What percentage of Chicago to Winnipeg flights are direct?

In the trailing 90 days, approximately 15.2% of flights from Chicago to Winnipeg were direct. For travelers opting for connecting flights, the median number of stopovers was 2. This indicates that a significant portion of routes involve at least one stop. Travelers should consider this when planning their journey.

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. This corresponds to a median direct flight duration of 157 minutes. For flights with one stop, the median duration extends to 7 hours and 25 minutes, or 445 minutes. Travelers should account for these differences when planning their travel itinerary.

How often do Chicago to Winnipeg flight prices drop?

Historically, flight prices for the Chicago to Winnipeg route have shown regular price drops. This suggests that travelers may frequently find opportunities to secure better deals. Monitoring prices consistently can be beneficial for those looking to purchase tickets for this route. This pattern has been observed over a trailing 30-day period.

Flights From Chicago

To Winnipeg

Cheap Flights from Chicago to Winnipeg

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 1 day ago

461 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)

Today’s best flight deals from Chicago to Winnipeg

Explore current cheapest deals departing from Chicago to Winnipeg

2026-10-27 – 2026-10-29
CHI - Winnipeg
74% AI deal score
$418
$299
Round trip
2026-09-27 – 2026-10-18
CHI - Winnipeg
68% AI deal score
$393
$321
Round trip
2026-09-27 – 2026-10-19
CHI - Winnipeg
68% AI deal score
$393
$321
Round trip
2026-09-27 – 2026-10-22
CHI - Winnipeg
68% AI deal score
$392
$321
Round trip
2026-09-27 – 2026-10-23
CHI - Winnipeg
68% AI deal score
$392
$321
Round trip
2026-10-15 – 2026-10-18
CHI - Winnipeg
73% AI deal score
$442
$322
Round trip
2026-09-22 – 2026-10-19
CHI - Winnipeg
73% AI deal score
$414
$322
Round trip
2026-09-22 – 2026-10-22
CHI - Winnipeg
73% AI deal score
$414
$322
Round trip
2026-09-22 – 2026-10-18
CHI - Winnipeg
73% AI deal score
$414
$322
Round trip
2026-09-25 – 2026-10-23
CHI - Winnipeg
69% AI deal score
$398
$322
Round trip

Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

Right now, only 2% of recent fares from Chicago to Winnipeg are considered a good price. If you are looking for cheap flights from Chicago to Winnipeg, current fares are significantly below the typical level for this route, which typically ranges from $457–$898, with a median of $669. New deals for this route show up several times a week, so keeping an eye on price alerts can be beneficial.

A typical journey from Chicago to Winnipeg takes about 2h 37m, including connections. This route is classified as a short-haul flight, covering a distance of 1138 km. While direct flights from Chicago to Winnipeg are available, most itineraries connect at least once, with a median of 2 stopovers when connecting.

The cheapest time to fly from Chicago to Winnipeg is typically during the spring months. April offers the lowest median fare at $152, followed by May with a median of $166. June also presents a relatively low median fare of $211, making these months the most economical for travel on this route.

How much is a round trip from Chicago to Winnipeg

Regular price: $341 - $624

Prices are currently below the regular range.

The regular price range for flights from Chicago to Winnipeg is $341 to $624. The current lowest deal is $299 with Frontier Airlines for travel from Oct 27-Oct 29.

now $299

Low $341

High $624

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

Lufthansa

Last-minute flights going from Chicago to Winnipeg

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$414

$322

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$414

$322

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$414

$322

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$416

$383

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$415

$383

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$432

$383

One-way

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

2 nights

Sep 22 - Sep 24

$527 → $319

40%

2 nights

Dec 5 - Dec 7

$537 → $342

36%

4 nights

Dec 3 - Dec 7

$531 → $373

30%

5 nights

Dec 8 - Dec 13

$529 → $381

28%

Popular Airports to fly from Chicago to Winnipeg

Chicago - Winnipeg route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Winnipeg are below the typical level at $299.

📅 Best time to fly

April offers the lowest median price

Historically, April is the cheapest month to fly, with a median price of $152.

⏱️ Flight duration

Direct flights take 2h 37m

The median flight duration is 2h 37m for direct flights and 17h 50m for connecting flights.

✈️ Airlines & availability

Connecting flights are more common

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

🏆 Airline highlight

Lufthansa offers direct flights

Lufthansa is one airline that offers direct flights on this route.

🎯 Booking tip

Deals appear regularly

Deals for flights on this route appear regularly, typically within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Winnipeg, providing a major hub for your travel needs.

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

💸 Flights from ~$305

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient option for flights to Winnipeg.

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

💸 Flights from ~$330

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative departure point for your journey to Winnipeg.

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

💸 Flights from ~$355

Winnipeg main airports to arrive at

Winnipeg James Armstrong Richardson International (YWG)

Cheapest

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

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

💸 Flights from ~$305

Airports nearby Winnipeg used as alternative

Hector International (FAR)

Cheapest

Hector International is a major regional hub that can be a useful alternative for US domestic flights.

📍 ~360 km from Winnipeg (requires international border crossing and approximately 3.5-hour drive).

💸 Flights from ~$319

Business & First Class Flight Deals to Winnipeg

$1,007

Save $258

Porter Airlines

Business Class

From ORD

Elite

Oct 09

Winnipeg, Canada

68% AI deal score

$1,282

$1,021

Save $261

WestJet

Business Class

From MDW

Elite

Sep 27

Winnipeg, Canada

68% AI deal score

$1,276

$1,037

Save $239

Porter Airlines

Business Class

From ORD

Elite

Oct 28

Winnipeg, Canada

67% AI deal score

$1,251

$1,007

Save $244

Porter Airlines

Business Class

From ORD

Elite

Oct 16

Winnipeg, Canada

67% AI deal score

$1,278

$1,021

Save $257

WestJet

Business Class

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 within 28-59 days of travel saw average prices of $192, while booking 60 or more days out resulted in significantly higher average prices of $450. These trends are based on observations over a trailing 90-day period.

Across the trailing quarter, a good price for a flight from Chicago to Winnipeg is considered to be $457 or less. The median price observed for this route was $669. Prices can vary, with 75% of observed fares being $898 or less. These figures provide a benchmark for travelers planning their trips.

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. In the trailing 270 days, the annual median price for this route was $669. These months typically present more budget-friendly options for travelers.

Related routes

More routes from Chicago

Flights from Chicago to Abu Dhabi Flights from Chicago to Accra Flights from Chicago to Addis Ababa Flights from Chicago to Adelaide Flights from Chicago to Ahmedabad Flights from Chicago to Albuquerque Flights from Chicago to Amman Flights from Chicago to Amsterdam Flights from Chicago to Athens Flights from Chicago to Atlanta Flights from Chicago to Austin Flights from Chicago to Barcelona

Flights to Winnipeg from other cities

Flights from Dubai to Winnipeg Flights from Edmonton to Winnipeg Flights from Glasgow to Winnipeg Flights from Halifax to Winnipeg Flights from Hamilton to Winnipeg Flights from Kelowna to Winnipeg Flights from Louisville to Winnipeg Flights from Melbourne to Winnipeg Flights from Montreal to Winnipeg Flights from New Delhi to Winnipeg Flights from Ottawa to Winnipeg Flights from Singapore to Winnipeg

Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

How much is a round trip from Chicago to Winnipeg

Regular price: $341 - $624

Prices are currently below the regular range.

The regular price range for flights from Chicago to Winnipeg is $341 to $624. The current lowest deal is $299 with Frontier Airlines for travel from Oct 27-Oct 29.

now $299

Low $341

High $624

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

Direct flights from Chicago to Winnipeg

Lufthansa

Last-minute flights going from Chicago to Winnipeg

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$414

$322

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$414

$322

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$414

$322

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$416

$383

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$415

$383

One-way

Tue, Sep 22

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$432

$383

One-way

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

2 nights

Sep 22 - Sep 24

$527 → $319

40%

2 nights

Dec 5 - Dec 7

$537 → $342

36%

4 nights

Dec 3 - Dec 7

$531 → $373

30%

5 nights

Dec 8 - Dec 13

$529 → $381

28%

Popular Airports to fly from Chicago to Winnipeg

Chicago - Winnipeg route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Winnipeg are below the typical level at $299.

📅 Best time to fly

April offers the lowest median price

Historically, April is the cheapest month to fly, with a median price of $152.

⏱️ Flight duration

Direct flights take 2h 37m

The median flight duration is 2h 37m for direct flights and 17h 50m for connecting flights.

✈️ Airlines & availability

Connecting flights are more common

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

🏆 Airline highlight

Lufthansa offers direct flights

Lufthansa is one airline that offers direct flights on this route.

🎯 Booking tip

Deals appear regularly

Deals for flights on this route appear regularly, typically within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Winnipeg, providing a major hub for your travel needs.

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

💸 Flights from ~$305

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient option for flights to Winnipeg.

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

💸 Flights from ~$330

Chicago Rockford International (RFD)

Chicago Rockford International Airport is an alternative departure point for your journey to Winnipeg.

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

💸 Flights from ~$355

Winnipeg main airports to arrive at

Winnipeg James Armstrong Richardson International (YWG)

Cheapest

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

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

💸 Flights from ~$305

Airports nearby Winnipeg used as alternative

Hector International (FAR)

Cheapest

Hector International is a major regional hub that can be a useful alternative for US domestic flights.

Winnipeg, Canada

67% AI deal score

$1,278

$1,021

Save $257

WestJet

Business Class

Frequently Asked Questions About Flights to Winnipeg

Cheap Flights from Chicago to Winnipeg

Today’s best flight deals from Chicago to Winnipeg

Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

How much is a round trip from Chicago to Winnipeg

The cheapest time to fly from Chicago to Winnipeg

Direct flights from Chicago to Winnipeg

Last-minute flights going from Chicago to Winnipeg

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

Popular Airports to fly from Chicago to Winnipeg

Chicago - Winnipeg route insights

Recent fares are below the typical level

April offers the lowest median price

Direct flights take 2h 37m

Connecting flights are more common

Lufthansa offers direct flights

Deals appear regularly

Chicago main airports to depart from

Winnipeg main airports to arrive at

Airports nearby Winnipeg used as alternative

Business & First Class Flight Deals to Winnipeg

Best Elite deals to Winnipeg

Oct 09

Oct 15

Oct 16

Oct 15

Oct 09

Oct 16

Oct 11

Oct 27

Oct 09

Sep 27

Oct 28

Oct 16

Frequently Asked Questions About Flights to Winnipeg

When is the best time to book flights from Chicago to Winnipeg?

What is a good price for a flight from Chicago to Winnipeg?

When is the cheapest time of year to fly from Chicago to Winnipeg?

What percentage of Chicago to Winnipeg flights are direct?

What's the flight time from Chicago to Winnipeg?

How often do Chicago to Winnipeg flight prices drop?

Related routes

More routes from Chicago

Flights to Winnipeg from other cities

Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

How much is a round trip from Chicago to Winnipeg

The cheapest time to fly from Chicago to Winnipeg

Direct flights from Chicago to Winnipeg

Last-minute flights going from Chicago to Winnipeg

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

Popular Airports to fly from Chicago to Winnipeg

Chicago - Winnipeg route insights

Recent fares are below the typical level

April offers the lowest median price

Direct flights take 2h 37m

Connecting flights are more common

Lufthansa offers direct flights

Deals appear regularly

Chicago main airports to depart from

Winnipeg main airports to arrive at

Airports nearby Winnipeg used as alternative

Business & First Class Flight Deals to Winnipeg

Best Elite deals to Winnipeg

Oct 09

Oct 15

Oct 16

Oct 15

Oct 09

Oct 16

Oct 11

Oct 27

Oct 09

Sep 27

Oct 28

Oct 16

Frequently Asked Questions About Flights to Winnipeg

When is the best time to book flights from Chicago to Winnipeg?

What is a good price for a flight from Chicago to Winnipeg?

When is the cheapest time of year to fly from Chicago to Winnipeg?