Cheap flights from Winnipeg to Chicago O'Hare Intl Airport

YWG — ORD
13 Dec — 20 Dec1
Return
1 adult
Economy
From?
To?
Tue 13/12
Tue 20/12

How far in advance should I book a flight from Winnipeg to Chicago O'Hare Intl Airport?

Travellers have found it’s best to book a flight 38 days in advance to save up to 52% 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 38 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 Winnipeg to Chicago O'Hare Intl Airport 1-2 weeks in advance for as low as C$ 846, or C$ 1,147 for flights within the next 24 hours.

What is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport?

Flights from Winnipeg to Chicago O'Hare Intl Airport lean towards being more expensive in August. Prices are generally better when you fly from Winnipeg to Chicago O'Hare Intl Airport in February, with the cheapest ticket starting at C$ 576.

When is the cheapest time to fly from Winnipeg to Chicago O'Hare Intl Airport (YWG - ORD)?

When flying from Winnipeg to Chicago O'Hare Intl Airport, 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 Winnipeg to O'Hare Intl in December, January 2022

The best prices found for YWG to ORD flights for December, January
21 Jan. - 28 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 53m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

4h 42m
C$ 396

Delta

Deal found 8/12

14 Jan. - 15 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

8h 47m
C$ 400

Delta

Deal found 6/12

21 Jan. - 28 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

4h 42m
C$ 459

Delta

Deal found 7/12

Winnipeg to O'Hare Intl 2022 flight deals

Cheap flights to O'Hare Intl from Winnipeg found for this year
29 Dec. - 16 Mar.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 39m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 08m
C$ 597

Air Canada

Deal found 7/12

21 Dec. - 28 Dec.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 39m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

13h 35m
C$ 617

Air Canada

Deal found 7/12

28 Dec. - 16 Mar.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

12h 05m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 30m
C$ 624

Air Canada

Deal found 7/12

Cheap Delta flights from Winnipeg to O'Hare Intl

21 Jan. - 28 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 53m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

4h 42m
C$ 396

Delta

Deal found 8/12

14 Jan. - 15 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

8h 47m
C$ 400

Delta

Deal found 6/12

26 Apr. - 1 May
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 59m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

6h 27m
C$ 445

Delta

Deal found 8/12

Cheap Air Canada flights from Winnipeg to O'Hare Intl

20 Feb. - 11 Apr.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

13h 22m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 15m
C$ 444

Air Canada

Deal found 7/12

26 Apr. - 1 May
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 24m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 47m
C$ 451

Air Canada

Deal found 7/12

26 Apr. - 1 May
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 24m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 47m
C$ 456

Air Canada

Deal found 6/12

Last minute flights from Winnipeg to O'Hare Intl

Late deals on round-trip flights to O'Hare Intl from Winnipeg, departing today and this week
13 Dec. - 27 Dec.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 39m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

14h 00m
C$ 659

United Airlines

Deal found 6/12

13 Dec. - 27 Dec.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

11h 43m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

4h 06m
C$ 710

Delta

Deal found 6/12

13 Dec. - 27 Dec.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 08m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

7h 10m
C$ 734

Air Canada

Deal found 7/12

One-way flights to O'Hare Intl from Winnipeg

The cheapest one-way flights from Winnipeg to O'Hare Intl
14 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
C$ 236

Delta

Deal found 6/12

9 Feb.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

2 stops

9h 34m
C$ 244

Air Canada

Deal found 6/12

7 Mar.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 56m
C$ 262

Air Canada

Deal found 6/12

Related info for your journey

Useful info, stats and facts about Winnipeg to O'Hare Intl flights.

What airport do you fly from for flights from Winnipeg to Chicago O'Hare Intl?

If you book a flight to Chicago O'Hare Intl from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 0 flights from Winnipeg to Chicago O'Hare Intl per day from 7 different airlines.

Which airlines flying from Winnipeg to Chicago O'Hare Intl have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like Air Canada, Endeavor Airlines, and Delta flying from Winnipeg to Chicago O'Hare Intl have implemented new flexible cancellation policies.

Can I find flights from Winnipeg to Chicago O'Hare Intl Airport for under C$ 400 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago O'Hare Intl Airport for under C$ 400. The cheapest flight booked recently is on Delta for just C$ 396, but on average you can expect to pay C$ 471.

Are there last-minute flights available from Winnipeg to Chicago O'Hare Intl Airport for under C$ 700?

There are currently 7+ open flights from Winnipeg to Chicago O'Hare Intl Airport within the next 7 days for less than C$ 700.

What are the cheapest airlines flying from Winnipeg to Chicago O'Hare Intl Airport round-trip?

Delta, at C$ 396, was found to be the cheapest airline from Winnipeg to Chicago O'Hare Intl Airport.Alternate airlines to your destination round-trip include Air Canada and United Airlines. Delta is priced at 44% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Winnipeg to Chicago O'Hare Intl Airport one-way?

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at C$ 236. Air Canada flights start at C$ 244 while deals on United Airlines start at C$ 281 one-way.

What are the most popular airlines that fly from Winnipeg to Chicago O'Hare Intl Airport?

Consider Endeavor Airlines, Air Canada or Delta when booking your flight. These represent the most popular airlines when flying from Winnipeg to Chicago O'Hare Intl Airport.

What are the cheapest flights from Winnipeg to Chicago O'Hare Intl Airport?

While on average a flight from Winnipeg to Chicago O'Hare Intl Airport is generally C$ 318, our data shows the cheapest flight currently is C$ 271. When looking at the most popular route, (Winnipeg - Chicago O'Hare Intl), you can expect to pay C$ 400 for that flight.

Top 5 airlines flying from Winnipeg to O'Hare Intl

The chart below displays the airlines Cheapflights users travelling from Winnipeg to O'Hare Intl choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Endeavor AirlinesCheapestC$ 196AverageC$ 914FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Endeavor Airlines flights
Air CanadaCheapestC$ 396AverageC$ 672FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
DeltaCheapestC$ 440AverageC$ 607FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
WestJetCheapestC$ 452AverageC$ 543FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
United AirlinesCheapestC$ 654AverageC$ 766FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights