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Manitoba

$167+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
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 July 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/12. 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 10/155:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Thu 10/227:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/12$311
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 10/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 10/47:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/12$312
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 10/165:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 10/197:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/13$315
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 10/157:45 am
ORD
-
YWG
2 stops17h 10m
Multiple Airlines
Thu 10/227:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 7/12$333
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 10/17:45 am
ORD
-
YWG
2 stops17h 10m
Multiple Airlines
Sun 10/47:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 7/12$346
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/215:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 8/287:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/12$347
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 9/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 10/67:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/15$350
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 9/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 10/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/15$352
This FlightHub deal was found by Cheapflights users on 7/15. 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 10/165:30 pm
ORD
-
YWG
1 stop17h 40m
WestJet
Fri 10/237:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 7/15$353
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/215:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Fri 8/287:00 am
YWG
-
ORD
2 stops24h 53m
Multiple Airlines
Deal found 7/12$361
This Trip.com deal was found by Cheapflights users on 7/15. 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 9/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 10/37:10 pm
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 7/15$367
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 8/710:25 am
MDW
-
YWG
1 stop9h 00m
Multiple Airlines
Sat 8/85:10 pm
YWG
-
MDW
1 stop16h 30m
Multiple Airlines
Deal found 7/15$490

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 July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(Kiwi.com)

One-way from

$167
(iWofly)

Popular in

January

Cheapest in

October

Average price

$782

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. 15% potential increase in price ($118 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 16, 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

Sat 9/26

8:03 am-3:19 pm

1 stop7h 16m

Winnipeg

Thu 10/1

9:20 am-4:18 pm

1 stop6h 58m

$548

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/12

8:03 am-3:19 pm

1 stop7h 16m

Winnipeg

Tue 9/15

9:20 am-4:18 pm

1 stop6h 58m

$563

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 8/21

9:24 am-7:49 pm

2 stops10h 25m

Winnipeg

Fri 8/28

4:15 pm-9:40 am

2 stops17h 25m

$602

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/25

8:03 am-5:58 pm

2 stops9h 55m

Winnipeg

Thu 10/1

9:20 am-4:18 pm

1 stop6h 58m

$637

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 8/11

9:59 am-8:40 am

2 stops22h 41m

Winnipeg

Tue 8/18

2:55 pm-9:45 am

3 stops18h 50m

$679

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 7/27

8:29 pm-7:54 pm

1 stop23h 25m

Winnipeg

Fri 8/28

9:20 am-4:19 pm

1 stop6h 59m

$719

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 7/28

11:45 am-7:54 pm

1 stop8h 09m

Winnipeg

Tue 8/25

12:15 pm-8:20 pm

1 stop8h 05m

$723

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/1

7:13 pm-3:08 pm

1 stop19h 55m

Winnipeg

Sun 10/4

6:40 am-6:19 pm

1 stop11h 39m

$739

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 8/2

7:09 am-4:20 pm

1 stop9h 11m

Winnipeg

Wed 8/12

5:00 am-1:22 pm

1 stop8h 22m

$749

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 9/11

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Tue 9/15

11:15 am-2:35 pm

2 stops27h 20m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/12

Showing 1-10 of 39 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, February is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $62). Flying from Chicago to Manitoba in January is currently the most expensive (average of $1,074). 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 16, 2026.

It’s optimal to fly from Chicago to Manitoba at noon. By choosing this option you can save up to 42% 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 July 16, 2026.

The most flights from CHI to CAMB are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 16, 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
9,993 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
9,993 reviews
United Airlines
7.4
Good
9,993 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

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 7h 16m. 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 Atlas Air (100%), Copa Airlines (79%) or SkyWest Airlines (74%) 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 $337, 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 $333 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, February is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $62). Flying from Chicago to Manitoba in January is currently the most expensive (average of $1,074). 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 July 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$208Average$405FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$362Average$756FlexibilityNo cancel feeOn-time69%

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