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Cheap flights from Chicago to Winnipeg from C$ 240

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Winnipeg departing on 10/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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Wed 3/4
Wed 10/4

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Cheap Chicago to Winnipeg (CHI to YWG) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg

Best price found

C$ 240

Fastest flight time

2h 24m

Direct flights

Tue, Wed, Fri, Sat and Sun

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago in the past 72 hours is C$ 240. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 465.
The fastest flight from Chicago to Winnipeg takes 2h 24m
Direct flights go from Chicago to Winnipeg on Tuesday, Wednesday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Air Canada.
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?

May. The cheapest time of year to fly to Winnipeg from Chicago is May. The most expensive is December.

What is the cheapest day to depart Chicago for Winnipeg?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Friday

When is the cheapest time to fly from Chicago to Winnipeg?

In the afternoon. Chicago to Winnipeg flights are approximately 51% more expensive at noon than in the afternoon

What is the cheapest airline that flies to Winnipeg from Chicago?

Air Canada. Air Canada is the most popular carrier operating from Chicago to Winnipeg

What is the cheapest Chicago to Winnipeg flight route?

Chicago Midway - Winnipeg. Fly from Chicago Midway to Winnipeg for the best Chicago - Winnipeg flight prices

How far in advance should you book Chicago to Winnipeg flights?

7 days before. The cheapest time to buy a flight from Chicago to Winnipeg is approximately 7 days to departure

Can stopping save me money on Chicago to Winnipeg flights?

You could potentially save up to 35% on your flight if you consider stops on a Chicago to Winnipeg flight.

When you’re planning your trip from Chicago to Winnipeg, the most popular airport-to-airport route is Chicago O'Hare Intl Airport to Winnipeg Airport. If you are looking for an alternate airport near Chicago O'Hare Intl Airport, Chicago Midway Airport is a great option and is located in Chicago. The least expensive flight option from Chicago to Winnipeg will typically be MDW — YWG during the month of March with an average price of C$ 465 RT.

Chicago O'Hare Intl Airport (ORD) to Winnipeg Airport (YWG)C$ 478
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Chicago Midway Airport (MDW) to Winnipeg Airport (YWG)C$ 465
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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
Multiple Airlines
24 Apr.
MDW7:00 a.m.Chicago Midway
7h 55m
1 stop
YWG2:55 p.m.Winnipeg
1 May
YWG8:00 a.m.Winnipeg
6h 39m
1 stop
MDW2:39 p.m.Chicago Midway
WestJet
21 Sep.
ORD5:55 p.m.Chicago O'Hare Intl
17h 49m
1 stop
YWG11:44 a.m.Winnipeg
28 Sep.
YWG8:30 a.m.Winnipeg
8h 39m
1 stop
ORD5:09 p.m.Chicago O'Hare Intl
Air Canada
11 Jun.
ORD6:00 a.m.Chicago O'Hare Intl
10h 00m
1 stop
YWG4:00 p.m.Winnipeg
13 Jun.
YWG5:00 a.m.Winnipeg
7h 54m
1 stop
ORD12:54 p.m.Chicago O'Hare Intl
Delta
10 May
MDW8:45 a.m.Chicago Midway
6h 40m
1 stop
YWG3:25 p.m.Winnipeg
12 May
YWG6:55 a.m.Winnipeg
6h 40m
1 stop
MDW1:35 p.m.Chicago Midway
Multiple Airlines
17 Apr.
ORD9:27 a.m.Chicago O'Hare Intl
14h 03m
1 stop
YWG11:30 p.m.Winnipeg
22 Apr.
YWG7:30 a.m.Winnipeg
13h 35m
1 stop
ORD9:05 p.m.Chicago O'Hare Intl
Undisclosed Carrier
1 May
ORD5:57 p.m.Chicago O'Hare Intl
21h 28m
1 stop
YWG3:25 p.m.Winnipeg
31 May
YWG3:20 p.m.Winnipeg
25h 45m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
C$ 1,077
Find similar

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, Delta and WestJet
Multiple Airlines
10 Apr.
MDW5:30 a.m.Chicago Midway
18h 00m
2 stops
YWG11:30 p.m.Winnipeg
Delta
20 Jul.
MDW7:06 p.m.Chicago Midway
4h 19m
1 stop
YWG11:25 p.m.Winnipeg
WestJet
4 Jul.
ORD6:00 a.m.Chicago O'Hare Intl
16h 43m
2 stops
YWG10:43 p.m.Winnipeg

Search last-minute flights to Winnipeg from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Winnipeg
Multiple Airlines
6 Apr.
ORD10:46 p.m.Chicago O'Hare Intl
25h 58m
1 stop
YWG12:44 a.m.Winnipeg
8 Apr.
YWG7:30 a.m.Winnipeg
13h 40m
1 stop
ORD9:10 p.m.Chicago O'Hare Intl
WestJet
7 Apr.
ORD6:00 a.m.Chicago O'Hare Intl
8h 55m
1 stop
YWG2:55 p.m.Winnipeg
13 Apr.
YWG5:00 a.m.Winnipeg
11h 35m
2 stops
ORD4:35 p.m.Chicago O'Hare Intl
C$ 1,239
Find similar
Undisclosed Carrier
7 Apr.
ORD5:55 p.m.Chicago O'Hare Intl
21h 00m
1 stop
YWG2:55 p.m.Winnipeg
13 Apr.
YWG5:00 a.m.Winnipeg
16h 21m
2 stops
ORD9:21 p.m.Chicago O'Hare Intl
C$ 1,399
Find similar
Multiple Airlines
6 Apr.
ORD9:40 p.m.Chicago O'Hare Intl
27h 04m
2 stops
YWG12:44 a.m.Winnipeg
8 Apr.
YWG7:30 a.m.Winnipeg
25h 01m
2 stops
ORD8:31 a.m.Chicago O'Hare Intl
Multiple Airlines
6 Apr.
ORD9:40 p.m.Chicago O'Hare Intl
27h 04m
2 stops
YWG12:44 a.m.Winnipeg
8 Apr.
YWG7:30 a.m.Winnipeg
32h 37m
3 stops
ORD4:07 p.m.Chicago O'Hare Intl
Multiple Airlines
6 Apr.
ORD9:44 p.m.Chicago O'Hare Intl
27h 00m
3 stops
YWG12:44 a.m.Winnipeg
8 Apr.
YWG7:30 a.m.Winnipeg
33h 11m
3 stops
ORD4:41 p.m.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
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 478Free CancellationRating
7.0
6,744 reviews
Search Air Canada flights

Undisclosed Carrier flights from Chicago to Winnipeg

Our best Undisclosed Carrier deals on Chicago to Winnipeg flight tickets
Undisclosed Carrier
1 May
ORD5:57 p.m.Chicago O'Hare Intl
21h 28m
1 stop
YWG3:25 p.m.Winnipeg
31 May
YWG3:20 p.m.Winnipeg
25h 45m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
C$ 1,077
Find similar
Undisclosed Carrier
7 Apr.
ORD5:55 p.m.Chicago O'Hare Intl
21h 00m
1 stop
YWG2:55 p.m.Winnipeg
13 Apr.
YWG5:00 a.m.Winnipeg
16h 21m
2 stops
ORD9:21 p.m.Chicago O'Hare Intl
C$ 1,399
Find similar
Undisclosed Carrier
7 Apr.
ORD6:25 a.m.Chicago O'Hare Intl
5h 12m
1 stop
YWG11:37 a.m.Winnipeg
13 Apr.
YWG7:00 a.m.Winnipeg
7h 54m
1 stop
ORD2:54 p.m.Chicago O'Hare Intl
C$ 1,496
Find similar

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets
Air Canada
11 Jun.
ORD6:00 a.m.Chicago O'Hare Intl
10h 00m
1 stop
YWG4:00 p.m.Winnipeg
13 Jun.
YWG5:00 a.m.Winnipeg
7h 54m
1 stop
ORD12:54 p.m.Chicago O'Hare Intl
Air Canada
25 Apr.
ORD8:35 p.m.Chicago O'Hare Intl
13h 20m
1 stop
YWG9:55 a.m.Winnipeg
2 May
YWG5:00 a.m.Winnipeg
7h 54m
1 stop
ORD12:54 p.m.Chicago O'Hare Intl
Air Canada
21 Sep.
ORD1:00 p.m.Chicago O'Hare Intl
2h 24m
YWG3:24 p.m.Winnipeg
28 Sep.
YWG11:50 a.m.Winnipeg
8h 20m
1 stop
ORD8:10 p.m.Chicago O'Hare Intl

  • How far is Chicago to Winnipeg by plane?

    A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 2h 24m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Winnipeg Airport?

    Prices for flights from Chicago to Winnipeg Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Winnipeg Airport?

  • How old do you have to be to fly from Chicago to Winnipeg Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.

  • What documentation or ID do you need to fly to Winnipeg Airport?

    The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.


Alternative routes for Chicago to Winnipeg

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
St. Louis to Winnipeg Flights
Fastest flight time5h 14m
Cheapest priceC$ 680

Similar Chicago to Winnipeg flights

Flexible with your destination? Broaden your search and find flights similar to your Chicago to Winnipeg route

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Winnipeg?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.

Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.

How can momondo help me find flights from Chicago to Winnipeg?

momondo helps you find the best flight between Chicago and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Chicago and alert you when they change.


An easier way to manage your Winnipeg trip

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