Cheap flights from Winnipeg to Chicago from C$ 194
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 26/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
1 Feb — 8 Feb1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Chicago are usually found in September or October, booked 64 days in advance, depart on a Friday or Wednesday and return on a Monday
Cheap flight deals from Winnipeg to Chicago
Enter your travel dates to find the best prices.
Best flights from Winnipeg to Chicago
Discover carefully curated flight deals from Winnipeg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 2 January 2026.
Sat 25/46:55 p.m.YWG - ORD
1 stop21h 48mWestJet
Thu 30/45:30 p.m.ORD - YWG
1 stop26h 45mWestJet
Deal found 31/12C$ 402
Thu 19/25:55 a.m.YWG - MDW
2 stops17h 46mMultiple Airlines
Sun 22/26:00 a.m.MDW - YWG
1 stop9h 09mMultiple Airlines
Deal found 1/1C$ 512
Tue 20/15:21 p.m.YWG - ORD
1 stop4h 22mMultiple Airlines
Fri 23/112:42 p.m.ORD - YWG
1 stop12h 11mMultiple Airlines
Deal found 1/1C$ 534
Mon 16/26:15 a.m.YWG - ORD
1 stop7h 20mWestJet
Sun 1/36:15 a.m.ORD - YWG
1 stop4h 46mWestJet
Deal found 1/1C$ 534
Mon 2/36:15 a.m.YWG - ORD
1 stop7h 20mWestJet
Wed 4/38:50 a.m.ORD - YWG
1 stop14h 46mWestJet
Deal found 30/12C$ 552
Tue 3/36:45 a.m.YWG - MDW
2 stops11h 55mWestJet
Sun 8/37:20 p.m.MDW - YWG
2 stops23h 49mWestJet
Deal found 31/12C$ 590
Tue 3/35:19 p.m.YWG - ORD
1 stop4h 11mWestJet
Sun 8/37:00 p.m.ORD - YWG
2 stops24h 09mWestJet
Deal found 31/12C$ 601
Tue 20/16:40 a.m.YWG - MDW
1 stop6h 29mWestJet
Fri 23/11:49 p.m.MDW - YWG
1 stop21h 14mWestJet
Deal found 1/1C$ 604
Wed 11/35:44 p.m.YWG - MDW
1 stop24h 56mWestJet
Tue 17/37:20 p.m.MDW - YWG
1 stop16h 40mWestJet
Deal found 1/1C$ 604
Fri 23/15:21 p.m.YWG - MDW
1 stop17h 44mWestJet
Thu 29/110:48 a.m.MDW - YWG
1 stop28h 19mWestJet
Deal found 1/1C$ 607
Wed 11/37:50 a.m.YWG - ORD
2 stops13h 44mWestJet
Tue 17/39:50 a.m.ORD - YWG
2 stops9h 19mWestJet
Deal found 1/1C$ 608
Sat 25/412:53 p.m.YWG - MDW
1 stop5h 52mWestJet
Thu 30/41:10 p.m.MDW - YWG
2 stops9h 50mWestJet
Deal found 1/1C$ 609
Mon 2/35:19 p.m.YWG - MDW
1 stop25h 21mWestJet
Wed 4/31:49 p.m.MDW - YWG
1 stop21h 12mWestJet
Deal found 31/12C$ 620
Direct flights from Winnipeg to Chicago
Explore direct flight options from Winnipeg to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 2 January 2026.
Mon 2/32:20 p.m.YWG - ORD
Nonstop2h 25mUnited Airlines
Wed 4/39:15 a.m.ORD - YWG
Nonstop2h 42mUnited Airlines
Deal found 31/12C$ 705
Sat 14/22:20 p.m.YWG - ORD
Nonstop2h 25mAir Canada
Sat 21/29:15 a.m.ORD - YWG
Nonstop2h 42mAir Canada
Deal found 31/12C$ 778
Fri 23/12:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Thu 29/19:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
Deal found 1/1C$ 795
Tue 20/12:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Fri 23/19:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
Deal found 1/1C$ 812
Thu 19/22:20 p.m.YWG - ORD
Nonstop2h 25mAir Canada
Sun 22/29:15 a.m.ORD - YWG
Nonstop2h 42mAir Canada
Deal found 1/1C$ 893
Mon 16/22:20 p.m.YWG - ORD
Nonstop2h 25mAir Canada
Sun 1/39:15 a.m.ORD - YWG
Nonstop2h 42mAir Canada
Deal found 1/1C$ 1,102
Sun 15/22:20 p.m.YWG - ORD
Nonstop2h 25mAir Canada
Sun 22/29:15 a.m.ORD - YWG
Nonstop2h 42mAir Canada
Deal found 1/1C$ 1,165
Last-minute flights from Winnipeg to Chicago
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated 2 January 2026 and is based on user searches.
Tue 6/15:21 p.m.YWG - MDW
1 stop19h 48mWestJet
Wed 7/17:16 p.m.MDW - YWG
1 stop21h 13mWestJet
Deal found 1/1C$ 1,268
Tue 20/18:05 p.m.YWG - ORD
2 stops39h 17mMultiple Airlines
Fri 23/112:42 p.m.ORD - YWG
1 stop12h 11mMultiple Airlines
Deal found 1/1C$ 445
Tue 20/16:40 a.m.YWG - MDW
1 stop6h 29mWestJet
Fri 23/11:49 p.m.MDW - YWG
1 stop21h 14mWestJet
Deal found 1/1C$ 604
Tue 20/19:00 p.m.YWG - ORD
2 stops13h 05mWestJet
Fri 23/110:35 a.m.ORD - YWG
2 stops14h 00mWestJet
Deal found 1/1C$ 615
Tue 20/12:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Fri 23/19:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
Deal found 1/1C$ 812
Tue 20/12:20 p.m.YWG - ORD
Nonstop2h 43mAir Canada
Fri 23/12:00 p.m.ORD - YWG
1 stop7h 44mAir Canada
Deal found 1/1C$ 818
Fri 23/16:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Thu 29/17:41 p.m.ORD - YWG
2 stops29h 12mMultiple Airlines
Deal found 1/1C$ 526
Fri 23/15:21 p.m.YWG - ORD
1 stop4h 22mWestJet
Thu 29/111:15 a.m.ORD - YWG
1 stop27h 52mWestJet
Deal found 1/1C$ 604
Fri 23/15:21 p.m.YWG - MDW
1 stop17h 44mWestJet
Thu 29/110:48 a.m.MDW - YWG
1 stop28h 19mWestJet
Deal found 1/1C$ 607
Fri 23/15:30 a.m.YWG - ORD
1 stop7h 31mAir Canada
Thu 29/19:10 a.m.ORD - YWG
Nonstop2h 47mAir Canada
Deal found 1/1C$ 777
Fri 23/12:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Thu 29/19:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
Deal found 1/1C$ 795
One-way flights from Winnipeg to Chicago
Search for one-way flight options from Winnipeg to Chicago. Find affordable one-way fares based on user searches. Data last updated 2 January 2026.
Mon 26/18:00 a.m.YWG - ORD
1 stop15h 46mMultiple Airlines
Deal found 31/12C$ 194
Mon 26/14:10 p.m.YWG - MDW
3 stops19h 55mMultiple Airlines
Deal found 31/12C$ 199
Fri 15/510:45 a.m.YWG - ORD
2 stops21h 14mMultiple Airlines
Deal found 31/12C$ 270
Thu 15/14:10 p.m.YWG - ORD
2 stops26h 33mMultiple Airlines
Deal found 1/1C$ 274
Sun 15/26:00 a.m.YWG - ORD
1 stop8h 12mPorter Airlines
Deal found 1/1C$ 279
Sun 15/212:10 p.m.YWG - ORD
2 stops21h 12mMultiple Airlines
Deal found 1/1C$ 333
Mon 26/15:21 p.m.YWG - MDW
1 stop19h 48mWestJet
Deal found 31/12C$ 336
Fri 15/52:15 p.m.YWG - ORD
Nonstop2h 21mUnited Airlines
Deal found 31/12C$ 383
Sun 21/67:00 a.m.YWG - ORD
Nonstop2h 21mUnited Airlines
Deal found 31/12C$ 387
Thu 15/15:30 a.m.YWG - ORD
1 stop7h 31mAir Canada
Deal found 1/1C$ 388
Sun 15/25:00 a.m.YWG - MDW
2 stops27h 54mWestJet
Deal found 1/1C$ 443
Sun 15/26:55 p.m.YWG - MDW
3 stops20h 25mMultiple Airlines
Deal found 1/1C$ 557
Find 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 2 January 2026.
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 2 January 2026.
Use the filters below to find and compare flights from Winnipeg to Chicago that are best for you.
Fly from
Winnipeg
Fly to
Chicago
Route
Depart
Return
Price
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 25/4
6:55 p.m.-4:43 p.m.
1 stop21h 48m
Chicago O'Hare Intl
Thu 30/4
5:30 p.m.-8:15 p.m.
1 stop26h 45m
C$ 402
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Thu 19/2
5:55 a.m.-11:41 p.m.
2 stops17h 46m
Chicago Midway
Sun 22/2
6:00 a.m.-3:09 p.m.
1 stop9h 09m
C$ 512
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Tue 20/1
5:21 p.m.-9:43 p.m.
1 stop4h 22m
Chicago O'Hare Intl
Fri 23/1
12:42 p.m.-12:53 a.m.
1 stop12h 11m
C$ 534
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 16/2
6:15 a.m.-1:35 p.m.
1 stop7h 20m
Chicago O'Hare Intl
Sun 1/3
6:15 a.m.-11:01 a.m.
1 stop4h 46m
C$ 534
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Mon 2/3
6:15 a.m.-1:35 p.m.
1 stop7h 20m
Chicago O'Hare Intl
Wed 4/3
8:50 a.m.-11:36 p.m.
1 stop14h 46m
C$ 552
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 3/3
6:45 a.m.-6:40 p.m.
2 stops11h 55m
Chicago Midway
Sun 8/3
7:20 p.m.-7:09 p.m.
2 stops23h 49m
C$ 590
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Tue 3/3
5:19 p.m.-9:30 p.m.
1 stop4h 11m
Chicago O'Hare Intl
Sun 8/3
7:00 p.m.-7:09 p.m.
2 stops24h 09m
C$ 601
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 20/1
6:40 a.m.-1:09 p.m.
1 stop6h 29m
Chicago Midway
Fri 23/1
1:49 p.m.-11:03 a.m.
1 stop21h 14m
C$ 604
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Wed 11/3
5:44 p.m.-6:40 p.m.
1 stop24h 56m
Chicago Midway
Tue 17/3
7:20 p.m.-12:00 p.m.
1 stop16h 40m
C$ 604
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 23/1
5:21 p.m.-11:05 a.m.
1 stop17h 44m
Chicago Midway
Thu 29/1
10:48 a.m.-3:07 p.m.
1 stop28h 19m
C$ 607
Flights are sorted by cheapest round-trip flights first.
Deals found on 31/12
Showing 1-10 of 28 results
1
2
3
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.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
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 26 December 2025.
The best time to book flights from Winnipeg to Chicago is 64 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, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 199). Flying from Winnipeg to Chicago in January is currently the most expensive (average of C$ 640). 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 2 January 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chicago as you normally would.
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 2 January 2026.
The most flights from YWG to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Winnipeg to Chicago?
What’s the top layover airport for flights from Winnipeg to Chicago?
Share of one-stop round-trip flights from Winnipeg to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Calgary (YYC) – chosen by Cheapflights users on 79% of one-stop itineraries from Winnipeg to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Winnipeg to Chicago?
Average round-trip fare for 1-stop flights from Winnipeg to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 407.
What’s the fastest layover option from Winnipeg to Chicago?
Shortest average travel time for 1-stop one-way flights from Winnipeg to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 3h 48m.
Which airport typically offers the quickest layover for flights from Winnipeg to Chicago?
Average layover duration for 1-stop one-way flights from Winnipeg to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 0h 56m.
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 2 January 2026.
Check out reviews from past customers who have flown with United Airlines,WestJet, andAir Canada from Winnipeg to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
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.
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 4 flights from Winnipeg to Chicago per day from 3 different airlines.
How long is the flight from Winnipeg to Chicago?
Airlines like WestJet fly from Winnipeg to Chicago in about 21h 48m. The time it takes to get you to your destination can typically vary by up to . There are 1136 km between Winnipeg and Chicago.
What are the cheapest airlines flying from Winnipeg to Chicago round-trip?
WestJet, at C$ 198, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Air Canada and United Airlines. WestJet is priced at 67% lower than the current average price of a flight leaving 3 months from now.
What are the most reliable airlines from Winnipeg to Chicago?
Before booking your flight to Chicago from Winnipeg, check out the most reliable airlines to get you to your destination on time: SkyWest Airlines (78%), Air Canada (78%), Avianca( 78%).
What are the cheapest flights from Winnipeg to Chicago?
Looking at all options, your cheapest flight can be booked for C$ 279. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 343 on average, our data indicates C$ 889 when flying from Winnipeg to Chicago.
Can I find deals for business class flights from Winnipeg to Chicago?
Yes. Cheapflights offers flight deals from Winnipeg to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Winnipeg to Chicago?
Currently, May is the cheapest month in which you can book a flight from Winnipeg to Chicago (average of C$ 199). Flying from Winnipeg to Chicago in January is currently the most expensive (average of C$ 640). 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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 2 January 2026.
Discover the top 3 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 2 January 2026.
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Winnipeg to Chicago?
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Winnipeg today with Cheapflights!
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.
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
We value your privacy
Cheapflights and its partners wish to use cookies or similar technologies to store and/or access information on and about your device and process personal data such as your IP address, device identifiers etc., in order to improve your experience on the site, to analyze navigation, to offer and measure personalized advertising, and to facilitate sharing on social networks. We also allow the use of third-party cookies (including those from our advertising partners) on our sites.
By clicking 'Accept', you consent to your data being processed by 0 vendors on this web site for the purposes described in this notice. You can review the vendors and their individual processing purposes on the .
To review individual processing purposes and cookie categories, please click ’Select individual purposes’. You can review and update your choices anytime by clicking the ’Privacy Preferences’ link in the page side navigation.