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Cheap flights from Chicago to Winnipeg from $118

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 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Winnipeg

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Winnipeg that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Winnipeg.

Cheap last minute flights

Planning a quick getaway from Chicago to Winnipeg? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Winnipeg, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Winnipeg

Find recent round-trip train or bus tickets from Chicago to Winnipeg.

All round-trip flight deals to Winnipeg

The cheapest plane tickets to Winnipeg found on KAYAK recently.
7:39 pm - 9:09 pmORD-YWG
25h 30m2 stops
7:30 am - 9:10 pmYWG-ORD
13h 40m1 stop
Mon, Dec 2 - Mon, Dec 9
7:39 pm - 3:10 pmORD-YWG
19h 31m2 stops
11:35 am - 9:37 amYWG-ORD
22h 02m2 stops
Mon, Dec 2 - Mon, Dec 9
9:50 am - 5:08 pmORD-YWG
7h 18m1 stop
11:00 am - 7:32 pmYWG-ORD
8h 32m1 stop
$474Air Canada
Find Deal
Thu, Dec 12 - Mon, Dec 16
8:45 am - 9:10 pmORD-YWG
12h 25m1 stop
7:30 am - 1:11 pmYWG-ORD
5h 41m1 stop
$480Air Canada
Find Deal
Sat, Jan 11 - Sun, Jan 19
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$524United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:10 am - 1:27 pmORD-YWG
6h 17m1 stop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$529United Airlines
Find Deal
Fri, Jan 17 - Sun, Jan 19
10:19 am - 4:47 pmMDW-YWG
6h 28m1 stop
12:45 pm - 5:47 pmYWG-MDW
5h 02m1 stop
$544Delta
Find Deal
Tue, Jan 14 - Sun, Jan 19
11:50 am - 4:47 pmORD-YWG
4h 57m1 stop
12:45 pm - 9:15 pmYWG-ORD
8h 30m2 stops
$554Delta
Find Deal
Tue, Jan 14 - Sun, Jan 19
2:15 pm - 4:54 pmMDW-YWG
26h 39m1 stop
5:37 pm - 5:47 pmYWG-MDW
24h 10m1 stop
$581WestJet
Find Deal
Mon, Dec 16 - Mon, Jan 6
6:55 am - 3:34 pmORD-YWG
8h 39m2 stops
6:20 am - 3:56 pmYWG-ORD
9h 36m1 stop
$600WestJet
Find Deal
Mon, Feb 10 - Sun, Feb 16
6:15 pm - 3:10 pmMDW-YWG
20h 55m1 stop
Thu, Dec 12
2:03 pm - 12:43 amMDW-YWG
10h 40m1 stop
Sun, Jan 12
9:03 am - 4:24 pmORD-YWG
7h 21m1 stop
$196Air Canada
Find Deal
Sat, Apr 12
8:45 am - 9:10 pmORD-YWG
12h 25m1 stop
$207Air Canada
Find Deal
Sat, Jan 11
12:58 pm - 3:28 pmORD-YWG
2h 30mnonstop
$236United Airlines
Find Deal
Fri, Feb 28
7:15 am - 1:03 pmORD-YWG
5h 48m1 stop
$237United Airlines
Find Deal
Sat, Apr 19
6:59 pm - 12:35 amMDW-YWG
29h 36m2 stops
$238WestJet
Find Deal
Sat, Jan 11
9:20 am - 4:53 pmMDW-YWG
7h 33m1 stop
$245Delta
Find Deal
Sat, Apr 26
1:05 pm - 3:08 pmMDW-YWG
26h 03m1 stop
$274WestJet
Find Deal
Tue, Apr 15
6:59 pm - 11:42 pmMDW-YWG
4h 43m1 stop
$278Delta
Find Deal
Sat, Jan 11
9:10 pm - 4:10 pmORD-YWG
19h 00m2 stops
7:30 am - 5:00 pmYWG-ORD
9h 30m1 stop
Thu, Nov 21 - Sun, Nov 24
6:00 am - 12:23 amORD-YWG
18h 23m2 stops
7:30 am - 5:00 pmYWG-ORD
9h 30m1 stop
Fri, Nov 22 - Sun, Nov 24
11:38 am - 12:43 amORD-YWG
13h 05m1 stop
7:30 am - 5:00 pmYWG-ORD
9h 30m1 stop
Fri, Nov 22 - Sun, Nov 24
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
8:30 am - 5:09 pmYWG-ORD
8h 39m1 stop
$1,018Air Canada
Find Deal
Thu, Nov 21 - Mon, Nov 25
7:10 am - 1:27 pmORD-YWG
6h 17m1 stop
8:30 am - 5:09 pmYWG-ORD
8h 39m1 stop
$1,027Air Canada
Find Deal
Thu, Nov 21 - Mon, Nov 25
9:45 am - 4:55 pmORD-YWG
7h 10m1 stop
6:55 am - 5:09 pmYWG-ORD
10h 14m2 stops
$1,263Delta
Find Deal
Thu, Nov 21 - Tue, Nov 26
2:17 pm - 11:27 pmMDW-YWG
9h 10m1 stop
6:55 am - 5:02 pmYWG-MDW
10h 07m2 stops
$1,263Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
$1,358United Airlines
Find Deal
Thu, Nov 21 - Tue, Nov 26
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
$1,519United Airlines
Find Deal
Thu, Nov 21 - Sun, Nov 24
9:30 am - 4:55 pmMDW-YWG
7h 25m1 stop
12:31 pm - 6:32 pmYWG-MDW
6h 01m1 stop
$1,613WestJet
Find Deal
Thu, Nov 21 - Sat, Nov 23
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$520Air Canada
Find Deal
Tue, Jan 14 - Sun, Jan 19
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$524United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$552Air Canada
Find Deal
Fri, Jan 17 - Sun, Jan 19
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
$584Air Canada
Find Deal
Fri, Dec 13 - Mon, Dec 16
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$588Air Canada
Find Deal
Sat, Jan 4 - Sat, Jan 11
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$595United Airlines
Find Deal
Mon, Dec 16 - Mon, Jan 6
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
$602United Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
12:56 pm - 3:28 pmORD-YWG
2h 32mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$625Air Canada
Find Deal
Fri, Jan 3 - Fri, Jan 10
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:45 pmYWG-ORD
2h 30mnonstop
$627United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
12:52 pm - 3:28 pmORD-YWG
2h 36mnonstop
2:15 pm - 4:51 pmYWG-ORD
2h 36mnonstop
$635Air Canada
Find Deal
Mon, Dec 16 - Mon, Jan 6

United Airlines flights from Chicago to Winnipeg

Our best United Airlines deals on Chicago to Winnipeg flight tickets
United Airlines
Jan 9
ORD12:56 pmChicago O'Hare Intl
2h 32m
YWG3:28 pmWinnipeg
Jan 12
YWG2:15 pmWinnipeg
2h 36m
ORD4:51 pmChicago O'Hare Intl
United Airlines
Jan 17
ORD7:10 amChicago O'Hare Intl
6h 17m
1 stop
YWG1:27 pmWinnipeg
Jan 19
YWG2:15 pmWinnipeg
2h 36m
ORD4:51 pmChicago O'Hare Intl
United Airlines
Dec 12
ORD7:10 amChicago O'Hare Intl
6h 17m
1 stop
YWG1:27 pmWinnipeg
Dec 16
YWG7:30 amWinnipeg
24h 23m
2 stops
ORD7:53 amChicago O'Hare Intl

WestJet flights from Chicago to Winnipeg

Our best WestJet deals on Chicago to Winnipeg flight tickets
WestJet
Dec 16
MDW2:15 pmChicago Midway
26h 39m
1 stop
YWG4:54 pmWinnipeg
Jan 6
YWG5:37 pmWinnipeg
24h 10m
1 stop
MDW5:47 pmChicago Midway
WestJet
Feb 10
ORD6:55 amChicago O'Hare Intl
8h 39m
2 stops
YWG3:34 pmWinnipeg
Feb 16
YWG6:20 amWinnipeg
9h 36m
1 stop
ORD3:56 pmChicago O'Hare Intl
WestJet
Jan 18
MDW11:19 amChicago Midway
24h 36m
1 stop
YWG11:55 amWinnipeg
Jan 25
YWG12:20 pmWinnipeg
20h 34m
2 stops
MDW8:54 amChicago 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 from Chicago to Winnipeg?

March. The cheapest time of year to fly to Winnipeg from Chicago is March. Most expensive is April

What is the cheapest day to depart Chicago for Winnipeg?

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

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

In the morning. Chicago to Winnipeg flights are approximately 17% 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?

45 days before. The cheapest time to buy a flight from Chicago to Winnipeg is approximately 45 days to departure

Can stopping save me money on Chicago to Winnipeg flights?

You could potentially save up to 30% on your flight if you consider stops on a Chicago to Winnipeg flight.

How have Chicago to Winnipeg flight prices changed over time?

What is the typical price of a round-trip flight between Chicago and Winnipeg?


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

$118

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 $118. The best round-trip flight deal from Chicago to Winnipeg found on momondo in the last 72 hours is $337.
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 32m, 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 $219Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
DeltaPriceFrom $510Free CancellationRating
8.0
8,756 reviews
Search Delta flights
United AirlinesPriceFrom $535Free CancellationRating
7.4
9,171 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 9,171 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 $735 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 $219, round-trip. It should be noted that an average Air Canada flight deal for this route in this time was higher, at $609 round-trip. Air Canada operates 7 flights out of Chicago into Winnipeg in an average week, so prices vary by time and availability. 8,237 Air Canada reviews by users on momondo have scored the airline at 7.0/10.


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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