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Manitoba

$112+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This oojo deal was found by Cheapflights users on 2/10. 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 oojo 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
Wed 5/277:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/10$228
This FlightHub deal was found by Cheapflights users on 2/9. 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 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 6/37:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/9$239
This Trip.com deal was found by Cheapflights users on 2/7. 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 5/155:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 5/197:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/7$240
This oojo deal was found by Cheapflights users on 2/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 5/64:55 pm
YWG
-
ORD
1 stop23h 45m
WestJet
Deal found 2/9$285
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/55:16 pm
MDW
-
YWG
1 stop21h 53m
Multiple Airlines
Sun 3/87:30 am
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Deal found 2/10$289
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/65:05 am
ORD
-
YWG
1 stop10h 04m
Multiple Airlines
Mon 3/92:40 pm
YWG
-
ORD
2 stops15h 28m
Multiple Airlines
Deal found 2/10$292
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 5/155:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 5/199:05 pm
YWG
-
ORD
2 stops21h 35m
Multiple Airlines
Deal found 2/7$296
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/48:16 pm
ORD
-
YWG
2 stops28h 23m
Multiple Airlines
Wed 3/117:30 am
YWG
-
ORD
1 stop10h 27m
Multiple Airlines
Deal found 2/10$302
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 4/86:00 am
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Fri 4/107:30 am
YWG
-
MDW
1 stop12h 37m
Multiple Airlines
Deal found 2/10$309
This oojo deal was found by Cheapflights users on 2/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 6/77:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/9$314
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 4/85:15 am
ORD
-
YWG
2 stops19h 25m
Multiple Airlines
Fri 4/106:15 am
YWG
-
ORD
1 stop7h 20m
Multiple Airlines
Deal found 2/10$318
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/66:05 am
MDW
-
YWG
1 stop9h 04m
Multiple Airlines
Mon 3/98:05 pm
YWG
-
MDW
2 stops16h 57m
Multiple Airlines
Deal found 2/10$349

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(oojo)

One-way from

$112
(Trip.com)

Popular in

January

Cheapest in

May

Average price

$752

Good round-trip deal

$661 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. 30% potential increase in price ($274 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 11, 2026.
Use the filters below to find and compare flights from Chicago to Manitoba that are best for you.

Fly from

Chicago

Fly to

Manitoba

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

5:16 pm-3:09 pm

1 stop21h 53m

Winnipeg

Sun 3/8

7:30 am-10:19 pm

1 stop14h 49m

$289

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/6

6:05 am-3:09 pm

1 stop9h 04m

Winnipeg

Sun 3/8

7:30 am-7:47 pm

1 stop12h 17m

$289

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/6

5:05 am-3:09 pm

1 stop10h 04m

Winnipeg

Mon 3/9

2:40 pm-6:08 am

2 stops15h 28m

$292

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/25

5:30 pm-12:00 pm

2 stops18h 30m

Winnipeg

Wed 5/27

7:00 am-4:40 pm

2 stops9h 40m

$296

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/15

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Tue 5/19

9:05 pm-6:40 pm

2 stops21h 35m

$296

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/29

5:30 pm-9:20 am

2 stops15h 50m

Winnipeg

Wed 6/3

7:00 am-4:40 pm

2 stops9h 40m

$299

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/8

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

Fri 4/10

7:30 am-8:07 pm

1 stop12h 37m

$309

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/8

5:15 am-12:40 am

2 stops19h 25m

Winnipeg

Fri 4/10

6:15 am-1:35 pm

1 stop7h 20m

$318

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/11

5:30 pm-5:25 pm

1 stop23h 55m

Winnipeg

Mon 6/1

7:00 am-4:40 pm

1 stop9h 40m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 3/9

2:20 pm-12:40 am

1 stop10h 20m

Winnipeg

Mon 3/16

6:15 am-1:35 pm

1 stop7h 20m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 31 results
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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 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 February 11, 2026.

It’s optimal to fly from Chicago to Manitoba in the afternoon. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the morning.

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 February 11, 2026.
Get a feel of what it's like to fly with United Airlines and Air Canada 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
9,273 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,273 reviews
United Airlines
7.4
Good
9,273 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Air Canada
7.1
Good
10,705 reviews
United Airlines
7.4
Good
9,273 reviews

Entertainment

7.1

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 18h 30m. Airlines will cover a distance of 706 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 SkyWest Airlines (59%), Air Canada (59%) or United Airlines (59%) 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 $1,031, our data shows the cheapest flight currently is $349. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $228 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.

See more FAQs

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Alternative routes for Chicago to Manitoba

See prices for flight routes from nearby airports that may be better suited for you.
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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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$356FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$643FlexibilityNo cancel feeOn-time69%

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