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Cheap flights from Ottawa to Chicago from C$ 211

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 28/4. 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.
Porter Airlines Logo
6:50 a.m. - 10:15 a.m.
YOW
-
MDW
4h 25m
1 stop
Porter Airlines Logo
11:00 a.m. - 4:44 p.m.
MDW
-
YOW
4h 44m
1 stop
C$ 328Porter Airlines
Thu, 9 Apr - Mon, 13 Apr
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YOW
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.
MDW
-
YOW
5h 29m
1 stop
C$ 365Porter Airlines
Wed, 11 Mar - Wed, 18 Mar
Porter Airlines Logo
6:45 a.m. - 10:15 a.m.
YOW
-
MDW
4h 30m
1 stop
Porter Airlines Logo
12:35 p.m. - 5:29 p.m.
MDW
-
YOW
3h 54m
1 stop
C$ 401Porter Airlines
Wed, 8 Apr - Sat, 11 Apr
Multiple Airlines Logo
10:35 a.m. - 10:45 p.m.
YOW
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
7:30 a.m. - 5:25 p.m.
MDW
-
YOW
8h 55m
1 stop
C$ 483Multiple Airlines
Thu, 19 Mar - Thu, 26 Mar
Multiple Airlines Logo
4:20 p.m. - 8:53 p.m.
YOW
-
MDW
29h 33m
1 stop
Multiple Airlines Logo
7:30 a.m. - 5:25 p.m.
MDW
-
YOW
8h 55m
1 stop
C$ 484Multiple Airlines
Thu, 19 Mar - Thu, 26 Mar
Multiple Airlines Logo
7:00 a.m. - 6:37 p.m.
YOW
-
MDW
12h 37m
2 stops
Multiple Airlines Logo
7:30 a.m. - 5:40 p.m.
MDW
-
YOW
9h 10m
1 stop
C$ 490Multiple Airlines
Sat, 2 May - Tue, 5 May
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.
YOW
-
MDW
4h 05m
1 stop
Porter Airlines Logo
4:15 p.m. - 10:29 p.m.
MDW
-
YOW
5h 14m
1 stop
C$ 495Porter Airlines
Fri, 6 Mar - Sun, 8 Mar
Multiple Airlines Logo
10:35 a.m. - 10:45 p.m.
YOW
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
7:30 a.m. - 12:59 p.m.
MDW
-
YOW
28h 29m
2 stops
C$ 498Multiple Airlines
Thu, 19 Mar - Thu, 26 Mar
Multiple Airlines Logo
10:35 a.m. - 10:45 p.m.
YOW
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
7:30 a.m. - 4:44 p.m.
MDW
-
YOW
8h 14m
2 stops
C$ 513Multiple Airlines
Thu, 19 Mar - Thu, 26 Mar
Multiple Airlines Logo
11:00 a.m. - 1:02 p.m.
YOW
-
MDW
27h 02m
2 stops
Multiple Airlines Logo
7:30 a.m. - 5:25 p.m.
MDW
-
YOW
8h 55m
1 stop
C$ 514Multiple Airlines
Mon, 16 Mar - Thu, 19 Mar

WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
7 May
YOW5:55 a.m.Ottawa
13h 19m
2 stops
MDW6:14 p.m.Chicago Midway
11 May
MDW6:30 a.m.Chicago Midway
16h 50m
2 stops
YOW12:20 a.m.Ottawa
C$ 584
WestJet
7 May
YOW5:55 a.m.Ottawa
13h 19m
2 stops
MDW6:14 p.m.Chicago Midway
11 May
MDW6:30 a.m.Chicago Midway
16h 50m
2 stops
YOW12:20 a.m.Ottawa
C$ 594
WestJet
21 May
YOW5:55 a.m.Ottawa
27h 48m
2 stops
MDW8:43 a.m.Chicago Midway
24 May
MDW9:22 a.m.Chicago Midway
7h 13m
2 stops
YOW5:35 p.m.Ottawa
C$ 610

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
9 Apr
YOW6:50 a.m.Ottawa
4h 25m
1 stop
MDW10:15 a.m.Chicago Midway
13 Apr
MDW11:00 a.m.Chicago Midway
4h 44m
1 stop
YOW4:44 p.m.Ottawa
C$ 328
Porter Airlines
11 Mar
YOW6:45 a.m.Ottawa
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
18 Mar
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 365
Porter Airlines
8 Apr
YOW6:45 a.m.Ottawa
4h 30m
1 stop
MDW10:15 a.m.Chicago Midway
11 Apr
MDW12:35 p.m.Chicago Midway
3h 54m
1 stop
YOW5:29 p.m.Ottawa
C$ 401

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 22 February 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 9/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 13/4

11:00 a.m.-4:44 p.m.

1 stop4h 44m

C$ 328

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 11/3

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Wed 18/3

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 365

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 8/4

6:45 a.m.-10:15 a.m.

1 stop4h 30m

Chicago Midway

Sat 11/4

12:35 p.m.-5:29 p.m.

1 stop3h 54m

C$ 401

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 19/3

10:35 a.m.-10:45 p.m.

1 stop13h 10m

Chicago Midway

Thu 26/3

7:30 a.m.-5:25 p.m.

1 stop8h 55m

C$ 483

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 19/3

4:20 p.m.-8:53 p.m.

1 stop29h 33m

Chicago Midway

Thu 26/3

7:30 a.m.-5:25 p.m.

1 stop8h 55m

C$ 484

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 2/5

7:00 a.m.-6:37 p.m.

2 stops12h 37m

Chicago Midway

Tue 5/5

7:30 a.m.-5:40 p.m.

1 stop9h 10m

C$ 490

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/3

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

1 stop4h 05m

Chicago Midway

Sun 8/3

4:15 p.m.-10:29 p.m.

1 stop5h 14m

C$ 495

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 19/3

10:35 a.m.-10:45 p.m.

1 stop13h 10m

Chicago Midway

Thu 26/3

7:30 a.m.-12:59 p.m.

2 stops28h 29m

C$ 498

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 19/3

10:35 a.m.-10:45 p.m.

1 stop13h 10m

Chicago Midway

Thu 26/3

7:30 a.m.-4:44 p.m.

2 stops8h 14m

C$ 513

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 16/3

11:00 a.m.-1:02 p.m.

2 stops27h 02m

Chicago Midway

Thu 19/3

7:30 a.m.-5:25 p.m.

1 stop8h 55m

C$ 514

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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$ 317Free CancellationRating
8.0
419 reviews
Search Porter Airlines flights

  • How do I get Price Alerts for flights from Ottawa to Chicago Midway Airport?

    Search flight deals from Ottawa to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Ottawa to Chicago Midway Airport with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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