Cheap flights from Winnipeg to Chicago

Round-trip
Economy
Winnipeg (YWG)
Chicago (CHI)
Depart
Return
Any month
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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 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 2021: compare Winnipeg to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YWG - CHI
Price
C$ 455 - C$ 753
CHI
Temperature
1 - 29 °C
CHI
Precipitation
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$ 455

From Winnipeg to Chicago

One-way from

C$ 489

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 Monday is a good option for securing a great price. You can expect to save up to 14% 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$ 436 1-2 weeks out and tickets from C$ 591 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$ 318. You can even find prices in April for less than C$ 318, as users have found deals to Chicago from as low as C$ 240. 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 afternoon could potentially save you up to 22% on airfare.

Cheap flights from Winnipeg to Chicago in July, August 2021

The best prices found for YWG to CHI flights for July, August
27 Aug - 11 Sep
C$ 623pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
27 Aug - 11 Sep
C$ 630pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg
27 Aug - 11 Sep
C$ 641pp
YWG
Winnipeg
WestJet
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
   
2 STOPS
YWG
Winnipeg

Winnipeg to Chicago 2021 flight deals

Cheap flights to Chicago from Winnipeg found for this year
2 Dec - 5 Dec
C$ 504pp
YWG
Winnipeg
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YWG
Winnipeg
2 Dec - 5 Dec
C$ 515pp
YWG
Winnipeg
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YWG
Winnipeg
6 Nov - 9 Nov
C$ 515pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg

Direct flights to Chicago from Winnipeg

Save time with Winnipeg to Chicago direct flight deals
6 Nov - 9 Nov
C$ 608pp
YWG
Winnipeg
Multiple Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air New Zealand
Direct
YWG
Winnipeg
6 Nov - 8 Nov
C$ 789pp
YWG
Winnipeg
Multiple Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air New Zealand
Direct
YWG
Winnipeg

Last minute flights from Winnipeg to Chicago

Late deals on round-trip flights to Chicago from Winnipeg, departing today and this week
8 Aug - 14 Aug
C$ 1,154pp
YWG
Winnipeg
WestJet
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
   
2 STOPS
YWG
Winnipeg
8 Aug - 12 Aug
C$ 1,185pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
8 Aug - 12 Aug
C$ 1,223pp
YWG
Winnipeg
WestJet
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
   
2 STOPS
YWG
Winnipeg

One-way flights to Chicago from Winnipeg

The cheapest one-way flights from Winnipeg to Chicago
3:30 a.m. - 5:57 p.m.
WestJet
2 stops
14h 27m
YWG - ORD
WestJet
C$ 489
WestJet
7:45 a.m. - 3:19 p.m.
Air Canada
1 stop
7h 34m
YWG - ORD
Air Canada
C$ 493
Air Canada
1:00 a.m. - 12:30 p.m.
Delta
2 stops
11h 30m
YWG - MDW
Delta
C$ 497
Delta

Related info for your journey

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

Flight FAQs

From Winnipeg to Chicago

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

Can I find flights from Winnipeg to Chicago for under C$ 628 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago for under C$ 628. The cheapest flight booked recently is on Delta for just C$ 504, but on average you can expect to pay C$ 577.

Are there direct flights from Winnipeg to Chicago for under C$ 628 on Cheapflights?

Cheapflights has 2 direct flights from Winnipeg to Chicago under C$ 628. A good price for a direct flight from Winnipeg to Chicago is less than C$ 699.

Are there last-minute flights available from Winnipeg to Chicago for under C$ 1,257?

There are currently 12+ open flights from Winnipeg to Chicago within the next 7 days for less than C$ 1,257.

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 United Airlines, Delta, and Air Canada fly from Winnipeg to Chicago in about 2h 13m. The time it takes to get you to your destination can typically vary by up to 5h 07m. 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$ 504, 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 United Airlines and Air Canada - these airlines can fly you to your destination from C$ 511 and C$ 518, respectively. These flights start at 7% 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 WestJet, with whom users have recently found tickets for as low as C$ 327. However, be on the lookout for offers from Air Canada and United Airlines, 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 duration and weather info for your trip from Winnipeg to Chicago.
Today's exchange rate
C$ 1 = $0.80
Flight duration
2h 28m
Average temperature for July in Chicago
29.0 °C
Avg rainfall for July in Chicago
95.0 mm

Airports servicing Winnipeg

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 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.
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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