Cheap flights from Winnipeg (YWG) to O'Hare Intl (ORD) from $164

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 7/24. 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.
YWG — ORD
Jun 25 — Jul 21

The best prices from Winnipeg to Chicago O'Hare Intl are usually found in March or November, booked 80 days in advance, depart on a Monday or Wednesday and return on a Thursday

Cheap flight deals from Winnipeg to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to O'Hare Intl (ORD). 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

May

Cheapest in

March

Average price

$504

Round-trip from

$223
High demand for flights, 23% potential price rise
Best time to find cheap flights, 12% potential price drop
Average for round-trip flights in June 2024
From Winnipeg to Chicago O'Hare Intl

What is the cheapest day to fly round-trip from Winnipeg to Chicago O'Hare Intl Airport?

Sunday is generally a great day to depart. Flying on this day could help you save up to 55%.

How far in advance should I book a flight from Winnipeg to Chicago O'Hare Intl Airport?

Find a great deal and save up to 12% by booking at least 17 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago O'Hare Intl Airport within the next two weeks, with the cheapest ticket starting at $326.

What is the cheapest month to fly from Winnipeg to Chicago O'Hare Intl Airport?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, May can be a great choice for travel to Chicago O'Hare Intl Airport. Flights to Chicago O'Hare Intl Airport from Winnipeg in May are about $502 on average during May, but can be found for as low as $296.

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

Unlike in the morning, when flights are generally more expensive, you can save up to 33% on flights from Winnipeg to Chicago O'Hare Intl Airport by exploring options for tickets in the afternoon.

Cheap Winnipeg to O'Hare Intl flights in June & July 2024

Find cheap flight options from Winnipeg to O'Hare Intl 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.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back soon for alternative fares.
Mon 7/18:30 amYWG - ORD
1 stop8h 27mWestJet
Wed 7/107:05 amORD - YWG
1 stop8h 17mWestJet
Deal found 6/20$313
Mon 7/18:30 amYWG - ORD
1 stop8h 27mWestJet
Wed 7/106:05 amORD - YWG
2 stops11h 39mWestJet
Deal found 6/20$321
Mon 7/15:20 pmYWG - ORD
1 stop23h 37mWestJet
Mon 7/89:45 amORD - YWG
1 stop13h 43mWestJet
Deal found 6/18$343
Thu 7/412:26 pmYWG - ORD
1 stop4h 29mWestJet
Mon 7/83:51 pmORD - YWG
1 stop7h 37mWestJet
Deal found 6/19$345
Thu 7/412:26 pmYWG - ORD
1 stop9h 31mWestJet
Mon 7/86:05 amORD - YWG
2 stops16h 38mWestJet
Deal found 6/19$349
Sat 7/136:30 amYWG - ORD
2 stops15h 10mWestJet
Thu 7/186:05 amORD - YWG
1 stop17h 23mWestJet
Deal found 6/20$350
Tue 7/237:30 amYWG - ORD
2 stops11h 00mWestJet
Fri 7/269:39 amORD - YWG
1 stop13h 49mWestJet
Deal found 6/20$355
Mon 7/226:50 amYWG - ORD
1 stop10h 07mWestJet
Tue 7/237:55 pmORD - YWG
1 stop19h 27mWestJet
Deal found 6/20$372
Sat 7/136:55 amYWG - ORD
1 stop14h 45mWestJet
Thu 7/189:39 amORD - YWG
1 stop13h 49mWestJet
Deal found 6/19$376

Winnipeg to O'Hare Intl 2024 flight deals

Discover exclusive flight deals for travel between Winnipeg and O'Hare Intl 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.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back soon for alternative fares.
Mon 7/18:30 amYWG - ORD
1 stop8h 27mWestJet
Wed 7/107:05 amORD - YWG
1 stop8h 17mWestJet
Deal found 6/20$313
Mon 7/18:30 amYWG - ORD
1 stop8h 27mWestJet
Wed 7/106:05 amORD - YWG
2 stops11h 39mWestJet
Deal found 6/20$321
Mon 7/15:20 pmYWG - ORD
1 stop23h 37mWestJet
Mon 7/89:45 amORD - YWG
1 stop13h 43mWestJet
Deal found 6/18$343
Thu 7/412:26 pmYWG - ORD
1 stop4h 29mWestJet
Mon 7/83:51 pmORD - YWG
1 stop7h 37mWestJet
Deal found 6/19$345
Sat 8/179:35 amYWG - ORD
2 stops11h 27mWestJet
Tue 8/206:05 amORD - YWG
1 stop5h 27mWestJet
Deal found 6/20$347
Thu 7/412:26 pmYWG - ORD
1 stop9h 31mWestJet
Mon 7/86:05 amORD - YWG
2 stops16h 38mWestJet
Deal found 6/19$349
Sat 7/136:30 amYWG - ORD
2 stops15h 10mWestJet
Thu 7/186:05 amORD - YWG
1 stop17h 23mWestJet
Deal found 6/20$350
Sat 8/176:55 amYWG - ORD
1 stop9h 55mWestJet
Tue 8/208:30 pmORD - YWG
1 stop26h 58mWestJet
Deal found 6/20$351
Sat 8/179:35 amYWG - ORD
2 stops11h 27mWestJet
Tue 8/2010:18 amORD - YWG
2 stops12h 54mWestJet
Deal found 6/20$352

Winnipeg to O'Hare Intl flights leaving soon

Find last-minute flight options from Winnipeg to O'Hare Intl for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,256,981 searches. Data last updated June 20, 2024.
Consider one of these great deals we found on last-minute flights from Winnipeg to Chicago. Users should be sure to double check the price, date, and time of their last-minute flight.
Thu 6/276:55 amYWG - ORD
1 stop8h 04mWestJet
Tue 7/26:05 amORD - YWG
1 stop17h 42mWestJet
Deal found 6/19$394
Thu 6/278:30 amYWG - ORD
1 stop8h 27mWestJet
Wed 7/34:00 pmORD - YWG
1 stop7h 47mWestJet
Deal found 6/19$479
Thu 6/276:55 amYWG - ORD
1 stop8h 04mWestJet
Tue 7/212:35 pmORD - YWG
2 stops11h 23mWestJet
Deal found 6/19$485
Thu 6/278:00 amYWG - ORD
2 stops16h 55mMultiple Airlines
Tue 7/25:18 pmORD - YWG
3 stops25h 39mMultiple Airlines
Deal found 6/19$488
Thu 6/278:00 amYWG - ORD
1 stop12h 47mMultiple Airlines
Tue 7/211:02 amORD - YWG
3 stops31h 55mMultiple Airlines
Deal found 6/19$491
Sat 6/296:55 amYWG - ORD
1 stop4h 49mWestJet
Wed 7/34:00 pmORD - YWG
1 stop7h 47mWestJet
Deal found 6/19$501
Wed 6/269:35 amYWG - ORD
2 stops13h 11mWestJet
Thu 7/46:00 amORD - YWG
1 stop9h 22mWestJet
Deal found 6/19$505
Thu 6/277:30 amYWG - ORD
2 stops12h 17mWestJet
Thu 7/411:30 amORD - YWG
2 stops11h 13mWestJet
Deal found 6/19$511
Fri 6/288:00 amYWG - ORD
1 stop11h 47mWestJet
Wed 7/34:00 pmORD - YWG
1 stop7h 47mWestJet
Deal found 6/19$517

One-way flights to O'Hare Intl from Winnipeg

Search for one-way flight options from Winnipeg to O'Hare Intl. 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.
Users traveling one-way from Winnipeg to Chicago can select one of these great deals. Users in need of a round-trip flight from Winnipeg to Chicago instead should update the search form at the top of page.
Wed 7/248:00 amYWG - ORD
1 stop12h 58mMultiple Airlines
Deal found 6/19$164
Thu 7/258:00 amYWG - ORD
1 stop12h 58mMultiple Airlines
Deal found 6/19$166
Wed 6/268:00 amYWG - ORD
1 stop8h 44mMultiple Airlines
Deal found 6/19$168
Fri 7/268:00 amYWG - ORD
1 stop12h 58mMultiple Airlines
Deal found 6/19$195
Tue 7/236:55 amYWG - ORD
1 stop14h 41mWestJet
Deal found 6/19$202
Tue 7/238:30 amYWG - ORD
2 stops16h 05mMultiple Airlines
Deal found 6/19$205
Tue 7/232:05 pmYWG - ORD
3 stops15h 26mMultiple Airlines
Deal found 6/19$209
Sun 7/216:50 amYWG - ORD
3 stops35h 29mMultiple Airlines
Deal found 6/19$220
Wed 7/248:00 amYWG - ORD
3 stops24h 12mMultiple Airlines
Deal found 6/19$221

Find flights from Winnipeg to O'Hare Intl within your budget

Customize your flight search to find flights from Winnipeg to O'Hare Intl 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

$343 - $606

Route

Depart

Return

Price

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 7/1

1 stop23h 37m

Chicago O'Hare Intl

Mon 7/8

1 stop13h 43m

$343

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 7/4

1 stop4h 29m

Chicago O'Hare Intl

Mon 7/8

1 stop7h 37m

$345

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 8/17

2 stops11h 27m

Chicago O'Hare Intl

Tue 8/20

1 stop5h 27m

$347

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 7/4

1 stop9h 31m

Chicago O'Hare Intl

Mon 7/8

2 stops16h 38m

$349

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Wed 10/23

1 stop15h 34m

Chicago O'Hare Intl

Thu 10/24

2 stops23h 03m

$411

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Thu 11/28

1 stop9h 09m

Chicago O'Hare Intl

Sat 11/30

1 stop18h 53m

$439

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 8/5

Nonstop2h 28m

Chicago O'Hare Intl

Sat 8/10

Nonstop2h 26m

$456

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Sat 7/13

Nonstop2h 28m

Chicago O'Hare Intl

Thu 7/18

Nonstop2h 26m

$466

WinnipegChicago O'Hare Intl

YWG - ORD

YWGORD

Winnipeg

Mon 8/5

2 stops10h 24m

Chicago O'Hare Intl

Sat 8/10

2 stops10h 00m

$606

Flights are sorted by cheapest first

Deals found on 6/18

How far ahead should I book a flight from Winnipeg to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to O'Hare Intl. Price data was last updated on June 14, 2024.
The price you pay for your flight from Winnipeg to Chicago O'Hare Intl Airport may vary depending on when you book. For the best chance of a lower fare, look to book 80 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 Winnipeg to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to O'Hare Intl. Price data was last updated on June 16, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Winnipeg to Chicago O'Hare Intl Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday mornings 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 Winnipeg to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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.

Temperature and rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated June 20, 2024.
Peruse reviews from past customers who have flown with WestJet, United Airlines and Air Canada from Winnipeg to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
10,000 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.6
Good
2,363 reviews
8.0
Very good
10,000 reviews

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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

Food

7.4

Boarding

8.2

Entertainment

8.0

Overall

8.0

Comfort

7.9

Crew

8.6

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to O'Hare Intl. 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 O'Hare Intl?

    For a flight from Winnipeg to Chicago O'Hare Intl, you will be flying from Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city. Winnipeg is the only Winnipeg airport and it handles 0 outbound flights to Chicago O'Hare Intl per day. 2 airlines have flights to Chicago O'Hare Intl from Winnipeg on a regular basis.

  • Can I find flights from Winnipeg to Chicago O'Hare Intl Airport for under $400 on Cheapflights?

    Yes, there are multiple flights from Winnipeg to Chicago O'Hare Intl Airport for under $400. The cheapest flight booked recently is on WestJet for just $343, but on average you can expect to pay $369.

  • Are there nonstop flights from Winnipeg to Chicago O'Hare Intl Airport for under $500 on Cheapflights?

    Cheapflights has at least 20 direct flights from Winnipeg to Chicago O'Hare Intl Airport under $500. A good price for a nonstop flight from Winnipeg to Chicago O'Hare Intl Airport is less than $665.

  • Are there last-minute flights available from Winnipeg to Chicago O'Hare Intl Airport for under $400?

    There are currently 20+ open flights from Winnipeg to Chicago O'Hare Intl Airport within the next 7 days for less than $400.

  • What is the cheapest airline to fly from Winnipeg to Chicago O'Hare Intl Airport round-trip?

    Cheapflights users have booked flights from Winnipeg to Chicago O'Hare Intl Airport round-trip from $343. You may be able to fly from Winnipeg to Chicago O'Hare Intl Airport for 35% less than the average price by searching for this airline.

  • What are the cheapest airlines to fly from Winnipeg to Chicago O'Hare Intl Airport one-way?

    $202 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Canada, with prices starting from $253 and $258, respectively.

  • What are the most reliable airlines from Winnipeg to Chicago O'Hare Intl Airport?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Winnipeg to Chicago O'Hare Intl Airport on time: SkyWest Airlines (88%), Air Canada (88%), United Airlines (88%).

  • What are the cheapest flights from Winnipeg to Chicago O'Hare Intl Airport?

    On average you can expect to pay $421 for a flight from Winnipeg to Chicago O'Hare Intl Airport. The cheapest flight overall is $221 while the most popular route, (Winnipeg - Chicago O'Hare Intl) is currently priced at $273.

  • What does YWG to ORD mean?

    Winnipeg Airport is YWG and Chicago O'Hare Intl Airport is ORD. 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.

  • Can I find deals for flights from Winnipeg to O'Hare Intl that include extra baggage allowance?

    The amount of baggage you can bring on your Winnipeg to O'Hare Intl 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 Winnipeg to O'Hare Intl with specific airlines?

    Yes, Cheapflights allows you to browse and filter Winnipeg to O'Hare Intl 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 Winnipeg to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Winnipeg to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to O'Hare Intl?

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

  • Can I find deals for business class flights from Winnipeg to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Winnipeg to O'Hare Intl 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 Winnipeg to O'Hare Intl that allow pets onboard?

    Many airlines flying from Winnipeg to O'Hare Intl 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 Winnipeg to O'Hare Intl?

    Yes, you can often find last-minute deals on Winnipeg to O'Hare Intl 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 Winnipeg to Chicago O'Hare Intl Airport flight deals updated?

    The Winnipeg to Chicago O'Hare Intl Airport flight deals you see on this page were last updated on 6/20.

  • What is the cheapest month to book a flight from Winnipeg to Chicago O'Hare Intl Airport?

    Currently, February is the cheapest month in which you can book a flight from Winnipeg to Chicago O'Hare Intl Airport (average of $244). Flying from Winnipeg to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $319). 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

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

Top 2 airlines flying from Winnipeg to O'Hare Intl

Discover the top 2 airlines that operate flights from Winnipeg to O'Hare Intl. 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$283Average$480FlexibilityNo cancel feeOn-time67%
DeltaCheapest$390Average$545FlexibilityNo cancel feeOn-timeN/A

Search flights from Winnipeg to O'Hare Intl by cabin class

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

Hourly flight availability from Winnipeg to O'Hare Intl

Find hourly flight availability from Winnipeg to O'Hare Intl. 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
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