Cheap flights from Chicago (CHI) to Winnipeg (YWG) from $121

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 7/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — YWG
Jun 25 — Jul 21

The best prices from Chicago to Winnipeg are usually found in March or May, booked 28 days in advance, depart on a Thursday or Monday and return on a Tuesday

Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). 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 June 20, 2024.

Popular in

July

Cheapest in

March

Round-trip from

$388

One-way from

$154
High demand for flights, 32% potential price rise
Best time to find cheap flights, 64% potential price drop
From Chicago (CHI) to Winnipeg
One-way flight from Chicago (CHI) to Winnipeg

What is the cheapest day to fly round-trip from Chicago to Winnipeg?

Saturday flights are generally found to be more expensive for flights from Chicago to Winnipeg. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Winnipeg.

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

To save up to 490% on this flight, we recommend booking at least 29 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Winnipeg from $610 1-2 weeks out and tickets from $1,097 for flights departing within the next 72 hours.

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

March can be a great time to fly to Winnipeg from Chicago with a flight ticket averaging about $582. Cheapflights users have found deals in the month of March for as cheap as $205. The most expensive prices can be found in the month of July.

What is the cheapest time of day to fly from CHI to YWG?

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 31% on airfare.

Cheap Chicago to Winnipeg flights in June & July 2024

Find cheap flight options from Chicago to Winnipeg specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,256,981 searches. Prices were last updated on June 20, 2024.
Check out some of the best flight deals from Chicago to Winnipeg in 2024. Check back in a little while for more flight options.
Thu 7/187:40 amMDW - YWG
1 stop7h 42mMultiple Airlines
Tue 7/238:30 amYWG - MDW
2 stops12h 20mMultiple Airlines
Deal found 6/19$299
Thu 7/187:40 amMDW - YWG
1 stop7h 42mMultiple Airlines
Thu 7/258:00 amYWG - MDW
1 stop9h 00mMultiple Airlines
Deal found 6/19$326
Wed 7/36:05 amORD - YWG
1 stop5h 31mWestJet
Fri 7/58:30 amYWG - ORD
1 stop8h 27mWestJet
Deal found 6/19$346
Thu 7/189:39 amORD - YWG
1 stop13h 49mWestJet
Mon 7/226:50 amYWG - ORD
1 stop10h 07mWestJet
Deal found 6/20$372
Thu 7/189:39 amORD - YWG
1 stop13h 49mWestJet
Fri 7/266:55 amYWG - ORD
1 stop14h 45mWestJet
Deal found 6/19$388
Fri 7/195:55 pmORD - YWG
1 stop17h 43mWestJet
Mon 7/225:28 pmYWG - ORD
1 stop23h 22mWestJet
Deal found 6/20$397
Thu 7/189:39 amORD - YWG
1 stop13h 49mWestJet
Sat 7/207:30 amYWG - ORD
2 stops16h 24mWestJet
Deal found 6/19$399
Fri 7/198:34 pmORD - YWG
2 stops20h 48mMultiple Airlines
Mon 7/223:20 pmYWG - ORD
2 stops23h 23mMultiple Airlines
Deal found 6/20$400
Fri 7/195:55 pmORD - YWG
1 stop17h 43mMultiple Airlines
Mon 7/298:50 pmYWG - ORD
2 stops33h 13mMultiple Airlines
Deal found 6/19$404

Chicago to Winnipeg 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Winnipeg in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,256,981 searches. Data last updated June 20, 2024.
Check out some of the best flight deals from Chicago to Winnipeg in 2024. Check back in a little while for more flight options.
Thu 7/187:40 amMDW - YWG
1 stop7h 42mMultiple Airlines
Tue 7/238:30 amYWG - MDW
2 stops12h 20mMultiple Airlines
Deal found 6/19$299
Sat 8/109:59 pmORD - YWG
1 stop17h 23mMultiple Airlines
Mon 8/128:00 amYWG - ORD
1 stop12h 58mMultiple Airlines
Deal found 6/19$323
Thu 7/187:40 amMDW - YWG
1 stop7h 42mMultiple Airlines
Thu 7/258:00 amYWG - MDW
1 stop9h 00mMultiple Airlines
Deal found 6/19$326
Sat 8/109:59 pmORD - YWG
1 stop17h 23mMultiple Airlines
Mon 8/128:00 amYWG - ORD
2 stops22h 01mMultiple Airlines
Deal found 6/19$345
Wed 7/36:05 amORD - YWG
1 stop5h 31mWestJet
Fri 7/58:30 amYWG - ORD
1 stop8h 27mWestJet
Deal found 6/19$346
Sat 9/75:55 pmORD - YWG
1 stop17h 43mWestJet
Sat 9/218:30 amYWG - ORD
1 stop8h 39mWestJet
Deal found 6/19$353
Tue 8/135:55 pmORD - YWG
1 stop17h 43mWestJet
Sat 8/177:30 amYWG - ORD
2 stops12h 18mWestJet
Deal found 6/19$363
Wed 9/48:16 pmORD - YWG
2 stops19h 11mMultiple Airlines
Tue 9/102:40 pmYWG - ORD
2 stops32h 54mMultiple Airlines
Deal found 6/18$368
Thu 7/189:39 amORD - YWG
1 stop13h 49mWestJet
Mon 7/226:50 amYWG - ORD
1 stop10h 07mWestJet
Deal found 6/20$372

One-way flights to Winnipeg from Chicago

Search for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,256,981 searches. Data last updated June 20, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Winnipeg. Those seeking round-trip flights from Chicago to Winnipeg should utilize the search form at the the top of the page.
Wed 7/179:59 pmORD - YWG
1 stop17h 23mMultiple Airlines
Deal found 6/19$121
Fri 7/195:55 pmORD - YWG
1 stop17h 43mWestJet
Deal found 6/19$154
Fri 7/198:34 pmORD - YWG
2 stops20h 48mMultiple Airlines
Deal found 6/19$162
Wed 7/176:46 pmORD - YWG
2 stops20h 36mMultiple Airlines
Deal found 6/19$164
Wed 7/177:26 amORD - YWG
3 stops31h 56mMultiple Airlines
Deal found 6/19$187
Sun 6/306:56 amMDW - YWG
1 stop8h 26mMultiple Airlines
Deal found 6/19$202
Sun 6/308:40 amMDW - YWG
2 stops9h 27mPorter Airlines
Deal found 6/19$291
Sun 6/304:00 pmORD - YWG
1 stop8h 07mAir Canada
Deal found 6/19$305
Sun 6/309:10 pmORD - YWG
3 stops20h 42mMultiple Airlines
Deal found 6/19$312

Find flights from Chicago to Winnipeg within your budget

Customize your flight search to find flights from Chicago to Winnipeg 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 3,256,981 searches. Data last updated June 20, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$299 - $584

Route

Depart

Return

Price

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/18

1 stop7h 42m

Winnipeg

Tue 7/23

2 stops12h 20m

$299

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 8/10

1 stop17h 23m

Winnipeg

Mon 8/12

1 stop12h 58m

$323

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/18

1 stop7h 42m

Winnipeg

Thu 7/25

1 stop9h 00m

$326

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 7/3

1 stop5h 31m

Winnipeg

Fri 7/5

1 stop8h 27m

$346

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/7

1 stop17h 43m

Winnipeg

Sat 9/21

1 stop8h 39m

$353

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 8/13

1 stop17h 43m

Winnipeg

Sat 8/17

2 stops12h 18m

$363

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 7/21

1 stop6h 26m

Winnipeg

Wed 7/24

1 stop6h 25m

$486

Chicago MidwayWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 7/17

2 stops9h 52m

Winnipeg

Fri 7/26

2 stops10h 17m

$507

Chicago O'Hare IntlWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 7/20

1 stop8h 05m

Winnipeg

Mon 7/29

Nonstop2h 28m

$584

Flights are sorted by cheapest first

Deals found on 6/19

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Winnipeg. Price data was last updated on June 14, 2024.
The price you pay for your flight from Chicago to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 28 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Winnipeg. Price data was last updated on June 16, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago 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.

Temperature and rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature and rainfall totals by month.

YWG

Temperature

3.2 - 68 °F

If weather is an important factor for your trip to Winnipeg, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated June 20, 2024.
See what other customers who have flown with WestJet, Air Canada and Porter Airlines from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

8.0
Very good
10,000 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.5
Good
372 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.4
Good
2,778 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.4
Good
10,000 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

7.0
Good
7,126 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. 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 into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 0 inbound flights from Chicago per day from 3 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • Can I find flights from Chicago to Winnipeg for under $300 on Cheapflights?

    Yes, there are multiple flights from Chicago to Winnipeg for under $300. The cheapest flight booked recently is on Multiple Airlines for just $299, but on average you can expect to pay $370.

  • Are there nonstop flights from Chicago to Winnipeg for under $600 on Cheapflights?

    Cheapflights has at least 10 direct flights from Chicago to Winnipeg under $600. A good price for a nonstop flight from Chicago to Winnipeg is less than $943.

  • What is the cheapest airline to fly from Chicago to Winnipeg round-trip?

    Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $346. This flight start at 40% lower than the current average price 3 months from now.

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

    One-way options have recently been found by users for as low as $154 on WestJet. Other airlines that offer cheap prices include Porter Airlines from $291 and Air Canada from $305 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (92%), Air Canada (92%) and United Airlines (92%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $262. On average you can expect to pay $491. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $323.

  • What does ORD to YWG mean?

    Chicago O'Hare Intl Airport is ORD and Winnipeg Airport is YWG. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Winnipeg that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Winnipeg flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Winnipeg with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Winnipeg flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Winnipeg that allow pets onboard?

    Many airlines flying from Chicago to Winnipeg offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Winnipeg?

    Yes, you can often find last-minute deals on Chicago to Winnipeg flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Winnipeg flight deals updated?

    The Chicago to Winnipeg flight deals you see on this page were last updated on 6/20.

  • What are the most popular airlines that fly from Chicago to Winnipeg?

  • What is the cheapest month to book a flight from Chicago to Winnipeg?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $388). Flying from Chicago to Winnipeg in August is currently the most expensive (average of $573). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Chicago to Winnipeg

Discover the top 3 airlines that operate flights from Chicago to Winnipeg. 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 3,256,981 searches. Data last updated June 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$160Average$562FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$456Average$822FlexibilityNo cancel feeOn-time69%
DeltaCheapest$462Average$618FlexibilityNo cancel feeOn-timeN/A

Search flights from Chicago to Winnipeg by cabin class

Find flights from Chicago to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Chicago to Winnipeg

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 20, 2024.
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
100%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.