Cheap flights from Winnipeg (YWG) to Chicago (ORD)
Cheapest round-trip I’ve found: $719 on WestJet, 1 stop(s), departing 2026-10-21. That’s $45 below the typical price for this route.
Deal score: Not enough data yet
1stops
19h 35mflight time
Oct 2026cheapest departure window
$764typical price
Best months to fly Winnipeg to Chicago
| Month | Cheapest seen |
|---|---|
| October | $719 |
How to book this fare
I don’t sell tickets — I track prices and point you to where to look. To book this fare:
- Search Winnipeg to Chicago on Google Flights for the dates shown above (Oct 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 cheap flights from Winnipeg
- Winnipeg to Bali — $1,575
- Winnipeg to Reykjavik — $867
- Winnipeg to Lisbon — $800
- Winnipeg to Montego Bay — $702
- Winnipeg to Honolulu — $639
- Winnipeg to Bangkok — $1,239
- Winnipeg to San Jose — $714
- Winnipeg to Delhi — $2,094
Prices last checked: 2026-07-24, 10:04:45 p.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.