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Cheap flights from Chicago to Winnipeg from $103

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 5/13. 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
0 bags

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Find the cheapest flights from Chicago to Winnipeg

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Winnipeg.
WestJet Logo
5:30 pm - 9:03 amORD-YWG
15h 33m1 stop
WestJet Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
$199WestJet
Find Deal
Tue, May 13 - Wed, Jun 11
WestJet Logo
5:30 pm - 8:19 pmORD-YWG
26h 49m1 stop
WestJet Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
$218WestJet
Find Deal
Thu, May 15 - Sun, May 18
 Logo
5:48 pm - 4:28 pmORD-YWG
22h 40m1 stop
 Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
Tue, May 6 - Fri, May 9
 Logo
5:10 am - 4:28 pmORD-YWG
11h 18m1 stop
 Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
Fri, May 30 - Mon, Jun 2
Delta Logo
11:05 am - 11:25 pmORD-YWG
12h 20m2 stops
Delta Logo
6:40 am - 4:30 pmYWG-ORD
9h 50m2 stops
$362Delta
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
5:30 am - 11:25 pmORD-YWG
17h 55m2 stops
Delta Logo
6:40 am - 6:37 pmYWG-ORD
11h 57m2 stops
$388Delta
Find Deal
Sat, May 31 - Wed, Jun 4
Air Canada Logo
1:02 pm - 3:31 pmORD-YWG
2h 29mnonstop
Air Canada Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
$441Air Canada
Find Deal
Sat, Jun 7 - Sat, Jun 14
Air Canada Logo
1:02 pm - 3:31 pmORD-YWG
2h 29mnonstop
Air Canada Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
$445Air Canada
Find Deal
Thu, Jun 5 - Mon, Jun 9
United Airlines Logo
7:10 am - 1:09 pmORD-YWG
5h 59m1 stop
United Airlines Logo
4:25 pm - 10:41 pmYWG-ORD
6h 16m1 stop
$535United Airlines
Find Deal
Sat, May 31 - Sat, May 31
United Airlines Logo
9:25 pm - 5:38 pmORD-YWG
20h 13m2 stops
United Airlines Logo
6:35 pm - 4:51 pmYWG-ORD
22h 16m2 stops
$537United Airlines
Find Deal
Wed, Jul 23 - Tue, Aug 5

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
May 13
ORD5:30 pmChicago O'Hare Intl
15h 33m
1 stop
YWG9:03 amWinnipeg
Jun 11
YWG8:30 amWinnipeg
8h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
WestJet
May 15
ORD5:30 pmChicago O'Hare Intl
26h 49m
1 stop
YWG8:19 pmWinnipeg
May 18
YWG8:30 amWinnipeg
8h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
WestJet
Oct 16
ORD5:30 pmChicago O'Hare Intl
15h 31m
1 stop
YWG9:01 amWinnipeg
Oct 24
YWG8:30 amWinnipeg
8h 13m
1 stop
ORD4:43 pmChicago O'Hare Intl

Air Canada flights from Chicago to Winnipeg

Our best Air Canada deals on Chicago to Winnipeg flight tickets
Air Canada
Jun 7
ORD1:02 pmChicago O'Hare Intl
2h 29m
YWG3:31 pmWinnipeg
Jun 14
YWG2:20 pmWinnipeg
2h 31m
ORD4:51 pmChicago O'Hare Intl
Air Canada
Jun 5
ORD1:02 pmChicago O'Hare Intl
2h 29m
YWG3:31 pmWinnipeg
Jun 9
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl
Air Canada
May 23
ORD7:58 pmChicago O'Hare Intl
2h 35m
YWG10:33 pmWinnipeg
May 25
YWG7:00 amWinnipeg
2h 31m
ORD9:31 amChicago O'Hare Intl

See travel insights to Winnipeg from

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 to Winnipeg?

In general, January is the cheapest month to fly from Chicago to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $319. If you’re not able to fly to Winnipeg in January, then September is your next best option. Flight prices from Chicago to Winnipeg during September average around $431.

What is the cheapest day to depart on your flight to Winnipeg?

The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $562. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $673.

What is the cheapest time of day to depart on your flight to Winnipeg?

The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $594. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $670 on average. Flights to Winnipeg from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Winnipeg flight route?

Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago - Winnipeg flight prices

How far in advance should I book a flight to Winnipeg?

You are more likely to see cheaper flights to Winnipeg from Chicago when booking 10 weeks ahead of your departure date. In general, you can expect to find flights to Winnipeg for around $540 when searching 10 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Winnipeg from Chicago for as low as $326 on momondo.

What cabin class options are available on Chicago to Winnipeg flights?

There are 3 cabin classes available to choose from on Chicago to Winnipeg flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Winnipeg flight prices changed over time?

As of April 2025, prices for Chicago to Winnipeg flights are approximately 3% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Winnipeg

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Winnipeg according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

$103

Fastest flight time

2h 29m

Direct flights

Every day

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago in the past 72 hours is $103. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $199.
The fastest flight from Chicago to Winnipeg takes 2h 29m
Direct flights go from Chicago to Winnipeg every day.
There is 1 airport near Winnipeg: Winnipeg (YWG)

  • How far is Chicago to Winnipeg by plane?

    A flight from Chicago to Winnipeg will travel around 716.4 mi. Flights usually cover this in 2h 29m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Chicago to Winnipeg Airport refresh 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 a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Winnipeg Airport.

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

    The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Winnipeg?

  • What is the most popular airline from Chicago to Winnipeg?


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 $230Free CancellationRating
7.0
9,207 reviews
Search Air Canada flights
United AirlinesPriceFrom $508Free CancellationRating
7.4
8,685 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Winnipeg

    United Airlines flies from Chicago to Winnipeg around 7 times per week, with 8,685 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $508 (round-trip), much lower than the average airfare cost of $662 for United Airlines flights on this route.

  • Air Canada Flights From Chicago to Winnipeg

    The best Air Canada deal for Chicago to Winnipeg flight tickets found on momondo in the last 72 hours was $230, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at $617 round-trip. Air Canada operates 7 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 9,195 Air Canada reviews by users on momondo have scored the airline at 7.0/10.


Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Scanterbury
Selkirk
Morden
Portage la Prairie

Why use momondo?

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

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

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?

Once you have performed a search for Chicago to Winnipeg 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.

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

If you are not ready to book a flight from Chicago to Winnipeg now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Winnipeg and let you know when they change.


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