Are direct flights from Chicago to Winnipeg always the best option?

Direct flights offer convenience by reducing travel time and avoiding layovers, but they are not always the cheapest option. Flights with one or more connections can sometimes be more affordable. Consider your priorities for cost versus travel time when making your choice.

Can flexible travel dates help on Chicago to Winnipeg flights?

Yes, being flexible with your travel dates can often lead to finding cheaper flights. Prices tend to vary significantly depending on the day of the week, season, and holidays. Adjusting your departure or return by a few days may result in notable savings.

What extra costs should I check before booking Chicago to Winnipeg flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Factor these into your total travel budget to avoid surprises.

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 7 days ago

483 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Chicago to Winnipeg

Explore current cheapest deals departing from Chicago to Winnipeg

2027-01-31 – 2027-02-05
CHI - Winnipeg
44% AI deal score
$383
$414
Round trip
2027-01-27 – 2027-02-05
CHI - Winnipeg
44% AI deal score
$359
$419
Round trip
2027-01-12 – 2027-02-05
CHI - Winnipeg
44% AI deal score
$327
$419
Round trip
2027-01-20 – 2027-02-05
CHI - Winnipeg
44% AI deal score
$340
$419
Round trip
2027-01-12 – 2027-01-25
CHI - Winnipeg
44% AI deal score
$339
$421
Round trip
2027-01-12 – 2027-01-22
CHI - Winnipeg
44% AI deal score
$344
$422
Round trip
2027-01-27 – 2027-02-01
CHI - Winnipeg
44% AI deal score
$378
$422
Round trip
2026-12-14 – 2027-01-11
CHI - Winnipeg
43% AI deal score
$426
$507
Round trip
2026-12-14 – 2026-12-16
CHI - Winnipeg
45% AI deal score
$525
$527
Round trip
2026-11-27 – 2026-12-16
CHI - Winnipeg
41% AI deal score
$351
$529
Round trip

Chicago to Winnipeg: Overview

Insights for flights from Chicago to Winnipeg

For flights from Chicago to Winnipeg, a typical journey of 34h 46m including connections can be expected. This route spans a distance of 1138 kilometers, classifying it as a short-haul flight. Given that most itineraries involve connections, the overall travel time reflects the stops and layovers.

When looking for cheap flights from Chicago to Winnipeg, fares typically range from $1204–$1417, with a median of $1331. Right now, current fares are below the typical level. However, 0% of recent fares were classified as a good price, indicating that finding deals on this route can be challenging. New deals for this route are also infrequent, suggesting that setting up a price alert could be beneficial.

Most itineraries for this route connect at least once, with only 5.2% of recent fares being direct flights from Chicago to Winnipeg. For connecting itineraries, the median number of stopovers is 2, which significantly contributes to the overall journey time. This means travelers should anticipate multiple stops when planning their trip.

The cheapest month to fly from Chicago to Winnipeg is October, with a median fare of $152. Another relatively affordable month is July, where the median fare is $1331. These months offer the best opportunities for finding more budget-friendly options on this route.

How much is a round trip from Chicago to Winnipeg

Regular price: $366 - $822

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

The regular price range for flights from Chicago to Winnipeg is between $366 and $822. The current lowest deal is $401 with Frontier Airlines, for travel from Dec 1-Dec 14.

now $401

Low $366

High $822

The cheapest time to fly from Chicago to Winnipeg

The cheapest month to fly from Chicago to Winnipeg is October, with a median price of $152. The most expensive month is July, with a median price of $1331. Prices are generally lower from July to October.

October

Cheapest

Flights from $152

July

Most Expensive

Flights from $1,331

Jul

Oct

Direct flights from Chicago to Winnipeg

United Airlines

Last-minute flights going from Chicago to Winnipeg

Wed, Oct 28

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

WestJet

$655

$1,492

One-way

Wed, Oct 28

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

WestJet

$662

$1,492

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$629

$1,579

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$624

$1,579

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$630

$1,674

One-way

Thu, Oct 29

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

WestJet

$639

$1,575

One-way

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

7 nights

Dec 10 - Dec 17

$500 → $411

18%

6 nights

Dec 1 - Dec 7

$501 → $424

15%

5 nights

Dec 11 - Dec 16

$515 → $438

15%

7 nights

Dec 8 - Dec 15

$500 → $424

15%

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 $401.

📅 Best time to fly

October is historically the cheapest month to fly.

Historically, the cheapest month to fly from Chicago to Winnipeg is October, with a median price of $152.

⏱️ Flight duration

Connecting flights average 34h 46m.

Connecting flights from Chicago to Winnipeg typically have a median duration of 34h 46m.

✈️ Airlines & availability

Connecting flights are dominant.

Only 5.2% of recent fares from Chicago to Winnipeg are direct, making connecting flights dominant.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one airline offering direct flights from Chicago to Winnipeg.

🎯 Booking tip

Deals are rare for this route.

Deals on flights from Chicago to Winnipeg are historically rare, so consider booking when you see a good price.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Winnipeg and is often the cheapest option from Chicago.

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

💸 Flights from ~$445

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 Winnipeg.

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

💸 Flights from ~$385

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.

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

💸 Flights from ~$319

Business & First Class Flight Deals to Winnipeg

Discover luxury on the budget with premium cabin class on flights from Chicago to Winnipeg.

Elite

Best Elite deals to Winnipeg

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Nov 18

Winnipeg, Canada

67% AI deal score

$1,164

$978

Save $186

Porter Airlines

Business Class

From ORD

Elite

Dec 01

Winnipeg, Canada

67% AI deal score

$1,187

$978

Save $209

Porter Airlines

Business Class

From ORD

Elite

Nov 17

Winnipeg, Canada

67% AI deal score

$1,165

$978

Save $187

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

66% AI deal score

$1,229

$1,072

Save $157

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

66% AI deal score

$1,229

$1,072

Save $157

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

66% AI deal score

$1,229

$1,072

Save $157

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

66% AI deal score

$1,229

$1,075

Save $154

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

66% AI deal score

$1,229

$1,075

Save $154

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

66% AI deal score

$1,226

$1,075

Save $151

Porter Airlines

Business Class

From ORD

Elite

Dec 01

Winnipeg, Canada

65% AI deal score

$1,211

$1,071

Save $140

Porter Airlines

Business Class

From ORD

Elite

Dec 15

Winnipeg, Canada

65% AI deal score

$1,207

$1,071

Save $136

Porter Airlines

Business Class

From ORD

Elite

Dec 01

Winnipeg, Canada

65% AI deal score

$1,200

$1,074

Save $126

Porter Airlines

Business Class

Frequently Asked Questions About Flights to Winnipeg

To find cheaper flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can also help you identify more affordable options. Setting up price alerts may notify you when fares drop.

Booking flights in advance often provides more competitive prices, though last-minute deals can sometimes appear. Prices can fluctuate, so monitoring fares over time may help you decide the best booking window. Weekday bookings are sometimes more affordable than weekend bookings.

Comparing nearby airports can sometimes reveal more affordable flight options or different schedules. While it may require additional travel time to and from these airports, the potential savings could be significant. Always factor in ground transportation costs and convenience when considering this option.

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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: $366 - $822

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

The regular price range for flights from Chicago to Winnipeg is between $366 and $822. The current lowest deal is $401 with Frontier Airlines, for travel from Dec 1-Dec 14.

now $401

Low $366

High $822

The cheapest time to fly from Chicago to Winnipeg

October

Cheapest

Flights from $152

July

Most Expensive

Flights from $1,331

Jul

Oct

Direct flights from Chicago to Winnipeg

United Airlines

Last-minute flights going from Chicago to Winnipeg

Wed, Oct 28

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

WestJet

$655

$1,492

One-way

Wed, Oct 28

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

WestJet

$662

$1,492

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$629

$1,579

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$624

$1,579

One-way

Wed, Oct 28

⌛ Last-Minute

ORD - Winnipeg

Chicago (ORD) - Winnipeg (YWG)

WestJet

$630

$1,674

One-way

Thu, Oct 29

⌛ Last-Minute

MDW - Winnipeg

Chicago (MDW) - Winnipeg (YWG)

WestJet

$639

$1,575

One-way

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

7 nights

Dec 10 - Dec 17

$500 → $411

18%

6 nights

Dec 1 - Dec 7

$501 → $424

15%

5 nights

Dec 11 - Dec 16

$515 → $438

15%

7 nights

Dec 8 - Dec 15

$500 → $424

15%

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 $401.

📅 Best time to fly

October is historically the cheapest month to fly.

Historically, the cheapest month to fly from Chicago to Winnipeg is October, with a median price of $152.

⏱️ Flight duration

Connecting flights average 34h 46m.

Connecting flights from Chicago to Winnipeg typically have a median duration of 34h 46m.

✈️ Airlines & availability

Connecting flights are dominant.

Only 5.2% of recent fares from Chicago to Winnipeg are direct, making connecting flights dominant.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one airline offering direct flights from Chicago to Winnipeg.

🎯 Booking tip

Deals are rare for this route.

Deals on flights from Chicago to Winnipeg are historically rare, so consider booking when you see a good price.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Winnipeg and is often the cheapest option from Chicago.

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

💸 Flights from ~$445

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 Winnipeg.

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

💸 Flights from ~$385

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.

Winnipeg, Canada

65% AI deal score

$1,200

$1,074

Save $126

Porter Airlines

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.

October is historically the cheapest month to fly.

Connecting flights average 34h 46m.

Connecting flights are dominant.

United Airlines offers direct flights.

Deals are rare for this route.

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

Nov 18

Dec 01

Nov 17

Dec 15

Dec 15

Dec 15

Dec 15

Dec 15

Dec 15

Dec 01

Dec 15

Dec 01

Frequently Asked Questions About Flights to Winnipeg

How can I find cheap flights from Chicago to Winnipeg?

When should I book flights from Chicago to Winnipeg?

Should I compare nearby airports for flights from Chicago to Winnipeg?

Are direct flights from Chicago to Winnipeg always the best option?

Can flexible travel dates help on Chicago to Winnipeg flights?

What extra costs should I check before booking Chicago to Winnipeg flights?

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.

October is historically the cheapest month to fly.

Connecting flights average 34h 46m.

Connecting flights are dominant.

United Airlines offers direct flights.

Deals are rare for this route.

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

Nov 18

Dec 01

Nov 17

Dec 15

Dec 15

Dec 15

Dec 15

Dec 15

Dec 15

Dec 01

Dec 15

Dec 01

Frequently Asked Questions About Flights to Winnipeg

How can I find cheap flights from Chicago to Winnipeg?

When should I book flights from Chicago to Winnipeg?

Should I compare nearby airports for flights from Chicago to Winnipeg?