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Cheap flights from Winnipeg to Chicago from C$ 165

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
31 Dec — 7 Jan1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 64 days in advance, depart on a Friday or Wednesday and return on a Monday

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Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Chicago
Explore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 1 December 2025.

Mon 15/129:00 p.m.YWG - ORD
2 stops18h 12mMultiple Airlines
Fri 19/1212:09 p.m.ORD - YWG
1 stop13h 17mMultiple Airlines
Deal found 1/12C$ 573
Tue 23/126:00 a.m.YWG - MDW
1 stop28h 05mMultiple Airlines
Tue 6/12:03 p.m.MDW - YWG
2 stops28h 03mMultiple Airlines
Deal found 1/12C$ 588
Wed 24/1212:10 p.m.YWG - MDW
1 stop27h 10mMultiple Airlines
Tue 6/12:03 p.m.MDW - YWG
2 stops28h 03mMultiple Airlines
Deal found 1/12C$ 651
Sat 6/128:20 p.m.YWG - ORD
2 stops40h 56mMultiple Airlines
Sat 13/121:24 p.m.ORD - YWG
1 stop25h 43mMultiple Airlines
Deal found 1/12C$ 664
Wed 24/127:05 a.m.YWG - ORD
1 stop8h 05mAir Canada
Tue 6/13:55 p.m.ORD - YWG
1 stop7h 59mAir Canada
Deal found 1/12C$ 678
Tue 23/128:00 a.m.YWG - ORD
1 stop26h 18mMultiple Airlines
Tue 6/17:57 p.m.ORD - YWG
2 stops43h 19mMultiple Airlines
Deal found 1/12C$ 691
Mon 15/128:00 a.m.YWG - MDW
2 stops24h 46mMultiple Airlines
Fri 19/123:10 p.m.MDW - YWG
1 stop10h 16mMultiple Airlines
Deal found 1/12C$ 697
Thu 25/122:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Tue 6/19:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
Deal found 1/12C$ 718
Mon 29/125:45 p.m.YWG - MDW
1 stop17h 21mWestJet
Mon 5/17:16 p.m.MDW - YWG
1 stop15h 47mWestJet
Deal found 29/11C$ 725
Thu 25/122:20 p.m.YWG - ORD
Nonstop2h 43mAir Canada
Tue 6/19:10 a.m.ORD - YWG
Nonstop2h 47mAir Canada
Deal found 1/12C$ 725
Thu 25/126:45 a.m.YWG - MDW
2 stops28h 21mWestJet
Tue 6/19:32 a.m.MDW - YWG
2 stops15h 03mWestJet
Deal found 1/12C$ 729
Fri 19/125:40 p.m.YWG - MDW
2 stops21h 48mMultiple Airlines
Fri 2/16:12 a.m.MDW - YWG
1 stop8h 55mMultiple Airlines
Deal found 29/11C$ 752

Cheap flight deals from Winnipeg to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 1 December 2025.

Round-trip from

C$ 317

One-way from

C$ 165

Popular in

December

Cheapest in

September

Average price

C$ 760

Good round-trip deal

C$ 843 or less

Good one-way deal

C$ 394 or less
WestJet
  • WestJet
  • 26/5-28/5
  • 2 total stops
  • 24h 43m total
  • Winnipeg to Chicago
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8/12
  • 8/12
  • 2 total stops
  • 21h 46m total
  • Winnipeg to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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

 
Customize your flight search to find flights from Winnipeg to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 1 December 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.

Fly from

Winnipeg

Fly to

Chicago

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 15/1

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Thu 22/1

5:40 a.m.-12:41 a.m.

2 stops19h 01m

C$ 351

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/3

9:00 p.m.-1:35 p.m.

1 stop16h 35m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 362

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Thu 5/3

6:15 a.m.-11:35 p.m.

2 stops17h 20m

Chicago O'Hare Intl

Mon 9/3

2:20 p.m.-10:40 p.m.

1 stop8h 20m

C$ 370

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 25/4

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

2 stops23h 48m

Chicago O'Hare Intl

Thu 30/4

5:30 p.m.-9:30 p.m.

1 stop28h 00m

C$ 386

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 10/1

12:55 p.m.-11:45 a.m.

2 stops22h 50m

Chicago Midway

Mon 12/1

4:31 p.m.-5:26 p.m.

1 stop24h 55m

C$ 388

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sat 10/1

12:10 p.m.-8:04 p.m.

1 stop7h 54m

Chicago O'Hare Intl

Mon 12/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

C$ 397

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 16/3

6:15 a.m.-1:35 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Sat 21/3

11:39 a.m.-3:09 p.m.

1 stop27h 30m

C$ 457

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 15/1

6:45 a.m.-6:32 p.m.

2 stops11h 47m

Chicago Midway

Thu 22/1

5:01 p.m.-3:07 p.m.

1 stop22h 06m

C$ 504

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 23/12

6:00 a.m.-10:05 a.m.

1 stop28h 05m

Chicago Midway

Tue 6/1

2:03 p.m.-6:06 p.m.

2 stops28h 03m

C$ 588

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Tue 3/3

5:00 a.m.-5:45 p.m.

2 stops12h 45m

Chicago Midway

Sun 8/3

9:30 a.m.-7:24 p.m.

2 stops9h 54m

C$ 591

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/11

Showing 1-10 of 26 results
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Winnipeg to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Chicago. Price data was last updated on 28 November 2025.

The best time to book flights from Winnipeg to Chicago is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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$ 203). Flying from Winnipeg to Chicago in December is currently the most expensive (average of C$ 608). 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?

Find hourly flight availability from Winnipeg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 1 December 2025.

One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.

Weekly flight availability from Winnipeg to Chicago

Explore weekly flight availability from Winnipeg to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 1 December 2025.

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

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

Share of one-stop round-trip flights from Winnipeg to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 79% of one-stop itineraries from Winnipeg to Chicago on Cheapflights.

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

Average round-trip fare for 1-stop flights from Winnipeg to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 422.

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

Shortest average travel time for 1-stop one-way flights from Winnipeg to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 3h 48m.

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

Average layover duration for 1-stop one-way flights from Winnipeg to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 0h 56m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 1 December 2025.
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
9,065 reviews
Check prices

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,065 reviews
United Airlines
7.4
Good
9,065 reviews
Check prices

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,186 reviews
United Airlines
7.4
Good
9,065 reviews
Check prices

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,493 reviews
United Airlines
7.4
Good
9,065 reviews
Check prices

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

  • How long is the flight from Winnipeg to Chicago?

    Airlines like WestJet fly from Winnipeg to Chicago in about 16h 35m. 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$ 202, 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 66% 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: SkyWest Airlines (84%), Air Canada (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$ 315. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 328 on average, our data indicates C$ 894 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$ 203). Flying from Winnipeg to Chicago in December is currently the most expensive (average of C$ 608). 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

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Alternative routes for Winnipeg to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to O'Hare Intl flights

Top 3 airlines flying from Winnipeg to Chicago

Discover the top 3 airlines that operate flights from Winnipeg to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 1 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 202AverageC$ 416FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 492AverageC$ 655FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 502AverageC$ 737FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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