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Cheap flights from Ottawa to Chicago from C$ 268

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 29/4. 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.
Multiple Airlines Logo
11:00 a.m. - 1:00 p.m.
YOW
-
MDW
27h 00m
2 stops
Multiple Airlines Logo
7:30 a.m. - 5:25 p.m.
MDW
-
YOW
8h 55m
1 stop
C$ 426Multiple Airlines
Thu, 23 Apr - Sat, 25 Apr
Multiple Airlines Logo
3:55 p.m. - 1:00 p.m.
YOW
-
MDW
22h 05m
1 stop
Multiple Airlines Logo
7:30 a.m. - 5:25 p.m.
MDW
-
YOW
8h 55m
1 stop
C$ 427Multiple Airlines
Thu, 23 Apr - Sat, 25 Apr
Multiple Airlines Logo
7:00 a.m. - 7:31 p.m.
YOW
-
MDW
13h 31m
2 stops
Multiple Airlines Logo
7:30 a.m. - 1:15 p.m.
MDW
-
YOW
28h 45m
1 stop
C$ 470Multiple Airlines
Tue, 21 Apr - Sun, 26 Apr
Multiple Airlines Logo
6:35 p.m. - 9:45 a.m.
YOW
-
MDW
16h 10m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:20 a.m.
MDW
-
YOW
8h 00m
1 stop
C$ 478Multiple Airlines
Thu, 28 May - Tue, 2 Jun
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:20 a.m.
MDW
-
YOW
8h 00m
1 stop
C$ 480Multiple Airlines
Sat, 30 May - Fri, 5 Jun
Multiple Airlines Logo
3:55 p.m. - 1:00 p.m.
YOW
-
MDW
22h 05m
1 stop
Multiple Airlines Logo
7:30 a.m. - 1:15 p.m.
MDW
-
YOW
28h 45m
1 stop
C$ 481Multiple Airlines
Tue, 21 Apr - Sun, 26 Apr
Multiple Airlines Logo
6:35 p.m. - 9:45 a.m.
YOW
-
MDW
16h 10m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:20 a.m.
MDW
-
YOW
8h 00m
1 stop
C$ 483Multiple Airlines
Thu, 28 May - Thu, 4 Jun
Multiple Airlines Logo
6:25 p.m. - 9:45 a.m.
YOW
-
MDW
16h 20m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:20 a.m.
MDW
-
YOW
8h 00m
1 stop
C$ 484Multiple Airlines
Sat, 30 May - Thu, 4 Jun
Multiple Airlines Logo
6:35 p.m. - 9:45 a.m.
YOW
-
MDW
16h 10m
1 stop
Multiple Airlines Logo
3:20 p.m. - 12:20 a.m.
MDW
-
YOW
8h 00m
1 stop
C$ 505Multiple Airlines
Thu, 28 May - Thu, 4 Jun
Multiple Airlines Logo
3:55 p.m. - 1:00 p.m.
YOW
-
MDW
22h 05m
1 stop
Multiple Airlines Logo
7:30 a.m. - 5:25 p.m.
MDW
-
YOW
8h 55m
1 stop
C$ 517Multiple Airlines
Mon, 20 Apr - Fri, 24 Apr

Porter Airlines flights from Ottawa to Chicago Midway Airport

Our best Porter Airlines deals on Ottawa to Chicago Midway Airport flight tickets
Porter Airlines
4 May
YOW11:00 a.m.Ottawa
4h 35m
1 stop
MDW2:35 p.m.Chicago Midway
7 May
MDW10:30 a.m.Chicago Midway
6h 24m
1 stop
YOW5:54 p.m.Ottawa
C$ 548
Porter Airlines
4 May
YOW11:00 a.m.Ottawa
4h 35m
1 stop
MDW2:35 p.m.Chicago Midway
11 May
MDW3:20 p.m.Chicago Midway
5h 24m
1 stop
YOW9:44 p.m.Ottawa
C$ 549
Porter Airlines
30 Apr
YOW6:50 a.m.Ottawa
4h 25m
1 stop
MDW10:15 a.m.Chicago Midway
7 May
MDW10:30 a.m.Chicago Midway
8h 34m
1 stop
YOW8:04 p.m.Ottawa
C$ 554

WestJet flights from Ottawa to Chicago Midway Airport

Our best WestJet deals on Ottawa to Chicago Midway Airport flight tickets
WestJet
20 Apr
YOW5:40 a.m.Ottawa
28h 07m
2 stops
MDW8:47 a.m.Chicago Midway
24 Apr
MDW10:41 a.m.Chicago Midway
12h 58m
2 stops
YOW12:39 a.m.Ottawa
C$ 976
WestJet
21 Apr
YOW5:40 a.m.Ottawa
28h 07m
2 stops
MDW8:47 a.m.Chicago Midway
26 Apr
MDW9:27 a.m.Chicago Midway
19h 08m
2 stops
YOW5:35 a.m.Ottawa
C$ 1,313
WestJet
12 Apr
YOW8:20 p.m.Ottawa
23h 16m
2 stops
MDW6:36 p.m.Chicago Midway
19 Apr
MDW7:16 p.m.Chicago Midway
28h 23m
2 stops
YOW12:39 a.m.Ottawa
C$ 1,339

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 8 April 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

Thu 23/4

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

2 stops27h 00m

Chicago Midway

Sat 25/4

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

1 stop8h 55m

C$ 426

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 23/4

3:55 p.m.-1:00 p.m.

1 stop22h 05m

Chicago Midway

Sat 25/4

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

1 stop8h 55m

C$ 427

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 21/4

7:00 a.m.-7:31 p.m.

2 stops13h 31m

Chicago Midway

Sun 26/4

7:30 a.m.-1:15 p.m.

1 stop28h 45m

C$ 470
Quickest round-trip

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 28/5

6:35 p.m.-9:45 a.m.

1 stop16h 10m

Chicago Midway

Tue 2/6

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 478

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 30/5

6:25 p.m.-9:45 a.m.

1 stop16h 20m

Chicago Midway

Fri 5/6

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 480

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 21/4

3:55 p.m.-1:00 p.m.

1 stop22h 05m

Chicago Midway

Sun 26/4

7:30 a.m.-1:15 p.m.

1 stop28h 45m

C$ 481

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 28/5

6:35 p.m.-9:45 a.m.

1 stop16h 10m

Chicago Midway

Thu 4/6

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 483

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 30/5

6:25 p.m.-9:45 a.m.

1 stop16h 20m

Chicago Midway

Thu 4/6

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 484

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 28/5

6:35 p.m.-9:45 a.m.

1 stop16h 10m

Chicago Midway

Thu 4/6

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 505

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 20/4

3:55 p.m.-1:00 p.m.

1 stop22h 05m

Chicago Midway

Fri 24/4

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

1 stop8h 55m

C$ 517

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 25m

Direct flights

None
The fastest flight from Ottawa to Chicago Midway Airport takes 4h 25m
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?

    There are 1048.7 km between Ottawa and Chicago Midway. Flights usually cover this in 4h 25m, 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$ 322Free CancellationRating
8.0
432 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

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

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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