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Manitoba

$134+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
May 2 — May 91
Sat 5/2
Sat 5/9
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 April 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/2311:28 am
ORD
-
YWG
1 stop27h 41m
Multiple Airlines
Mon 4/279:05 pm
YWG
-
ORD
2 stops13h 18m
Multiple Airlines
Deal found 3/30$316
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 6/105:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 6/137:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 3/29$322
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 5/76:50 am
ORD
-
YWG
2 stops15h 20m
Multiple Airlines
Sun 5/107:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 3/30$325
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/275:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 5/49:05 pm
YWG
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 3/29$340
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/76:00 am
MDW
-
YWG
2 stops16h 10m
Multiple Airlines
Sun 5/104:25 pm
YWG
-
MDW
1 stop17h 20m
Multiple Airlines
Deal found 3/29$349
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/85:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 5/169:05 pm
YWG
-
ORD
2 stops34h 50m
Multiple Airlines
Deal found 3/29$353
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 6/135:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 6/229:05 pm
YWG
-
ORD
2 stops13h 17m
Multiple Airlines
Deal found 3/29$357
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/131:18 pm
ORD
-
YWG
2 stops35h 37m
Multiple Airlines
Wed 5/207:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 3/29$369
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/73:20 pm
MDW
-
YWG
1 stop23h 59m
Porter Airlines
Sun 5/107:00 pm
YWG
-
MDW
1 stop14h 45m
Porter Airlines
Deal found 3/29$399
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 6/53:20 pm
MDW
-
YWG
1 stop9h 35m
Multiple Airlines
Sun 6/78:45 pm
YWG
-
MDW
1 stop12h 55m
Multiple Airlines
Deal found 3/29$440
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/112:56 pm
MDW
-
YWG
1 stop24h 13m
Multiple Airlines
Tue 4/146:55 pm
YWG
-
MDW
2 stops27h 19m
Multiple Airlines
Deal found 3/29$503
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/133:20 pm
MDW
-
YWG
2 stops26h 38m
Multiple Airlines
Wed 5/206:40 am
YWG
-
MDW
1 stop6h 39m
Multiple Airlines
Deal found 3/29$521

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 April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$316
(Kiwi.com)

One-way from

$134
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$546

Good round-trip deal

$1,004 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. 23% potential increase in price ($184 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 2, 2026.
Use the filters below to find and compare flights from Chicago to Manitoba that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 5/7

6:00 am-10:10 pm

2 stops16h 10m

Winnipeg

Sun 5/10

6:05 pm-9:45 am

1 stop15h 40m

$361

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/12

1:49 pm-3:19 pm

2 stops25h 30m

Winnipeg

Tue 5/19

7:00 am-4:40 pm

1 stop9h 40m

$400

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 5/5

11:48 am-7:49 pm

1 stop8h 01m

Winnipeg

Wed 5/6

9:20 am-4:18 pm

1 stop6h 58m

$614

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 7/8

9:49 am-3:08 pm

1 stop5h 19m

Winnipeg

Tue 7/14

7:45 am-6:25 pm

2 stops10h 40m

$667

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 6/4

6:24 am-11:26 pm

1 stop17h 02m

Winnipeg

Mon 6/8

6:40 am-8:31 pm

2 stops13h 51m

$706

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 6/4

9:23 am-11:26 pm

1 stop14h 03m

Winnipeg

Wed 6/10

6:40 am-6:31 pm

2 stops11h 51m

$706

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 5/13

10:30 am-11:18 pm

2 stops12h 48m

Winnipeg

Wed 5/20

5:10 am-10:20 pm

2 stops17h 10m

$711

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 8/18

2:00 pm-11:27 pm

1 stop9h 27m

Winnipeg

Mon 8/24

6:40 am-1:11 pm

1 stop6h 31m

$716

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/13

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Wed 5/20

11:40 am-2:35 pm

2 stops26h 55m

$718

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/3

9:23 am-2:55 pm

1 stop5h 32m

Winnipeg

Mon 6/8

6:40 am-6:31 pm

2 stops11h 51m

$718

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 36 resultsSorted by cheapest first
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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 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 April 2, 2026.

It’s optimal to fly from Chicago to Manitoba in the evening. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight in the morning.

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 April 2, 2026.

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).

How much does it cost to fly round-trip from Chicago to Manitoba?

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 April 2, 2026.
Get a feel of what it's like to fly with United Airlines 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
9,533 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,533 reviews
United Airlines
7.4
Good
9,533 reviews

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 12h 48m. Airlines will cover a distance of 706 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 (64%), Air Canada (64%) or United Airlines (64%) 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 $316 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$356FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$226Average$509FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$649FlexibilityNo cancel feeOn-time69%

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