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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 February or November, booked 31 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
$290 - $530
YWG
Temperature
14 - 80.6 °F
YWG
Rainfall
0.5 - 3.3 inches

Popular in

March

High demand for flights, 18% potential price rise

Cheapest in

February

Best time to find cheap flights, 33% potential price drop

Round-trip from

$290

From Chicago to Winnipeg

One-way from

$186

One-way flight 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.

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

To save on the cost of your flight from Chicago to Winnipeg, book at least 51 days before your planned departure. Booking around this time can save you about 7% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $319 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $319.

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

Flights from Chicago to Winnipeg lean towards being more expensive in December. Prices are generally better when you fly from Chicago to Winnipeg in November, with the cheapest ticket starting at $112.

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 September, October 2020

The best prices found for CHI to YWG flights for September, October
20 Oct - 23 Oct
$381pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
20 Oct - 23 Oct
$759pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
3 Oct - 4 Oct
$789pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to Winnipeg 2020 flight deals

Cheap flights to Winnipeg from Chicago found for this year
20 Oct - 23 Oct
$381pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
20 Dec - 17 Jan
$427pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
20 Dec - 3 Jan
$448pp
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Winnipeg from Chicago

The cheapest one-way flights from Chicago to Winnipeg
1:06 am - 12:04 pm
Delta
1 Stop
10h 58m
MDW - YWG
Delta
$186
Delta
11:37 am - 3:46 pm
Delta
1 Stop
4h 09m
ORD - YWG
Delta
$206
Delta
10:37 am - 2:52 pm
Delta
1 Stop
4h 15m
ORD - YWG
Delta
$221
Delta

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.

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 Multiple Airlines for just $381, but on average you can expect to pay $483.

Are there nonstop flights from Chicago to Winnipeg for under $400 on Cheapflights?

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

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 3h 54m. Delta provides one of the quickest options available for as low as $779.

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

Delta, at $448, was found to be the cheapest airline from Chicago to Winnipeg..

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

To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $186.

Destination information for Winnipeg

Things to know before you go. Useful info for your trip from Chicago to Winnipeg
Today's exchange rate
$1 = C$ 1.34
Average temperature for September in Winnipeg
69.8 °F
Avg rainfall for September in Winnipeg
1.9 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Winnipeg

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