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Cheap flights from Chicago (CHI) to Winnipeg (YWG)

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The best prices from Chicago to Winnipeg are usually found in April or October, booked 49 days in advance, depart on a Sunday or Tuesday and return on a Wednesday

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

CHI - YWG
Price
$396 - $546
YWG
Temperature
14 - 80.6 °F
YWG
Rainfall
0.5 - 3.3 inches

Popular in

May

High demand for flights, 15% potential price rise

Cheapest in

April

Best time to find cheap flights, 15% potential price drop

Average price

$416

Average for round-trip flights in January 2021

Round-trip from

$396

From Chicago to Winnipeg

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 Chicago to Winnipeg?

Sunday flights are generally found to be more expensive for flights from Chicago to Winnipeg. 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 Winnipeg.

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

It’s optimal to fly from Chicago to Winnipeg at noon. By choosing this option you can save up to 44% on the cost of your flight, compared to a flight in the evening.

Cheap flights from Chicago to Winnipeg in January, February 2021

The best prices found for CHI to YWG flights for January, February
22 Jan - 24 Jan
$581pp
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
22 Jan - 24 Jan
$633pp
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
22 Jan - 24 Jan
$737pp
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to Winnipeg 2021 flight deals

Cheap flights to Winnipeg from Chicago found for this year
6 Mar - 6 Aug
$406pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
6 Mar - 6 Aug
$415pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
25 May - 29 May
$429pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Winnipeg from Chicago

Save time with Chicago to Winnipeg direct flight deals
9 Apr - 11 Apr
$572pp
ORD
Chicago O'Hare Intl
Air Canada
Non-Stop
YWG
Winnipeg
YWG
Winnipeg
Air Canada
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Winnipeg

Late deals on round-trip flights to Winnipeg from Chicago, departing today and this week
22 Jan - 24 Jan
$581pp
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
22 Jan - 24 Jan
$633pp
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
22 Jan - 24 Jan
$737pp
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl

Related info for your journey

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

Flight FAQs

From Chicago to Winnipeg

Are flight prices decreasing from Chicago to Winnipeg due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Winnipeg for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

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

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Chicago to Winnipeg 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 Chicago to Winnipeg have flexible cancellations due to COVID-19?

United Airlines, Delta, and Air Canada are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Winnipeg for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Winnipeg for under $400. The cheapest flight booked recently is on Air Canada for just $394, but on average you can expect to pay $462.

Are there nonstop flights from Chicago to Winnipeg for under $600 on Cheapflights?

Cheapflights has at least 1 direct flight from Chicago to Winnipeg under $600. A good price for a nonstop flight from Chicago to Winnipeg is less than $572.

Are there last-minute flights available from Chicago to Winnipeg for under $600?

There are currently 3+ open flights from Chicago to Winnipeg within the next 7 days for less than $600.

Is Chicago weather warmer or cooler than Winnipeg?

Expect the weather to be around 84 °F on average in July. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Winnipeg is generally colder than in Chicago.

How long is the flight from Chicago to Winnipeg?

A quick flight from Chicago to Winnipeg can take about 2h 34m. United Airlines provides one of the quickest options available for as low as $443. This flight may include one or multiple stops.

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

Air Canada, at $394, was found to be the cheapest airline from Chicago to Winnipeg.Alternate airlines to your destination round-trip include United Airlines and Delta. Air Canada is 15% cheaper than the average price of flights available within the next 90 days to this destination.

Destination information for Winnipeg

Things to know before you go. Useful info for your trip from Chicago to Winnipeg
Today's exchange rate
$1 = C$ 1.28
Flight duration
2h 31m
Average temperature for January in Winnipeg
14.0 °F
Avg rainfall for January in Winnipeg
0.9 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Winnipeg

Top 3 airlines flying from Chicago to Winnipeg

The chart below displays the airlines Cheapflights users traveling from Chicago to Winnipeg 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
Delta
$153 $356 No cancel fee N/A
United Airlines
$228 $645 No cancel fee 69%
Air Canada
$240 $732 No cancel fee 67%
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