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Cheap flights from Winnipeg to Chicago from C$ 240

YWG — CHI
15 Oct — 22 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

Mon 19/107:00 a.m. -
1 stop9h 40m
Thu 22/105:30 p.m. -
1 stop7h 25m
Deal found 14/9C$ 408
Sun 18/107:00 a.m. -
1 stop9h 40m
Mon 19/105:30 p.m. -
1 stop17h 40m
Deal found 13/9C$ 470
Fri 23/107:00 a.m. -
1 stop9h 40m
Tue 27/106:20 p.m. -
2 stops23h 50m
Deal found 13/9C$ 478
Thu 22/107:00 a.m. -
1 stop9h 40m
Tue 27/106:20 p.m. -
2 stops23h 50m
Deal found 14/9C$ 482
Wed 21/104:55 p.m. -
1 stop23h 45m
Fri 23/105:30 p.m. -
1 stop7h 25m
Deal found 11/9C$ 486
Sat 24/109:20 a.m. -
1 stop26h 20m
Sun 25/106:20 p.m. -
1 stop16h 25m
Deal found 10/9C$ 506
Sat 17/102:55 p.m. -
1 stop25h 45m
Mon 19/105:30 p.m. -
1 stop17h 40m
Deal found 13/9C$ 513
Thu 15/106:15 a.m. -
1 stop28h 45m
Sun 18/103:20 p.m. -
1 stop25h 05m
Deal found 13/9C$ 514
Tue 24/115:00 a.m. -
1 stop12h 40m
Sun 29/116:20 p.m. -
1 stop14h 55m
Deal found 14/9C$ 515
Fri 25/98:10 p.m. -
1 stop14h 50m
Wed 30/93:20 p.m. -
1 stop17h 20m
Deal found 11/9C$ 572
Thu 19/118:35 p.m. -
2 stops16h 58m
Mon 23/118:42 p.m. -
1 stop20h 48m
Deal found 9/9C$ 842
Thu 22/106:05 p.m. -
1 stop16h 55m
Tue 27/106:44 p.m. -
2 stops16h 21m
Deal found 14/9C$ 897

Find flight deals from Winnipeg to Chicago

Round-trip from

C$ 408

One-way from

C$ 240

Popular in

January

Cheapest in

November

Average price

C$ 785

Good round-trip deal

C$ 797 or less

Good one-way deal

C$ 455 or less
WestJet
  • WestJet
  • 19/10-22/10
  • 2 total stops
  • 17h 05m total
  • Winnipeg to Chicago
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WestJet
  • WestJet
  • 18/10-31/12
  • 1 total stop
  • 9h 40m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 81 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 52 potential savings vs. average RT price).
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Average for round-trip flights in September 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 3/11

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

1 stop7h 37m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 306

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Mon 19/10

4:15 p.m.-11:00 a.m.

2 stops18h 45m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 318

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 23/10

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

1 stop6h 54m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 328

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Sun 18/10

10:30 p.m.-4:40 p.m.

2 stops18h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 331

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sat 7/11

8:35 p.m.-5:47 p.m.

2 stops21h 12m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 339

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sun 11/10

4:55 p.m.-11:43 p.m.

3 stops30h 48m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 342

WinnipegChicago

YWG Winnipeg - ORD Chicago O'Hare Intl

YWGORD

Winnipeg

Fri 9/10

6:00 a.m.-3:03 p.m.

3 stops33h 03m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 342

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sun 18/10

9:05 p.m.-2:35 p.m.

3 stops41h 30m

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

Thu 26/11

6:00 a.m.-12:53 a.m.

3 stops18h 53m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 376

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sat 10/10

2:55 p.m.-2:35 p.m.

3 stops23h 40m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 413

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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, November is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 677). Flying from Winnipeg to Chicago in June is currently the most expensive (average of C$ 961). 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 (6 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$ 539 and C$ 921 in October.
The cheapest round-trip price found within the last 5 days was C$ 408 on WestJet (19 Oct-22 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
10,209 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Comfort

7.3

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
10,209 reviews
United Airlines
7.4
Good
10,209 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Comfort

7.3

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
3,443 reviews
United Airlines
7.4
Good
10,209 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Comfort

7.3

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
11,630 reviews
United Airlines
7.4
Good
10,209 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Comfort

7.3

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 7 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 Delta fly from Winnipeg to Chicago in about 5h 18m. The time it takes to get you to your destination can typically vary by up to 17h 49m. There are 1162 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$ 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 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: Air Canada (86%), SkyWest Airlines (85%), United Airlines( 85%).

  • 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$ 482 on average, our data indicates C$ 1,145 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$ 677). Flying from Winnipeg to Chicago in June is currently the most expensive (average of C$ 961). 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$ 689AverageC$ 962FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 707AverageC$ 873FlexibilityNo 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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