HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Manitoba

$149+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
May 29 — Jun 51
Fri 5/29
Fri 6/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Manitoba with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 29, 2026.

This Trip.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/296:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Deal found 4/26$251
This Trip.com deal was found by Cheapflights users on 4/26. 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.
Sat 5/235:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
Mon 5/257:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/26$255
This Trip.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 6/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/26$256
This Trip.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/275:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
Tue 6/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/27$291
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 6/29:05 pm
YWG
-
ORD
2 stops34h 50m
Multiple Airlines
Deal found 4/26$299
This FlightHub deal was found by Cheapflights users on 4/26. 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.
Mon 5/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/296:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Deal found 4/26$308
This FlightHub deal was found by Cheapflights users on 4/27. 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.
Mon 5/115:30 pm
ORD
-
YWG
1 stop17h 40m
WestJet
Mon 6/17:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/27$320
This Trip.com deal was found by Cheapflights users on 4/27. 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.
Mon 5/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 6/16:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Deal found 4/27$323
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/255:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 6/19:05 pm
YWG
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 4/27$327
This FlightHub deal was found by Cheapflights users on 4/24. 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 stop7h 25m
WestJet
Sun 10/256:15 am
YWG
-
ORD
1 stop7h 20m
WestJet
Deal found 4/24$343
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/153:20 pm
MDW
-
YWG
1 stop23h 59m
Multiple Airlines
Sat 5/236:05 am
YWG
-
MDW
2 stops15h 57m
Multiple Airlines
Deal found 4/24$374
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/1910:30 am
MDW
-
YWG
1 stop23h 15m
Multiple Airlines
Thu 5/216:05 pm
YWG
-
MDW
1 stop20h 30m
Multiple Airlines
Deal found 4/28$449

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 April 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(Trip.com)

One-way from

$149
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$535

Good round-trip deal

$755 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 ($178 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($58 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 April 29, 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

Thu 8/6

3:20 pm-8:40 am

1 stop17h 20m

Winnipeg

Sun 8/9

6:05 pm-9:40 am

1 stop15h 35m

$474

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/23

10:30 am-8:40 am

1 stop22h 10m

Winnipeg

Sat 5/30

9:05 pm-11:12 am

2 stops14h 07m

$530

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/27

9:23 am-4:51 pm

1 stop7h 28m

Winnipeg

Wed 6/3

4:15 pm-2:35 pm

2 stops22h 20m

$595

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 5/19

10:30 am-5:58 pm

2 stops31h 28m

Winnipeg

Thu 5/21

4:15 pm-2:35 pm

2 stops22h 20m

$623

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/5

9:22 am-12:55 am

2 stops15h 33m

Winnipeg

Sun 6/7

5:42 pm-6:18 pm

1 stop24h 36m

$647

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 9/2

9:20 am-11:40 pm

2 stops14h 20m

Winnipeg

Sat 9/5

7:00 am-6:05 pm

2 stops11h 05m

$656

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 7/22

12:27 pm-11:29 pm

1 stop11h 02m

Winnipeg

Sun 7/26

10:30 pm-4:59 pm

2 stops18h 29m

$667

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/13

3:20 pm-5:58 pm

2 stops26h 38m

Winnipeg

Sun 5/17

11:40 am-2:35 pm

2 stops26h 55m

$722

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/13

9:22 am-5:15 pm

2 stops7h 53m

Winnipeg

Sun 5/17

11:55 am-5:56 pm

1 stop6h 01m

$735

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 6/24

9:17 am-12:55 am

2 stops15h 38m

Winnipeg

Sun 6/28

10:30 pm-6:18 pm

2 stops19h 48m

$743

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 38 resultsSorted by cheapest first
1
2
3
4

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 April 29, 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 April 29, 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 April 29, 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
9,680 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

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
9,680 reviews
United Airlines
7.4
Good
9,680 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

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 15h 33m. Airlines will cover a distance of 722 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 $833, 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 $317 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 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 April 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$356FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$226Average$509FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$661FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.