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Manitoba

$109+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Apr 6 — Apr 131
Mon 4/6
Mon 4/13
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 March 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/2. 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 4/286:08 pm
ORD
-
YWG
2 stops21h 17m
Multiple Airlines
Thu 5/77:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 3/2$248
This Trip.com deal was found by Cheapflights users on 3/4. 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.
Fri 5/155:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 5/197:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 3/4$253
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 5/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 5/277:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 3/5$259
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/2211:07 am
ORD
-
YWG
2 stops13h 33m
Multiple Airlines
Sun 4/268:00 am
YWG
-
ORD
1 stop8h 40m
Multiple Airlines
Deal found 3/4$271
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 5/155:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 5/199:05 pm
YWG
-
ORD
2 stops13h 18m
Multiple Airlines
Deal found 3/4$280
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 5/145:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/229:05 pm
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 3/5$298
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/2311:00 am
MDW
-
YWG
1 stop21h 40m
Multiple Airlines
Sun 4/269:05 pm
YWG
-
MDW
2 stops22h 26m
Multiple Airlines
Deal found 3/3$300
This Kiwi.com deal was found by Cheapflights users on 3/3. 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 4/226:15 am
MDW
-
YWG
1 stop8h 54m
Multiple Airlines
Sun 4/269:05 pm
YWG
-
MDW
2 stops22h 26m
Multiple Airlines
Deal found 3/3$301
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 4/184:28 pm
ORD
-
YWG
1 stop22h 41m
Multiple Airlines
Sat 4/259:00 pm
YWG
-
ORD
1 stop19h 40m
Multiple Airlines
Deal found 3/4$303
This Trip.com deal was found by Cheapflights users on 3/3. 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.
Thu 9/105:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 9/147:10 pm
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 3/3$304
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/102:20 pm
ORD
-
YWG
1 stop10h 20m
Multiple Airlines
Mon 4/209:00 pm
YWG
-
ORD
2 stops20h 00m
Multiple Airlines
Deal found 3/5$317
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 4/196:00 am
MDW
-
YWG
1 stop9h 09m
Multiple Airlines
Sun 4/269:05 pm
YWG
-
MDW
2 stops25h 14m
Multiple Airlines
Deal found 3/5$318

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 March 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$712

Good round-trip deal

$780 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. 29% potential increase in price ($264 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 7, 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

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/11

8:42 am-3:20 pm

1 stop6h 38m

Winnipeg

Mon 6/1

4:55 pm-4:40 pm

1 stop23h 45m

$520

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/16

9:29 am-9:42 pm

2 stops12h 13m

Winnipeg

Thu 4/23

8:05 pm-8:47 am

2 stops12h 42m

$629

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/15

7:16 pm-9:42 pm

2 stops26h 26m

Winnipeg

Sun 4/19

5:20 pm-6:36 pm

1 stop25h 16m

$640

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 4/3

5:05 am-11:13 am

3 stops30h 08m

Winnipeg

Thu 4/30

6:00 am-10:23 am

2 stops28h 23m

$644

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/8

9:30 am-7:09 pm

2 stops9h 39m

Winnipeg

Thu 4/9

5:00 am-5:54 pm

2 stops12h 54m

$662

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 7/23

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Fri 7/31

5:38 pm-9:34 pm

1 stop3h 56m

$686

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 5/11

9:23 am-4:51 pm

1 stop7h 28m

Winnipeg

Mon 6/1

6:40 am-1:19 pm

1 stop6h 39m

$704

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/2

9:35 am-11:13 am

3 stops25h 38m

Winnipeg

Sun 4/5

8:20 pm-12:29 pm

2 stops16h 09m

$706
Quickest round-trip

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/11

9:18 am-11:52 am

Nonstop2h 34m

Winnipeg

Mon 6/1

7:00 am-9:34 am

Nonstop2h 34m

$724

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/9

9:18 am-11:52 am

Nonstop2h 34m

Winnipeg

Sun 4/12

2:00 pm-4:35 pm

Nonstop2h 35m

$726

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/4

Showing 1-10 of 31 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 March 7, 2026.

It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the morning.

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 March 7, 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
9,404 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

Boarding

7.7

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
9,404 reviews
United Airlines
7.4
Good
9,404 reviews

Food

6.6

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

Boarding

7.7

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 2h 34m. 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 (67%), Air Canada (67%) or United Airlines (67%) 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 $951, our data shows the cheapest flight currently is $349. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $280 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

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

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 March 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$356FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$226Average$509FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$626FlexibilityNo cancel feeOn-time69%

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