Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Chicago from C$ 223

YWG — CHI
1 Oct — 8 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Chicago

Thu 22/107:00 a.m. -
1 stop9h 40m
Fri 23/105:30 p.m. -
1 stop7h 25m
Deal found 26/8C$ 416
Thu 10/92:55 p.m. -
1 stop25h 45m
Sun 13/95:30 p.m. -
1 stop7h 25m
Deal found 27/8C$ 447
Thu 1/1012:00 p.m. -
1 stop28h 40m
Sun 4/105:30 p.m. -
1 stop7h 25m
Deal found 29/8C$ 450
Thu 1/109:20 a.m. -
1 stop6h 58m
Sun 4/105:30 p.m. -
1 stop7h 25m
Deal found 28/8C$ 494
Wed 21/109:05 p.m. -
1 stop19h 35m
Fri 23/105:30 p.m. -
1 stop7h 25m
Deal found 26/8C$ 504
Wed 30/99:20 a.m. -
1 stop6h 58m
Sun 4/105:30 p.m. -
1 stop7h 25m
Deal found 30/8C$ 509
Thu 24/99:20 a.m. -
1 stop6h 58m
Thu 1/105:30 p.m. -
1 stop7h 25m
Deal found 27/8C$ 520
Fri 25/99:20 a.m. -
1 stop6h 58m
Mon 28/95:30 p.m. -
1 stop7h 25m
Deal found 30/8C$ 532
Thu 1/106:05 p.m. -
1 stop20h 30m
Sun 4/1011:45 a.m. -
1 stop22h 00m
Deal found 28/8C$ 556
Sat 26/912:41 p.m. -
1 stop5h 18m
Wed 30/95:11 p.m. -
2 stops21h 57m
Deal found 27/8C$ 812
Sun 22/115:00 a.m. -
2 stops13h 04m
Wed 2/1210:24 a.m. -
2 stops9h 26m
Deal found 31/8C$ 838
Mon 23/115:00 a.m. -
2 stops11h 18m
Wed 2/1210:24 a.m. -
2 stops9h 26m
Deal found 31/8C$ 848

Find flight deals from Winnipeg to Chicago

Round-trip from

C$ 447

One-way from

C$ 223

Popular in

January

Cheapest in

April

Average price

C$ 844

Good round-trip deal

C$ 850 or less

Good one-way deal

C$ 562 or less
WestJet
  • WestJet
  • 10/9-13/9
  • 2 total stops
  • 33h 10m total
  • Winnipeg to Chicago
Search Deals
WestJet
  • WestJet
  • 11/10
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals
Price to beat on a round-trip flight from Winnipeg to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Winnipeg to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 1/10

6:00 a.m.-7:48 p.m.

2 stops13h 48m

Chicago O'Hare Intl

Sun 4/10

5:30 p.m.-8:15 p.m.

1 stop26h 45m

C$ 634

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 20/10

9:20 a.m.-4:19 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Wed 28/10

2:50 p.m.-9:57 p.m.

1 stop7h 07m

C$ 674

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 20/10

9:20 a.m.-4:19 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Tue 27/10

2:50 p.m.-9:57 p.m.

1 stop7h 07m

C$ 674

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 26/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

Chicago O'Hare Intl

Wed 30/9

9:45 a.m.-7:54 p.m.

1 stop10h 09m

C$ 736

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 5/12

7:00 a.m.-2:37 p.m.

1 stop7h 37m

Chicago O'Hare Intl

Mon 7/12

11:45 a.m.-10:45 a.m.

1 stop23h 00m

C$ 765

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 25/2

7:00 a.m.-2:12 p.m.

1 stop7h 12m

Chicago O'Hare Intl

Sun 28/2

9:46 a.m.-10:45 a.m.

1 stop24h 59m

C$ 810

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 24/11

5:00 a.m.-6:04 p.m.

2 stops13h 04m

Chicago Midway

Wed 2/12

10:24 a.m.-7:50 p.m.

2 stops9h 26m

C$ 838

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 5/12

7:15 a.m.-3:38 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Mon 7/12

9:15 a.m.-11:39 a.m.

Nonstop2h 24m

C$ 863

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sun 22/11

5:00 a.m.-6:04 p.m.

2 stops13h 04m

Chicago Midway

Wed 2/12

10:24 a.m.-4:34 p.m.

1 stop6h 10m

C$ 894

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 17/10

9:20 a.m.-4:14 p.m.

1 stop6h 54m

Chicago O'Hare Intl

Sat 17/10

8:30 p.m.-5:58 p.m.

2 stops21h 28m

C$ 896

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/8

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

Best time to book a flight from Winnipeg to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Winnipeg with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Chicago

What is the cheapest month to book a flight from Winnipeg to Chicago?

Currently, November is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 676). Flying from Winnipeg to Chicago in June is currently the most expensive (average of C$ 960). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to CHI?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chicago as you normally would.

Weekly flight availability from Winnipeg to Chicago

The most flights from YWG to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Winnipeg to Chicago?

Airfare is below average for this route at the moment.
Winnipeg to Chicago flights typically cost between C$ 587 and C$ 920 in October.
The cheapest round-trip price found within the last 5 days was C$ 450 on WestJet (1 Oct-4 Oct).

What’s the top layover airport for flights from Winnipeg to Chicago?

Calgary (YYC) – chosen by Cheapflights users on 88% of one-stop itineraries from Winnipeg to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Chicago?

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 328.

What’s the fastest layover option from Winnipeg to Chicago?

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 4h 06m.

Which airport typically offers the quickest layover for flights from Winnipeg to Chicago?

Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 1h 04m.

Reviews of airlines servicing Chicago

Check out reviews from past customers who have flown with United Airlines,WestJet, andAir Canada from Winnipeg to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,151 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
United Airlines
7.4
Good
10,151 reviews
United Airlines
7.4
Good
10,151 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
WestJet
7.2
Good
3,444 reviews
United Airlines
7.4
Good
10,151 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
Air Canada
7.1
Good
11,566 reviews
United Airlines
7.4
Good
10,151 reviews
Check prices

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.7

Crew

8.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

Related info for your journey

  • What airport do you fly from for flights from Winnipeg to Chicago?

    If you book a flight to Chicago from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 6 flights from Winnipeg to Chicago per day from 3 different airlines.

  • How long is the flight from Winnipeg to Chicago?

    Airlines like Porter Airlines fly from Winnipeg to Chicago in about 6h 59m. The time it takes to get you to your destination can typically vary by up to . There are 1136 km between Winnipeg and Chicago.

  • What are the cheapest airlines flying from Winnipeg to Chicago round-trip?

    WestJet, at C$ 272, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include United Airlines and Air Canada. WestJet is priced at 68% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Winnipeg to Chicago?

    Before booking your flight to Chicago from Winnipeg, check out the most reliable airlines to get you to your destination on time: Air New Zealand (84%), SkyWest Airlines (84%), United Airlines( 84%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 228. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 509 on average, our data indicates C$ 1,508 when flying from Winnipeg to Chicago.

  • Can I find deals for flights from Winnipeg to Chicago that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Chicago.

  • Can I find deals for business class flights from Winnipeg to Chicago?

    Yes. Cheapflights offers flight deals from Winnipeg to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 676). Flying from Winnipeg to Chicago in June is currently the most expensive (average of C$ 960). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Winnipeg to Chicago

Winnipeg to O'Hare Intl flights

Top 3 airlines flying from Winnipeg to Chicago

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 272AverageC$ 529FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 688AverageC$ 961FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 707AverageC$ 872FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

How does Cheapflights help users find flights from Winnipeg to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Winnipeg today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Winnipeg.

Can Cheapflights find flights from Winnipeg to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Winnipeg to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.