Prices are in Canadian Dollars.

Cheap flights from Winnipeg to Chicago-O'Hare Intl

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Winnipeg to Chicago-O'Hare Intl are usually found in May or January, booked 24 days in advance, depart on a Sunday or Wednesday and return on a Monday

How to find the cheapest flight from
Winnipeg (YWG) to Chicago-O'Hare Intl (ORD)

YWG - ORD
Price
C$ 459 - C$ 760
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$ 465

Average for round-trip flights in January 2021

Round-trip from

C$ 459

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.
What is the cheapest day to fly round-trip from Winnipeg to Chicago-O'Hare Intl?

Sunday flights are found to be more expensive to fly from Winnipeg to Chicago-O'Hare Intl. 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 Chicago-O'Hare Intl.

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$ 440. For sooner than that we have options available in the next 3 days from C$ 596.

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$ 320. You can even find prices in April for less than C$ 320, as users have found deals to Chicago-O'Hare Intl from as low as C$ 242. 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%.

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

A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago-O'Hare Intl in the afternoon. If you’re flexible enough to do this you can expect to save up to 20% on your trip compared to booking a flight at noon.

Cheap flights from Winnipeg to Chicago-O'Hare Intl in January, February 2021

The best prices found for YWG to ORD flights for January, February
22 Jan - 29 Jan
C$ 787pp
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
22 Jan - 29 Jan
C$ 1,151pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg
22 Jan - 29 Jan
C$ 1,172pp
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
10 May - 14 May
C$ 521pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
10 May - 14 May
C$ 527pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
10 May - 14 May
C$ 529pp
YWG
Winnipeg
WestJet
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
 
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
10 May - 14 May
C$ 615pp
YWG
Winnipeg
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YWG
Winnipeg
10 May - 14 May
C$ 625pp
YWG
Winnipeg
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YWG
Winnipeg
10 May - 14 May
C$ 628pp
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 Winnipeg to Chicago-O'Hare Intl flights.

Flight FAQs

From Winnipeg to Chicago-O'Hare Intl

Can I find flights from Winnipeg to Chicago-O'Hare Intl for under C$ 634 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago-O'Hare Intl for under C$ 634. The cheapest flight booked recently is on Air Canada for just C$ 521, but on average you can expect to pay C$ 1,131.

What safety measures are being taken by airlines flying from Winnipeg to Chicago O'Hare Intl to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Delta is one of them. New policies for travellers booking flights from Winnipeg to Chicago O'Hare Intl include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially-distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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.

Are there direct flights from Winnipeg to Chicago-O'Hare Intl for under C$ 634 on Cheapflights?

Cheapflights has 3 direct flights from Winnipeg to Chicago-O'Hare Intl under C$ 634. A good price for a direct flight from Winnipeg to Chicago-O'Hare Intl is less than C$ 623.

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 less than Chicago-O'Hare Intl. We can gather that this will continue over the next 15 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$ 575, 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$ 522), Delta (C$ 528), and WestJet (C$ 529) 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 info for your trip from Winnipeg to Chicago-O'Hare Intl
Today's exchange rate
C$ 1 = $0.79
Flight duration
2h 28m
Average temperature for January in Chicago-O'Hare Intl
2.0 °C
Avg rainfall for January in Chicago-O'Hare Intl
46.0 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
Home North America USA Illinois Chicago Chicago-O'Hare Intl Cheap flights from Winnipeg to Chicago-O'Hare Intl