Chicago to Winnipeg flights

Routavio compares airline fares from several flight booking sites. Search Chicago to Winnipeg to see the lowest price before you book.

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Lowest fare seen

€165Seen on 12 Oct 2026

Last checked

30 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €165

Lowest observed

12 Jan 2027

Frontier Airlines · 2 stops · One way

Cheapest observed day · Last checked: 12 Oct 2026

Departure

06:00

When to fly

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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.

One-way fare

One-way fare · No data: click and we will search

Airlines seen: United Airlines, Air Canada, Alaska Airlines, Delta Air Lines, Frontier Airlines, Porter Airlines Canada, WestJet (7)
Reported fastest flight: 2h 48m
Non-stop: Yes

Short answer

Routavio has seen Frontier Airlines fares from Chicago to Winnipeg. These are prices Routavio's searches returned on the dates shown, not quotes; run a live search for today's fare. Lowest fare seen: €165 on 12 Oct 2026.

Chicago → WinnipegTue 12 Jan 2027 · €165Last checked: 12 Oct 2026

About this route

Explore the fares we observed from Chicago to Winnipeg. Prices move often, so pick your dates to see the latest options.

Route distance: 1,154 km
Reported fastest flight: 2h 48m
Alternative airports: CGX, DPA, MDW, PWK, RFD

Route-level information; individual journeys vary.
Published schedules report non-stop service with United Airlines. Check current timetables.

A clearer picture of your fare

Observed, not guaranteed

Every price is a fare we actually saw, and it may change at any time.

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How our prices work

Price alert

Price alert for Chicago → Winnipeg

If the observed fare for this date drops, we will email you. At most one message a day.

Airport to city: straight-line distance

Chicago Midway International Airport (MDW) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 14 km.
Chicago O'Hare International Airport (ORD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 25 km.
Chicago Rockford International Airport (RFD) → Chicago, city gazetteer reference point (41.8781, -87.6298): ≈ 126 km.
Winnipeg / James Armstrong Richardson International Airport (YWG) → Winnipeg, city gazetteer reference point (49.8861, -97.1529): ≈ 7 km.

Approximate distances calculated from coordinates, not road distances or travel times. These airports serve the city; they are not confirmed endpoints of an offer.

Frequently asked

How much was a flight from Chicago to Winnipeg?

A fare of €165 was seen on 12 Oct 2026. Fares change, so search your dates for the current price.

Are there direct flights from Chicago to Winnipeg?

Yes. Published schedules report non-stop flights on this route with United Airlines.

Which airlines fly from Chicago to Winnipeg?

Routavio has seen these carriers on the route: United Airlines, Air Canada, Alaska Airlines, Delta Air Lines, Frontier Airlines, Porter Airlines Canada, WestJet (7).

How long does the flight from Chicago to Winnipeg take?

Across the 80 fares Routavio observed, the average journey time is 20h 04m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.

How many of the observed Chicago to Winnipeg fares were non-stop?

1 of the 80 fares we observed were non-stop; the rest included at least one stop. That describes our observations, not every flight that operates.

How observed prices work, what "No data" means and what a fare includes: Read the flight price guide · Price and schedule freshness on Routavio