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Manitoba

$81+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
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 November 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$191
(Kiwi.com)

One-way from

$81
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$554

Good round-trip deal

$1,004 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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Highest demand for flights based on searches. 5% potential increase in price ($28 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 November 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 November 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/117:23 pmMDW - YWG
1 stop19h 44mMultiple Airlines
Sun 12/147:30 amYWG - MDW
1 stop10h 42mMultiple Airlines
Deal found 11/11$191
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Wed 12/246:05 amORD - YWG
1 stop9h 02mMultiple Airlines
Wed 1/77:30 amYWG - ORD
1 stop15h 09mMultiple Airlines
Deal found 11/12$218
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sat 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
Mon 12/158:00 amYWG - ORD
1 stop27h 08mMultiple Airlines
Deal found 11/12$227
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:11 amORD - YWG
2 stops18h 30mMultiple Airlines
Mon 1/128:00 amYWG - ORD
1 stop27h 22mMultiple Airlines
Deal found 11/13$229
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Fri 12/126:11 amORD - YWG
1 stop8h 56mMultiple Airlines
Fri 12/195:40 pmYWG - ORD
2 stops30h 32mMultiple Airlines
Deal found 11/12$284
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/119:14 pmORD - YWG
2 stops17h 53mMultiple Airlines
Sun 12/147:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 11/11$285
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Tue 11/256:05 amMDW - YWG
2 stops18h 36mMultiple Airlines
Fri 11/287:30 amYWG - MDW
1 stop7h 10mMultiple Airlines
Deal found 11/12$302
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Tue 12/24:22 pmORD - YWG
1 stop22h 45mMultiple Airlines
Sat 12/66:15 amYWG - ORD
2 stops17h 58mMultiple Airlines
Deal found 11/12$331
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sat 12/1312:45 pmMDW - YWG
1 stop11h 57mMultiple Airlines
Mon 12/158:05 pmYWG - MDW
2 stops16h 56mMultiple Airlines
Deal found 11/12$469
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sat 12/139:59 amMDW - YWG
1 stop6h 56mWestJet
Mon 12/156:45 amYWG - MDW
2 stops11h 33mWestJet
Deal found 11/12$482

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 November 14, 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

MDW - YWG

MDWYWG

Chicago Midway

Thu 12/11

7:23 pm-3:07 pm

1 stop19h 44m

Winnipeg

Sun 12/14

7:30 am-6:12 pm

1 stop10h 42m

$191

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 12/24

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

Wed 1/7

7:30 am-10:39 pm

1 stop15h 09m

$218

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 12/13

1:24 pm-3:07 pm

1 stop25h 43m

Winnipeg

Mon 12/15

8:00 am-11:08 am

1 stop27h 08m

$227

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/23

5:40 am-3:07 pm

1 stop9h 27m

Winnipeg

Sun 1/25

7:30 am-10:46 pm

1 stop15h 16m

$227

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 12/15

7:10 am-6:03 pm

1 stop10h 53m

Winnipeg

Mon 1/12

8:00 am-11:22 am

1 stop27h 22m

$272

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 12/12

6:11 am-3:07 pm

1 stop8h 56m

Winnipeg

Fri 12/19

5:40 pm-12:12 am

2 stops30h 32m

$284

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 11/25

6:05 am-12:41 am

2 stops18h 36m

Winnipeg

Fri 11/28

7:30 am-2:40 pm

1 stop7h 10m

$302

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 3/9

12:33 pm-6:05 pm

2 stops29h 32m

Winnipeg

Tue 3/31

8:05 pm-10:05 am

1 stop14h 00m

$308

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 3/9

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Tue 3/31

12:10 pm-7:20 pm

1 stop7h 10m

$326

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 12/2

4:22 pm-3:07 pm

1 stop22h 45m

Winnipeg

Sat 12/6

6:15 am-12:13 am

2 stops17h 58m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 26 results
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2
3

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, May is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $91). Flying from Chicago to Manitoba in November is currently the most expensive (average of $613). 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 November 14, 2025.

It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight at noon.

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 November 14, 2025.

The most flights from CHI to CAMB are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 November 14, 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
9,016 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,016 reviews
United Airlines
7.4
Good
9,016 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,449 reviews
United Airlines
7.4
Good
9,016 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Comfort

7.3

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 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 (91%), United Airlines (91%) or Air Canada (88%) 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 $1,090, our data shows the cheapest flight currently is $1,004. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $201 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, May is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $91). Flying from Chicago to Manitoba in November is currently the most expensive (average of $613). 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 November 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$614FlexibilityNo cancel feeOn-time69%

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