Cheap flights from Chicago to Winnipeg

Round-trip
Economy
Chicago (CHI)
Winnipeg (YWG)
Wed 2/24
Wed 3/3
Any month
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Flight information for Chicago to Winnipeg
(CHI to YWG)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg
Best Price Found $501 The best flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $501
Fastest flight time 2h 36m The fastest flight from Chicago to Winnipeg takes 2h 36m.
Direct flights None There are no direct flights from Chicago to Winnipeg. Popular non-direct routes for this connection are Chicago Midway - Winnipeg and Chicago O'Hare Intl - Winnipeg.
Airports in Winnipeg 1 airport There is 1 airport near Winnipeg: Winnipeg (YWG)

How to get the cheapest flight ticket from Chicago to Winnipeg

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly from Chicago to Winnipeg?
April
The cheapest time of year to fly to Winnipeg from Chicago is April. Most expensive is May
What is the cheapest day to depart Chicago for Winnipeg?
Sunday
The cheapest day of the week is typically Sunday. The most expensive is typically Monday
When is the cheapest time to fly from Chicago to Winnipeg?
at noon
Chicago to Winnipeg flights are approximately 44% more expensive in the evening than at noon
What is the cheapest airline that flies to Winnipeg from Chicago?
WestJet
WestJet, Air Canada, and Delta are the most popular carriers operating from Chicago to Winnipeg
What is the cheapest Chicago to Winnipeg flight route?
Chicago O'Hare Intl - Winnipeg
Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago - Winnipeg flight prices
How far in advance should you book Chicago to Winnipeg flights?
49 days before
The cheapest time to buy a flight from Chicago to Winnipeg is approximately 49 days to departure
60
Days before departure
0

Easily compare round-trip flights from Chicago to Winnipeg

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Winnipeg by changing tabs
Air Canada
Jul 11
2h 34m
Chicago O'Hare Intl
2h 34m
6:28 am
Winnipeg
Jul 17
6:51 am
Winnipeg
2h 27m
9:18 am
Chicago O'Hare Intl
Air Canada
Feb 15
5h 40m
Chicago O'Hare Intl
5h 40m
1 stop
10:55 am
Winnipeg
Apr 2
6:51 am
Winnipeg
2h 27m
9:18 am
Chicago O'Hare Intl
Multiple Airlines
Feb 15
5h 54m
Chicago O'Hare Intl
5h 54m
1 stop
11:09 am
Winnipeg
Apr 2
6:51 am
Winnipeg
2h 27m
9:18 am
Chicago O'Hare Intl

Best airlines flying from Chicago to Winnipeg

Compare and see reviews for airlines that fly from Chicago to Winnipeg with momondo
AirlineRatingFree CancellationPrice
Delta
PriceFrom $153
Free Cancellation
Rating
8.3
8.2

Boarding

8.5

Comfort

8.8

Crew

7.8

Entertainment

8.1

Food

Reviews

Pros: I appreciate the choice of snacks.

Cons: The coffee served on the flight was lukewarm.

1 / 9
United Airlines
PriceFrom $228
Free Cancellation
Rating
6.6
6.4

Boarding

7.0

Comfort

7.3

Crew

6.0

Entertainment

6.6

Food

Reviews

Pros: It was meh....

Cons: I got no notification that the flight was going to be 1 hour earlier

1 / 6
Air Canada
PriceFrom $240
Free Cancellation
Rating
5.9
8.0

Boarding

6.0

Comfort

7.3

Crew

4.0

Entertainment

3.3

Food

Reviews

Pros: The flight attendants were fabulous on this flight.

Cons: Older plane that showed lots of grime from past travelers. The seats in my row had old spills that seemed to have run down the backs of the seats and dried over. Gross!

1 / 1

Which airlines flying from Chicago to Winnipeg have COVID-19 safety policies in place?

Many airlines have put safety measures in place to reduce the spread of COVID-19. One is Delta. Usage of HEPA filters, scheduled sanitation, enhanced cleaning of aircrafts, pre-flight testing, and mask policies are some of the implemented practices made by airlines to help keep you safe as you depart from Chicago to Winnipeg. Keep in mind that policies will vary by airline.

Are airlines flying from Chicago to Winnipeg offering flexible cancellation due to COVID-19?

Some of our partner airlines flying from Chicago to Winnipeg are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are United Airlines, Delta, and Air Canada. You can search for the full list of airlines like United Airlines that are offering this flexibility.


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