Cheap Flights from Winnipeg to Chicago
No deal from Winnipeg to Chicago has cleared our price bar yet. What we have seen on the route is below.
Across 4 months of observations from Winnipeg to Chicago, the lowest round-trip fare we recorded was $358, in August. The typical fare was $563. August was the cheapest month we saw and October the dearest.
The most recent price we saw on this route was $738 on Delta, seen Oct 16. It is an unverified observation and may have changed.
See every deal <a href="/from/winnipeg">from Winnipeg</a>, <a href="/to/chicago">to Chicago</a>, or the return direction <a href="/from/chicago/to/winnipeg">Chicago to Winnipeg</a>.
Latest price we saw: Winnipeg to Chicago
The most recent round-trip fare our sweep found on this route. It is not verified and may have changed since the date shown.
| From | Price | Per mile | Travel dates | Airline | Seen | Check price |
|---|---|---|---|---|---|---|
| Winnipeg (YWG) to Chicago (ORD) | $738 | 52.2¢ | Nov 29 – Dec 5 | Delta | Oct 16 | Check price |
Price history: Winnipeg to Chicago
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $497 | $623 | 23 |
| Sep 2026 | $410 | $575 | 54 |
| Aug 2026 | $358 | $558 | 27 |
| Jul 2026 | $495 | $495 | 1 |
Frequently asked questions
How many flight deals from Winnipeg to Chicago are on Sparkflights right now?
There are 0 verified deals from Winnipeg to Chicago on the board right now. The list refreshes hourly.
What is the lowest price ever seen from Winnipeg to Chicago?
The lowest fare we've recorded from Winnipeg to Chicago is $358, based on 105 price observations over 4 months.
How much does a flight from Winnipeg to Chicago cost?
The typical round-trip fare we observed from Winnipeg to Chicago is $563, against a recorded low of $358. These are observations, not quotes.
When is the cheapest month to fly Winnipeg to Chicago?
August was the cheapest month we observed from Winnipeg to Chicago and October the dearest, over 4 months of data.
What is the current price from Winnipeg to Chicago?
The most recent fare our sweep saw from Winnipeg to Chicago is $738, on Oct 16. It is an unverified observation rather than a verified deal, so check it before booking.