Cheap flights from Chicago (CHI) to Winnipeg (YWG)

CHI — YWG
Feb 7 — Feb 141

The best prices from Chicago to Winnipeg are usually found in May or October, booked 59 days in advance, depart on a Friday or Saturday and return on a Thursday

How to find the cheapest flight from Chicago (CHI) to Winnipeg (YWG)

All the information you need to plan the best CHI to YWG flight in 2023: compare Chicago to Winnipeg flight prices with the expected peak season, weather and rainfall in Winnipeg.

CHI - YWG

Price

$577 - $897

YWG

Temperature

3.2 - 68 °F

YWG

Rainfall

0.8 - 3.1 inches

Popular inMarchHigh demand for flights, 24% potential price rise
Cheapest inMayBest time to find cheap flights, 16% potential price drop
Round-trip from$577From Chicago (CHI) to Winnipeg
One-way from$226One-way flight from Chicago (CHI) to Winnipeg

What is the cheapest day to fly round-trip from Chicago to Winnipeg?

Tuesday flights are generally found to be more expensive for flights from Chicago to Winnipeg. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Winnipeg.

How far in advance should I book a flight from Chicago to Winnipeg?

To save up to 59% on this flight, we recommend booking at least 60 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Winnipeg from $849 1-2 weeks out and tickets from $1,094 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago to Winnipeg?

May can be a great time to fly to Winnipeg from Chicago with a flight ticket averaging about $686. Cheapflights users have found deals in the month of May for as cheap as $433. The most expensive prices can be found in the month of March.

When is the cheapest time to fly from Chicago to Winnipeg (CHI - YWG)?

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 34% on airfare.

Cheap flights from Chicago to Winnipeg in February, March 2023

The best prices found for CHI to YWG flights for February, March
Mar 7 - Mar 9
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

18h 44m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

11h 43m
$342

Multiple Airlines

Pick Dates

Deal found 1/30

Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

25h 15m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

21h 42m
$364

Multiple Airlines

Pick Dates

Deal found 2/1

Mar 1 - Mar 3
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

22h 03m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

26h 09m
$403

Multiple Airlines

Pick Dates

Deal found 2/1

Chicago to Winnipeg 2023 flight deals

Cheap flights to Winnipeg from Chicago found for this year
Mar 7 - Mar 9
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

18h 44m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

11h 43m
$342

Multiple Airlines

Pick Dates

Deal found 1/30

Mar 1 - Mar 8
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

25h 15m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

21h 42m
$364

Multiple Airlines

Pick Dates

Deal found 2/1

Mar 1 - Mar 3
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

22h 03m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

26h 09m
$403

Multiple Airlines

Pick Dates

Deal found 2/1

Cheap Air Canada flights from Chicago to Winnipeg

May 3 - May 6
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 37m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 01m
$404

Air Canada

Pick Dates

Deal found 1/30

Jul 12 - Jul 18
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 37m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 09m
$405

Air Canada

Pick Dates

Deal found 2/1

Jun 1 - Jun 5
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 37m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 09m
$406

Air Canada

Pick Dates

Deal found 1/31

Cheap Delta flights from Chicago to Winnipeg

Mar 11 - Mar 18
MDW

Chicago Midway

YWG

Winnipeg

1 stop

5h 44m
YWG

Winnipeg

MDW

Chicago Midway

1 stop

4h 51m
$499

Delta

Pick Dates

Deal found 1/31

Jul 4 - Jul 12
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 25m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

5h 16m
$500

Delta

Pick Dates

Deal found 1/31

Jul 3 - Jul 12
MDW

Chicago Midway

YWG

Winnipeg

1 stop

5h 55m
YWG

Winnipeg

MDW

Chicago Midway

2 stops

10h 49m
$509

Delta

Pick Dates

Deal found 1/31

Last minute flights from Chicago to Winnipeg

Late deals on return flights to Winnipeg from Chicago, departing today and this week
Feb 7 - Feb 9
ORD

Chicago O'Hare Intl

YWG

Winnipeg

3 stops

33h 02m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

10h 02m
$495

Multiple Airlines

Pick Dates

Deal found 1/30

Feb 9 - Feb 12
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

10h 14m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 05m
$695

Multiple Airlines

Pick Dates

Deal found 1/30

Feb 11 - Feb 12
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

12h 13m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

24h 08m
$700

United Airlines

Pick Dates

Deal found 1/30

One-way flights to Winnipeg from Chicago

The cheapest one-way flights from Chicago to Winnipeg
May 28
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 27m
$192

Delta

Pick Dates

Deal found 1/30

May 28
MDW

Chicago Midway

YWG

Winnipeg

1 stop

5h 57m
$192

Delta

Pick Dates

Deal found 1/30

Feb 21
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 53m
$226

Air Canada

Pick Dates

Deal found 1/31

Reviews of Airlines Servicing Winnipeg

Delta
7.9
Good
2,046 reviews

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 10

Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.

Delta
7.9
Good
2,046 reviews
Delta
7.9
Good
2,046 reviews

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 10

Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.

United Airlines
7.6
Good
1,184 reviews
Delta
7.9
Good
2,046 reviews

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 10

Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.

WestJet
7.0
Good
479 reviews
Delta
7.9
Good
2,046 reviews

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 10

Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.

Aeromexico
7.0
Good
457 reviews
Delta
7.9
Good
2,046 reviews

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 10

Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.

Air Canada
6.6
Okay
649 reviews
Delta
7.9
Good
2,046 reviews

Food

7.2

Entertainment

7.8

Overall

7.9

Boarding

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 10

Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.

Related info for your journey

Useful info, stats and facts about Chicago to Winnipeg flights.

What airport do you fly into for flights to Winnipeg from Chicago?

Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 0 inbound flights from Chicago per day from 4 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

Which airlines flying from Chicago to Winnipeg have flexible cancellations due to COVID-19?

Air Canada, Delta, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Winnipeg for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Winnipeg for under $400. The cheapest flight booked recently is on Multiple Airlines for just $342, but on average you can expect to pay $417.

Are there last-minute flights available from Chicago to Winnipeg for under $500?

There are currently 8+ open flights from Chicago to Winnipeg within the next 7 days for less than $500.

What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

Flying on Air Canada is currently your cheapest option to Winnipeg, with prices starting at $404. Another option worth looking into is United Airlines, starting at $479 round trip. These flights start at 41% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

One-way options have recently been found by users for as low as $192 on Delta. Other airlines that offer cheap prices include Air Canada from $226 and United Airlines from $314 one-way.

What are the most popular airlines that fly from Chicago to Winnipeg?

Before booking your flight from Chicago to Winnipeg check out the most popular airlines for this route: Air Canada, Delta or United Airlines.

What are the cheapest flights from Chicago to Winnipeg?

The cheapest flight price from Chicago to Winnipeg is $183. On average you can expect to pay $911. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $342.

Top 4 airlines flying from Chicago to Winnipeg

The chart below displays the airlines Cheapflights users traveling from Chicago to Winnipeg choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Air CanadaCheapest$191Average$605FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
United AirlinesCheapest$386Average$636FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
WestJetCheapest$432Average$494FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
DeltaCheapest$466Average$705FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.