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Cheap flights from Ottawa to Chicago from C$ 220

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 13/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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 a.m. - 10:10 a.m.
YOW
-
MDW
4h 10m1 stop
Multiple Airlines Logo
1:00 p.m. - 11:58 p.m.
MDW
-
YOW
9h 58m1 stop
C$ 423Multiple Airlines
Thu, 5 Feb - Mon, 9 Feb
Multiple Airlines Logo
3:55 p.m. - 12:02 a.m.
YOW
-
MDW
9h 07m1 stop
Multiple Airlines Logo
8:22 a.m. - 12:25 a.m.
MDW
-
YOW
15h 03m2 stops
C$ 430Multiple Airlines
Thu, 15 Jan - Sat, 17 Jan
Multiple Airlines Logo
7:00 a.m. - 10:10 a.m.
YOW
-
MDW
4h 10m1 stop
Multiple Airlines Logo
1:00 p.m. - 11:58 p.m.
MDW
-
YOW
9h 58m1 stop
C$ 433Multiple Airlines
Fri, 6 Feb - Mon, 9 Feb
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.
YOW
-
MDW
4h 05m1 stop
Porter Airlines Logo
4:15 p.m. - 8:54 p.m.
MDW
-
YOW
3h 39m1 stop
C$ 439Porter Airlines
Fri, 6 Feb - Sun, 8 Feb
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.
YOW
-
MDW
4h 05m1 stop
Porter Airlines Logo
4:15 p.m. - 8:54 p.m.
MDW
-
YOW
3h 39m1 stop
C$ 442Porter Airlines
Fri, 6 Feb - Sun, 8 Feb
Multiple Airlines Logo
7:00 a.m. - 11:13 p.m.
YOW
-
MDW
17h 13m2 stops
Multiple Airlines Logo
4:15 p.m. - 7:59 a.m.
MDW
-
YOW
14h 44m1 stop
C$ 448Multiple Airlines
Sun, 1 Feb - Sun, 8 Feb
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.
YOW
-
MDW
4h 05m1 stop
Porter Airlines Logo
4:15 p.m. - 7:59 a.m.
MDW
-
YOW
14h 44m1 stop
C$ 452Porter Airlines
Thu, 5 Feb - Sun, 8 Feb
Multiple Airlines Logo
7:00 a.m. - 10:10 a.m.
YOW
-
MDW
4h 10m1 stop
Multiple Airlines Logo
1:00 p.m. - 11:58 p.m.
MDW
-
YOW
9h 58m1 stop
C$ 456Multiple Airlines
Fri, 30 Jan - Mon, 2 Feb
Multiple Airlines Logo
7:00 a.m. - 10:10 a.m.
YOW
-
MDW
4h 10m1 stop
Multiple Airlines Logo
1:00 p.m. - 11:58 p.m.
MDW
-
YOW
9h 58m1 stop
C$ 457Multiple Airlines
Thu, 29 Jan - Mon, 2 Feb
Porter Airlines Logo
8:40 a.m. - 3:20 p.m.
YOW
-
MDW
7h 40m1 stop
Porter Airlines Logo
11:00 a.m. - 6:09 p.m.
MDW
-
YOW
6h 09m1 stop
C$ 460Porter Airlines
Sun, 8 Feb - Wed, 18 Feb

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
6 Feb
YOW7:00 a.m.Ottawa
4h 05m
1 stop
MDW10:05 a.m.Chicago Midway
8 Feb
MDW4:15 p.m.Chicago Midway
3h 39m
1 stop
YOW8:54 p.m.Ottawa
C$ 439
Find similar
Porter Airlines
6 Feb
YOW7:00 a.m.Ottawa
4h 05m
1 stop
MDW10:05 a.m.Chicago Midway
8 Feb
MDW4:15 p.m.Chicago Midway
3h 39m
1 stop
YOW8:54 p.m.Ottawa
C$ 442
Find similar
Porter Airlines
5 Feb
YOW7:00 a.m.Ottawa
4h 05m
1 stop
MDW10:05 a.m.Chicago Midway
8 Feb
MDW4:15 p.m.Chicago Midway
14h 44m
1 stop
YOW7:59 a.m.Ottawa
C$ 452
Find similar

WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
19 Mar
YOW5:40 a.m.Ottawa
7h 49m
2 stops
MDW12:29 p.m.Chicago Midway
23 Mar
MDW6:34 p.m.Chicago Midway
29h 05m
2 stops
YOW12:39 a.m.Ottawa
C$ 585
Find similar
WestJet
9 Jan
YOW5:40 a.m.Ottawa
8h 08m
2 stops
MDW12:48 p.m.Chicago Midway
17 Jan
MDW9:32 a.m.Chicago Midway
14h 10m
2 stops
YOW12:42 a.m.Ottawa
C$ 858
Find similar
WestJet
9 Jan
YOW5:40 a.m.Ottawa
28h 12m
2 stops
MDW8:52 a.m.Chicago Midway
17 Jan
MDW9:32 a.m.Chicago Midway
14h 10m
2 stops
YOW12:42 a.m.Ottawa
C$ 873
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 96,600 searches. Data last updated 31 December 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 5/2

7:00 a.m.-10:10 a.m.

1 stop4h 10m

Chicago Midway

Mon 9/2

1:00 p.m.-11:58 p.m.

1 stop9h 58m

C$ 423

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 15/1

3:55 p.m.-12:02 a.m.

1 stop9h 07m

Chicago Midway

Sat 17/1

8:22 a.m.-12:25 a.m.

2 stops15h 03m

C$ 430

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/2

7:00 a.m.-10:10 a.m.

1 stop4h 10m

Chicago Midway

Mon 9/2

1:00 p.m.-11:58 p.m.

1 stop9h 58m

C$ 433

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/2

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Sun 8/2

4:15 p.m.-8:54 p.m.

1 stop3h 39m

C$ 439

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/2

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Sun 8/2

4:15 p.m.-8:54 p.m.

1 stop3h 39m

C$ 442

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 1/2

7:00 a.m.-11:13 p.m.

2 stops17h 13m

Chicago Midway

Sun 8/2

4:15 p.m.-7:59 a.m.

1 stop14h 44m

C$ 448

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 5/2

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Sun 8/2

4:15 p.m.-7:59 a.m.

1 stop14h 44m

C$ 452

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 30/1

7:00 a.m.-10:10 a.m.

1 stop4h 10m

Chicago Midway

Mon 2/2

1:00 p.m.-11:58 p.m.

1 stop9h 58m

C$ 456

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 29/1

7:00 a.m.-10:10 a.m.

1 stop4h 10m

Chicago Midway

Mon 2/2

1:00 p.m.-11:58 p.m.

1 stop9h 58m

C$ 457

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 8/2

8:40 a.m.-3:20 p.m.

1 stop7h 40m

Chicago Midway

Wed 18/2

11:00 a.m.-6:09 p.m.

1 stop6h 09m

C$ 460

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?

    There are 1048.7 km between Ottawa and Chicago Midway. 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 were last updated today.

  • How many operators does momondo search for flights from Ottawa Airport to Chicago Midway Airport?

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Ottawa Airport to Chicago Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Ottawa to Chicago Midway Airport?

Best airlines flying from Ottawa to Chicago Midway Airport

Compare and see reviews for airlines that fly from Ottawa to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 328Free CancellationRating
8.0
403 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

It is quick and easy to find Ottawa to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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 offers price alerts on flights to Chicago from Ottawa. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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