Cheap flights from Winnipeg to Chicago from C$ 217
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 28/7. Fares are subject to change and may not be available on all flights or dates of travel.
Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in June or February, booked 67 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday
Cheap flight deals from Winnipeg to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 28 March 2025.
Round-trip from | C$ 319 |
---|---|
One-way from | C$ 217 |
Popular in | August |
Cheapest in | June |
Average price | C$ 643 |
Good round-trip deal | C$ 554 or less |
Good one-way deal | C$ 302 or less |
Find flight deals from Winnipeg to Chicago
Cheapest flights from Winnipeg to ChicagoExplore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 March 2025.
Explore the most affordable flight options available from Winnipeg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 March 2025.
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Chicago 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 629,999 searches. Data last updated 28 March 2025.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 8/5
8:30 a.m.-4:44 p.m.
1 stop8h 14m
Chicago O'Hare Intl
Sun 11/5
5:30 p.m.-11:41 a.m.
1 stop18h 11m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 1/5
8:30 a.m.-4:44 p.m.
1 stop8h 14m
Chicago O'Hare Intl
Sun 4/5
4:55 p.m.-9:26 p.m.
3 stops28h 31m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 26/4
2:20 p.m.-4:48 p.m.
Nonstop2h 28m
Chicago O'Hare Intl
Wed 7/5
12:57 p.m.-3:31 p.m.
Nonstop2h 34m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 5/5
2:20 p.m.-4:48 p.m.
Nonstop2h 28m
Chicago O'Hare Intl
Mon 12/5
9:17 p.m.-1:09 p.m.
1 stop15h 52m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Tue 22/4
6:40 a.m.-7:00 p.m.
2 stops12h 20m
Chicago O'Hare Intl
Fri 25/4
6:59 p.m.-11:28 p.m.
1 stop4h 29m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 27/5
8:30 a.m.-1:15 p.m.
1 stop4h 45m
Chicago Midway
Wed 28/5
7:25 p.m.-11:25 p.m.
1 stop4h 00m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Thu 24/4
5:00 a.m.-4:40 p.m.
1 stop11h 40m
Chicago Midway
Thu 1/5
8:30 a.m.-4:28 p.m.
1 stop7h 58m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 22/4
6:40 a.m.-5:19 p.m.
1 stop10h 39m
Chicago Midway
Fri 25/4
7:00 p.m.-11:28 p.m.
1 stop4h 28m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Wed 30/7
11:45 a.m.-8:45 a.m.
2 stops21h 00m
Chicago Midway
Mon 4/8
5:20 p.m.-10:46 p.m.
2 stops29h 26m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 28/7
8:30 a.m.-4:44 p.m.
1 stop8h 14m
Best time to book a flight from Winnipeg to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Winnipeg with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Winnipeg to Chicago
How far ahead should I book a flight from Winnipeg to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Chicago. Price data was last updated on 21 March 2025.
The best time to book flights from Winnipeg to Chicago is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Winnipeg to Chicago?
Currently, January is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 261). Flying from Winnipeg to Chicago in March is currently the most expensive (average of C$ 355). 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 YWG to CHI?
Find hourly flight availability from Winnipeg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 March 2025.
One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 23% on airfare.
What is the cheapest day to fly from Winnipeg to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Chicago. Price data was last updated on 16 December 2024.
Travelers seeking maximum savings on their Winnipeg to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, 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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 28 March 2025.
Get a feel of what it's like to fly with Delta, Porter Airlines and United Airlines from Winnipeg to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Overall
Food
Comfort
Boarding
Crew
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Overall
Food
Comfort
Boarding
Crew
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Overall
Food
Comfort
Boarding
Crew
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Overall
Food
Comfort
Boarding
Crew
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Overall
Food
Comfort
Boarding
Crew
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Overall
Food
Comfort
Boarding
Crew
Reviews
Aaron,Oct 2024
TUS - LAX
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Winnipeg to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Winnipeg to Chicago
Discover the top 4 airlines that operate flights from Winnipeg to Chicago. 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 629,999 searches. Data last updated 28 March 2025.
Fly with Cheapflights
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How does Cheapflights help users find flights from Winnipeg to Chicago?
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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Chicago?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Winnipeg.
Can Cheapflights find flights from Winnipeg to Chicago with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Chicago, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Winnipeg to Chicago become cheaper?
Yes, Cheapflights offers price alerts on Winnipeg to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.