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Manitoba

$146+ 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
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 August 3, 2026.

This Mytrip deal was found by Cheapflights users on 7/31. 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.
Mon 9/147:25 am
ORD
-
YWG
2 stops10h 33m
Multiple Airlines
Mon 9/218:45 pm
YWG
-
ORD
2 stops18h 07m
Multiple Airlines
Deal found 7/31$337
This Mytrip deal was found by Cheapflights users on 8/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:55 am
ORD
-
YWG
1 stop15h 00m
Multiple Airlines
Wed 9/2311:15 am
YWG
-
ORD
2 stops8h 33m
Multiple Airlines
Deal found 8/2$345
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Sun 9/138:40 pm
ORD
-
YWG
1 stop13h 05m
Multiple Airlines
Sun 9/206:05 pm
YWG
-
ORD
1 stop14h 55m
Multiple Airlines
Deal found 7/31$351
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/3010:20 am
MDW
-
YWG
1 stop24h 59m
Porter Airlines
Sun 9/611:15 am
YWG
-
MDW
2 stops23h 45m
Porter Airlines
Deal found 7/31$478
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sat 8/2910:20 am
MDW
-
YWG
1 stop10h 00m
Multiple Airlines
Sat 9/55:10 pm
YWG
-
MDW
1 stop21h 25m
Multiple Airlines
Deal found 7/30$480
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/3010:20 am
MDW
-
YWG
1 stop24h 59m
Multiple Airlines
Sun 9/66:05 pm
YWG
-
MDW
1 stop16h 55m
Multiple Airlines
Deal found 7/31$484
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Thu 9/33:20 pm
MDW
-
YWG
1 stop9h 35m
Multiple Airlines
Sun 9/66:05 pm
YWG
-
MDW
1 stop16h 55m
Multiple Airlines
Deal found 8/2$488
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:20 am
MDW
-
YWG
1 stop10h 00m
Multiple Airlines
Thu 9/36:15 am
YWG
-
MDW
1 stop8h 20m
Multiple Airlines
Deal found 7/30$573
This Gotogate deal was found by Cheapflights users on 7/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1311:45 am
MDW
-
YWG
2 stops30h 13m
Porter Airlines
Sun 9/2011:40 am
YWG
-
MDW
2 stops23h 20m
Porter Airlines
Deal found 7/30$602
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Sun 8/2310:20 am
MDW
-
YWG
2 stops24h 23m
Porter Airlines
Sun 8/308:45 pm
YWG
-
MDW
1 stop13h 00m
Porter Airlines
Deal found 7/31$609
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 9/211:45 am
MDW
-
YWG
2 stops26h 30m
Multiple Airlines
Wed 9/912:41 pm
YWG
-
MDW
1 stop5h 38m
Multiple Airlines
Deal found 8/3$622
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/1710:25 am
MDW
-
YWG
1 stop9h 24m
Porter Airlines
Wed 8/1912:15 pm
YWG
-
MDW
1 stop21h 30m
Porter Airlines
Deal found 7/29$626

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 August 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$337
(Mytrip)

One-way from

$146
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$683

Good round-trip deal

$1,046 or less

Good one-way deal

$337 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. 10% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Manitoba.
Search Deals
Price to beat on a one-way 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 August 3, 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

Sat 8/29

10:20 am-8:20 pm

1 stop10h 00m

Winnipeg

Sat 9/5

9:05 pm-2:35 pm

2 stops17h 30m

$527

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 8/17

10:25 am-7:49 pm

1 stop9h 24m

Winnipeg

Wed 8/19

12:15 pm-9:45 am

1 stop21h 30m

$626

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/30

8:03 am-3:19 pm

1 stop7h 16m

Winnipeg

Sat 10/3

9:20 am-4:18 pm

1 stop6h 58m

$647

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 9/16

9:45 am-10:43 am

2 stops24h 58m

Winnipeg

Wed 9/23

11:15 am-7:40 am

2 stops20h 25m

$674

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 9/11

11:45 am-5:58 pm

2 stops30h 13m

Winnipeg

Fri 9/18

4:15 pm-2:35 pm

2 stops22h 20m

$676

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 10/6

9:46 am-10:43 am

2 stops24h 57m

Winnipeg

Tue 10/20

11:40 am-2:20 pm

2 stops26h 40m

$684

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 9/13

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Sun 9/20

11:40 am-11:00 am

2 stops23h 20m

$687

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 10/7

1:55 pm-11:19 pm

2 stops9h 24m

Winnipeg

Wed 10/21

8:00 am-11:52 pm

2 stops15h 52m

$721

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 9/23

9:59 am-4:54 pm

1 stop6h 55m

Winnipeg

Sat 9/26

12:41 pm-5:59 pm

1 stop5h 18m

$733

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/15

9:29 am-11:19 pm

2 stops13h 50m

Winnipeg

Wed 10/21

6:40 am-10:33 pm

2 stops15h 53m

$746

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 40 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 month to book a flight from Chicago to Manitoba?

Currently, September is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $435). Flying from Chicago to Manitoba in January is currently the most expensive (average of $1,231). 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 August 3, 2026.

It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 37% 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 August 3, 2026.

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 August 3, 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
10,058 reviews

Food

6.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.4
Good
10,058 reviews
United Airlines
7.4
Good
10,058 reviews

Food

6.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

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 9h 24m. Airlines will cover a distance of 722 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 Atlas Air (100%), Copa Airlines (75%) or SkyWest Airlines (69%) 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 $726, our data shows the cheapest flight currently is $337. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $348 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, September is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $435). Flying from Chicago to Manitoba in January is currently the most expensive (average of $1,231). 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.

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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$208Average$405FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$362Average$762FlexibilityNo cancel feeOn-time69%

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