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Manitoba

$105+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Aug 29 — Sep 51
Fri 8/29
Fri 9/5
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 August 24, 2025.

Round-trip from

$179
(Kiwi.com)

One-way from

$105
(Trip.com)

Popular in

February

Cheapest in

May

Average price

$448

Good round-trip deal

$532 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. 2% potential increase in price ($11 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 August 2025
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Price to beat on a round-trip 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 August 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Fri 12/52:20 pmORD - YWG
1 stop8h 21mWestJet
Mon 12/86:15 amYWG - ORD
1 stop7h 20mWestJet
Deal found 8/23$179
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:30 pmORD - YWG
1 stop15h 31mWestJet
Tue 9/308:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 8/24$209
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Fri 10/175:30 pmORD - YWG
1 stop18h 11mWestJet
Mon 10/208:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 8/23$211
This oojo deal was found by Cheapflights users on 8/22. 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.
Thu 10/165:30 pmORD - YWG
1 stop21h 00mWestJet
Fri 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 8/22$230
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2311:45 amORD - YWG
2 stops12h 45mMultiple Airlines
Tue 9/308:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 8/24$236
This Kiwi.com deal was found by Cheapflights users on 8/22. 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.
Sun 10/55:30 pmORD - YWG
1 stop15h 31mWestJet
Sat 10/186:30 pmYWG - ORD
1 stop22h 13mWestJet
Deal found 8/22$241
This Trip.com deal was found by Cheapflights users on 8/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:30 pmORD - YWG
1 stop15h 31mWestJet
Sat 10/46:30 pmYWG - ORD
1 stop22h 13mWestJet
Deal found 8/24$243
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Fri 10/175:05 amORD - YWG
1 stop11h 17mMultiple Airlines
Mon 10/208:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 8/23$244
This Mytrip deal was found by Cheapflights users on 8/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:01 pmORD - YWG
Nonstop2h 30mAir Canada
Thu 10/27:20 pmYWG - ORD
1 stop21h 22mAir Canada
Deal found 8/24$256
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Fri 9/56:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
Mon 9/88:15 pmYWG - MDW
2 stops19h 43mMultiple Airlines
Deal found 8/23$293
This Kiwi.com deal was found by Cheapflights users on 8/22. 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.
Fri 10/316:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Wed 11/52:40 pmYWG - MDW
2 stops27h 59mMultiple Airlines
Deal found 8/22$294
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Fri 10/176:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
Mon 10/209:05 pmYWG - MDW
2 stops16h 33mMultiple Airlines
Deal found 8/23$402

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 August 24, 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

Fri 12/5

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Mon 12/8

6:15 am-1:35 pm

1 stop7h 20m

$179

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/23

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

Tue 9/30

8:30 am-4:43 pm

1 stop8h 13m

$209

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/17

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Mon 10/20

8:30 am-4:43 pm

1 stop8h 13m

$211

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/16

5:30 pm-2:30 pm

1 stop21h 00m

Winnipeg

Fri 10/24

8:30 am-4:43 pm

1 stop8h 13m

$230

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 10/5

5:30 pm-11:26 am

2 stops17h 56m

Winnipeg

Sat 10/18

8:30 am-4:43 pm

1 stop8h 13m

$230

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/23

11:45 am-12:30 am

2 stops12h 45m

Winnipeg

Tue 9/30

8:30 am-4:43 pm

1 stop8h 13m

$236

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 10/2

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

Sat 10/4

6:30 pm-4:43 pm

1 stop22h 13m

$243

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 10/17

5:05 am-4:22 pm

1 stop11h 17m

Winnipeg

Mon 10/20

8:30 am-4:43 pm

1 stop8h 13m

$244

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 9/5

6:20 am-4:22 pm

1 stop10h 02m

Winnipeg

Mon 9/8

8:15 pm-3:58 pm

2 stops19h 43m

$293

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 10/31

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Wed 11/5

2:40 pm-6:39 pm

2 stops27h 59m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/23

Showing 1-10 of 32 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 $496). 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 August 24, 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 August 24, 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 August 24, 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
8,937 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

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
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

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
8,937 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

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 8h 21m. 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 (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 $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 $288 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 $496). 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 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 August 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$542FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$619FlexibilityNo cancel feeOn-time69%

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