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$110+ Cheap flights from Chicago (CHI) to Manitoba

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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
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Cheap flight deals from Chicago to Manitoba

Keep the following information in mind while searching for Chicago to Manitoba flight deals. Data was last updated March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(Mytrip)

One-way from

$110
(Mytrip)

Popular in

February

Cheapest in

January

Average price

$635

Good round-trip deal

$573 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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From Chicago (CHI) to Manitoba
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One-way flight from Chicago (CHI) to Manitoba
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Manitoba.
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Price to beat on a one-way flight from Chicago (CHI) to Manitoba.
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Find flight deals from Chicago to Manitoba

Cheapest flights from Chicago to Manitoba
Explore the most affordable flight options available from Chicago to Manitoba. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

This Mytrip deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:30 pmORD - YWG
1 stop18h 11mWestJet
Mon 5/58:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 3/25$255
This Mytrip deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/84:35 pmORD - YWG
2 stops23h 20mMultiple Airlines
Sun 5/118:30 amYWG - ORD
1 stop8h 14mMultiple Airlines
Deal found 3/25$290
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/18:30 amMDW - YWG
2 stops16h 01mMultiple Airlines
Mon 5/59:00 amYWG - MDW
1 stop14h 47mMultiple Airlines
Deal found 3/25$340
This Gotogate deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2412:57 pmORD - YWG
Nonstop2h 34mAir Canada
Sun 4/272:20 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 3/25$451
This Mytrip deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/125:20 pmMDW - YWG
2 stops29h 26mPorter Airlines
Mon 6/1611:45 amYWG - MDW
2 stops28h 39mPorter Airlines
Deal found 3/25$463
This United Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/248:25 pmORD - YWG
1 stop14h 37mUnited Airlines
Fri 4/252:20 pmYWG - ORD
Nonstop2h 28mUnited Airlines
Deal found 3/25$515
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/241:16 pmMDW - YWG
1 stop7h 03mDelta
Sun 4/275:43 pmYWG - MDW
2 stops14h 57mDelta
Deal found 3/25$517
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/265:20 pmORD - YWG
1 stop6h 02mDelta
Sat 11/16:40 amYWG - ORD
2 stops9h 54mDelta
Deal found 3/25$543
This Flighttix deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/267:00 pmMDW - YWG
1 stop4h 28mWestJet
Sun 4/275:43 pmYWG - MDW
1 stop20h 39mWestJet
Deal found 3/24$570

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Manitoba 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 2,558,603 searches. Data last updated March 26, 2025.
Use the filters below to find and compare flights from Chicago to Manitoba that are best for you.

Fly from

Chicago

Fly to

Manitoba

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/1

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Mon 5/5

8:30 am-4:44 pm

1 stop8h 14m

$255

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/8

4:35 pm-3:55 pm

2 stops23h 20m

Winnipeg

Sun 5/11

8:30 am-4:44 pm

1 stop8h 14m

$290

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/1

8:30 am-12:31 am

2 stops16h 01m

Winnipeg

Mon 5/5

9:00 am-11:47 pm

1 stop14h 47m

$340

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/24

12:57 pm-3:31 pm

Nonstop2h 34m

Winnipeg

Sun 4/27

2:20 pm-4:48 pm

Nonstop2h 28m

$451

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 6/12

5:20 pm-10:46 pm

2 stops29h 26m

Winnipeg

Mon 6/16

11:45 am-4:24 pm

2 stops28h 39m

$463

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/24

8:25 pm-11:02 am

1 stop14h 37m

Winnipeg

Fri 4/25

2:20 pm-4:48 pm

Nonstop2h 28m

$515

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/24

1:16 pm-8:19 pm

1 stop7h 03m

Winnipeg

Sun 4/27

5:43 pm-8:40 am

2 stops14h 57m

$517

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/24

1:45 pm-11:25 pm

2 stops9h 40m

Winnipeg

Sat 5/31

6:40 am-12:41 pm

2 stops6h 01m

$548

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 4/26

7:00 pm-11:28 pm

1 stop4h 28m

Winnipeg

Sun 4/27

5:43 pm-2:22 pm

1 stop20h 39m

$570

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 5/15

6:00 am-4:28 pm

1 stop10h 28m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 17 results
1
2

Best time to book a flight from Chicago to Manitoba

Have a flexible travel schedule? Discover the best time to fly to Manitoba 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.

Cheapflights Insights

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

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $358). Flying from Chicago to Manitoba in April is currently the most expensive (average of $508). 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 CHI to MB?

Find hourly flight availability from Chicago to Manitoba. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 26, 2025.

When flying from Chicago to Manitoba, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Manitoba by month

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

In terms of precipitation, rainfall in Manitoba ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Manitoba when rainfall is around 0.8 in.

Temperature in Manitoba by month

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

If weather is an important factor for your trip to Manitoba, 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 Manitoba

Get insights into the airlines that provide service to Manitoba. 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 Manitoba. Reviews last updated March 26, 2025.
See what other customers who have flown with Delta, Porter Airlines and United Airlines from Chicago to Manitoba have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,891 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,608 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
8,960 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Food

7.3

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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

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

    One-way options have recently been found by users for as low as $158 on WestJet. Other airlines that offer cheap prices include United Airlines from $231 and Air Canada from $236 one-way.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Manitoba consider choosing SkyWest Airlines (80%), Air Canada (80%) or United Airlines (80%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Manitoba?

    While on average a flight from Chicago to Manitoba is generally $409, our data shows the cheapest flight currently is $157. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $255 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Manitoba 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 Chicago to Manitoba?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $358). Flying from Chicago to Manitoba in April is currently the most expensive (average of $508). 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 Chicago to Manitoba

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chicago to Manitoba

Discover the top 2 airlines that operate flights from Chicago to Manitoba. 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 2,558,603 searches. Data last updated March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$232Average$617FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$535Average$666FlexibilityNo cancel feeOn-time69%
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