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$ 444 - C$ 736
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$ 444

From Winnipeg to Chicago

One-way from

C$ 309

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$ 426 1-2 weeks out and tickets from C$ 577 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$ 310. You can even find prices in April for less than C$ 310, as users have found deals to Chicago from as low as C$ 235. 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 May, June 2021

The best prices found for YWG to CHI flights for May, June
11 Jun - 13 Jun
C$ 566pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg
2 Jun - 9 Jun
C$ 567pp
YWG
Winnipeg
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg
11 Jun - 13 Jun
C$ 571pp
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 2021 flight deals

Cheap flights to Chicago from Winnipeg found for this year
28 Jul - 1 Aug
C$ 559pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg
28 Jul - 1 Aug
C$ 560pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
11 Jun - 13 Jun
C$ 566pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg

One-way flights to Chicago from Winnipeg

The cheapest one-way flights from Winnipeg to Chicago
4:40 a.m. - 10:56 a.m.
Air Canada
1 stop
6h 16m
YWG - ORD
Air Canada
C$ 310
2:30 a.m. - 7:49 p.m.
Delta
3 stops
17h 19m
YWG - MDW
Delta
C$ 602
Delta
6:51 a.m. - 9:18 a.m.
Aer Lingus
Direct
2h 27m
YWG - ORD
Aer Lingus
C$ 1,688
Kiwi.com

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 is 1 flight from Winnipeg to Chicago per day from 4 different airlines.

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.

Can I find flights from Winnipeg to Chicago for under C$ 614 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago for under C$ 614. The cheapest flight booked recently is on Delta for just C$ 559, but on average you can expect to pay C$ 850.

Are there direct flights from Winnipeg to Chicago for under C$ 614 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.

What days are direct flights available from Winnipeg to Chicago?

Direct flights can be found on the following days: Sunday, Monday, Friday, Saturday.

How many flights depart from Winnipeg to Chicago on average per day?

Travellers can expect 1 flight from Winnipeg to Chicago on average per day.
Morning (6am - Noon) - 100% of flight departures

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 Delta, Air Canada, and WestJet fly from Winnipeg to Chicago in about 5h 12m. The time it takes to get you to your destination can typically vary by up to 6h 58m. Airlines will cover a distance of 1141 km. 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$ 559, 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 WestJet - these airlines can fly you to your destination from C$ 567 and C$ 734, respectively.

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

The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as C$ 310. However, be on the lookout for offers from Delta and Aer Lingus, 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 = $0.82
Average temperature for May in Chicago
22.0 °C
Avg rainfall for May in Chicago
109.0 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

Hourly flight availability from Winnipeg to Chicago

See what time of day planes typically take off from Winnipeg towards Chicago.
Morning 6 AM to noon 63% of flight departures
Afternoon Noon to 6 PM 36% of flight departures
Early morning Midnight to 6 AM 1% of flight departures
Evening 6 PM to midnight 0% of flight departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Winnipeg to Chicago
See how many times per day planes take to the skies headed from Winnipeg to Chicago.
Sunday
1 daily flight
Monday
2 daily flights
Tuesday
1 daily flight
Wednesday
2 daily flights
Thursday
0 flights
Friday
1 daily flight
Saturday
0 flights
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