RareNonstop · 5h
CHI to SJUPuerto Rico
San Juan
$162
usually $340
−52%
Most monthly lows $287–$340. Cheaper than every other month on record (3).
Flights · CHI → YUL
Chicago to Montreal
Best fare, round trip
$261
Too little price history on this route to compare — the fare is shown as found.
Found
- Depart
- Sat 12 Dec
- Return
- Fri 18 Dec
- Stay
- 6 nights
- Flight
- Nonstop · 2h
- Airline
Air Canada
Cached fare — the booking search re-prices live before you pay.
CanadaMontrealFrench North America — cheap transatlantic fares in, and a summer festival calendar that never stops.Best windowJun–SepAirportsTrudeau (YUL)Every route into MontrealFare seasonality
When this route gets cheap.
The cheapest itinerary we are tracking flies Air Canada nonstop and takes about 2 hours outbound, on a 6-night trip. At $261 for 1,183 km each way, that works out to about $110 per 1,000 km flown. That is above the $41 per 1,000 km typical of short-haul fares here. We have 3 months of cached prices for this route so far — not enough to call a fare cheap or expensive, so we publish the price without a percentage. Fare history here is still too short to name a cheap season. The best time to be in Montreal: Jun–Sep.
The 5 days we hold a cached fare for
Press a date to compare its fares
The median cached fare across this calendar is 64% higher than when tracking began on 15 Aug — $246 then versus $404 now, across 16 recorded snapshots. This is a calendar-level trend, so an individual deal above can be lower. The lowest single day we have seen here is $236, on 24 Dec.
These are the only days we have a cached price for on this route so far — not the only days it flies. The search above covers any date.
Cached fares · checked 17 Oct 2026
We are still collecting this route's months — 3 months of cached prices so far, too few to chart.
Route facts
- Airports
- O’Hare (ORD) · Midway (MDW) ↔ Trudeau (YUL)
- Flight time
- ≈2 hours outbound
- Distance
- ≈1,183 km each way
- Airlines on the board
- Air Canada
- Itineraries
- Nonstop available
- Best months to visit
- Jun–Sep
Good to know
CHI → YUL, answered.
How far in advance should I book CHI → Montreal?
We do not publish a number for this, because we cannot measure it yet. Answering it honestly means watching the same departure date on this route over many weeks as it approaches, and that archive is still filling up — so any "book N days ahead" figure here would be borrowed from somewhere else rather than measured. Our guide Why flight prices change covers the levers we can measure.
Are there nonstop flights from Chicago to Montreal?
Yes — the current board includes nonstop fares (Air Canada). The outbound leg runs around 2 hours.
Are these prices guaranteed?
No — these are cached fares found on real searches (this one on 17 October). Airlines reprice constantly, so the booking search re-checks the live price before you pay. Fresher finds are far more likely to still be available.
Next step
Sleeping in Montreal?
Lock the flight first — then compare stays for 12–18 Dec · 6 nights.
Browse hotelsMissed it?
Cached fares expire. This route has a feed of its own — follow it and the next CHI → YUL drop reaches you as soon as we find it.
Follow this route’s feedKeep browsing
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