Cheap flights from Winnipeg (YWG) to Chicago (CHI) from $154
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 6/5. 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 Thursday
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 mayo 8, 2024.
Popular in | August |
|---|---|
Cheapest in | November |
Average price | $463 |
Round-trip from | $223 |
What is the cheapest day to fly round-trip from Winnipeg to Chicago?
Flights from Winnipeg to Chicago are found to be more expensive on Friday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.
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 $545.
What is the cheapest month to fly from Winnipeg to Chicago?
Due to multiple factors, expect to potentially pay more when booking in August. For low rates, November can be a great choice for travel to Chicago. Flights to Chicago from Winnipeg in November are about $514 on average during November, but can be found for as low as $272.
When is the cheapest time to fly from Winnipeg to Chicago (YWG - CHI)?
A simple way to save on the total cost of your ticket is to fly from Winnipeg to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight in the afternoon.
Cheap WestJet flights from Winnipeg to Chicago
Explore cheap flight options specifically provided by WestJet 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 2,752,338 searches. Data last updated mayo 8, 2024.
Peruse some of the lowest-priced WestJet flights we've found from Winnipeg to Chicago. Make sure to check back often as deals are often changing.
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 2,752,338 searches. Data last updated mayo 8, 2024.
To aid your search, here are some of the cheapest Air Canada flights we've found from Winnipeg to Chicago. Check back soon if you're not seeing flights that suit your needs.
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 2,752,338 searches. Prices were last updated on mayo 8, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
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 2,752,338 searches. Data last updated mayo 8, 2024.
Scroll through some of the best deals on flights from Winnipeg to Chicago in 2024. Check back regularly for other flight deals.
Non-stop 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 2,752,338 searches. Data last updated mayo 8, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Winnipeg to Chicago. Search for alternative flights from Winnipeg to Chicago by utilizing the search form above.
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 2,752,338 searches. Data last updated mayo 8, 2024.
Have a look at some of the flights available from Winnipeg to Chicago departing last-minute. It's wise to confirm all flight details are correct before booking.
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 2,752,338 searches. Data last updated mayo 8, 2024.
Take a look at some of the best available options we've come across on one-way flights from Winnipeg to Chicago. Users in need of a round-trip flight from Winnipeg to Chicago instead should update the search form at the top of page.
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 2,752,338 searches. Data last updated mayo 8, 2024.
Fly from
Fly to
Budget
$296 - $496
Route
Depart
Return
Price
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
mié. 9/18
1 stop6h 07m
Chicago Midway
mar. 9/24
1 stop4h 36m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
sáb. 5/25
2 stops9h 18m
Chicago Midway
mié. 5/29
2 stops13h 51m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
mar. 6/4
2 stops9h 38m
Chicago O'Hare Intl
mar. 6/11
1 stop7h 34m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
mié. 9/18
1 stop15h 59m
Chicago O'Hare Intl
mar. 9/24
1 stop17h 21m
WinnipegChicago Midway
YWG - MDW
YWGMDW
Winnipeg
mié. 9/18
1 stop9h 59m
Chicago Midway
mar. 9/24
2 stops13h 25m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
dom. 5/26
1 stop12h 35m
Chicago O'Hare Intl
mar. 5/28
2 stops20h 45m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
mar. 6/4
3 stops26h 55m
Chicago O'Hare Intl
mar. 6/11
3 stops47h 09m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
lun. 6/24
Nonstop2h 28m
Chicago O'Hare Intl
sáb. 6/29
1 stop8h 07m
WinnipegChicago O'Hare Intl
YWG - ORD
YWGORD
Winnipeg
sáb. 6/8
Nonstop2h 28m
Chicago O'Hare Intl
mar. 6/11
1 stop7h 10m
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 May 3, 2024.
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 16 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 May 5, 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 $179 while a round-trip flight costs $363. Price data was last updated on May 5, 2024.
Currently, February is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of $244). Flying from Winnipeg to Chicago in June is currently the most expensive (average of $348). 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
$248
February
$244
March
$280
April
$258
May
$278
June
$348
July
$330
August
$274
September
$258
October
$248
November
$270
December
$248
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 | 23 - 73.4 °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 mayo 8, 2024.
Read through reviews of airlines operating flights from Winnipeg to Chicago, such as WestJet, Air Canada and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
Boarding
Comfort
Crew
Food
Entertainment
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.
Overall
Boarding
Comfort
Crew
Food
Entertainment
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.
Overall
Boarding
Comfort
Crew
Food
Entertainment
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.
Overall
Boarding
Comfort
Crew
Food
Entertainment
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.
Overall
Boarding
Comfort
Crew
Food
Entertainment
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 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 2,752,338 searches. Data last updated mayo 8, 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.
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to Chicago flexibly with Cheapflights today.
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Yes! Start tracking prices for Winnipeg to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.