Cheap flights from Winnipeg to Chicago

YWG — CHI
10 Dec — 17 Dec1
Return
1 adult
Economy
From?
To?
Sat 10/12
Sat 17/12

The best prices from Winnipeg to Chicago are usually found in February or September, booked 38 days in advance, depart on a Tuesday or Wednesday and return on a Monday

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

All the information you need to plan the best YWG to CHI flight in 2022: compare Winnipeg to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

YWG - CHI

Price

C$ 463 - C$ 628

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

Popular inAugustHigh demand for flights, 17% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 11% potential price drop
Round-trip fromC$ 624From Winnipeg to Chicago (CHI)
One-way fromC$ 474One-way flight from Winnipeg to Chicago (CHI)

What is the cheapest day to fly round-trip from Winnipeg to Chicago?

Monday is generally a great day to depart. Flying on this day could help you save up to 34%.

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

Find a great deal and save up to 52% by booking at least 38 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago within the next two weeks, with the cheapest ticket starting at C$ 819.

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

The best pricing can be found in the month of February. Prices to Chicago from Winnipeg average C$ 699. You can even find prices in February for less than C$ 699, as users have found deals to Chicago from as low as C$ 568. The month of August 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 20%.

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 30% on airfare.

Cheap flights from Winnipeg to Chicago in December, January 2022

The best prices found for YWG to CHI flights for December, January
20 Jan. - 23 Jan.
YWG

Winnipeg

MDW

Chicago Midway

1 stop

7h 19m
MDW

Chicago Midway

YWG

Winnipeg

2 stops

12h 57m
C$ 457

Delta

Deal found 4/12

27 Jan. - 30 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

4h 52m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

5h 32m
C$ 457

Delta

Deal found 4/12

9 Dec. - 11 Dec.
YWG

Winnipeg

MDW

Chicago Midway

1 stop

12h 30m
MDW

Chicago Midway

YWG

Winnipeg

1 stop

24h 18m
C$ 475

Multiple Airlines

Deal found 4/12

Cheap Air Canada flights from Winnipeg to Chicago

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 12m
C$ 450

Air Canada

Deal found 5/12

23 Apr. - 30 Apr.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 55m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

9h 10m
C$ 486

Air Canada

Deal found 4/12

26 Apr. - 1 May
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 24m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

10h 17m
C$ 502

Air Canada

Deal found 4/12

Cheap United Airlines flights from Winnipeg to Chicago

30 Mar. - 5 Apr.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 58m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

8h 05m
C$ 463

United Airlines

Deal found 4/12

20 Jan. - 23 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

11h 21m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

1 stop

15h 55m
C$ 543

United Airlines

Deal found 4/12

30 Mar. - 5 Apr.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

6h 49m
ORD

Chicago O'Hare Intl

YWG

Winnipeg

2 stops

18h 45m
C$ 622

United Airlines

Deal found 4/12

One-way flights to Chicago from Winnipeg

The cheapest one-way flights from Winnipeg to Chicago
20 Jan.
YWG

Winnipeg

MDW

Chicago Midway

1 stop

7h 19m
C$ 264

Delta

Deal found 3/12

20 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

7h 53m
C$ 264

Delta

Deal found 3/12

7 Jan.
YWG

Winnipeg

ORD

Chicago O'Hare Intl

1 stop

8h 10m
C$ 403

Air Canada

Deal found 3/12

Related info for your journey

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

What airport do you fly from for flights from Winnipeg to Chicago?

If you book a flight to Chicago 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 per day from 7 different airlines.

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 Air Canada, Endeavor Airlines, and Delta flying from Winnipeg to Chicago have implemented new flexible cancellation policies.

Can I find flights from Winnipeg to Chicago for under C$ 500 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago for under C$ 500. The cheapest flight booked recently is on Air Canada for just C$ 450, but on average you can expect to pay C$ 513.

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

Air Canada, at C$ 450, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. Air Canada is priced at 35% 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 one-way?

The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 264. However, be on the lookout for offers from Air Canada and WestJet, as they are both options that can get you from Winnipeg to Chicago for a low price.

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

Endeavor Airlines, Air Canada and Delta are the most popular airlines when flying from Winnipeg to Chicago.

What are the cheapest flights from Winnipeg to Chicago?

Looking at all options, your cheapest flight can be booked for C$ 267. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 457 on average our data indicates C$ 279 when flying from Winnipeg to Chicago.

Top 5 airlines flying from Winnipeg to Chicago

The chart below displays the airlines Cheapflights users travelling from Winnipeg to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Endeavor AirlinesCheapestC$ 193AverageC$ 902FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Endeavor Airlines flights
Air CanadaCheapestC$ 391AverageC$ 663FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
WestJetCheapestC$ 446AverageC$ 536FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
DeltaCheapestC$ 503AverageC$ 601FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapestC$ 645AverageC$ 755FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights