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Cheap flights from Winnipeg to Chicago from C$ 271

YWG — CHI
15 Dec — 22 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 14/129:35 p.m. -
2 stops17h 55m
Mon 21/125:58 a.m. -
1 stop7h 42m
Deal found 14/11C$ 555
Thu 10/129:35 p.m. -
2 stops24h 54m
Sun 13/1210:29 p.m. -
1 stop15h 11m
Deal found 10/11C$ 556
Mon 7/129:35 p.m. -
2 stops17h 55m
Wed 9/128:30 a.m. -
2 stops15h 40m
Deal found 12/11C$ 588
Mon 7/129:35 p.m. -
2 stops17h 55m
Thu 10/1210:29 p.m. -
2 stops17h 56m
Deal found 12/11C$ 602
Mon 7/129:35 p.m. -
2 stops14h 58m
Thu 10/125:02 p.m. -
2 stops23h 23m
Deal found 12/11C$ 625
Fri 11/129:35 p.m. -
2 stops25h 25m
Fri 18/125:58 a.m. -
1 stop7h 42m
Deal found 13/11C$ 634
Mon 7/125:45 p.m. -
1 stop22h 08m
Wed 9/1210:36 a.m. -
2 stops13h 34m
Deal found 12/11C$ 635
Sun 6/129:35 p.m. -
2 stops19h 31m
Thu 10/125:02 p.m. -
2 stops23h 23m
Deal found 12/11C$ 649
Tue 1/1212:10 p.m. -
2 stops34h 25m
Sat 5/128:30 a.m. -
2 stops25h 50m
Deal found 13/11C$ 652
Thu 10/129:35 p.m. -
2 stops19h 31m
Sun 13/128:37 p.m. -
3 stops27h 33m
Deal found 10/11C$ 678
Mon 14/127:00 a.m. -
1 stop28h 28m
Tue 15/1212:39 p.m. -
1 stop11h 00m
Deal found 14/11C$ 759
Sat 12/129:35 p.m. -
2 stops19h 31m
Sat 19/128:35 p.m. -
3 stops27h 35m
Deal found 14/11C$ 813

Find flight deals from Winnipeg to Chicago

Round-trip from

C$ 528

One-way from

C$ 271

Popular in

June

Cheapest in

February

Average price

C$ 800

Good round-trip deal

C$ 884 or less

Good one-way deal

C$ 539 or less
18/1-21/1
  • 18/1-21/1
  • 3 total stops
  • 44h 34m total
  • Winnipeg to Chicago
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15/12-31/12
  • 15/12-31/12
  • 2 total stops
  • 25h 25m total
  • Winnipeg to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 93 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 November 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

Tue 1/12

9:35 p.m.-2:00 p.m.

2 stops17h 25m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 298

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 23/12

7:00 a.m.-12:01 a.m.

1 stop18h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 331

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 15/12

9:35 p.m.-4:16 p.m.

2 stops19h 41m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 344

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Tue 1/12

9:35 p.m.-11:33 a.m.

2 stops14h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 345

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 5/12

9:35 p.m.-10:25 a.m.

2 stops13h 50m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 348

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 3/12

9:35 p.m.-4:16 p.m.

2 stops19h 41m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 364

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 11/12

7:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 367

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sat 5/12

9:35 p.m.-7:20 a.m.

2 stops34h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 368

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 4/12

7:55 p.m.-5:40 p.m.

1 stop22h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 370

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 4/12

9:35 p.m.-11:33 a.m.

2 stops14h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 382

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 39 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 773). Flying from Winnipeg to Chicago in October is currently the most expensive (average of C$ 1,077). 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 Tuesday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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

Calgary (YYC) – chosen by Cheapflights users on 83% 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$ 377.

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
10,495 reviews
Check prices

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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
7.3
Good
10,495 reviews
United Airlines
7.3
Good
10,495 reviews
Check prices

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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
3,436 reviews
United Airlines
7.3
Good
10,495 reviews
Check prices

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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
11,897 reviews
United Airlines
7.3
Good
10,495 reviews
Check prices

Entertainment

7.1

Overall

7.3

Boarding

7.7

Comfort

7.3

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

  • How long is the flight from Winnipeg to Chicago?

    Airlines like Porter Airlines, WestJet, and United Airlines fly from Winnipeg to Chicago in about 2h 31m. The time it takes to get you to your destination can typically vary by up to 8h 54m. 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$ 279, 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 69% 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 (95%), Air Canada (87%), Air New Zealand( 87%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 432. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 528 on average, our data indicates C$ 884 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 773). Flying from Winnipeg to Chicago in October is currently the most expensive (average of C$ 1,077). 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$ 279AverageC$ 544FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 708AverageC$ 988FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 726AverageC$ 907FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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