$152+ Cheap flights from Winnipeg (YWG) to Chicago (CHI)
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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Winnipeg to Chicago 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.Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in June or May, booked 69 days in advance, depart on a Wednesday or Friday and return on a Friday
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 June 12, 2025.
Round-trip from | $240 (Trip.com) |
|---|---|
One-way from | $152 (Kiwi.com) |
Popular in | April |
Cheapest in | June |
Average price | $408 |
Good round-trip deal | $340 or less |
Good one-way deal | $227 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 June 12, 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 June 12, 2025.
This Trip.com deal was found by Cheapflights users on 6/10. 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.
This Mytrip deal was found by Cheapflights users on 6/9. 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.
This Delta deal was found by Cheapflights users on 6/11. 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.
This United Airlines deal was found by Cheapflights users on 6/10. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 6/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. 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.
This oojo deal was found by Cheapflights users on 6/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/9. 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.
This FlightHub deal was found by Cheapflights users on 6/12. 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.
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 2,558,603 searches. Data last updated June 12, 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
Fri 10/3
8:30 am-4:43 pm
1 stop8h 13m
Chicago O'Hare Intl
Sun 10/5
1:40 pm-9:25 pm
1 stop7h 45m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 6/23
9:00 am-9:38 am
1 stop24h 38m
Chicago O'Hare Intl
Mon 6/30
10:43 am-7:24 pm
2 stops32h 41m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 9/19
12:40 pm-6:07 pm
1 stop5h 27m
Chicago Midway
Tue 9/23
1:00 pm-11:32 pm
2 stops10h 32m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 8/28
2:20 pm-4:51 pm
Nonstop2h 31m
Chicago O'Hare Intl
Tue 9/2
7:15 am-1:09 pm
1 stop5h 54m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Wed 8/6
5:00 am-1:13 pm
1 stop8h 13m
Chicago O'Hare Intl
Sun 8/10
9:55 am-4:18 pm
1 stop6h 23m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 8/2
8:35 am-4:50 pm
1 stop8h 15m
Chicago O'Hare Intl
Sat 8/9
6:00 am-11:31 am
1 stop5h 31m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 7/25
9:00 am-9:42 pm
1 stop12h 42m
Chicago Midway
Mon 7/28
6:20 pm-1:43 pm
2 stops19h 23m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Mon 6/23
11:45 am-8:45 am
2 stops21h 00m
Chicago Midway
Mon 6/30
5:50 pm-10:46 pm
2 stops28h 56m
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Sun 8/24
11:45 am-4:24 pm
2 stops28h 39m
Chicago Midway
Sun 8/31
9:40 am-10:46 pm
2 stops13h 06m
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Fri 8/1
9:00 am-9:30 pm
1 stop12h 30m
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 June 9, 2025.
The price you pay for your flight from Winnipeg to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Winnipeg to Chicago?
Currently, August is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $245). Flying from Winnipeg to Chicago in March is currently the most expensive (average of $321). 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 June 12, 2025.
A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the morning.
Weekly flight availability from Winnipeg to Chicago
Explore weekly flight availability from Winnipeg to Chicago. 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 June 12, 2025.
The most flights from YWG to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).
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 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
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 June 12, 2025.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as Porter Airlines, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Mary,Jun 2025
FLL - YYZ
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Mary,Jun 2025
FLL - YYZ
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Mary,Jun 2025
FLL - YYZ
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Mary,Jun 2025
FLL - YYZ
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Mary,Jun 2025
FLL - YYZ
Food
Boarding
Entertainment
Overall
Comfort
Crew
Reviews
Mary,Jun 2025
FLL - YYZ
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 2 airlines flying from Winnipeg to Chicago
Discover the top 2 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 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$230 | Average$572 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$443 | Average$562 | FlexibilityNo cancel fee | On-time69% |