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Manitoba

$102+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
oct. 15 — oct. 221
mer. 10/15
mer. 10/22
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 septembre 15, 2025.

Round-trip from

$191
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$556

Good round-trip deal

$490 or less

Good one-way deal

$268 or less
From Chicago (CHI) to Manitoba
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One-way flight from Chicago (CHI) to Manitoba
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Highest demand for flights based on searches. 0% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septembre 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
lun. 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
dim. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$208
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sam. 10/115:30 pmORD - YWG
2 stops17h 56mWestJet
ven. 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$216
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dim. 10/125:30 pmORD - YWG
1 stop15h 31mWestJet
ven. 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$218
This oojo deal was found by Cheapflights users on 9/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/165:30 pmORD - YWG
1 stop18h 11mWestJet
ven. 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/13$232
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
lun. 10/65:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mer. 10/83:12 pmORD - YWG
1 stop25h 10mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$234
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
lun. 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
jeu. 10/169:05 pmYWG - ORD
1 stop19h 38mWestJet
Deal found 9/14$235
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sam. 10/115:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$236
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
jeu. 10/95:05 amORD - YWG
1 stop11h 17mMultiple Airlines
ven. 10/178:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 9/14$238
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/105:30 pmORD - YWG
1 stop18h 11mWestJet
mer. 10/159:05 pmYWG - ORD
1 stop19h 38mWestJet
Deal found 9/14$241
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
mar. 10/281:56 pmMDW - YWG
1 stop25h 11mMultiple Airlines
mar. 11/49:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
Deal found 9/12$256
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
ven. 10/106:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
lun. 10/139:05 pmYWG - MDW
2 stops16h 33mMultiple Airlines
Deal found 9/12$327

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 septembre 15, 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

jeu. 10/9

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

dim. 10/12

8:30 am-4:43 pm

1 stop8h 13m

$208

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jeu. 10/16

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

ven. 10/24

8:30 am-4:43 pm

1 stop8h 13m

$232

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven. 10/10

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

mer. 10/15

9:05 pm-4:43 pm

1 stop19h 38m

$241

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

ven. 10/10

5:30 pm-5:40 pm

1 stop24h 10m

Winnipeg

lun. 10/13

9:00 am-11:44 pm

1 stop14h 44m

$244

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 10/28

1:56 pm-3:07 pm

1 stop25h 11m

Winnipeg

mar. 11/4

9:00 pm-12:41 pm

2 stops15h 41m

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sam. 10/4

1:40 pm-9:25 pm

1 stop7h 45m

Winnipeg

dim. 10/5

4:25 pm-11:59 pm

1 stop7h 34m

$262

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 11/17

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

dim. 11/23

12:55 pm-1:35 pm

3 stops24h 40m

$316

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

ven. 10/10

6:20 am-4:22 pm

1 stop10h 02m

Winnipeg

lun. 10/13

9:05 pm-1:38 pm

2 stops16h 33m

$327

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mar. 10/28

6:00 am-5:26 pm

1 stop11h 26m

Winnipeg

mar. 11/4

8:00 am-9:33 pm

1 stop13h 33m

$329

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mer. 10/22

6:08 am-11:27 pm

1 stop17h 19m

Winnipeg

sam. 10/25

8:30 am-4:43 pm

1 stop8h 13m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 37 results
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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 December is currently the most expensive (average of $501). 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 septembre 15, 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.

Weekly flight availability from Chicago to Manitoba

Explore weekly flight availability from Chicago to Manitoba. 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 septembre 15, 2025.

The most flights from CHI to CAMB are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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 septembre 15, 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada from Chicago to Manitoba by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,931 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,931 reviews
United Airlines
7.4
Good
8,931 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,931 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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.

  • How long is the flight from Chicago to Manitoba?

    Departing from Chicago to Manitoba will take you 15h 31m. Airlines will cover a distance of 706 mi.

  • 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 (76%), Air Canada (76%) or United Airlines (76%) 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 $663, our data shows the cheapest flight currently is $183. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $239 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 December is currently the most expensive (average of $501). 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 septembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$615FlexibilityNo cancel feeOn-time69%

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