Cheap flights from Chicago to Winnipeg

Round-trip
Economy
Chicago (CHI)
Winnipeg (YWG)
Tue 7/20
Tue 7/27
Any month
Compare vs. momondo |

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$534The best flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $534
Fastest flight time4h 4mThe fastest flight from Chicago to Winnipeg takes 4h 4m
Direct flightsNoneThere 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 Winnipeg1 airportThere 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?

Tuesday
The cheapest day of the week is typically Tuesday. 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 48% more expensive in the morning 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 18
ORD6:20 amChicago O'Hare Intl
5h 30m
1 stop
YWG11:50 amWinnipeg
Jul 24
YWG1:55 amWinnipeg
5h 50m
1 stop
ORD7:45 amChicago O'Hare Intl
Delta
Oct 20
ORD1:25 pmChicago O'Hare Intl
6h 28m
1 stop
YWG7:53 pmWinnipeg
Oct 27
YWG2:30 amWinnipeg
5h 50m
1 stop
ORD8:20 amChicago O'Hare Intl
Air Canada
Aug 6
ORD5:00 amChicago O'Hare Intl
6h 26m
1 stop
YWG11:26 amWinnipeg
Aug 11
YWG4:40 amWinnipeg
6h 16m
1 stop
ORD10:56 amChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Winnipeg

If you're looking for one-way flights from Chicago to Winnipeg, view some of our deals below provided by Air Canada
Air Canada
Jul 2
ORD5:30 pmChicago O'Hare Intl
37h 00m
2 stops
YWG6:30 amWinnipeg
Air Canada
Jul 2
ORD4:55 amChicago O'Hare Intl
49h 35m
1 stop
YWG6:30 amWinnipeg
Multiple Airlines
Jul 2
ORD7:55 pmChicago O'Hare Intl
56h 10m
3 stops
YWG4:05 amWinnipeg

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
8.1
8.3

Boarding

8.4

Comfort

8.3

Crew

7.9

Entertainment

8.1

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10
United Airlines
PriceFrom $228
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.

1 / 10
Air Canada
PriceFrom $240
Free Cancellation
Rating
7.1
7.3

Boarding

7.2

Comfort

7.8

Crew

7.2

Entertainment

5.9

Food

Reviews

Pros: I managed to get a comfortable seating

1 / 10

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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