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Manitoba

$121+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$246
(oojo)

One-way from

$121
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$628

Good round-trip deal

$641 or less

Good one-way deal

$252 or less
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. 1% potential increase in price ($9 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 July 2025
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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 July 3, 2025.

This oojo deal was found by Cheapflights users on 7/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:30 pmORD - YWG
1 stop15h 31mWestJet
Fri 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 7/3$246
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 10/111:45 amORD - YWG
2 stops12h 45mMultiple Airlines
Mon 10/139:00 amYWG - ORD
1 stop15h 10mMultiple Airlines
Deal found 7/1$254
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 8/156:20 amMDW - YWG
1 stop10h 03mMultiple Airlines
Fri 8/226:00 amYWG - MDW
2 stops17h 27mMultiple Airlines
Deal found 7/1$364
This oojo deal was found by Cheapflights users on 7/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1512:43 pmMDW - YWG
2 stops11h 48mWestJet
Fri 8/228:15 pmYWG - MDW
2 stops13h 21mWestJet
Deal found 7/1$497
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/219:15 amMDW - YWG
1 stop7h 36mDelta
Sat 8/2312:43 pmYWG - MDW
1 stop4h 54mDelta
Deal found 7/1$510

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 July 3, 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

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 9/2

5:30 pm-2:30 pm

1 stop21h 00m

Winnipeg

Tue 9/9

8:30 am-4:43 pm

1 stop8h 13m

$246

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/1

11:45 am-12:30 am

2 stops12h 45m

Winnipeg

Mon 10/13

9:00 am-12:10 am

1 stop15h 10m

$254

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 8/15

6:20 am-4:23 pm

1 stop10h 03m

Winnipeg

Fri 8/22

6:00 am-11:27 pm

2 stops17h 27m

$364

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 8/15

12:43 pm-12:31 am

2 stops11h 48m

Winnipeg

Fri 8/22

8:15 pm-9:36 am

2 stops13h 21m

$497

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/21

9:15 am-4:51 pm

1 stop7h 36m

Winnipeg

Sat 8/23

12:43 pm-5:37 pm

1 stop4h 54m

$510

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/29

11:39 am-9:31 pm

3 stops33h 52m

$121

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 7/23

5:34 pm-9:31 pm

3 stops27h 57m

$123

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/10

7:15 am-4:51 pm

2 stops9h 36m

$185

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 7/15

1:02 pm-3:31 pm

Nonstop2h 29m

$200

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/15

9:24 am-4:50 pm

1 stop7h 26m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 13 results
1
2

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, August is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $358). Flying from Chicago to Manitoba in December is currently the most expensive (average of $497). 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 July 3, 2025.

When flying from Chicago to Manitoba, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 July 3, 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).

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 July 3, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta, and 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.
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,982 reviews
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,861 reviews
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,917 reviews
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 cheapest airlines to fly from Chicago to Manitoba one-way?

    One-way options have recently been found by users for as low as $185 on Delta. Other airlines that offer cheap prices include United Airlines from $200 and WestJet from $216 one-way.

  • 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 (83%), Air Canada (83%) or United Airlines (83%) 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 $696, our data shows the cheapest flight currently is $194. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $252 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, August is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $358). Flying from Chicago to Manitoba in December is currently the most expensive (average of $497). 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 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$354Average$641FlexibilityNo cancel feeOn-time69%

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