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Cheap flights from Winnipeg to Chicago from C$ 296

YWG — CHI
29 Nov — 6 Dec1
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

Mon 14/127:55 p.m. -
1 stop16h 40m
Wed 16/126:20 p.m. -
1 stop14h 55m
Deal found 25/10C$ 555
Sat 5/1211:00 a.m. -
1 stop25h 34m
Tue 8/124:00 p.m. -
2 stops24h 25m
Deal found 28/10C$ 621
Fri 20/119:35 p.m. -
2 stops17h 09m
Fri 27/116:20 p.m. -
1 stop14h 55m
Deal found 28/10C$ 645
Wed 25/119:35 p.m. -
2 stops17h 09m
Wed 2/128:15 a.m. -
2 stops15h 55m
Deal found 28/10C$ 666
Mon 23/119:35 p.m. -
3 stops28h 08m
Fri 27/115:26 p.m. -
2 stops22h 59m
Deal found 28/10C$ 680
Sun 13/124:45 p.m. -
2 stops18h 47m
Tue 15/128:30 a.m. -
1 stop29h 10m
Deal found 29/10C$ 684
Sat 21/119:35 p.m. -
2 stops26h 43m
Tue 24/116:20 p.m. -
1 stop14h 55m
Deal found 28/10C$ 687
Sun 22/119:35 p.m. -
2 stops15h 46m
Tue 24/119:09 a.m. -
2 stops15h 01m
Deal found 28/10C$ 773
Sun 13/127:55 p.m. -
2 stops14h 42m
Tue 15/1212:28 p.m. -
1 stop25h 12m
Deal found 29/10C$ 947
Thu 26/119:35 p.m. -
2 stops15h 59m
Thu 3/123:36 p.m. -
1 stop32h 08m
Deal found 29/10C$ 971
Sat 5/129:35 p.m. -
2 stops19h 31m
Tue 8/125:30 p.m. -
2 stops15h 45m
Deal found 28/10C$ 1,013
Sat 21/1112:44 p.m. -
1 stop4h 55m
Tue 24/119:09 a.m. -
2 stops15h 01m
Deal found 28/10C$ 1,059

Find flight deals from Winnipeg to Chicago

Round-trip from

C$ 555

One-way from

C$ 296

Popular in

June

Cheapest in

April

Average price

C$ 978

Good round-trip deal

C$ 940 or less

Good one-way deal

C$ 550 or less
14/12-16/12
  • 14/12-16/12
  • 2 total stops
  • 31h 35m total
  • Winnipeg to Chicago
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11/12-31/12
  • 11/12-31/12
  • 2 total stops
  • 25h 25m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 103 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Price to beat on a round-trip flight from Winnipeg to Chicago (CHI).
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Price to beat on a one-way flight from Winnipeg to Chicago (CHI).
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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 10/12

12:40 p.m.-11:35 a.m.

2 stops23h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 362

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Thu 10/12

9:35 p.m.-4:33 p.m.

3 stops43h 58m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 379

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 3/3

7:00 a.m.-7:42 p.m.

2 stops13h 42m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 389

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 10/12

9:35 p.m.-4:06 p.m.

2 stops19h 31m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 389

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 22/12

7:00 a.m.-2:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 422

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 5/3

6:54 a.m.-1:02 p.m.

1 stop7h 08m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 432

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Tue 10/11

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

1 stop8h 37m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 462

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sat 14/11

8:00 p.m.-5:47 p.m.

3 stops46h 47m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 517

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 28/3

7:10 p.m.-2:31 p.m.

1 stop19h 21m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 547

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 2/3

8:00 a.m.-7:42 p.m.

1 stop12h 42m

Chicago Midway

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 561

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 42 resultsSorted by cheapest first
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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, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 720). Flying from Winnipeg to Chicago in October is currently the most expensive (average of C$ 1,056). 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.

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

Calgary (YYC) – chosen by Cheapflights users on 86% 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$ 358.

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
7.3
Good
10,453 reviews
Check prices

Food

6.7

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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
7.3
Good
10,453 reviews
United Airlines
7.3
Good
10,453 reviews
Check prices

Food

6.7

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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
3,442 reviews
United Airlines
7.3
Good
10,453 reviews
Check prices

Food

6.7

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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
11,833 reviews
United Airlines
7.3
Good
10,453 reviews
Check prices

Food

6.7

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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 2 flights from Winnipeg to Chicago per day from 3 different airlines.

  • How long is the flight from Winnipeg to Chicago?

    Airlines like Porter Airlines, American Airlines, and Delta fly from Winnipeg to Chicago in about 7h 01m. The time it takes to get you to your destination can typically vary by up to 4h 44m. There are 1136 km between Winnipeg and Chicago. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    WestJet, at C$ 274, 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: Copa Airlines (93%), Air Canada (86%), Air New Zealand( 86%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 324. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 566 on average, our data indicates C$ 1,012 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, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 720). Flying from Winnipeg to Chicago in October is currently the most expensive (average of C$ 1,056). 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$ 274AverageC$ 533FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 694AverageC$ 968FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 712AverageC$ 889FlexibilityNo 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.

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