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Manitoba

$110+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/104:35 pmORD - YWG
2 stops26h 26mMultiple Airlines
Sun 12/147:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 12/9$666
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Mon 12/2210:37 amORD - YWG
1 stop33h 31mMultiple Airlines
Mon 1/58:00 amYWG - ORD
2 stops36h 04mMultiple Airlines
Deal found 12/11$707
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/115:00 amORD - YWG
2 stops14h 35mMultiple Airlines
Wed 12/174:55 pmYWG - ORD
1 stop27h 28mMultiple Airlines
Deal found 12/10$771
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/102:49 pmMDW - YWG
2 stops33h 01mMultiple Airlines
Sun 12/147:30 amYWG - MDW
1 stop10h 42mMultiple Airlines
Deal found 12/9$789
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/259:10 amORD - YWG
Nonstop2h 47mUnited Airlines
Sun 12/282:20 pmYWG - ORD
Nonstop2h 43mUnited Airlines
Deal found 12/10$806
This Air Canada deal was found by Cheapflights users on 12/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:30 pmORD - YWG
1 stop13h 19mAir Canada
Tue 12/305:30 amYWG - ORD
1 stop14h 15mAir Canada
Deal found 12/11$839
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/253:10 pmMDW - YWG
2 stops24h 20mMultiple Airlines
Sun 12/287:30 amYWG - MDW
1 stop14h 42mMultiple Airlines
Deal found 12/10$858
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/258:21 pmORD - YWG
2 stops29h 05mMultiple Airlines
Sun 12/285:40 pmYWG - ORD
1 stop8h 12mMultiple Airlines
Deal found 12/10$880
This Justfly.com deal was found by Cheapflights users on 12/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:50 pmMDW - YWG
1 stop21h 55mWestJet
Wed 12/175:45 pmYWG - MDW
1 stop24h 33mWestJet
Deal found 12/10$1,034
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/117:44 amMDW - YWG
2 stops16h 58mMultiple Airlines
Wed 12/178:20 pmYWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 12/10$1,041
This FlightHub deal was found by Cheapflights users on 12/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:50 amMDW - YWG
1 stop29h 17mWestJet
Sun 12/288:05 pmYWG - MDW
2 stops15h 01mWestJet
Deal found 12/11$1,157
This Justfly.com deal was found by Cheapflights users on 12/9. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:50 pmMDW - YWG
1 stop9h 54mWestJet
Sun 12/145:45 pmYWG - MDW
1 stop24h 33mWestJet
Deal found 12/9$1,165

Find flight deals from Chicago to Manitoba

Keep the following information in mind while searching for Chicago to Manitoba flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$110
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$681

Good round-trip deal

$680 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
Search Deals
From Chicago (CHI) to Manitoba
Search Deals
One-way flight from Chicago (CHI) to Manitoba
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Manitoba.
Search Deals

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 December 12, 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 1/25

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

Sun 2/1

7:30 am-10:19 pm

1 stop14h 49m

$269

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 6/5

5:30 pm-11:40 am

1 stop18h 10m

Winnipeg

Sun 6/7

8:30 am-4:43 pm

1 stop8h 13m

$320

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 1/25

8:43 pm-12:41 am

3 stops27h 58m

Winnipeg

Sun 2/1

8:20 pm-9:03 pm

2 stops24h 43m

$354

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-11:33 am

2 stops18h 03m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$376

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 1/10

6:10 am-12:41 am

2 stops18h 31m

Winnipeg

Thu 1/15

8:20 pm-10:10 am

1 stop13h 50m

$378

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 1/10

5:15 am-12:41 am

3 stops19h 26m

Winnipeg

Thu 1/15

12:10 pm-9:12 am

2 stops21h 02m

$391

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 2/18

1:28 pm-11:32 am

2 stops22h 04m

Winnipeg

Sun 2/22

7:30 am-7:59 pm

1 stop12h 29m

$393

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/23

7:00 am-12:39 am

2 stops17h 39m

Winnipeg

Mon 4/27

8:30 am-4:43 pm

1 stop8h 13m

$412

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/23

7:00 am-12:39 am

2 stops17h 39m

Winnipeg

Thu 4/30

8:30 am-4:43 pm

1 stop8h 13m

$412

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 1/30

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Mon 2/2

6:15 am-1:35 pm

1 stop7h 20m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 28 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 $89). Flying from Chicago to Manitoba in November is currently the most expensive (average of $614). 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 December 12, 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 December 12, 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 December 12, 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
9,095 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Air Canada
7.1
Good
10,516 reviews
United Airlines
7.4
Good
9,095 reviews

Entertainment

7.1

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 18h 10m. 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 (73%), United Airlines (73%) or Air Canada (70%) 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 $923, our data shows the cheapest flight currently is $322. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $241 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 $89). Flying from Chicago to Manitoba in November is currently the most expensive (average of $614). 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 3 airlines flying from Chicago to Manitoba

Discover the top 3 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$675FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$645FlexibilityNo cancel feeOn-time69%

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