Cheap flights from Winnipeg to Chicago from C$ 250

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Flight information for Winnipeg to Chicago
(YWG to CHI)

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

Best price found

C$ 250

Fastest flight time

4h 32m

Direct flights

None

Airports in Chicago

3 airports
The best one-way flight to Chicago from Winnipeg in the past 72 hours is C$ 250. The best round-trip flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is C$ 693.
The fastest flight from Winnipeg to Chicago takes 4h 32m
There are no direct flights from Winnipeg to Chicago. Popular non-direct routes for this connection are Winnipeg Airport - Chicago O'Hare Intl Airport and Winnipeg Airport - Chicago Midway Airport.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Winnipeg to Chicago

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 Winnipeg to Chicago?

September. The cheapest time of year to fly to Chicago from Winnipeg is September. The most expensive is August.

What is the cheapest day to depart Winnipeg for Chicago?

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

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

in the evening. Winnipeg to Chicago flights are approximately 32% more expensive at noon than in the evening

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

WestJet. Air Canada, Delta, and Endeavor Airlines are the most popular carriers operating from Winnipeg to Chicago

What is the cheapest Winnipeg to Chicago flight route?

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

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

37 days before. The cheapest time to buy a flight from Winnipeg to Chicago is approximately 37 days to departure

If you are looking to fly from Winnipeg to Chicago, you are most likely going to fly from Winnipeg Airport to Chicago O'Hare Intl Airport, the most popular airports on that route. You may be looking for an airport near Chicago O'Hare Intl Airport to land at when travelling from Winnipeg and Chicago Midway Airport, located in Chicago is a great option. In March, C$ 361 is typically the cheapest round trip price you’ll find from Winnipeg to Chicago which you can find when you fly YWG — MDW.

Winnipeg Airport (YWG) to Chicago O'Hare Intl Airport (ORD)C$ 404
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Winnipeg Airport (YWG) to Chicago Midway Airport (MDW)C$ 361
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Easily compare round-trip flights from Winnipeg to Chicago

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 Winnipeg to Chicago by changing tabs
Delta
16 Apr.
YWG2:55 a.m.Winnipeg
6h 46m
1 stop
MDW9:41 a.m.Chicago Midway
19 Apr.
MDW10:26 a.m.Chicago Midway
8h 59m
1 stop
YWG7:25 p.m.Winnipeg
Delta
2 Aug.
YWG2:15 a.m.Winnipeg
10h 09m
2 stops
ORD12:24 p.m.Chicago O'Hare Intl
6 Aug.
ORD2:00 a.m.Chicago O'Hare Intl
6h 25m
1 stop
YWG8:25 a.m.Winnipeg
United Airlines
5 Apr.
YWG1:10 a.m.Winnipeg
9h 38m
2 stops
ORD10:48 a.m.Chicago O'Hare Intl
26 Apr.
ORD3:25 a.m.Chicago O'Hare Intl
13h 40m
2 stops
YWG5:05 p.m.Winnipeg
C$ 1,186
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Delta
16 Apr.
YWG2:55 a.m.Winnipeg
6h 46m
1 stop
MDW9:41 a.m.Chicago Midway
19 Apr.
MDW5:36 a.m.Chicago Midway
10h 16m
2 stops
YWG3:52 p.m.Winnipeg
Delta
16 Apr.
YWG1:00 a.m.Winnipeg
11h 20m
2 stops
ORD12:20 p.m.Chicago O'Hare Intl
19 Apr.
ORD2:00 a.m.Chicago O'Hare Intl
5h 45m
1 stop
YWG7:45 a.m.Winnipeg
Delta
16 Apr.
YWG1:00 a.m.Winnipeg
11h 20m
2 stops
ORD12:20 p.m.Chicago O'Hare Intl
19 Apr.
ORD4:51 a.m.Chicago O'Hare Intl
11h 01m
2 stops
YWG3:52 p.m.Winnipeg

Find the cheapest one-way flights from Winnipeg to Chicago

If you're looking for one-way flights from Winnipeg to Chicago, view some of our deals below provided by Air Canada, Delta and Endeavor Airlines
Multiple Airlines
17 Apr.
YWG12:15 p.m.Winnipeg
18h 02m
1 stop
MDW6:17 a.m.Chicago Midway
Air Canada
19 Jul.
YWG1:30 a.m.Winnipeg
7h 55m
1 stop
ORD9:25 a.m.Chicago O'Hare Intl
Delta
31 Mar.
YWG8:33 a.m.Winnipeg
4h 13m
1 stop
ORD12:46 p.m.Chicago O'Hare Intl

Search last-minute flights to Chicago from Winnipeg

Find and compare round-trip flight prices for your last-minute flight from Winnipeg to Chicago
Delta
25 Mar.
YWG2:55 a.m.Winnipeg
9h 24m
2 stops
ORD12:19 p.m.Chicago O'Hare Intl
3 Apr.
ORD2:00 a.m.Chicago O'Hare Intl
5h 33m
1 stop
YWG7:33 a.m.Winnipeg
C$ 1,657
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Delta
25 Mar.
YWG2:55 a.m.Winnipeg
9h 24m
2 stops
ORD12:19 p.m.Chicago O'Hare Intl
3 Apr.
ORD6:30 a.m.Chicago O'Hare Intl
12h 59m
2 stops
YWG7:29 p.m.Winnipeg
C$ 1,877
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Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
AirlineRatingFree CancellationPrice
United AirlinesPriceFrom C$ 415Free CancellationRating
7.2
1,656 reviews
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DeltaPriceFrom C$ 423Free CancellationRating
7.8
772 reviews
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Air CanadaPriceFrom C$ 431Free CancellationRating
7.3
323 reviews
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WestJetPriceFrom C$ 455Free CancellationRating
7.3
144 reviews
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Endeavor AirlinesPriceFrom C$ 519Free CancellationRating
10.0
1 review
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Delta flights from Winnipeg to Chicago

Our best Delta deals on Winnipeg to Chicago flight tickets
Delta
16 Apr.
YWG2:55 a.m.Winnipeg
6h 46m
1 stop
MDW9:41 a.m.Chicago Midway
19 Apr.
MDW10:26 a.m.Chicago Midway
8h 59m
1 stop
YWG7:25 p.m.Winnipeg
Delta
2 Aug.
YWG2:15 a.m.Winnipeg
10h 09m
2 stops
ORD12:24 p.m.Chicago O'Hare Intl
6 Aug.
ORD2:00 a.m.Chicago O'Hare Intl
6h 25m
1 stop
YWG8:25 a.m.Winnipeg
Delta
16 Apr.
YWG2:55 a.m.Winnipeg
6h 46m
1 stop
MDW9:41 a.m.Chicago Midway
19 Apr.
MDW5:36 a.m.Chicago Midway
10h 16m
2 stops
YWG3:52 p.m.Winnipeg

  • How far is Winnipeg to Chicago by plane?

    A flight from Winnipeg to Chicago will travel around 1153.0 km. 6h 46m is a normal flight duration for this route.


Similar Winnipeg to Chicago flights

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

Why use momondo?

Finding the right flight to Chicago from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.

Once you have performed a search for Winnipeg to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

Yes momondo offers price alerts on flights to Chicago from Winnipeg. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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