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Manitoba

$140+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
may. 24 — may. 311
dom. 5/24
dom. 5/31
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 abril 24, 2026.

This FlightHub deal was found by Cheapflights users on 4/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/275:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
mar. 6/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/21$314
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
sáb. 5/235:30 pm
ORD
-
YWG
1 stop26h 50m
Multiple Airlines
sáb. 5/307:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 4/23$319
This Trip.com deal was found by Cheapflights users on 4/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/295:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
jue. 6/44:55 pm
YWG
-
ORD
1 stop23h 45m
WestJet
Deal found 4/22$323
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
vie. 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
jue. 6/46:00 am
YWG
-
ORD
2 stops17h 01m
Multiple Airlines
Deal found 4/22$329
This FlightHub deal was found by Cheapflights users on 4/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/285:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
jue. 6/47:10 pm
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 4/22$347
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
mié. 9/25:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
sáb. 9/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/22$355
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
jue. 5/285:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
jue. 6/46:00 am
YWG
-
ORD
2 stops17h 01m
Multiple Airlines
Deal found 4/22$369
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
jue. 5/79:37 pm
ORD
-
YWG
2 stops27h 18m
Multiple Airlines
sáb. 5/307:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 4/23$377
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
jue. 5/285:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
lun. 6/19:05 pm
YWG
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 4/19$383
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
mié. 9/26:55 am
ORD
-
YWG
2 stops15h 15m
Multiple Airlines
sáb. 9/57:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 4/22$385
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
jue. 6/43:20 pm
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
mar. 6/93:15 pm
YWG
-
MDW
2 stops19h 54m
Multiple Airlines
Deal found 4/20$388
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
mar. 5/1910:30 am
MDW
-
YWG
1 stop22h 10m
Multiple Airlines
mar. 5/269:05 pm
YWG
-
MDW
2 stops14h 04m
Multiple Airlines
Deal found 4/21$395

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 abril 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$314
(FlightHub)

One-way from

$140
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$597

Good round-trip deal

$757 or less

Good one-way deal

$624 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. 22% potential increase in price ($176 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($57 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 abril 24, 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

dom. 5/10

8:05 pm-10:54 am

1 stop14h 49m

Winnipeg

dom. 5/17

9:05 pm-4:40 pm

1 stop19h 35m

$491

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mié. 6/3

12:20 pm-8:40 am

3 stops20h 20m

Winnipeg

mar. 6/9

5:25 pm-4:40 pm

2 stops23h 15m

$532

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 5/7

3:20 pm-8:40 am

1 stop17h 20m

Winnipeg

sáb. 5/30

9:25 am-9:45 am

1 stop24h 20m

$549

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 6/2

9:22 am-8:40 am

2 stops23h 18m

Winnipeg

mié. 6/3

4:15 pm-9:40 am

2 stops17h 25m

$579

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mié. 5/6

1:59 pm-3:25 pm

2 stops25h 26m

Winnipeg

jue. 5/14

9:05 pm-4:40 pm

1 stop19h 35m

$583

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

mié. 6/3

2:47 pm-3:19 pm

1 stop24h 32m

Winnipeg

vie. 6/5

9:20 am-4:15 pm

1 stop6h 55m

$599

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 6/9

9:17 am-12:55 am

2 stops15h 38m

Winnipeg

jue. 6/11

6:00 am-6:31 pm

2 stops12h 31m

$656

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 6/5

1:59 pm-10:54 am

1 stop20h 55m

Winnipeg

vie. 6/12

7:00 am-6:18 pm

2 stops11h 18m

$663

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 5/7

1:22 pm-12:55 am

2 stops11h 33m

Winnipeg

sáb. 5/30

6:15 am-4:12 pm

2 stops9h 57m

$668

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

jue. 5/7

3:20 pm-6:03 pm

2 stops26h 43m

Winnipeg

lun. 5/11

4:15 pm-2:35 pm

2 stops22h 20m

$696

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 36 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 abril 24, 2026.

It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 27% 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 abril 24, 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).

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 abril 24, 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
9,643 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,643 reviews
United Airlines
7.4
Good
9,643 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 14h 49m. 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 (57%), Air Canada (57%) or United Airlines (57%) 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 $824, our data shows the cheapest flight currently is $608. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $319 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 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 abril 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$405FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$226Average$509FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$230Average$641FlexibilityNo cancel feeOn-time69%

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