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Manitoba

$112+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
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 June 23, 2025.

Round-trip from

$263
(Kiwi.com)

One-way from

$112
(Mytrip)

Popular in

February

Cheapest in

May

Average price

$575

Good round-trip deal

$641 or less

Good one-way deal

$252 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. 4% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/21. 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 9/256:00 amORD - YWG
1 stop10h 22mMultiple Airlines
Wed 10/19:00 amYWG - ORD
1 stop13h 28mMultiple Airlines
Deal found 6/21$263
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 10/96:15 amMDW - YWG
1 stop10h 07mMultiple Airlines
Tue 10/149:00 amYWG - MDW
1 stop13h 58mMultiple Airlines
Deal found 6/21$308
This Flightnetwork deal was found by Cheapflights users on 6/21. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/58:40 amORD - YWG
1 stop6h 29mAir Canada
Tue 8/1212:00 pmYWG - ORD
1 stop8h 16mAir Canada
Deal found 6/21$356
This oojo deal was found by Cheapflights users on 6/21. 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.
Fri 9/55:30 pmORD - YWG
1 stop21h 00mWestJet
Wed 9/108:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 6/21$367
This United Airlines deal was found by Cheapflights users on 6/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/57:54 pmORD - YWG
Nonstop2h 39mUnited Airlines
Wed 9/107:00 amYWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 6/23$394
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/52:00 pmORD - YWG
2 stops9h 27mDelta
Wed 9/108:35 amYWG - ORD
1 stop6h 25mDelta
Deal found 6/23$429
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/69:21 amMDW - YWG
1 stop7h 31mDelta
Wed 7/96:45 amYWG - MDW
2 stops11h 55mDelta
Deal found 6/22$472
This Kiwi.com deal was found by Cheapflights users on 6/23. 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.
Thu 7/105:20 pmMDW - YWG
1 stop17h 30mPorter Airlines
Mon 7/146:10 amYWG - MDW
1 stop26h 35mPorter Airlines
Deal found 6/23$552
This oojo deal was found by Cheapflights users on 6/23. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1212:43 pmMDW - YWG
2 stops11h 48mWestJet
Wed 9/36:30 amYWG - MDW
2 stops14h 56mWestJet
Deal found 6/23$591

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 June 23, 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 9/25

6:00 am-4:22 pm

1 stop10h 22m

Winnipeg

Wed 10/1

9:00 am-10:28 pm

1 stop13h 28m

$263

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 8/5

8:40 am-3:09 pm

1 stop6h 29m

Winnipeg

Tue 8/12

12:00 pm-8:16 pm

1 stop8h 16m

$356

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/5

5:30 pm-2:30 pm

1 stop21h 00m

Winnipeg

Wed 9/10

8:30 am-4:43 pm

1 stop8h 13m

$367

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 7/28

6:20 am-12:31 am

2 stops18h 11m

Winnipeg

Mon 9/8

9:00 am-6:18 pm

1 stop9h 18m

$390

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/5

7:54 pm-10:33 pm

Nonstop2h 39m

Winnipeg

Wed 9/10

7:00 am-9:31 am

Nonstop2h 31m

$394

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/5

2:00 pm-11:27 pm

2 stops9h 27m

Winnipeg

Wed 9/10

8:35 am-3:00 pm

1 stop6h 25m

$429

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 7/6

9:21 am-4:52 pm

1 stop7h 31m

Winnipeg

Wed 7/9

6:45 am-6:40 pm

2 stops11h 55m

$472

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/10

5:20 pm-10:50 am

1 stop17h 30m

Winnipeg

Mon 7/14

6:10 am-8:45 am

1 stop26h 35m

$552

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 8/12

12:43 pm-12:31 am

2 stops11h 48m

Winnipeg

Wed 9/3

6:30 am-9:26 pm

2 stops14h 56m

$591

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/5

6:00 am-4:22 pm

1 stop10h 22m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 18 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 $495). 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 June 23, 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 June 23, 2025.

The most flights from CHI to CAMB are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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 June 23, 2025.
See what other customers who have flown with Porter Airlines, Delta 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.
Porter Airlines
8.0
Very good
292 reviews

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
292 reviews
Porter Airlines
8.0
Very good
292 reviews

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,966 reviews
Porter Airlines
8.0
Very good
292 reviews

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,831 reviews
Porter Airlines
8.0
Very good
292 reviews

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,887 reviews
Porter Airlines
8.0
Very good
292 reviews

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,604 reviews
Porter Airlines
8.0
Very good
292 reviews

Entertainment

7.0

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 $173 on United Airlines. Other airlines that offer cheap prices include Delta from $179 and Air Canada from $221 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 (86%), Air Canada (86%) or United Airlines (86%) 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 $685, our data shows the cheapest flight currently is $201. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $238 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 $495). 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 June 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$284Average$648FlexibilityNo cancel feeOn-time69%

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