Cheap flights from Winnipeg to Chicago

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The best prices from Winnipeg to Chicago are usually found in January or April, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Monday

How to find the cheapest flight from
Winnipeg (YWG) to Chicago (CHI)

YWG - CHI
Price
C$ 480 - C$ 794
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Popular in

August

High demand for flights, 28% potential price rise

Cheapest in

January

Best time to find cheap flights, 17% potential price drop

Round-trip from

C$ 480

From Winnipeg to Chicago

One-way from

C$ 342

One-way flight from Winnipeg to Chicago

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?

Departing on a Tuesday is a good option for securing a great price. You can expect to save up to 18% when planning your travel around this day of the week.

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

To save up to 86% on this flight, we recommend booking at least 34 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Winnipeg to Chicago from C$ 460 1-2 weeks out and tickets from C$ 623 for flights departing within the next 72 hours.

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

The best pricing can be found in the month of April. Prices to Chicago from Winnipeg average C$ 335. You can even find prices in April for less than C$ 335, as users have found deals to Chicago from as low as C$ 253. The month of January appears to be one of the more expensive times to travel to Chicago from Winnipeg. Flying in the targeted month can save you up to 10%.

When is the cheapest time to fly from Winnipeg to Chicago (YWG - CHI)?

One of the essential ways to save on airfare from Winnipeg to Chicago 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 43% on airfare.

Winnipeg to Chicago 2020 flight deals

Cheap flights to Chicago from Winnipeg found for this year
2 Dec - 4 Dec
C$ 486pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg
2 Dec - 4 Dec
C$ 496pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg
2 Dec - 4 Dec
C$ 498pp
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg

One-way flights to Chicago from Winnipeg

The cheapest one-way flights from Winnipeg to Chicago
2:30 a.m. - 6:05 p.m.
Air Canada
2 stops
15h 35m
YWG - ORD
Air Canada
C$ 342
KAYAK
5:55 a.m. - 4:08 p.m.
Delta
2 stops
10h 13m
YWG - ORD
Delta
C$ 1,276
Delta
2:00 a.m. - 5:05 p.m.
United Airlines
3 stops
15h 05m
YWG - ORD
United Airlines
C$ 1,814
United

Related info for your journey

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

Flight FAQs

From Winnipeg to Chicago

Can I find flights from Winnipeg to Chicago for under C$ 530 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago for under C$ 530. The cheapest flight booked recently is on Delta for just C$ 486, but on average you can expect to pay C$ 547.

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

Airlines globally have implemented additional safety measures to accommodate you. Delta is one of them. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Winnipeg to Chicago. Policies will vary by airline.

Which airlines flying from Winnipeg to Chicago 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 have implemented new flexible cancellation policies.

Are there direct flights from Winnipeg to Chicago for under C$ 530 on Cheapflights?

There are no direct flights from Winnipeg to Chicago, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Is Winnipeg weather warmer or cooler than Chicago?

With an average temperature of 29 °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 are hotter than in Winnipeg.

How long is the flight from Winnipeg to Chicago?

Airlines like Air Canada, Delta, and United Airlines fly from Winnipeg to Chicago in about 6h 22m. The time it takes to get you to your destination can typically vary by up to 10h 46m. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

What are the cheapest airlines to flying from Winnipeg to Chicago round-trip?

Currently priced at C$ 487, Delta will fly you from Winnipeg to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and United Airlines - these airlines can fly you to your destination from C$ 547 and C$ 601, respectively. These flights start at 15% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Winnipeg to Chicago one-way?

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as C$ 313. However, be on the lookout for offers from Air Canada and Delta, as they are both options that can get you from Winnipeg to Chicago for a low price.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Winnipeg to Chicago
Today's exchange rate
C$ 1 = $0.76
Average temperature for October in Chicago
18.0 °C
Avg rainfall for October in Chicago
66.0 mm

Airports servicing Winnipeg

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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