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

CHI — YWG
Feb 1 — Feb 81

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, 25% potential price rise
Cheapest inMayBest time to find cheap flights, 14% potential price drop
Round-trip from$577From Chicago (CHI) to Winnipeg
One-way from$248One-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 $847 1-2 weeks out and tickets from $1,108 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 $674. 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 January, February 2023

The best prices found for CHI to YWG flights for January, February
Feb 18 - Feb 22
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 20m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 00m
$398

Multiple Airlines

Pick Dates

Deal found 1/25

Feb 23 - Mar 2
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

11h 31m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 21m
$402

Multiple Airlines

Pick Dates

Deal found 1/24

Feb 14 - Feb 21
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 53m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 00m
$419

Air Canada

Pick Dates

Deal found 1/24

Chicago to Winnipeg 2023 flight deals

Cheap flights to Winnipeg from Chicago found for this year
Jul 21 - Jul 25
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 37m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 09m
$386

Air Canada

Pick Dates

Deal found 1/25

Jul 23 - Aug 29
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 25m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 09m
$390

Multiple Airlines

Pick Dates

Deal found 1/24

Mar 28 - Mar 30
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 40m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 20m
$391

Multiple Airlines

Pick Dates

Deal found 1/24

Cheap Air Canada flights from Chicago to Winnipeg

Jul 21 - Jul 25
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 37m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 09m
$386

Air Canada

Pick Dates

Deal found 1/25

Feb 14 - Feb 21
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 53m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 00m
$419

Air Canada

Pick Dates

Deal found 1/24

Jul 25 - Aug 29
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 37m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 56m
$422

Air Canada

Pick Dates

Deal found 1/24

Cheap Delta flights from Chicago to Winnipeg

May 25 - May 31
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 27m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 27m
$477

Delta

Pick Dates

Deal found 1/25

Jul 25 - Aug 28
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 25m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

10h 38m
$523

Delta

Pick Dates

Deal found 1/24

Mar 7 - Mar 15
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

11h 05m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

10h 12m
$534

Delta

Pick Dates

Deal found 1/24

Last minute flights from Chicago to Winnipeg

Late deals on return flights to Winnipeg from Chicago, departing today and this week
Feb 3 - Feb 5
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

14h 12m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 51m
$714

Multiple Airlines

Pick Dates

Deal found 1/25

Feb 3 - Feb 5
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 12m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 51m
$738

Multiple Airlines

Pick Dates

Deal found 1/25

Feb 3 - Feb 5
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

12h 45m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

10h 46m
$769

Multiple Airlines

Pick Dates

Deal found 1/25

One-way flights to Winnipeg from Chicago

The cheapest one-way flights from Chicago to Winnipeg
Mar 28
MDW

Chicago Midway

YWG

Winnipeg

1 stop

15h 00m
$165

Multiple Airlines

Pick Dates

Deal found 1/24

Mar 20
MDW

Chicago Midway

YWG

Winnipeg

1 stop

22h 55m
$169

Multiple Airlines

Pick Dates

Deal found 1/26

Mar 28
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

26h 25m
$170

Multiple Airlines

Pick Dates

Deal found 1/24

Reviews of Airlines Servicing Winnipeg

Delta
7.9
Good
2,000 reviews

Boarding

8.0

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 10

I make a reservation and I have access to carry one bag on cabinets and one carry on bag, after I bought the reservation I called the airline to confirm and the answer was right I HAVE ACCESS TO CARRY ONE CARRY-ON BAG AND ONE IN STORE; at the time to checking in I get charged for $60 dollars on the flight going out and $30 dollars for the flight comes back. So I need the money back to my account for those changes thanks for the atención on this request

Delta
7.9
Good
2,000 reviews
Delta
7.9
Good
2,000 reviews

Boarding

8.0

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 10

I make a reservation and I have access to carry one bag on cabinets and one carry on bag, after I bought the reservation I called the airline to confirm and the answer was right I HAVE ACCESS TO CARRY ONE CARRY-ON BAG AND ONE IN STORE; at the time to checking in I get charged for $60 dollars on the flight going out and $30 dollars for the flight comes back. So I need the money back to my account for those changes thanks for the atención on this request

United Airlines
7.6
Good
1,147 reviews
Delta
7.9
Good
2,000 reviews

Boarding

8.0

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 10

I make a reservation and I have access to carry one bag on cabinets and one carry on bag, after I bought the reservation I called the airline to confirm and the answer was right I HAVE ACCESS TO CARRY ONE CARRY-ON BAG AND ONE IN STORE; at the time to checking in I get charged for $60 dollars on the flight going out and $30 dollars for the flight comes back. So I need the money back to my account for those changes thanks for the atención on this request

Aeromexico
7.0
Good
454 reviews
Delta
7.9
Good
2,000 reviews

Boarding

8.0

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 10

I make a reservation and I have access to carry one bag on cabinets and one carry on bag, after I bought the reservation I called the airline to confirm and the answer was right I HAVE ACCESS TO CARRY ONE CARRY-ON BAG AND ONE IN STORE; at the time to checking in I get charged for $60 dollars on the flight going out and $30 dollars for the flight comes back. So I need the money back to my account for those changes thanks for the atención on this request

Air Canada
6.6
Okay
649 reviews
Delta
7.9
Good
2,000 reviews

Boarding

8.0

Comfort

7.9

Overall

7.9

Entertainment

7.8

Crew

8.5

Food

7.2

Reviews

1 / 10

I make a reservation and I have access to carry one bag on cabinets and one carry on bag, after I bought the reservation I called the airline to confirm and the answer was right I HAVE ACCESS TO CARRY ONE CARRY-ON BAG AND ONE IN STORE; at the time to checking in I get charged for $60 dollars on the flight going out and $30 dollars for the flight comes back. So I need the money back to my account for those changes thanks for the atención on this request

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 Air Canada for just $386, but on average you can expect to pay $419.

Are there last-minute flights available from Chicago to Winnipeg for under $800?

There are currently 6+ open flights from Chicago to Winnipeg within the next 7 days for less than $800.

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 $386. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $434 and $477, respectively. These flights start at 42% 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 $194 and Undisclosed Carrier from $248 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 $391.

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
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