Cheap flights from Winnipeg to Chicago-O'Hare Intl

Round-trip
Economy
Winnipeg (YWG)
Chicago (ORD)
Depart
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Any month
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How to find the cheapest flight from
Winnipeg (YWG) to Chicago-O'Hare Intl (ORD)

All the information you need to plan the best YWG to ORD flight in 2021: compare Winnipeg to Chicago-O'Hare Intl flight prices with the expected peak season, weather and rainfall in Chicago-O'Hare Intl.
YWG - ORD
Price
C$ 446 - C$ 738
ORD
Temperature
2 - 30 °C
ORD
Rainfall
39 - 123 mm

Popular in

August

High demand for flights, 33% potential price rise

Cheapest in

May

Best time to find cheap flights, 10% potential price drop

Average price

C$ 468

Average for round-trip flights in June 2021

Round-trip from

C$ 446

From Winnipeg to Chicago-O'Hare Intl

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Winnipeg to Chicago-O'Hare Intl?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 34 days in advance, which can save you up to 86% on flights from Winnipeg to Chicago-O'Hare Intl compared to booking the week you need them. Waiting 34 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 427. For sooner than that we have options available in the next 3 days from C$ 579.

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

The best pricing can be found in the month of April. Prices to Chicago-O'Hare Intl from Winnipeg average C$ 311. You can even find prices in April for less than C$ 311, as users have found deals to Chicago-O'Hare Intl from as low as C$ 235. The month of January appears to be one of the more expensive times to travel to Chicago-O'Hare Intl from Winnipeg. Flying in the targeted month can save you up to 10%.

Cheap flights from Winnipeg to Chicago-O'Hare Intl in June, July 2021

The best prices found for YWG to ORD flights for June, July
17 Jul - 24 Jul
C$ 583pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
15 Jul - 31 Jul
C$ 585pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
20 Jul - 27 Jul
C$ 606pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg

Winnipeg to Chicago-O'Hare Intl 2021 flight deals

Cheap flights to Chicago-O'Hare Intl from Winnipeg found for this year
4 Aug - 11 Aug
C$ 527pp
YWG
Winnipeg
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg
4 Aug - 11 Aug
C$ 531pp
YWG
Winnipeg
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
15 Sep - 19 Sep
C$ 535pp
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg

Direct flights to Chicago-O'Hare Intl from Winnipeg

Save time with Winnipeg to Chicago-O'Hare Intl direct flight deals
31 Oct - 4 Nov
C$ 584pp
YWG
Winnipeg
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YWG
Winnipeg
31 Oct - 4 Nov
C$ 591pp
YWG
Winnipeg
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YWG
Winnipeg

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Winnipeg</span> to <span class="emphasized">Chicago-O'Hare Intl</span> flights.

Flight FAQs

From Winnipeg to Chicago-O'Hare Intl

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 4 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 United Airlines, Delta, and Air Canada 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 for under C$ 616 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago-O'Hare Intl for under C$ 616. The cheapest flight booked recently is on Air Canada for just C$ 527, but on average you can expect to pay C$ 601.

Are there direct flights from Winnipeg to Chicago-O'Hare Intl for under C$ 616 on Cheapflights?

Cheapflights has 2 direct flights from Winnipeg to Chicago-O'Hare Intl under C$ 616. A good price for a direct flight from Winnipeg to Chicago-O'Hare Intl is less than C$ 588.

Does it rain more in Winnipeg or Chicago-O'Hare Intl?

When travelling, we recommend packing in preparation to handle common weather conditions. The rainfall in Winnipeg is typically similar to Chicago-O'Hare Intl. We can gather that this will continue over the next 20 days.

Is Winnipeg weather warmer or cooler than Chicago-O'Hare Intl?

With an average temperature of 30 °C, peak weather can be found in July. As a traveller, expect to see changes in flight prices during that period. The temperatures in Chicago-O'Hare Intl are hotter than in Winnipeg.

How long is the flight from Winnipeg to Chicago-O'Hare Intl?

For as low as C$ 592, United Airlines can have you in Chicago-O'Hare Intl from Winnipeg in 2h 13m. Both multi-stop and direct flights can be found to your destination and back.

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

According to our current data, Air Canada (C$ 528), Delta (C$ 535), and United Airlines (C$ 584) offers the cheapest pricing from Winnipeg to Chicago-O'Hare Intl.

Destination information for Chicago-O'Hare Intl

Things to know before you go - useful duration and weather info for your trip from Winnipeg to Chicago-O'Hare Intl.
Today's exchange rate
C$ 1 = $0.82
Average temperature for June in Chicago-O'Hare Intl
28.0 °C
Avg rainfall for June in Chicago-O'Hare Intl
88.0 mm

Airports servicing Winnipeg

Airports servicing Chicago

Top 4 airlines flying from Winnipeg to Chicago-O'Hare Intl

The chart below displays the airlines Cheapflights users travelling from Winnipeg to Chicago-O'Hare Intl choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
WestJet
C$ 185 C$ 332 No cancel fee 60%
Search WestJet flights
Delta
C$ 269 C$ 405 No cancel fee N/A
Search Delta flights
Air Canada
C$ 339 C$ 418 No cancel fee 67%
Search Air Canada flights
United Airlines
C$ 366 C$ 502 No cancel fee 69%
Search United Airlines flights
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