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Manitoba

$85+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
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 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(Kiwi.com)

One-way from

$85
(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 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/276:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Wed 12/37:30 amYWG - ORD
1 stop11h 16mMultiple Airlines
Deal found 11/19$233
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/69:00 pmYWG - ORD
2 stops25h 24mMultiple Airlines
Deal found 11/17$289
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/276:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Tue 12/29:00 pmYWG - ORD
2 stops17h 31mMultiple Airlines
Deal found 11/19$301
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/286:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Wed 12/37:30 amYWG - ORD
1 stop11h 16mMultiple Airlines
Deal found 11/19$308
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 11/286:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
Mon 12/19:00 pmYWG - MDW
2 stops35h 46mMultiple Airlines
Deal found 11/18$309
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 11/236:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
Sun 12/77:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Deal found 11/18$344
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 11/236:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
Mon 12/19:00 pmYWG - MDW
2 stops35h 46mMultiple Airlines
Deal found 11/18$347
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/266:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Thu 1/19:05 amYWG - ORD
2 stops8h 09mMultiple Airlines
Deal found 11/17$354
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 11/296:35 pmORD - YWG
1 stop20h 32mMultiple Airlines
Fri 12/57:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 11/18$357
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 11/236:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Mon 12/19:00 pmYWG - ORD
2 stops18h 12mMultiple Airlines
Deal found 11/18$364
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/2910:32 amORD - YWG
1 stop10h 36mMultiple Airlines
Wed 12/37:30 amYWG - ORD
1 stop11h 16mMultiple Airlines
Deal found 11/19$365
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 11/286:00 amORD - YWG
1 stop9h 07mMultiple Airlines
Sun 11/307:30 amYWG - ORD
1 stop28h 04mMultiple Airlines
Deal found 11/17$367

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 19, 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

Sun 2/8

6:20 am-3:09 pm

1 stop8h 49m

Winnipeg

Thu 2/19

8:05 pm-10:10 am

1 stop14h 05m

$266

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/23

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Sun 1/25

6:55 pm-1:35 pm

1 stop18h 40m

$303

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 11/28

6:00 am-3:07 pm

1 stop9h 07m

Winnipeg

Wed 12/3

7:30 am-6:46 pm

1 stop11h 16m

$308

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 11/28

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

Mon 12/1

9:00 pm-8:46 am

2 stops35h 46m

$309

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 11/23

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

Sun 12/7

7:30 am-10:12 pm

1 stop14h 42m

$344

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 11/23

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

Mon 12/1

9:00 pm-8:46 am

2 stops35h 46m

$347

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 12/1

5:00 am-6:03 pm

1 stop13h 03m

Winnipeg

Tue 12/2

9:00 pm-6:46 pm

2 stops21h 46m

$364

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 12/2

4:22 pm-3:07 pm

1 stop22h 45m

Winnipeg

Sat 12/6

5:45 pm-11:40 am

1 stop17h 55m

$369

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/3

10:37 am-7:08 pm

1 stop32h 31m

Winnipeg

Sat 1/10

9:00 pm-11:35 am

2 stops14h 35m

$420

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 11/30

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

Wed 12/3

7:30 am-2:04 pm

2 stops30h 34m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 36 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, 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 19, 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 19, 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 19, 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
9,023 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

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
9,023 reviews
United Airlines
7.4
Good
9,023 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

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
10,462 reviews
United Airlines
7.4
Good
9,023 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

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.

  • 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 (83%), United Airlines (83%) or Air Canada (82%) 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 $202 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

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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 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$614FlexibilityNo cancel feeOn-time69%

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