Cheap flights from Winnipeg to Chicago
The best prices from Winnipeg to Chicago are usually found in February or September, booked 38 days in advance, depart on a Tuesday or Wednesday and return on a Monday
How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)
All the information you need to plan the best YWG to CHI flight in 2022: compare Winnipeg to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YWG - CHI Price | C$ 463 - C$ 628 |
|---|---|
CHI Temperature | -5 - 23 °C |
CHI Rainfall | 43 - 125 mm |
| Popular in | August | High demand for flights, 17% potential price rise |
|---|---|---|
| Cheapest in | February | Best time to find cheap flights, 11% potential price drop |
| Round-trip from | C$ 624 | From Winnipeg to Chicago (CHI) |
| One-way from | C$ 474 | One-way flight from Winnipeg to Chicago (CHI) |
What is the cheapest day to fly round-trip from Winnipeg to Chicago?
Monday is generally a great day to depart. Flying on this day could help you save up to 34%.
How far in advance should I book a flight from Winnipeg to Chicago?
Find a great deal and save up to 52% by booking at least 38 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago within the next two weeks, with the cheapest ticket starting at C$ 819.
What is the cheapest month to fly from Winnipeg to Chicago?
The best pricing can be found in the month of February. Prices to Chicago from Winnipeg average C$ 699. You can even find prices in February for less than C$ 699, as users have found deals to Chicago from as low as C$ 568. The month of August appears to be one of the more expensive times to travel to Chicago from Winnipeg. Flying in the targeted month can save you up to 20%.
When is the cheapest time to fly from Winnipeg to Chicago (YWG - CHI)?
One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 30% on airfare.
Cheap flights from Winnipeg to Chicago in December, January 2022
The best prices found for YWG to CHI flights for December, January
Winnipeg
Chicago Midway
1 stop
7h 19mChicago Midway
Winnipeg
2 stops
12h 57mDelta
Winnipeg
Chicago O'Hare Intl
1 stop
4h 52mChicago O'Hare Intl
Winnipeg
1 stop
5h 32mDelta
Winnipeg
Chicago Midway
1 stop
12h 30mChicago Midway
Winnipeg
1 stop
24h 18mMultiple Airlines
Cheap Air Canada flights from Winnipeg to Chicago
Winnipeg
Chicago O'Hare Intl
1 stop
6h 24mChicago O'Hare Intl
Winnipeg
1 stop
7h 12mAir Canada
Winnipeg
Chicago O'Hare Intl
1 stop
7h 55mChicago O'Hare Intl
Winnipeg
1 stop
9h 10mAir Canada
Winnipeg
Chicago O'Hare Intl
1 stop
6h 24mChicago O'Hare Intl
Winnipeg
1 stop
10h 17mAir Canada
Cheap United Airlines flights from Winnipeg to Chicago
Winnipeg
Chicago O'Hare Intl
1 stop
7h 58mChicago O'Hare Intl
Winnipeg
1 stop
8h 05mUnited Airlines
Winnipeg
Chicago O'Hare Intl
1 stop
11h 21mChicago O'Hare Intl
Winnipeg
1 stop
15h 55mUnited Airlines
Winnipeg
Chicago O'Hare Intl
1 stop
6h 49mChicago O'Hare Intl
Winnipeg
2 stops
18h 45mUnited Airlines
One-way flights to Chicago from Winnipeg
The cheapest one-way flights from Winnipeg to Chicago
Winnipeg
Chicago Midway
1 stop
7h 19mDelta
Winnipeg
Chicago O'Hare Intl
1 stop
7h 53mDelta
Winnipeg
Chicago O'Hare Intl
1 stop
8h 10mAir Canada
Related info for your journey
Useful info, stats and facts about Winnipeg to Chicago flights.
What airport do you fly from for flights from Winnipeg to Chicago?
If you book a flight to Chicago from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 0 flights from Winnipeg to Chicago per day from 7 different airlines.
Which airlines flying from Winnipeg to Chicago have flexible cancellations due to COVID-19?
Due to the rapidly changing circumstances due to COVID-19, airlines like Air Canada, Endeavor Airlines, and Delta flying from Winnipeg to Chicago have implemented new flexible cancellation policies.
Can I find flights from Winnipeg to Chicago for under C$ 500 on Cheapflights?
Yes, there are multiple flights from Winnipeg to Chicago for under C$ 500. The cheapest flight booked recently is on Air Canada for just C$ 450, but on average you can expect to pay C$ 513.
What are the cheapest airlines flying from Winnipeg to Chicago round-trip?
Air Canada, at C$ 450, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. Air Canada is priced at 35% lower than the current average price of a flight leaving 3 months from now.
What are the cheapest airlines to fly from Winnipeg to Chicago one-way?
The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 264. However, be on the lookout for offers from Air Canada and WestJet, as they are both options that can get you from Winnipeg to Chicago for a low price.
What are the most popular airlines that fly from Winnipeg to Chicago?
Endeavor Airlines, Air Canada and Delta are the most popular airlines when flying from Winnipeg to Chicago.
What are the cheapest flights from Winnipeg to Chicago?
Looking at all options, your cheapest flight can be booked for C$ 267. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 457 on average our data indicates C$ 279 when flying from Winnipeg to Chicago.