Cheap flights from Chicago to Winnipeg from C$ 201

Return
1 adult
Economy
From?
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Thu 7/7
Thu 14/7

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

C$ 201

Fastest flight time

6h 01m

Direct flights

None

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago in the past 72 hours is C$ 201. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is C$ 727.
The fastest flight from Chicago to Winnipeg takes 6h 01m
There are no direct flights from Chicago to Winnipeg. Popular non-direct routes for this connection are Chicago Midway Airport - Winnipeg Airport and Chicago O'Hare Intl Airport - Winnipeg 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?

December

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

What is the cheapest day to depart Chicago for Winnipeg?

Monday

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

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

in the morning

Chicago to Winnipeg flights are approximately 32% more expensive in the afternoon than in the morning

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?

60 days before

The cheapest time to buy a flight from Chicago to Winnipeg is approximately 60 days to departure

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 July with an average price of C$ 490 RT.

Chicago O'Hare Intl Airport (ORD) to Winnipeg Airport (YWG)C$ 492
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Chicago Midway Airport (MDW) to Winnipeg Airport (YWG)C$ 490
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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
Air Canada
21 Oct.
ORD4:48 a.m.Chicago O'Hare Intl
8h 34m
1 stop
YWG1:22 p.m.Winnipeg
23 Oct.
YWG9:50 a.m.Winnipeg
7h 58m
1 stop
ORD5:48 p.m.Chicago O'Hare Intl
Multiple Airlines
15 Oct.
ORD2:25 a.m.Chicago O'Hare Intl
6h 03m
1 stop
YWG8:28 a.m.Winnipeg
19 Oct.
YWG1:55 a.m.Winnipeg
6h 55m
1 stop
ORD8:50 a.m.Chicago O'Hare Intl
WestJet
19 Aug.
ORD1:10 p.m.Chicago O'Hare Intl
20h 38m
1 stop
YWG9:48 a.m.Winnipeg
24 Aug.
YWG1:00 a.m.Winnipeg
11h 26m
1 stop
ORD12:26 p.m.Chicago O'Hare Intl
United Airlines
1 Sep.
ORD2:00 a.m.Chicago O'Hare Intl
5h 28m
1 stop
YWG7:28 a.m.Winnipeg
6 Sep.
YWG9:50 a.m.Winnipeg
6h 00m
1 stop
ORD3:50 p.m.Chicago O'Hare Intl
Delta
13 Oct.
ORD1:10 p.m.Chicago O'Hare Intl
6h 02m
1 stop
YWG7:12 p.m.Winnipeg
21 Oct.
YWG2:30 a.m.Winnipeg
9h 50m
2 stops
ORD12:20 p.m.Chicago O'Hare Intl
Air Canada
13 Oct.
ORD2:00 a.m.Chicago O'Hare Intl
8h 00m
1 stop
YWG10:00 a.m.Winnipeg
21 Oct.
YWG1:55 a.m.Winnipeg
6h 55m
1 stop
ORD8:50 a.m.Chicago 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, Delta and Endeavor Airlines
Air Canada
17 Nov.
ORD2:30 a.m.Chicago O'Hare Intl
11h 10m
2 stops
YWG1:40 p.m.Winnipeg
Multiple Airlines
1 Sep.
ORD4:10 a.m.Chicago O'Hare Intl
24h 15m
1 stop
YWG4:25 a.m.Winnipeg
WestJet
19 Jul.
ORD1:10 p.m.Chicago O'Hare Intl
20h 38m
1 stop
YWG9:48 a.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
Air Canada
10 Jul.
ORD4:10 p.m.Chicago O'Hare Intl
14h 07m
1 stop
YWG6:17 a.m.Winnipeg
16 Jul.
YWG2:55 p.m.Winnipeg
13h 50m
1 stop
ORD4:45 a.m.Chicago O'Hare Intl
Multiple Airlines
7 Jul.
ORD1:10 p.m.Chicago O'Hare Intl
6h 01m
1 stop
YWG7:11 p.m.Winnipeg
9 Jul.
YWG1:00 a.m.Winnipeg
11h 26m
1 stop
ORD12:26 p.m.Chicago O'Hare Intl
Delta
7 Jul.
ORD1:10 p.m.Chicago O'Hare Intl
6h 01m
1 stop
YWG7:11 p.m.Winnipeg
11 Jul.
YWG1:00 a.m.Winnipeg
11h 34m
2 stops
ORD12:34 p.m.Chicago O'Hare Intl
C$ 1,016
Find similar
WestJet
7 Jul.
ORD2:00 a.m.Chicago O'Hare Intl
13h 05m
2 stops
YWG3:05 p.m.Winnipeg
9 Jul.
YWG1:00 a.m.Winnipeg
11h 26m
1 stop
ORD12:26 p.m.Chicago O'Hare Intl
C$ 1,141
Find similar
Air Canada
7 Jul.
ORD4:25 p.m.Chicago O'Hare Intl
13h 18m
1 stop
YWG5:43 a.m.Winnipeg
8 Jul.
YWG2:55 p.m.Winnipeg
13h 50m
1 stop
ORD4:45 a.m.Chicago O'Hare Intl
Multiple Airlines
7 Jul.
ORD1:10 p.m.Chicago O'Hare Intl
6h 01m
1 stop
YWG7:11 p.m.Winnipeg
8 Jul.
YWG1:00 a.m.Winnipeg
10h 17m
2 stops
ORD11:17 a.m.Chicago O'Hare Intl

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets
Air Canada
21 Oct.
ORD4:48 a.m.Chicago O'Hare Intl
8h 34m
1 stop
YWG1:22 p.m.Winnipeg
23 Oct.
YWG9:50 a.m.Winnipeg
7h 58m
1 stop
ORD5:48 p.m.Chicago O'Hare Intl
Air Canada
13 Oct.
ORD2:00 a.m.Chicago O'Hare Intl
8h 00m
1 stop
YWG10:00 a.m.Winnipeg
21 Oct.
YWG1:55 a.m.Winnipeg
6h 55m
1 stop
ORD8:50 a.m.Chicago O'Hare Intl
Air Canada
8 Sep.
ORD2:00 a.m.Chicago O'Hare Intl
8h 00m
1 stop
YWG10:00 a.m.Winnipeg
12 Sep.
YWG1:55 a.m.Winnipeg
11h 28m
1 stop
ORD1:23 p.m.Chicago O'Hare Intl

Delta flights from Chicago to Winnipeg

Our best Delta deals on Chicago to Winnipeg flight tickets
Delta
13 Oct.
ORD1:10 p.m.Chicago O'Hare Intl
6h 02m
1 stop
YWG7:12 p.m.Winnipeg
21 Oct.
YWG2:30 a.m.Winnipeg
9h 50m
2 stops
ORD12:20 p.m.Chicago O'Hare Intl
Delta
19 Jul.
ORD1:10 p.m.Chicago O'Hare Intl
6h 01m
1 stop
YWG7:11 p.m.Winnipeg
26 Jul.
YWG1:00 a.m.Winnipeg
11h 34m
2 stops
ORD12:34 p.m.Chicago O'Hare Intl
Delta
15 Oct.
MDW11:45 a.m.Chicago Midway
6h 58m
1 stop
YWG6:43 p.m.Winnipeg
19 Oct.
YWG2:30 a.m.Winnipeg
6h 55m
1 stop
MDW9:25 a.m.Chicago Midway

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

    Due to the global impact of COVID-19, some of our airline partners operating flights from Chicago to Winnipeg, such as Air Canada may have flexible change policies in place. Use our site to search for all of the airlines offering this flexibility to you.

  • How far is Chicago to Winnipeg by plane?

    A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 5h 28m by plane in normal conditions.



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 time6h 08m
Cheapest priceC$ 845

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?

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.

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

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.

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.


Here's why travellers choose to use momondo
Flexible Travel
momondo understands the need for flexibility and we have a filter specifically for flights with no change fees.
Expert Insights
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