What percentage of Chicago to Winnipeg flights are direct?

Historically, approximately 15.2% of flights from Chicago to Winnipeg have been direct. For journeys requiring connections, the median number of stopovers was 2. This data is based on observations over the trailing 90 days.

What's the flight time from Chicago to Winnipeg?

The typical direct flight time from Chicago to Winnipeg is 2 hours and 37 minutes, covering a distance of 1138 kilometers. For flights with one stop, the median duration extends to 7 hours and 25 minutes. This represents a significant increase compared to direct routes, with one-stop flights taking an average of 445 minutes versus 157 minutes for direct flights.

How often do Chicago to Winnipeg flight prices drop?

Historically, flight prices for the Chicago to Winnipeg route have shown regular fluctuations. This indicates that price drops are a consistent occurrence for this particular route. Travelers may find opportunities to secure more favorable fares across the trailing 30 days.

Flights From Chicago

To Winnipeg

Cheap Flights from Chicago to Winnipeg

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Winnipeg

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to Winnipeg

Explore current cheapest deals departing from Chicago to Winnipeg

2026-10-09 – 2026-10-16
CHI - Winnipeg
75% AI deal score
$404
$300
Round trip
2026-10-01 – 2026-10-22
CHI - Winnipeg
68% AI deal score
$361
$300
Round trip
2026-10-02 – 2026-10-23
CHI - Winnipeg
68% AI deal score
$361
$300
Round trip
2026-10-05 – 2026-10-12
CHI - Winnipeg
75% AI deal score
$404
$300
Round trip
2026-10-11 – 2026-10-18
CHI - Winnipeg
75% AI deal score
$404
$300
Round trip
2026-10-04 – 2026-10-11
CHI - Winnipeg
75% AI deal score
$404
$300
Round trip
2026-10-01 – 2026-10-23
CHI - Winnipeg
68% AI deal score
$361
$300
Round trip
2026-10-08 – 2026-10-15
CHI - Winnipeg
75% AI deal score
$404
$302
Round trip
2026-09-01 – 2026-10-01
CHI - Winnipeg
68% AI deal score
$373
$306
Round trip
2026-10-05 – 2026-10-19
CHI - Winnipeg
68% AI deal score
$370
$311
Round trip

Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

Only 2% of recent fares from Chicago to Winnipeg were classified as a good price. Fares for this route typically range from $457–$898, with a median of $669. Right now, fares are significantly below the typical level, indicating a potentially favorable time to find cheap flights from Chicago to Winnipeg.

For travelers wondering when is the cheapest time to fly from Chicago to Winnipeg, the data shows that April is the most affordable month, with a median fare of $152. Following closely, May offers a median fare of $166, and June presents a median of $211. These months generally provide more budget-friendly options for this route.

A typical journey from Chicago to Winnipeg takes about 2h 37m, including connections. This is considered a short-haul route, covering a distance of 1138 km. While the non-stop flight time is also 2h 37m, most itineraries involve connections, with a median connecting journey time of 17h 50m.

Most itineraries for flights from Chicago to Winnipeg connect at least once, with only 15.2% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2. New deals for this route show up several times a week, so keeping an eye on price alerts can be beneficial.

How much is a round trip from Chicago to Winnipeg

Regular price: $334 - $614

Prices are currently below the regular range.

The regular price range for flights from Chicago to Winnipeg is $334-$614. The current lowest deal is $300 with WestJet for travel from Oct 4-Oct 11.

now $300

Low $334

High $614

The cheapest time to fly from Chicago to Winnipeg

The cheapest month to fly from Chicago to Winnipeg is May, with a median price of $167. The most expensive month is August, with a median price of $882. Prices are generally lower from January to September.

May

Cheapest

Flights from $167

August

Most Expensive

Flights from $882

Jan

May

Jun

Jul

Aug

Sep

Oct

Direct flights from Chicago to Winnipeg

Air Canada

Last-minute flights going from Chicago to Winnipeg

Wed, Aug 5

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

Contour Airlines

$532

$502

One-way

Fri, Aug 7

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Porter Airlines

$590

$550

One-way

Sat, Aug 8

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Frontier Airlines

$584

$484

One-way

Sun, Aug 9

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Frontier Airlines

$560

$469

One-way

Mon, Aug 10

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Porter Airlines

$559

$541

One-way

Tue, Aug 11

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

Frontier Airlines

$469

$392

One-way

Biggest price drops on these dates for flights from Chicago to Winnipeg

3 nights

Aug 18 - Aug 21

$524 → $393

25%

1 night

Oct 22 - Oct 23

$423 → $312

26%

1 night

Oct 18 - Oct 19

$422 → $312

26%

3 nights

Oct 19 - Oct 22

$422 → $314

26%

Popular Airports to fly from Chicago to Winnipeg

Chicago - Winnipeg route insights

💸 Price insights

Fares are below the typical level

Recent fares from Chicago to Winnipeg are below the typical level of $669.

📅 Best time to fly

Fly in April for the best prices

Historically, April, May, and June offer the lowest median prices, starting at $152.

⏱️ Flight duration

Direct flights average 2h 37m

The typical direct flight from Chicago to Winnipeg takes 2 hours and 37 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Only 15.2% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

Air Canada offers direct flights

Air Canada is one airline offering direct flights on the Chicago to Winnipeg route.

🎯 Booking tip

Deals appear regularly

Deals on flights from Chicago to Winnipeg appear regularly over a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International offers a wide range of flights from Chicago to Winnipeg, often with competitive pricing.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$309

Chicago Midway International (MDW)

Chicago Midway International is a convenient option for flights to Winnipeg, located closer to the city center.

📍 ~14 km from Chicago city center (reachable by car or train)

💸 Flights from ~$339

Chicago Rockford International (RFD)

Chicago Rockford International provides an alternative departure point for flights to Winnipeg.

📍 ~126 km from Chicago city center (reachable by car)

💸 Flights from ~$375

Winnipeg main airports to arrive at

Winnipeg James Armstrong Richardson International (YWG)

Cheapest

Winnipeg James Armstrong Richardson International Airport is a convenient arrival point for flights to Winnipeg.

📍 ~7 km from city center (reachable by car)

💸 Flights from ~$309

Airports nearby Winnipeg used as alternative

Hector International (FAR)

Cheapest

Hector International is a major regional hub with multiple US carriers, commonly used by Manitoba residents for US domestic flights.

📍 ~370 km from Winnipeg (requires international border crossing and ~3.5-hour drive).

💸 Flights from ~$248

Business & First Class Flight Deals to Winnipeg

68% AI deal score

$2,085

$1,450

Save $635

Frequently Asked Questions About Flights to Winnipeg

Historically, the optimal booking window for flights from Chicago to Winnipeg is typically 14-27 days before departure. During this period, the average price observed was $179. Booking 28-59 days out saw average prices increase to $192. For those booking 60 or more days in advance, the average price was significantly higher, at $450, across the trailing 90 days of observations.

Across the trailing 90 days, a good price for a flight from Chicago to Winnipeg was considered to be $457. This threshold represents the 25th percentile of prices observed. The median price for this route was $669, while prices at the 75th percentile reached $898.

Historically, the cheapest months to fly from Chicago to Winnipeg include April, with a median price of $152, and May, with a median price of $166. June also offered competitive prices, with a median of $211. These prices are notably lower than the annual median price for the route, which stood at $669 across the trailing 270 days.

Related routes

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Flights to Winnipeg from other cities

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Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

How much is a round trip from Chicago to Winnipeg

Regular price: $334 - $614

Prices are currently below the regular range.

The regular price range for flights from Chicago to Winnipeg is $334-$614. The current lowest deal is $300 with WestJet for travel from Oct 4-Oct 11.

now $300

Low $334

High $614

The cheapest time to fly from Chicago to Winnipeg

May

Cheapest

Flights from $167

August

Most Expensive

Flights from $882

Jan

May

Jun

Jul

Aug

Sep

Oct