Cheap flights from Chicago (CHI) to Manitoba

CHI — YWG
Dec 10 — Dec 171

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

Travelers have found it’s best to book a flight 60 days in advance to save up to 76% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Manitoba 1-2 weeks in advance for as low as $849, or $1,243 for flights within the next 24 hours.

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

December is one of the best times of the year to fly to Manitoba from Chicago. Prices for December average $640 per person but you can even find prices for as low as $352. The most expensive prices can be found in the month of March. Opting for a December flight can save you 40% on your journey compared to booking in March

When is the cheapest time to fly from Chicago to Manitoba (CHI - MB)?

When flying from Chicago to Manitoba, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to Manitoba in December, January 2022

The best prices found for CHI to Manitoba flights for December, January
Jan 10 - Jan 17
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

32h 40m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

24h 49m
$380

Multiple Airlines

Pick Dates

Deal found 12/5

Jan 10 - Jan 17
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 10m
$395

Air Canada

Pick Dates

Deal found 12/5

Dec 12 - Dec 19
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 55m
$409

Multiple Airlines

Pick Dates

Deal found 12/3

Chicago to Manitoba 2022 flight deals

Cheap flights to Manitoba from Chicago found for this year
Dec 12 - Dec 19
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 55m
$409

Multiple Airlines

Pick Dates

Deal found 12/3

Dec 20 - Jan 5
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

16h 15m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

13h 57m
$455

Multiple Airlines

Pick Dates

Deal found 12/4

Dec 20 - Jan 5
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

16h 15m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

12h 02m
$521

Multiple Airlines

Pick Dates

Deal found 12/4

Cheap Air Canada flights from Chicago to Manitoba

Jan 10 - Jan 17
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 10m
$395

Air Canada

Pick Dates

Deal found 12/5

Jan 9 - Jan 16
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

13h 54m
$415

Air Canada

Pick Dates

Deal found 12/4

Jan 24 - Feb 14
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

9h 36m
$424

Air Canada

Pick Dates

Deal found 12/4

Cheap Delta flights from Chicago to Manitoba

Jan 24 - Jan 27
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

5h 32m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
$414

Delta

Pick Dates

Deal found 12/4

Jan 24 - Jan 27
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

12h 52m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
$423

Delta

Pick Dates

Deal found 12/4

Jan 24 - Jan 27
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

12h 52m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

11h 54m
$427

Delta

Pick Dates

Deal found 12/4

Last minute flights from Chicago to Manitoba

Late deals on return flights to Manitoba from Chicago, departing today and this week
Dec 12 - Dec 19
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 55m
$409

Multiple Airlines

Pick Dates

Deal found 12/3

Dec 12 - Dec 19
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

9h 39m
$597

Multiple Airlines

Pick Dates

Deal found 12/3

Dec 12 - Dec 19
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

9h 10m
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

13h 57m
$689

Delta

Pick Dates

Deal found 12/4

One-way flights to Manitoba from Chicago

The cheapest one-way flights from Chicago to Manitoba
Jan 9
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 12m
$567

Delta

Pick Dates

Deal found 12/4

Jan 9
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

8h 37m
$625

Delta

Pick Dates

Deal found 12/4

Related info for your journey

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

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

Some of the carriers operating flights from Chicago to Manitoba that may be offering flexible cancellation policies are Air Canada, Delta, and United Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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

Yes, there are multiple flights from Chicago to Manitoba for under $400. The cheapest flight booked recently is on Multiple Airlines for just $354, but on average you can expect to pay $435.

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

There are currently 5+ open flights from Chicago to Manitoba within the next 7 days for less than $500.

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

The most popular airlines flying from Chicago to Manitoba are Air Canada, Delta and United Airlines. Something to consider prior to booking your flight.

What are the cheapest flights from Chicago to Manitoba?

While on average a flight from Chicago to Manitoba is generally $1,066, our data shows the cheapest flight currently is $500. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $354 for that flight.

Destination points for flights from Chicago to Manitoba

Select to see more specific information for flights from Chicago to all places in Manitoba

Top 4 airlines flying from Chicago to Manitoba

The chart below displays the airlines Cheapflights users traveling from Chicago to Manitoba choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Air CanadaCheapest$236Average$618FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
United AirlinesCheapest$386Average$652FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
WestJetCheapest$432Average$494FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
DeltaCheapest$473Average$672FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights