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Cheap flights from Chicago to Winnipeg from $110

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 5/6. 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 - 9:01 amORD-YWG
15h 31m1 stop
WestJet Logo
6:30 pm - 4:44 pmYWG-ORD
22h 14m1 stop
$231WestJet
Find Deal
Sun, May 18 - Sat, May 24
 Logo
7:47 pm - 4:28 pmORD-YWG
20h 41m2 stops
 Logo
8:30 am - 4:44 pmYWG-ORD
8h 14m1 stop
Tue, Apr 29 - Thu, May 1
Porter Airlines Logo
9:40 am - 10:46 pmMDW-YWG
13h 06m2 stops
Porter Airlines Logo
6:10 am - 4:54 pmYWG-MDW
10h 44m1 stop
$397Porter Airlines
Find Deal
Thu, Jun 12 - Sun, Jun 15
Porter Airlines Logo
9:40 am - 10:46 pmMDW-YWG
13h 06m2 stops
Porter Airlines Logo
11:45 am - 8:45 amYWG-MDW
21h 00m2 stops
$403Porter Airlines
Find Deal
Thu, Jun 12 - Sun, Jun 15
Air Canada Logo
12:57 pm - 3:31 pmORD-YWG
2h 34mnonstop
Air Canada Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
$470Air Canada
Find Deal
Sun, May 18 - Sun, May 25
Air Canada Logo
12:57 pm - 3:31 pmORD-YWG
2h 34mnonstop
Air Canada Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
$489Air Canada
Find Deal
Sun, May 18 - Sun, May 25
Delta Logo
6:24 am - 11:57 amORD-YWG
5h 33m1 stop
Delta Logo
6:40 am - 4:30 pmYWG-ORD
9h 50m2 stops
$500Delta
Find Deal
Fri, May 23 - Sun, May 25
United Airlines Logo
12:57 pm - 3:31 pmORD-YWG
2h 34mnonstop
United Airlines Logo
2:20 pm - 4:48 pmYWG-ORD
2h 28mnonstop
$515United Airlines
Find Deal
Sat, May 3 - Sun, May 4
United Airlines Logo
1:02 pm - 3:31 pmORD-YWG
2h 29mnonstop
United Airlines Logo
5:00 am - 12:55 pmYWG-ORD
7h 55m1 stop
$520United Airlines
Find Deal
Wed, Jun 4 - Sun, Jun 8
Delta Logo
9:20 am - 4:58 pmMDW-YWG
7h 38m1 stop
Delta Logo
12:40 pm - 6:07 pmYWG-MDW
5h 27m1 stop
$534Delta
Find Deal
Wed, Sep 10 - Sat, Sep 13

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
May 18
ORD5:30 pmChicago O'Hare Intl
15h 31m
1 stop
YWG9:01 amWinnipeg
May 24
YWG6:30 pmWinnipeg
22h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
WestJet
Jun 4
ORD1:40 pmChicago O'Hare Intl
7h 46m
1 stop
YWG9:26 pmWinnipeg
Jun 8
YWG5:30 pmWinnipeg
23h 14m
1 stop
ORD4:44 pmChicago O'Hare Intl
WestJet
Aug 2
ORD1:40 pmChicago O'Hare Intl
7h 46m
1 stop
YWG9:26 pmWinnipeg
Aug 8
YWG6:15 pmWinnipeg
18h 24m
1 stop
ORD12:39 pmChicago O'Hare Intl

Porter Airlines flights from Chicago to Winnipeg

Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
Porter Airlines
Jun 12
MDW9:40 amChicago Midway
13h 06m
2 stops
YWG10:46 pmWinnipeg
Jun 15
YWG6:10 amWinnipeg
10h 44m
1 stop
MDW4:54 pmChicago Midway
Porter Airlines
Jun 12
MDW9:40 amChicago Midway
13h 06m
2 stops
YWG10:46 pmWinnipeg
Jun 15
YWG11:45 amWinnipeg
21h 00m
2 stops
MDW8:45 amChicago Midway
Porter Airlines
Jun 11
MDW9:40 amChicago Midway
13h 06m
2 stops
YWG10:46 pmWinnipeg
Jun 15
YWG6:10 amWinnipeg
10h 44m
1 stop
MDW4:54 pmChicago Midway

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 $568 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 9% 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

$110

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Winnipeg

1 airport
The best one-way flight to Winnipeg from Chicago in the past 72 hours is $110. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $231.
The fastest flight from Chicago to Winnipeg takes 2h 24m
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 24m, 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 $232Free CancellationRating
7.0
9,035 reviews
Search Air Canada flights
United AirlinesPriceFrom $535Free CancellationRating
7.4
8,619 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 8,619 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Winnipeg in the last 72 hours was $535 (round-trip), much lower than the average airfare cost of $665 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 $232, 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. 9,035 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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