Statistics on Chicago-Winnipeg (Manitoba) flights: what is the right price and when to buy your plane ticket?
Best time to go: what is the RIGHT price for a round-trip flight to Winnipeg (Manitoba) (from: Chicago)
The average price to go to Winnipeg (Manitoba) from Chicago airport is $ 536 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 479 (in may) and $ 615 (in august), which is a saving of $ 58 or a surplus of $ 79 (compared to the average price) depending on the period you leave.
The analysis of all prices reveals that the most frequent price is between $540 to $594 and it is generally more economical to leave on a thursday and return on a wednesday on a flight with 1 or more layovers.
Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Winnipeg (Manitoba) before booking your flight.
If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Chicago-Winnipeg (Manitoba) plane ticket.
How are these data calculated?
We have studied a sample of 4921 airfare prices from previous years for flights to Winnipeg (Manitoba) from Chicago and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.
Average price depending on the departure month
Data analysis:
By leaving in may, the price of the plane ticket will statistically be the cheapest ($ 479, saving $ 58 compared to the average price over the year which is $ 536). Conversely, august will be the most expensive ($ 615).
Flight Chicago-Winnipeg (Manitoba): when is the best time to go for the best price?
| Month | Good price* | Average price | Our opinion |
|---|---|---|---|
| January | $ 399 | $ 510 | fair price |
| February | $ 434 | $ 523 | fair price |
| March | $ 431 | $ 532 | fair price |
| April | $ 448 | $ 521 | fair price |
| May | $ 397 | $ 479 the cheapest | very good price |
| June | $ 393 | $ 556 | fair price |
| July | $ 484 | $ 570 | fair price |
| August | $ 478 | $ 615 the most expensive | very high price |
| September | $ 369 | $ 490 | good price |
| October | $ 393 | $ 548 | fair price |
| November | $ 401 | $ 498 | fair price |
| December | $ 466 | $ 584 | fair price |
*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!
Price breakdown to travel from Chicago to Winnipeg (Manitoba)
Data analysis:
The prices for flights from Chicago to Winnipeg (Manitoba) range from $216 to $972. 3% of tickets were purchased at the minimum price (from $216 to $270), 1% at the maximum price (from $918 to $972). The majority of plane tickets were purchased in the range of $540 to $594 (14% of tickets).
Cheapest airlines for the Chicago->Winnipeg (Manitoba) flight
There are 9 companies that serve Chicago from Winnipeg (Manitoba) airport: United, Air Canada, Spirit Airlines, WestJet, Porter Airlines, Frontier Airlines, Delta, Swoop and Allegiant Air.
Data analysis:
Of the 4921 flights analyzed in previous years, United was the airline that offered the best fare most often in the flight ticket search results (26% of the time) on the Chicago->Winnipeg (Manitoba) route.
Direct flight or flight with layover?
Data analysis:
To get the best price for the Chicago-Winnipeg (Manitoba) flight, you should take a flight with one or more layovers (you will save an average of $ 274 compared to a direct flight).
Which day of the week to leave?
Data analysis:
Statistically, Chicago-Winnipeg (Manitoba) flights departing on a thursday are cheaper than on other days of the week. By choosing a thursday as your departure date, you can save an average of $35. On the other hand, departing on a sunday may cost you an additional $37.
Which day of the week to come back?
Data analysis:
Statistically, return flights from Winnipeg (Manitoba) to Chicago departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday for your return date, you will save an average of $51. Conversely, departing from Winnipeg (Manitoba) on a saturday may cost you an additional $48.
Top prices Chicago-Winnipeg (Manitoba)
| Round trip | Dates | Price | |
|---|---|---|---|
| Chicago → Winnipeg (Manitoba) | 08-05 to 13-05-2025 | $ 507 | direct flight with United |
| Chicago → Winnipeg (Manitoba) | 10-05 to 20-05-2025 | $ 201 | layover flight with WestJet |
| Chicago → Winnipeg (Manitoba) | 12-05 to 19-05-2025 | $ 315 | layover flight with WestJet |
| Chicago → Winnipeg (Manitoba) | 14-05 to 18-05-2025 | $ 509 | direct flight with Air Canada |
| Chicago → Winnipeg (Manitoba) | 22-05 to 29-05-2025 | $ 377 | layover flight with Sun Country |
| Chicago → Winnipeg (Manitoba) | 23-05 to 29-05-2025 | $ 336 | layover flight with Sun Country |
| Chicago → Winnipeg (Manitoba) | 03-06 to 24-06-2025 | $ 328 | layover flight with Spirit Airlines |
| Chicago → Winnipeg (Manitoba) | 04-06 to 23-06-2025 | $ 315 | layover flight with WestJet |
| Chicago → Winnipeg (Manitoba) | 10-06 to 18-06-2025 | $ 507 | direct flight with United |
| Chicago → Winnipeg (Manitoba) | 18-06 to 24-06-2025 | $ 307 | layover flight with Frontier Airlines |
When to book your flight Chicago - Winnipeg (Manitoba) to get the cheapest price?
Statistically, you will make the biggest savings by buying your plane ticket between 1 to 2 months in advance. However, you may end up paying a high price if you book between 8 to 9 months in advance.
Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Chicago-Winnipeg (Manitoba) flight, it is recommended to book your ticket on a monday.
How far in advance should I buy my flight?
Data analysis:
To get the cheapest flight ticket from Chicago to Winnipeg (Manitoba), it is recommended to buy it 1 to 2 months before departure (it is then on average 479 $, which is a saving of 57 $ compared to the overall average price). On the other hand, if you buy your ticket 8 to 9 months in advance, you will pay the full price (79 $ more than the average price).
Depending on the departure month
The best time to buy your Chicago to Winnipeg (Manitoba) flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.
| Departure on... | How far in advance should I book? |
|---|---|
| January | Best time: 1 to 2 months before departure (average price: 466 $) |
| February | - |
| March | Best time: 1 to 2 months before departure (average price: 460 $) |
| April | Best time: 1 to 2 months before departure (average price: 511 $) |
| May | Best time: 1 to 2 months before departure (average price: 427 $) |
| June | Best time: 2 to 3 months before departure (average price: 455 $) Other interesting period(s): 1 to 2 months ($ 461) |
| July | Best time: 3 to 4 months before departure (average price: 484 $) Other interesting period(s): 1 to 2 months ($ 515), 2 to 3 months ($ 513) |
| August | Best time: 1 to 2 months before departure (average price: 502 $) Other interesting period(s): 2 to 3 months ($ 523) |
| September | Best time: 1 to 2 months before departure (average price: 440 $) |
| October | Best time: 1 to 2 months before departure (average price: 432 $) Other interesting period(s): 2 to 3 months ($ 480) |
| November | Best time: 1 to 2 months before departure (average price: 468 $) |
| December | Best time: 1 to 2 months before departure (average price: 542 $) Other interesting period(s): 2 to 3 months ($ 576) |
What day of the week should I book my flight ticket?
Data analysis:
Statistically, monday is the day when plane tickets for Chicago->Winnipeg (Manitoba) are the cheapest. So, by buying your plane ticket on a monday, you will save $14. Conversely, by buying it on a sunday, you may end up paying $13 more.
Chicago to Winnipeg (Manitoba): flight price when booking today
Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.
| Month | Current price | Our opinion | |
|---|---|---|---|
| April 2025 | $ 614 $614 to $614 | high price | Find a flight |
| May 2025 | $ 432 $199 to $683 | very good price | Find a flight |
| June 2025 | $ 394 $270 to $539 | very good price | Find a flight |
| July 2025 | $ 543 $433 to $700 | very good price | Find a flight |
Data analysis:
Compared to the average price, may, june and july are cheaper to travel to Winnipeg (Manitoba). So it may be interesting to book now to leave during these months!