Cheap flights from Ottawa to Chicago

One-way fares from $376 · YOW → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Ottawa
Cheapest fare
$376

WestJet · Wed, Nov 18

Cheapest month
November

from $376

Direct flights
Not recently

Usually 1+ stop

Quickest trip
3h 40m

1,040 km

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Cheapest month to fly from Ottawa to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $376

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

WestJet
Depart05:30 Wed, Nov 18YOW → ORD 8h 27m · 2 stops
$376one way, per person
View deal
Porter Airlines Canada
Depart07:00 Sun, Nov 15YOW → ORD 3h 40m · 1 stop
$414one way, per person
View deal
Porter Airlines Canada
Depart07:05 Mon, Nov 9YOW → ORD 7h 02m · 1 stop
$450one way, per person
View deal
Porter Airlines Canada
Depart07:05 Sun, Nov 8YOW → ORD 7h 07m · 1 stop
$476one way, per person
View deal
American Airlines
Depart07:00 Fri, Nov 13YOW → ORD 3h 40m · 1 stop
$635one way, per person
View deal
See every date in November 2026 →

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Where to stay, what to do and getting around, from our travel partners.

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About flights from Ottawa to Chicago

Ottawa (YOW) and Chicago (CHI) are about 1,040 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 3h 40m. Over the next few months, one-way fares start from $376, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Ottawa to Chicago?

The cheapest one-way fare we've seen recently is $376 with WestJet, departing Wednesday, November 18, 2026.

What is the cheapest month to fly from Ottawa to Chicago?

November 2026 currently has the lowest fares, from $376 one way.

Are there direct flights from Ottawa to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Ottawa to Chicago?

The quickest journey we've seen takes about 3h 40m. Ottawa and Chicago are around 1,040 km apart.

Which airlines fly from Ottawa to Chicago?

Recent fares on this route were with WestJet, Porter Airlines Canada and American Airlines.

More cheap flights from Ottawa

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