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Manitoba

$92+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$228
(Kiwi.com)

One-way from

$92
(Trip.com)

Popular in

February

Cheapest in

May

Good round-trip deal

$316 or less

Good one-way deal

$332 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. 20% potential increase in price ($153 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Price to beat on a round-trip flight from Chicago (CHI) to Manitoba.
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Price to beat on a one-way 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 January 8, 2026.

This Trip.com deal was found by Cheapflights users on 1/6. 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.
Wed 9/301:40 pmORD - YWG
1 stop9h 30mWestJet
Sun 10/48:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 1/6$222
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 3/132:20 pmORD - YWG
1 stop8h 20mMultiple Airlines
Sun 3/154:10 pmYWG - ORD
2 stops23h 49mMultiple Airlines
Deal found 1/8$228
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/202:20 pmORD - YWG
1 stop8h 20mWestJet
Fri 2/276:15 amYWG - ORD
1 stop7h 20mWestJet
Deal found 1/6$229
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 7/111:40 pmORD - YWG
1 stop7h 45mWestJet
Fri 7/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 1/7$230
This Trip.com deal was found by Cheapflights users on 1/6. 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.
Mon 5/115:30 pmORD - YWG
1 stop18h 10mWestJet
Mon 6/18:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 1/6$240
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 2/65:40 amORD - YWG
1 stop9h 29mMultiple Airlines
Sun 2/87:30 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 1/7$246
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/28:43 pmORD - YWG
2 stops18h 47mMultiple Airlines
Mon 2/98:00 amYWG - ORD
1 stop27h 22mMultiple Airlines
Deal found 1/6$252
This FlightHub deal was found by Cheapflights users on 1/6. 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.
Mon 2/22:20 pmORD - YWG
1 stop10h 20mWestJet
Mon 2/96:15 amYWG - ORD
1 stop7h 20mWestJet
Deal found 1/6$253
This Trip.com deal was found by Cheapflights users on 1/7. 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.
Sun 6/285:30 pmORD - YWG
1 stop24h 10mWestJet
Thu 7/98:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 1/7$254
This FlightHub deal was found by Cheapflights users on 1/8. 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.
Fri 6/55:30 pmORD - YWG
1 stop18h 10mWestJet
Sun 6/78:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 1/8$256
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/211:20 pmMDW - YWG
2 stops35h 21mMultiple Airlines
Sun 1/258:20 pmYWG - MDW
1 stop13h 50mMultiple Airlines
Deal found 1/7$292
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 3/37:30 amMDW - YWG
2 stops17h 10mMultiple Airlines
Wed 3/48:20 pmYWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 1/7$300

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 January 8, 2026.
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

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Sun 3/15

4:10 pm-3:59 pm

2 stops23h 49m

$228

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 2/20

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Fri 2/27

6:15 am-1:35 pm

1 stop7h 20m

$229

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

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 2/20

2:20 pm-12:40 am

1 stop10h 20m

Winnipeg

Fri 2/27

4:10 pm-4:53 pm

2 stops24h 43m

$258

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/11

5:30 pm-1:00 pm

2 stops19h 30m

Winnipeg

Mon 6/1

8:30 am-4:43 pm

1 stop8h 13m

$269

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 1/21

1:20 pm-12:41 am

2 stops35h 21m

Winnipeg

Sun 1/25

8:20 pm-10:10 am

1 stop13h 50m

$292

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

7:30 am-12:40 am

2 stops17h 10m

Winnipeg

Wed 3/4

8:20 pm-10:05 am

1 stop13h 45m

$300

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/13

6:00 am-3:09 pm

1 stop9h 09m

Winnipeg

Sun 3/15

7:30 am-10:19 pm

1 stop14h 49m

$306

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 6/27

1:40 pm-11:10 pm

1 stop9h 30m

Winnipeg

Fri 7/10

8:30 am-4:43 pm

1 stop8h 13m

$315

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 2/15

6:00 am-3:09 pm

1 stop9h 09m

Winnipeg

Sun 2/22

7:30 am-7:59 pm

1 stop12h 29m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 30 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 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 January 8, 2026.

It’s optimal to fly from Chicago to Manitoba in the evening. By choosing this option you can save up to 13% 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 January 8, 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).

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 January 8, 2026.
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
9,139 reviews

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
Air Canada
7.1
Good
10,603 reviews
United Airlines
7.4
Good
9,139 reviews

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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 20m. 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 (51%), Air Canada (51%) or United Airlines (51%) 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 $731, our data shows the cheapest flight currently is $316. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $221 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

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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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$675FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$585FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$636FlexibilityNo cancel feeOn-time69%

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