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Manitoba

$99+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
nov 15 — nov 221
sáb 11/15
sáb 11/22
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 outubro 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$302
(Kiwi.com)

One-way from

$99
(Trip.com)

Popular in

February

Cheapest in

May

Average price

$574

Good round-trip deal

$493 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. 0% potential increase in price ($4 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 October 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 outubro 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
seg 10/275:28 pmMDW - YWG
1 stop23h 58mMultiple Airlines
seg 11/39:00 pmYWG - MDW
2 stops14h 38mMultiple Airlines
Deal found 10/13$282
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
seg 12/13:43 pmORD - YWG
2 stops23h 47mMultiple Airlines
seg 12/86:15 amYWG - ORD
1 stop7h 20mMultiple Airlines
Deal found 10/16$314
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
qui 11/206:05 amMDW - YWG
2 stops18h 36mMultiple Airlines
dom 11/237:30 amYWG - MDW
1 stop15h 03mMultiple Airlines
Deal found 10/15$328
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
sex 11/75:11 amORD - YWG
1 stop9h 56mMultiple Airlines
dom 11/97:30 amYWG - ORD
2 stops15h 58mMultiple Airlines
Deal found 10/15$328
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
qui 10/235:30 pmORD - YWG
1 stop15h 31mMultiple Airlines
dom 10/268:05 pmYWG - ORD
2 stops27h 39mMultiple Airlines
Deal found 10/15$374
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
dom 11/306:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
dom 12/77:30 amYWG - MDW
1 stop10h 34mMultiple Airlines
Deal found 10/16$377
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
qui 11/135:11 amORD - YWG
2 stops19h 30mMultiple Airlines
sex 11/147:30 amYWG - ORD
1 stop9h 26mMultiple Airlines
Deal found 10/16$397
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
sex 12/191:27 pmORD - YWG
1 stop11h 26mMultiple Airlines
seg 12/294:55 pmYWG - ORD
2 stops46h 54mMultiple Airlines
Deal found 10/16$402
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
qua 11/122:06 pmMDW - YWG
2 stops34h 33mMultiple Airlines
qua 11/198:20 pmYWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 10/15$419
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
dom 11/307:57 pmORD - YWG
2 stops41h 55mMultiple Airlines
dom 12/76:55 pmYWG - ORD
1 stop18h 40mMultiple Airlines
Deal found 10/16$419
This Trip.com deal was found by Cheapflights users on 10/15. 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.
qui 11/206:00 amORD - YWG
1 stop17h 36mWestJet
dom 11/2312:40 pmYWG - ORD
1 stop24h 55mWestJet
Deal found 10/15$421
This Mytrip deal was found by Cheapflights users on 10/15. 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.
qua 11/127:58 pmORD - YWG
3 stops27h 52mMultiple Airlines
qua 11/197:30 amYWG - ORD
2 stops12h 57mMultiple Airlines
Deal found 10/15$428

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 outubro 16, 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

seg 10/27

5:28 pm-5:26 pm

1 stop23h 58m

Winnipeg

seg 11/3

9:00 pm-11:38 am

2 stops14h 38m

$282

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

seg 1/5

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

dom 1/11

7:30 am-10:49 am

1 stop27h 19m

$302

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

seg 12/1

3:43 pm-3:30 pm

2 stops23h 47m

Winnipeg

seg 12/8

6:15 am-1:35 pm

1 stop7h 20m

$314

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

qui 11/20

6:05 am-12:41 am

2 stops18h 36m

Winnipeg

dom 11/23

7:30 am-10:33 pm

1 stop15h 03m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sex 11/7

5:11 am-3:07 pm

1 stop9h 56m

Winnipeg

dom 11/9

7:30 am-11:28 pm

2 stops15h 58m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

qua 2/18

1:45 pm-12:36 am

1 stop10h 51m

Winnipeg

ter 2/24

6:15 am-10:23 pm

2 stops16h 08m

$364

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

dom 11/30

6:05 am-3:07 pm

1 stop9h 02m

Winnipeg

dom 12/7

7:30 am-6:04 pm

1 stop10h 34m

$387

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

qui 11/13

5:11 am-12:41 am

2 stops19h 30m

Winnipeg

sex 11/14

7:30 am-4:56 pm

1 stop9h 26m

$397

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sex 12/19

1:27 pm-12:53 am

1 stop11h 26m

Winnipeg

seg 12/29

4:55 pm-3:49 pm

2 stops46h 54m

$402

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sex 10/31

6:20 am-3:07 pm

1 stop8h 47m

Winnipeg

qua 11/5

4:55 pm-5:22 pm

1 stop24h 27m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 29 results
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2
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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 $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 outubro 16, 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 outubro 16, 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 outubro 16, 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
8,982 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,982 reviews
United Airlines
7.4
Good
8,982 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
Air Canada
7.1
Good
10,306 reviews
United Airlines
7.4
Good
8,982 reviews

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 (89%), Air Canada (89%) or United Airlines (89%) 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 $1,111, our data shows the cheapest flight currently is $435. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $284 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 $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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 outubro 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$585FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$618FlexibilityNo cancel feeOn-time69%

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