Winnipeg to Chicago flights (YWG → ORD)
Looking for Winnipeg to Chicago flights? Cheapest round-trip I’ve found: $755 on Air Canada, 1 stop(s), departing 2026-12-23. That’s $66 below the typical price for this route. Cheap flights from Winnipeg to Chicago change daily — I re-check this route three times a day.
Deal score: Average price — cheaper than 43% of prices I’ve seen on this route.
Best months to fly Winnipeg to Chicago
| Month | Cheapest seen |
|---|---|
| September | $446 |
| October | $530 |
| December | $571 |
| August | $690 |
| February | $736 |
| November | $766 |
How to book this fare
I don’t sell tickets — I track prices and point you to where to look. To book Winnipeg to Chicago flights:
- Search Winnipeg to Chicago on Google Flights for the dates shown above (Dec 2026) — the fare I found is usually still available there.
- Compare the same dates on metasearch sites like Skyscanner or KAYAK to confirm you’re seeing the lowest price.
- Book directly with the airline when you can — it’s often the same price and makes changes or cancellations much easier.
Fares change constantly. If the price has moved, check back — I re-check this route daily.
Other Winnipeg to … flights
- Winnipeg to Melbourne flights — $1,615
- Winnipeg to Sydney flights — $1,706
- Winnipeg to Bucharest flights — $1,580
- Winnipeg to Perth flights — $3,132
- Winnipeg to Santiago flights — $1,112
- Winnipeg to Adelaide flights — $2,832
- Winnipeg to Bangkok flights — $1,376
- Winnipeg to Calgary flights — $179
All flights to Chicago · All flights from Winnipeg
Prices last checked: 2026-09-25, 6:06:18 a.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.