HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Manitoba

$104+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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

Keep the following information in mind while searching for Chicago to Manitoba flight deals. Data was last updated April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Trip.com)

One-way from

$104
(Flightnetwork)

Popular in

February

Cheapest in

January

Average price

$726

Good round-trip deal

$562 or less

Good one-way deal

$203 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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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

Find 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 2, 2025.

This Trip.com deal was found by Cheapflights users on 4/1. 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 5/35:30 pmORD - YWG
1 stop18h 11mWestJet
Thu 5/88:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 4/1$206
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 6/95:10 amORD - YWG
1 stop11h 18mMultiple Airlines
Tue 6/108:30 amYWG - ORD
1 stop8h 14mMultiple Airlines
Deal found 3/31$271
This Flightnetwork deal was found by Cheapflights users on 3/31. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1612:57 pmORD - YWG
Nonstop2h 34mAir Canada
Fri 5/232:20 pmYWG - ORD
Nonstop2h 31mAir Canada
Deal found 3/31$424
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Sat 5/39:40 amMDW - YWG
2 stops24h 46mPorter Airlines
Thu 5/811:25 amYWG - MDW
2 stops21h 20mPorter Airlines
Deal found 4/1$491
This United deal was found by Cheapflights users on 4/1. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:58 pmORD - YWG
Nonstop2h 35mUnited Airlines
Tue 6/102:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 4/1$509
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/167:25 pmMDW - YWG
1 stop4h 00mDelta
Fri 5/238:30 amYWG - MDW
1 stop4h 45mDelta
Deal found 3/31$534
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/12:00 pmORD - YWG
2 stops9h 29mDelta
Tue 7/812:40 pmYWG - ORD
1 stop7h 03mDelta
Deal found 3/31$543
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Sat 5/39:40 amMDW - YWG
2 stops24h 46mMultiple Airlines
Thu 5/811:25 amYWG - MDW
2 stops21h 20mMultiple Airlines
Deal found 4/1$547
This Justfly.com deal was found by Cheapflights users on 4/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/289:20 amMDW - YWG
1 stop14h 12mWestJet
Fri 11/75:00 amYWG - MDW
2 stops13h 36mWestJet
Deal found 4/1$552

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 2, 2025.
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

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/3

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

Thu 5/8

8:30 am-4:44 pm

1 stop8h 14m

$206

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 6/9

5:10 am-4:28 pm

1 stop11h 18m

Winnipeg

Tue 6/10

8:30 am-4:44 pm

1 stop8h 14m

$271

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/16

12:57 pm-3:31 pm

Nonstop2h 34m

Winnipeg

Fri 5/23

2:20 pm-4:51 pm

Nonstop2h 31m

$424

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/3

9:40 am-10:26 am

2 stops24h 46m

Winnipeg

Thu 5/8

11:25 am-8:45 am

2 stops21h 20m

$491

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/31

7:58 pm-10:33 pm

Nonstop2h 35m

Winnipeg

Tue 6/10

2:20 pm-4:51 pm

Nonstop2h 31m

$509

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 5/16

7:25 pm-11:25 pm

1 stop4h 00m

Winnipeg

Fri 5/23

6:40 am-1:15 pm

1 stop6h 35m

$534

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 7/1

2:00 pm-11:29 pm

2 stops9h 29m

Winnipeg

Tue 7/8

12:40 pm-7:43 pm

1 stop7h 03m

$543

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/3

9:40 am-10:26 am

2 stops24h 46m

Winnipeg

Thu 5/8

11:25 am-8:45 am

2 stops21h 20m

$547

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 4/17

10:20 am-11:28 pm

1 stop13h 08m

Winnipeg

Sun 4/20

8:35 am-2:22 pm

1 stop5h 47m

$606

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/16

5:30 pm-2:30 pm

1 stop21h 00m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 18 results
1
2

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, August is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $358). Flying from Chicago to Manitoba in April is currently the most expensive (average of $506). 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 2, 2025.

When flying from Chicago to Manitoba, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 2, 2025.

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).

Rainfall in Manitoba by month

Plan your trip to Manitoba by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Manitoba ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Manitoba when rainfall is around 0.8 in.

Temperature in Manitoba by month

Plan your trip to Manitoba by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Manitoba, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 2, 2025.
See what other customers who have flown with Delta, Porter Airlines and United Airlines from Chicago to Manitoba have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,898 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
7.9
Good
278 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,615 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,022 reviews
Delta
8.0
Very good
7,898 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 cheapest airlines to fly from Chicago to Manitoba one-way?

    One-way options have recently been found by users for as low as $104 on WestJet. Other airlines that offer cheap prices include Delta from $194 and Air Canada from $211 one-way.

  • 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 (80%), Air Canada (80%) or United Airlines (80%) 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 $416, our data shows the cheapest flight currently is $157. When looking at the most popular route, (Chicago O'Hare Intl - Winnipeg), you can expect to pay $267 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, August is the cheapest month in which you can book a flight from Chicago to Manitoba (average of $358). Flying from Chicago to Manitoba in April is currently the most expensive (average of $506). 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.

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 Toronto Island flights
Midway to Pearson Intl flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Québec City flights
Midway to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Abbotsford flights
Midway to Calgary flights
St. Louis to Pearson Intl flights
O'Hare Intl to Winnipeg flights
O'Hare Intl to Ottawa flights
O'Hare Intl to Halifax flights
St. Louis to Vancouver Intl flights
O'Hare Intl to Edmonton flights
Midway to Québec City flights
St. Louis to Calgary flights
St. Louis to Pierre Elliott Trudeau Intl flights
Midway to Edmonton flights
Midway to Ottawa flights
Midway to Halifax flights
Midway to Winnipeg flights
O'Hare Intl to Victoria flights
O'Hare Intl to St. John's flights
O'Hare Intl to Saskatoon flights
St. Louis to Halifax flights
O'Hare Intl to Charlottetown flights
St. Louis to Winnipeg flights
Midway to Saskatoon flights
St. Louis to Québec City flights
Midway to St. John's flights
Midway to Victoria flights
St. Louis to St. John's flights
O'Hare Intl to Hamilton flights
St. Louis to Edmonton flights
O'Hare Intl to Fredericton flights
O'Hare Intl to Thunder Bay flights
O'Hare Intl to Sydney flights
Midway to Thunder Bay flights
Peoria to Pierre Elliott Trudeau Intl flights
Peoria to Vancouver Intl flights
O'Hare Intl to Deer Lake flights
O'Hare Intl to London flights
St. Louis to Ottawa flights
O'Hare Intl to Regina flights
O'Hare Intl to Kelowna flights

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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$232Average$617FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$535Average$665FlexibilityNo 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.