HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Feb 24 — Mar 31
Tue 2/24
Tue 3/3
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 January 25, 2026.

This Trip.com deal was found by Cheapflights users on 1/25. 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 6/35:30 pm
ORD
-
YWG
1 stop7h 00m
WestJet
Thu 6/48:30 am
YWG
-
ORD
1 stop8h 13m
WestJet
Deal found 1/25$281
This FlightHub deal was found by Cheapflights users on 1/25. 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 6/55:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 6/77:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/25$295
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Mon 3/92:20 pm
ORD
-
YWG
1 stop8h 20m
Multiple Airlines
Mon 3/168:00 am
YWG
-
ORD
1 stop10h 21m
Multiple Airlines
Deal found 1/23$314
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Thu 2/2611:05 am
MDW
-
YWG
1 stop24h 27m
Multiple Airlines
Sun 3/18:20 pm
YWG
-
MDW
1 stop13h 45m
Multiple Airlines
Deal found 1/23$325
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Sat 2/1412:50 pm
MDW
-
YWG
1 stop10h 45m
Multiple Airlines
Fri 2/208:20 pm
YWG
-
MDW
1 stop15h 35m
Multiple Airlines
Deal found 1/23$326
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Tue 4/284:28 pm
ORD
-
YWG
2 stops25h 12m
Multiple Airlines
Thu 5/78:30 am
YWG
-
ORD
1 stop8h 13m
Multiple Airlines
Deal found 1/24$327
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Sat 2/1412:50 pm
MDW
-
YWG
1 stop10h 45m
Multiple Airlines
Mon 2/238:20 pm
YWG
-
MDW
1 stop13h 50m
Multiple Airlines
Deal found 1/23$339
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Sat 2/1412:50 pm
MDW
-
YWG
1 stop10h 45m
Multiple Airlines
Thu 2/195:55 am
YWG
-
MDW
2 stops17h 46m
Multiple Airlines
Deal found 1/23$341
This Trip.com deal was found by Cheapflights users on 1/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:30 pm
ORD
-
YWG
1 stop16h 30m
WestJet
Sat 6/68:30 am
YWG
-
ORD
1 stop8h 13m
WestJet
Deal found 1/23$341
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Sat 2/1412:50 pm
MDW
-
YWG
1 stop10h 45m
Multiple Airlines
Tue 2/178:05 pm
YWG
-
MDW
1 stop14h 05m
Multiple Airlines
Deal found 1/23$342
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Sat 2/1412:50 pm
MDW
-
YWG
1 stop10h 45m
Multiple Airlines
Sun 2/228:05 pm
YWG
-
MDW
1 stop14h 05m
Multiple Airlines
Deal found 1/23$347
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Thu 2/1211:05 am
MDW
-
YWG
1 stop12h 30m
Multiple Airlines
Fri 2/208:20 pm
YWG
-
MDW
1 stop15h 35m
Multiple Airlines
Deal found 1/23$359

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 January 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$281
(Trip.com)

One-way from

$140
(Trip.com)

Popular in

January

Cheapest in

May

Average price

$1,231

Good round-trip deal

$976 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 January 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 January 25, 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

Sat 2/14

12:50 pm-11:35 pm

1 stop10h 45m

Winnipeg

Thu 2/19

8:05 pm-10:10 am

1 stop14h 05m

$342

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 2/14

12:50 pm-11:35 pm

1 stop10h 45m

Winnipeg

Sun 2/22

8:05 pm-10:10 am

1 stop14h 05m

$347

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 3/10

7:41 pm-3:09 pm

1 stop19h 28m

Winnipeg

Tue 3/17

8:05 pm-7:46 pm

2 stops23h 41m

$347

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 2/14

12:50 pm-11:35 pm

1 stop10h 45m

Winnipeg

Fri 2/20

9:00 pm-11:55 am

2 stops14h 55m

$368

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 2/12

11:05 am-11:35 pm

1 stop12h 30m

Winnipeg

Fri 2/20

9:00 pm-11:55 am

2 stops14h 55m

$401

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 2/11

6:15 am-12:40 am

2 stops18h 25m

Winnipeg

Wed 2/18

8:05 pm-10:10 am

1 stop14h 05m

$409

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 2/11

6:15 am-12:40 am

2 stops18h 25m

Winnipeg

Tue 2/17

8:05 pm-10:10 am

1 stop14h 05m

$409

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 2/14

1:29 pm-11:35 pm

2 stops10h 06m

Winnipeg

Mon 2/23

8:20 pm-10:10 am

1 stop13h 50m

$426

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 2/13

10:35 am-12:39 am

2 stops14h 04m

Winnipeg

Wed 2/18

7:30 am-4:52 pm

1 stop9h 22m

$450

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 2/9

11:05 am-12:39 am

1 stop13h 34m

Winnipeg

Tue 2/17

8:05 pm-10:10 am

1 stop14h 05m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 32 results
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 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 January 25, 2026.

It’s optimal to fly from Chicago to Manitoba in the evening. By choosing this option you can save up to 22% 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 January 25, 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).

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 January 25, 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
9,200 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
9,200 reviews
United Airlines
7.4
Good
9,200 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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
10,655 reviews
United Airlines
7.4
Good
9,200 reviews

Overall

7.4

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

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.

  • 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 (54%), Air Canada (54%) or United Airlines (54%) 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 $1,160, our data shows the cheapest flight currently is $973. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $314 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

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.

Alternative routes for Chicago to Manitoba

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Calgary flights
O'Hare Intl to Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
Midway to Vancouver Intl flights
Midway to Pearson Intl flights
St. Louis to Vancouver Intl flights
O'Hare Intl to Toronto Island flights
Midway to Toronto Island flights
Midway to Pierre Elliott Trudeau Intl flights
Midway to Calgary flights
O'Hare Intl to Abbotsford flights
St. Louis to Pearson Intl flights
O'Hare Intl to Québec City flights
O'Hare Intl to Winnipeg flights
O'Hare Intl to Ottawa flights
St. Louis to Calgary flights
O'Hare Intl to Halifax flights
St. Louis to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Edmonton flights
O'Hare Intl to Kelowna flights
Midway to Québec City flights
Midway to Ottawa flights
Midway to Winnipeg flights
Midway to Halifax flights
O'Hare Intl to Hamilton flights
Peoria to Vancouver Intl flights
St. Louis to Halifax flights
O'Hare Intl to St. John's flights
Midway to Kelowna flights
O'Hare Intl to London flights
Midway to Edmonton flights
O'Hare Intl to Charlottetown flights
O'Hare Intl to Saskatoon flights
O'Hare Intl to Regina flights
O'Hare Intl to Fredericton flights
St. Louis to Québec City flights
Midway to St. John's flights
St. Louis to Edmonton flights
St. Louis to Victoria flights
Moline to Pearson Intl flights
St. Louis to Kelowna flights
O'Hare Intl to Thunder Bay flights
O'Hare Intl to Victoria flights
St. Louis to Winnipeg flights
St. Louis to Ottawa flights
Midway to Thunder Bay flights
Moline to Calgary flights
St. Louis to St. John's flights

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 January 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$330FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$515FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$641FlexibilityNo 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.