
Multiple Airlines Logo
10:35 am - 10:45 pm
YOW
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
7:30 am - 4:44 pm
MDW
-
YOW
8h 14m
2 stops
$375Multiple Airlines
Thu, Mar 19 - Thu, Mar 26
Multiple Airlines Logo
11:00 am - 1:02 pm
YOW
-
MDW
27h 02m
2 stops
Multiple Airlines Logo
7:30 am - 5:25 pm
MDW
-
YOW
8h 55m
1 stop
$376Multiple Airlines
Mon, Mar 16 - Thu, Mar 19

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
Apr 9
YOW6:50 amOttawa
4h 25m
1 stop
MDW10:15 amChicago Midway
Apr 13
MDW11:00 amChicago Midway
4h 44m
1 stop
YOW4:44 pmOttawa
$240
Porter Airlines
Mar 11
YOW6:45 amOttawa
4h 20m
1 stop
MDW10:05 amChicago Midway
Mar 18
MDW11:00 amChicago Midway
5h 29m
1 stop
YOW5:29 pmOttawa
$267
Porter Airlines
Apr 8
YOW6:45 amOttawa
4h 30m
1 stop
MDW10:15 amChicago Midway
Apr 11
MDW12:35 pmChicago Midway
3h 54m
1 stop
YOW5:29 pmOttawa
$293

WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
May 7
YOW5:55 amOttawa
13h 19m
2 stops
MDW6:14 pmChicago Midway
May 11
MDW6:30 amChicago Midway
16h 50m
2 stops
YOW12:20 amOttawa
$427
WestJet
May 7
YOW5:55 amOttawa
13h 19m
2 stops
MDW6:14 pmChicago Midway
May 11
MDW6:30 amChicago Midway
16h 50m
2 stops
YOW12:20 amOttawa
$434
WestJet
May 7
YOW6:55 amOttawa
10h 17m
2 stops
MDW4:12 pmChicago Midway
May 11
MDW6:36 pmChicago Midway
21h 59m
2 stops
YOW5:35 pmOttawa
$447

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 February 22, 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

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/9

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Mon 4/13

11:00 am-4:44 pm

1 stop4h 44m

$240

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 3/11

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Wed 3/18

11:00 am-5:29 pm

1 stop5h 29m

$267

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 4/8

6:45 am-10:15 am

1 stop4h 30m

Chicago Midway

Sat 4/11

12:35 pm-5:29 pm

1 stop3h 54m

$293

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/19

10:35 am-10:45 pm

1 stop13h 10m

Chicago Midway

Thu 3/26

7:30 am-5:25 pm

1 stop8h 55m

$353

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/19

4:20 pm-8:53 pm

1 stop29h 33m

Chicago Midway

Thu 3/26

7:30 am-5:25 pm

1 stop8h 55m

$354

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 5/2

7:00 am-6:37 pm

2 stops12h 37m

Chicago Midway

Tue 5/5

7:30 am-5:40 pm

1 stop9h 10m

$358

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/6

7:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Sun 3/8

4:15 pm-10:29 pm

1 stop5h 14m

$362

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/19

10:35 am-10:45 pm

1 stop13h 10m

Chicago Midway

Thu 3/26

7:30 am-12:59 pm

2 stops28h 29m

$364

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/19

10:35 am-10:45 pm

1 stop13h 10m

Chicago Midway

Thu 3/26

7:30 am-4:44 pm

2 stops8h 14m

$375

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/16

11:00 am-1:02 pm

2 stops27h 02m

Chicago Midway

Thu 3/19

7:30 am-5:25 pm

1 stop8h 55m

$376

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 05m

Direct flights

None
The fastest flight from Ottawa to Chicago Midway Airport takes 4h 05m
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
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.

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