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Cheap flights from Winnipeg to Chicago from C$ 186

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 25/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
23 Dec — 30 Dec1
1 adult

The best prices from Winnipeg to Chicago are usually found in June or May, booked 71 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 18 December 2024.

Round-trip from

C$ 408

One-way from

C$ 186

Popular in

January

Cheapest in

June

Average price

C$ 666
19/1-24/1
  • 19/1-24/1
  • 2 total stops
  • 22h 32m total
  • Winnipeg to Chicago
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25/3
  • 25/3
  • 1 total stop
  • 9h 08m total
  • Winnipeg to Chicago
Search Deals
High demand for flights, 4% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Winnipeg to Chicago

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 18 December 2024.

Mon 30/1211:35 a.m.YWG - ORD
2 stops20h 12mMultiple Airlines
Sun 2/211:10 a.m.ORD - YWG
2 stops27h 58mMultiple Airlines
Deal found 16/12C$ 713
Mon 30/125:00 a.m.YWG - MDW
1 stop11h 40mPorter Airlines
Sun 2/21:05 p.m.MDW - YWG
1 stop10h 35mPorter Airlines
Deal found 16/12C$ 738
Mon 30/125:55 p.m.YWG - ORD
1 stop15h 02mUnited Airlines
Sun 2/27:10 a.m.ORD - YWG
1 stop6h 17mUnited Airlines
Deal found 16/12C$ 776
Mon 30/127:00 p.m.YWG - MDW
1 stop15h 20mMultiple Airlines
Sun 2/21:26 p.m.MDW - YWG
2 stops21h 19mMultiple Airlines
Deal found 16/12C$ 804
Mon 30/128:00 p.m.YWG - MDW
2 stops21h 11mWestJet
Sun 2/21:26 p.m.MDW - YWG
2 stops21h 56mWestJet
Deal found 16/12C$ 941
Mon 30/122:15 p.m.YWG - ORD
Nonstop2h 36mAir Canada
Sun 2/27:20 a.m.ORD - YWG
1 stop9h 08mAir Canada
Deal found 16/12C$ 958
Mon 30/128:00 p.m.YWG - ORD
2 stops37h 21mWestJet
Fri 3/15:30 p.m.ORD - YWG
2 stops31h 05mWestJet
Deal found 17/12C$ 1,155

Find flights from Winnipeg to Chicago within your budget

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 18 December 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 19/1

7:30 a.m.-9:32 p.m.

1 stop14h 02m

Chicago Midway

Fri 24/1

6:40 a.m.-3:10 p.m.

1 stop8h 30m

C$ 408

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 15/1

7:30 a.m.-5:55 a.m.

2 stops22h 25m

Chicago O'Hare Intl

Wed 22/1

3:56 p.m.-12:39 a.m.

3 stops32h 43m

C$ 473

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 19/1

7:30 a.m.-2:51 p.m.

1 stop7h 21m

Chicago O'Hare Intl

Fri 24/1

10:53 a.m.-5:18 p.m.

1 stop6h 25m

C$ 527

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Wed 15/1

5:37 p.m.-9:58 p.m.

1 stop4h 21m

Chicago O'Hare Intl

Wed 22/1

11:05 a.m.-11:42 p.m.

2 stops12h 37m

C$ 571

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sun 19/1

12:45 p.m.-5:47 p.m.

1 stop5h 02m

Chicago Midway

Fri 24/1

9:34 a.m.-4:47 p.m.

2 stops7h 13m

C$ 620

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 4/4

12:15 p.m.-6:30 p.m.

1 stop6h 15m

Chicago O'Hare Intl

Mon 7/4

5:00 a.m.-1:09 p.m.

1 stop8h 09m

C$ 623

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 17/1

5:37 p.m.-3:30 p.m.

1 stop21h 53m

Chicago O'Hare Intl

Sun 19/1

4:58 p.m.-7:10 p.m.

2 stops26h 12m

C$ 637

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 16/1

5:00 a.m.-6:14 p.m.

2 stops13h 14m

Chicago Midway

Thu 23/1

10:19 a.m.-4:47 p.m.

1 stop6h 28m

C$ 671

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Mon 30/12

5:00 a.m.-4:40 p.m.

1 stop11h 40m

Chicago Midway

Sun 2/2

1:05 p.m.-11:40 p.m.

1 stop10h 35m

C$ 738

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 25/3

7:30 a.m.-4:38 p.m.

1 stop9h 08m

C$ 186

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

Showing 1-10 of 13 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.

Travel insights for flights from Winnipeg to Chicago

Get recent, data-driven insights about flights from Winnipeg to Chicago including ideal travel times, pricing trends, and more.

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 13 December 2024.

The best time to book flights from Winnipeg to Chicago is 70 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, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in May is currently the most expensive (average of C$ 342). 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 18 December 2024.

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 evening tend to be the most expensive. A flight in the morning could potentially save you up to 16% on airfare.

What is the cheapest day to fly from Winnipeg to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Chicago. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 18 December 2024.
Get a feel of what it's like to fly with United Airlines, Delta and WestJet from Winnipeg to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,604 reviews
Check prices

Crew

8.6

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,604 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Crew

8.6

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
283 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Crew

8.6

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
9,059 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Crew

8.6

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Crew

8.6

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Canada
7.0
Good
8,382 reviews
Delta
8.0
Very good
8,604 reviews
Check prices

Crew

8.6

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 is 1 flight from Winnipeg to Chicago per day from 4 different airlines.

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

    Air Canada, at C$ 527, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Delta and WestJet. Air Canada is priced at 22% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Winnipeg to Chicago one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as C$ 299. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Winnipeg to Chicago for a low price.

  • 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%), United Airlines (84%), Air Canada( 80%).

  • What are the cheapest flights from Winnipeg to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 244. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 427 on average our data indicates C$ 660 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$ 261). Flying from Winnipeg to Chicago in May is currently the most expensive (average of C$ 342). 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 4 airlines flying from Winnipeg to Chicago

Discover the top 4 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 18 December 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 393AverageC$ 702FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 495AverageC$ 595FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 525AverageC$ 882FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 563AverageC$ 748FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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