Cheap flights from Winnipeg to Chicago from C$ 214
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 17/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
The best prices from Winnipeg to Chicago are usually found in November or March, booked 16 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 9 May 2024.
Popular in | August |
|---|---|
Cheapest in | November |
Round-trip from | C$ 354 |
One-way from | C$ 342 |
What is the cheapest day to fly round-trip from Winnipeg to Chicago?
Tuesday is generally a great day to depart. Flying on this day could help you save up to 16%.
How far in advance should I book a flight from Winnipeg to Chicago?
Find a great deal and save up to 115% by booking at least 17 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$ 749.
What is the cheapest month to fly from Winnipeg to Chicago?
The best pricing can be found in the month of November. Prices to Chicago from Winnipeg average C$ 706. You can even find prices in November for less than C$ 706, as users have found deals to Chicago from as low as C$ 374. 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 16%.
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 in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 14% on airfare.
Cheap Air Canada flights from Winnipeg to Chicago
Explore cheap flight options specifically provided by Air Canada for the route between Winnipeg and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 9 May 2024.
Check out some of the cheapest Air Canada flights we've come across from Winnipeg to Chicago. It's recommended that users confirm their flight details before booking.
Cheap United Airlines flights from Winnipeg to Chicago
Explore cheap flight options specifically provided by United Airlines for the route between Winnipeg and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 9 May 2024.
Browse through some of the cheapest United Airlines flights travelling from Winnipeg to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Cheap Winnipeg to Chicago flights in May & June 2024
Find cheap flight options from Winnipeg to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 437,143 searches. Prices were last updated on 9 May 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Winnipeg to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Winnipeg and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 9 May 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Direct flights to Chicago from Winnipeg
Discover non-stop flight options from Winnipeg to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 9 May 2024.
Consider booking one of these non-stop flights heading from Winnipeg to Chicago. Those looking to potentially save on 1 or 2-stop flights from Winnipeg to Chicago should utilize the search form at the top of the page.
Winnipeg to Chicago flights leaving soon
Find last-minute flight options from Winnipeg to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 9 May 2024.
Book one of these great deals on flights from Winnipeg to Chicago. Tip: verify your flight details before completing your reservation.
One-way flights to Chicago from Winnipeg
Search for one-way flight options from Winnipeg to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 9 May 2024.
Users in need of a one-way flight from Winnipeg to Chicago can choose from these deals. For those needing a return trip from Winnipeg, there is a search form available above.
Find flights from Winnipeg to Chicago within your budget
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 437,143 searches. Data last updated 9 May 2024.
Fly from
Fly to
Budget
C$ 407 - C$ 691
Route
Depart
Return
Price
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Wed 18/9
1 stop6h 07m
Chicago Midway
Tue 24/9
1 stop4h 36m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Fri 7/6
2 stops10h 09m
Chicago Midway
Fri 14/6
2 stops10h 05m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Wed 18/9
2 stops10h 29m
Chicago Midway
Tue 24/9
2 stops25h 18m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Sun 26/5
1 stop4h 07m
Chicago Midway
Tue 28/5
2 stops12h 54m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Sun 26/5
1 stop4h 07m
Chicago Midway
Tue 28/5
1 stop22h 53m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 3/6
1 stop12h 35m
Chicago O'Hare Intl
Mon 10/6
3 stops25h 43m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
Fri 14/6
2 stops9h 47m
Chicago Midway
Mon 17/6
2 stops10h 07m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Mon 24/6
Nonstop2h 28m
Chicago O'Hare Intl
Sat 29/6
1 stop8h 07m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
Wed 29/5
Nonstop2h 28m
Chicago O'Hare Intl
Sun 2/6
1 stop6h 55m
When is the best time to 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 3 May 2024.
The best time to book flights from Winnipeg to Chicago is 16 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.
When is the cheapest time 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 5 May 2024.
Average price of flights to Chicago by month
Plan your trip from Winnipeg to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Winnipeg to Chicago is currently C$ 252 while a round-trip flight costs C$ 536. Price data was last updated on 5 May 2024.
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 August is currently the most expensive (average of C$ 439). 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.
January
C$ 359
February
C$ 418
March
C$ 445
April
C$ 458
May
C$ 525
June
C$ 555
July
C$ 592
August
C$ 603
September
C$ 473
October
C$ 513
November
C$ 464
December
C$ 480
Temperature and rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.
CHI Temperature | -5 - 23 °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 9 May 2024.
Get a feel of what it's like to fly with Air Canada, United Airlines and Delta 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.
Boarding
Overall
Entertainment
Food
Crew
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Entertainment
Food
Crew
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Entertainment
Food
Crew
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Entertainment
Food
Crew
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Entertainment
Food
Crew
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Boarding
Overall
Entertainment
Food
Crew
Comfort
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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 ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Winnipeg to Chicago
Discover the top 6 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 437,143 searches. Data last updated 9 May 2024.
Search flights from Winnipeg to Chicago by cabin class
Find flights from Winnipeg to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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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.