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Manitoba

$170+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Jul 23 — Jul 301
Thu 7/23
Thu 7/30
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 June 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/22. 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 9/223:20 pm
ORD
-
YWG
1 stop9h 35m
Multiple Airlines
Sat 9/2611:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 6/22$333
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 9/203:20 pm
ORD
-
YWG
1 stop28h 29m
Porter Airlines
Sat 9/264:15 pm
YWG
-
ORD
2 stops18h 45m
Porter Airlines
Deal found 6/21$341
This Mytrip deal was found by Cheapflights users on 6/21. 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.
Fri 8/289:50 am
ORD
-
YWG
1 stop13h 30m
Multiple Airlines
Tue 9/811:15 am
YWG
-
ORD
2 stops10h 20m
Multiple Airlines
Deal found 6/21$368
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/1810:25 am
MDW
-
YWG
1 stop23h 20m
Multiple Airlines
Sat 7/2511:15 am
YWG
-
MDW
2 stops22h 25m
Multiple Airlines
Deal found 6/18$374
This Mytrip deal was found by Cheapflights users on 6/19. 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.
Thu 7/239:50 am
ORD
-
YWG
1 stop15h 05m
Multiple Airlines
Sun 7/266:05 pm
YWG
-
ORD
1 stop14h 55m
Multiple Airlines
Deal found 6/19$375
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 9/65:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 9/1311:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 6/20$377
This Trip.com deal was found by Cheapflights users on 6/20. 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 9/65:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 9/139:05 pm
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 6/20$389
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 9/127:00 am
ORD
-
YWG
2 stops10h 58m
Multiple Airlines
Sat 9/199:05 pm
YWG
-
ORD
1 stop19h 35m
Multiple Airlines
Deal found 6/21$391
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/262:41 pm
ORD
-
YWG
2 stops29h 34m
Multiple Airlines
Tue 9/17:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 6/22$418
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/103:15 pm
MDW
-
YWG
1 stop18h 30m
Multiple Airlines
Fri 8/148:45 pm
YWG
-
MDW
1 stop12h 55m
Multiple Airlines
Deal found 6/19$474
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/103:15 pm
MDW
-
YWG
2 stops19h 28m
Porter Airlines
Fri 8/148:45 pm
YWG
-
MDW
1 stop12h 55m
Porter Airlines
Deal found 6/19$475
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/2810:20 am
MDW
-
YWG
1 stop10h 10m
Multiple Airlines
Tue 9/89:05 pm
YWG
-
MDW
2 stops13h 53m
Multiple Airlines
Deal found 6/21$508

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 June 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$333
(Kiwi.com)

One-way from

$170
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$877

Good round-trip deal

$865 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. 14% potential increase in price ($116 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 June 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 June 23, 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 7/18

10:25 am-9:45 am

1 stop23h 20m

Winnipeg

Sat 7/25

6:15 am-9:40 am

1 stop27h 25m

$377

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/19

8:03 am-3:19 pm

1 stop7h 16m

Winnipeg

Wed 9/23

11:40 am-8:20 pm

2 stops8h 40m

$550

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/21

9:19 am-9:45 am

2 stops24h 26m

Winnipeg

Tue 7/28

4:15 pm-9:40 am

2 stops17h 25m

$603

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/14

9:19 am-8:40 am

2 stops23h 21m

Winnipeg

Tue 7/21

4:15 pm-9:40 am

2 stops17h 25m

$629

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/14

1:18 pm-12:55 am

2 stops11h 37m

Winnipeg

Tue 7/21

6:40 am-1:09 pm

1 stop6h 29m

$742

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 7/16

10:25 am-5:58 pm

2 stops31h 33m

Winnipeg

Mon 7/20

11:15 am-9:40 am

2 stops22h 25m

$742

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 9/6

9:59 am-10:10 pm

2 stops12h 11m

Winnipeg

Sun 9/13

3:58 pm-1:20 pm

1 stop21h 22m

$742

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 8/28

8:09 am-5:58 pm

2 stops9h 49m

Winnipeg

Tue 9/8

11:15 am-9:35 pm

2 stops10h 20m

$774

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 7/18

9:54 am-11:29 pm

1 stop13h 35m

Winnipeg

Wed 7/22

6:40 am-6:18 pm

1 stop11h 38m

$782

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 7/8

1:18 pm-12:55 am

2 stops11h 37m

Winnipeg

Tue 7/14

6:15 am-6:25 pm

2 stops12h 10m

$784

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 38 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 June 23, 2026.

It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 34% 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 June 23, 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 June 23, 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
9,875 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,875 reviews
United Airlines
7.4
Good
9,875 reviews

Food

6.6

Boarding

7.7

Entertainment

7.1

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 24m. 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 (79%), Air Canada (79%) or United Airlines (79%) 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 $1,108, our data shows the cheapest flight currently is $494. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $341 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

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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 June 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$208Average$405FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$362Average$699FlexibilityNo cancel feeOn-time69%

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