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 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Winnipeg

Explore current cheapest deals departing from Chicago to Winnipeg

Round trip

Sort by: Cheapest

October 26 - October 30

Cheapest

Best

ORD - Winnipeg

$459

$322

Round trip

October 26 - October 29

Cheapest

Best

ORD - Winnipeg

$459

$322

Round trip

September 8 - September 21

Earliest

ORD - Winnipeg

$406

$329

Round trip

September 11 - September 15

ORD - Winnipeg

$454

$334

Round trip

September 11 - September 22

ORD - Winnipeg

$409

$334

Round trip

September 14 - October 13

ORD - Winnipeg

$394

$336

Round trip

October 18 - October 29

ORD - Winnipeg

$427

$337

Round trip

October 18 - October 30

ORD - Winnipeg

$424

$337

Round trip

September 11 - September 25

ORD - Winnipeg

$406

$338

Round trip

September 8 - September 11

Earliest

ORD - Winnipeg

$455

$338

Round trip

Unlock all 500+ flight deals to Winnipeg and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Winnipeg

Right now, 8% of recent fares for flights from Chicago to Winnipeg are considered a good price. Fares for this route typically range from $387 to $490, with a median of $401. Currently, prices are near the typical level. New deals show up several times a week for this route.

When looking for cheap flights from Chicago to Winnipeg, the cheapest time to fly is generally during the spring months. April stands out as the most affordable, with a median fare of $152. Following closely, May offers a median fare of $166, and June presents a median of $211. These months offer significantly lower prices compared to the typical range.

A typical journey from Chicago to Winnipeg takes about 8h 21m, including connections. This is because most itineraries connect at least once. The overall distance for this route is 1138 km, classifying it as a short-haul flight.

Most itineraries for this route connect at least once, with only 25.7% of recent fares being direct flights from Chicago to Winnipeg. For itineraries that do include connections, the median number of stopovers is 2.

How much is a round trip from Chicago to Winnipeg

Regular price: $377 - $611

Prices are currently below the regular range for flights from Chicago to Winnipeg.

The regular price range for flights from Chicago to Winnipeg is between $377 and $611. The current lowest deal is $322 with WestJet, for travel from Oct 26 to Oct 30.

now $322

Low $377

High $611

The cheapest time to fly from Chicago to Winnipeg

The cheapest month to fly from Chicago to Winnipeg is April, with a median price of $152. The most expensive month is October, with a median price of $464. Prices are generally lower from January to July.

April

Cheapest

Flights from $152

October

Most Expensive

Flights from $464

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Direct flights from Chicago to Winnipeg

United Airlines

Last-minute flights going from Chicago to Winnipeg

Tue, Jun 16

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Porter Airlines

$523

$656

One-way

Tue, Jun 16

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

JetBlue Airways

$453

$757

One-way

Wed, Jun 17

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Porter Airlines

$523

$656

One-way

Wed, Jul 1

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

JetBlue Airways

$535

$576

One-way

Thu, Jul 2

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Porter Airlines

$594

$474

One-way

Fri, Jul 3

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

Porter Airlines

$591

$375

One-way

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

3 nights

Jul 3 - Jul 6

$591 → $375

37%

3 nights

Jul 6 - Jul 9

$580 → $366

37%

2 nights

Jul 10 - Jul 12

$570 → $397

30%

3 nights

Jul 17 - Jul 20

$563 → $419

26%

Popular Airports to fly from Chicago to Winnipeg

Chicago - Winnipeg route insights

💸 Price insights

Recent fares are near the typical level

Recent fares from Chicago to Winnipeg are near the typical level for the route.

📅 Best time to fly

Fly in April for prices as low as $152

Historically, April is the cheapest month to fly, with median prices around $152.

⏱️ Flight duration

Flights typically take 8h 21m

The median flight duration from Chicago to Winnipeg is 8 hours and 21 minutes.

✈️ Airlines & availability

Connecting flights are dominant on this route

Only 25.7% of recent deals are direct, with connecting flights having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers that has offered direct flights on this route.

🎯 Booking tip

Deals appear regularly for this route

Deals for flights from Chicago to Winnipeg appear regularly, about 0.4 times per day.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Fly from O'Hare International for a convenient and often cheapest option to Winnipeg.

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

💸 Flights from ~$322

Chicago Midway International (MDW)

Chicago Midway International offers another departure choice for flights to Winnipeg.

📍 ~15 km from Chicago city center (reachable by car or train).

💸 Flights from ~$366

Chicago Rockford International (RFD)

Consider Chicago Rockford International as an alternative departure point for your trip to Winnipeg.

📍 ~110 km from Chicago city center (reachable by car).

💸 Flights from ~$448

Winnipeg main airports to arrive at

Winnipeg James Armstrong Richardson International (YWG)

Cheapest

Winnipeg James Armstrong Richardson International Airport is the primary airport for flights arriving in Winnipeg.

📍 ~10 km from city center (reachable by car)

💸 Flights from ~$322

Airports nearby Winnipeg used as alternative

Grand Forks International (GFK)

Grand Forks International is a useful alternative for US domestic flights, offering low-cost carrier options.

📍 ~220 km from Winnipeg (reachable by car, requires international border crossing)

💸 Flights from ~$321

Hector International (FAR)

Cheapest

Hector International is a reliable alternative for transborder travel with more destination options and better connectivity.

📍 ~330 km from Winnipeg (reachable by car, requires international border crossing)

💸 Flights from ~$259

Brandon Municipal (YBR)

Brandon Municipal is the closest domestic Canadian alternative, requiring no international border crossing.

📍 ~200 km from Winnipeg (reachable by car)

💸 Flights from ~$546

Minot International (MOT)

Minot International provides additional US domestic network access for travelers in Western Manitoba.

📍 ~370 km from Winnipeg (reachable by car, requires international border crossing)

💸 Flights from ~$275

Business & First Class Flight Deals to Winnipeg

Winnipeg, Canada

36% AI deal score

$2,107

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 for a flight has been around $179. Booking within 28-59 days prior to travel shows an average price of $192. For those planning further in advance, booking 60+ days out has historically resulted in significantly higher average prices, around $450.

Across the trailing quarter, a good price for a flight from Chicago to Winnipeg has typically been considered to be $387 or less. The median price observed for this route in the trailing 90 days was $401. Prices tend to increase beyond this point, with 75% of observed prices being $490 or less.

Historically, the cheapest months to fly from Chicago to Winnipeg have been April, May, and June. April typically sees a median price of $152, while May's median price is around $166. June also offers competitive prices, with a median of $211. These months are considerably more affordable than the annual median price of $401 for this route.

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