Cheap flights from Winnipeg to Chicago from C$ 171
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 18/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — CHI
26 Jan — 2 Feb1
Round-trip
1 adult
Economy
The best prices from Winnipeg to Chicago are usually found in March or June, booked 70 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 21 January 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 21 January 2025.
Thu 13/36:20 a.m.YWG - ORD
1 stop9h 36mWestJet
Mon 17/34:45 p.m.ORD - YWG
2 stops18h 30mWestJet
Deal found 20/1C$ 468
Thu 13/36:00 a.m.YWG - ORD
2 stops9h 56mMultiple Airlines
Mon 17/37:42 p.m.ORD - YWG
3 stops29h 02mMultiple Airlines
Deal found 21/1C$ 518
Sun 9/28:15 p.m.YWG - MDW
1 stop15h 55mMultiple Airlines
Sun 16/21:05 p.m.MDW - YWG
1 stop10h 45mMultiple Airlines
Deal found 21/1C$ 593
Mon 10/27:30 a.m.YWG - ORD
1 stop5h 41mAir Canada
Wed 12/210:53 a.m.ORD - YWG
1 stop6h 25mAir Canada
Deal found 20/1C$ 625
Thu 13/32:15 p.m.YWG - ORD
Nonstop2h 22mUnited Airlines
Mon 17/37:10 a.m.ORD - YWG
1 stop6h 17mUnited Airlines
Deal found 21/1C$ 630
Wed 19/212:45 p.m.YWG - ORD
2 stops8h 08mDelta
Wed 26/210:10 a.m.ORD - YWG
1 stop6h 33mDelta
Deal found 20/1C$ 640
Fri 28/38:50 a.m.YWG - MDW
1 stop5h 25mDelta
Tue 1/41:16 p.m.MDW - YWG
1 stop6h 59mDelta
Deal found 20/1C$ 643
Sun 9/211:35 a.m.YWG - MDW
2 stops24h 35mPorter Airlines
Sat 15/21:05 p.m.MDW - YWG
2 stops28h 54mPorter Airlines
Deal found 21/1C$ 728
Fri 28/38:50 a.m.YWG - MDW
1 stop9h 28mWestJet
Tue 1/42:55 p.m.MDW - YWG
2 stops9h 39mWestJet
Deal found 20/1C$ 757
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 21 January 2025.
Thu 13/36:00 a.m.YWG - ORD
2 stops9h 56mWestJet
Mon 17/34:45 p.m.ORD - YWG
2 stops18h 30mWestJet
Deal found 21/1C$ 476
Thu 13/36:00 a.m.YWG - ORD
2 stops9h 56mMultiple Airlines
Mon 17/37:42 p.m.ORD - YWG
3 stops29h 02mMultiple Airlines
Deal found 21/1C$ 518
Sun 9/27:30 a.m.YWG - ORD
1 stop5h 41mAir Canada
Sat 15/24:00 p.m.ORD - YWG
1 stop7h 23mAir Canada
Deal found 21/1C$ 617
Thu 13/32:15 p.m.YWG - ORD
Nonstop2h 22mUnited Airlines
Mon 17/37:10 a.m.ORD - YWG
1 stop6h 17mUnited Airlines
Deal found 21/1C$ 630
Fri 28/38:50 a.m.YWG - MDW
1 stop5h 25mDelta
Tue 1/41:16 p.m.MDW - YWG
1 stop6h 59mDelta
Deal found 20/1C$ 643
Sun 9/211:35 a.m.YWG - MDW
2 stops24h 35mPorter Airlines
Sat 15/21:05 p.m.MDW - YWG
2 stops28h 54mPorter Airlines
Deal found 21/1C$ 728
Sun 9/28:15 p.m.YWG - MDW
1 stop15h 55mMultiple Airlines
Sun 16/21:05 p.m.MDW - YWG
1 stop10h 45mMultiple Airlines
Deal found 21/1C$ 593
Sat 29/35:43 p.m.YWG - ORD
1 stop4h 02mDelta
Tue 1/411:20 a.m.ORD - YWG
1 stop27h 48mDelta
Deal found 20/1C$ 662
Fri 28/38:50 a.m.YWG - MDW
1 stop9h 28mWestJet
Tue 1/42:55 p.m.MDW - YWG
2 stops9h 39mWestJet
Deal found 20/1C$ 757
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 21 January 2025.
Thu 13/32:15 p.m.YWG - ORD
Nonstop2h 22mUnited Airlines
Mon 17/312:58 p.m.ORD - YWG
Nonstop2h 30mUnited Airlines
Deal found 21/1C$ 763
Mon 3/22:15 p.m.YWG - ORD
Nonstop2h 36mAir Canada
Thu 6/212:56 p.m.ORD - YWG
Nonstop2h 32mAir Canada
Deal found 20/1C$ 777
Last-minute flights from Winnipeg to Chicago
Discover last-minute flight deals from Winnipeg to Chicago. Data last updated 21 January 2025 and is based on user searches.
Mon 27/18:00 a.m.YWG - ORD
1 stop12h 13mMultiple Airlines
Mon 27/110:47 p.m.ORD - YWG
2 stops18h 50mMultiple Airlines
Deal found 20/1C$ 615
Mon 27/16:55 a.m.YWG - MDW
1 stop5h 51mWestJet
Mon 27/16:59 p.m.MDW - YWG
1 stop16h 56mWestJet
Deal found 20/1C$ 917
Mon 27/16:55 a.m.YWG - ORD
1 stop4h 25mWestJet
Mon 27/17:10 p.m.ORD - YWG
1 stop16h 45mWestJet
Deal found 20/1C$ 956
Mon 27/12:15 p.m.YWG - ORD
Nonstop2h 36mAir Canada
Mon 27/18:30 p.m.ORD - YWG
1 stop11h 58mAir Canada
Deal found 20/1C$ 1,025
Sun 9/28:15 p.m.YWG - MDW
1 stop15h 55mMultiple Airlines
Sun 16/21:05 p.m.MDW - YWG
1 stop10h 45mMultiple Airlines
Deal found 21/1C$ 593
Sun 9/28:15 p.m.YWG - ORD
2 stops21h 05mMultiple Airlines
Sun 16/21:32 p.m.ORD - YWG
2 stops19h 36mMultiple Airlines
Deal found 21/1C$ 597
Sun 9/27:30 a.m.YWG - ORD
1 stop5h 41mAir Canada
Sat 15/24:00 p.m.ORD - YWG
1 stop7h 23mAir Canada
Deal found 21/1C$ 617
Sun 9/211:35 a.m.YWG - MDW
2 stops24h 35mPorter Airlines
Sat 15/21:05 p.m.MDW - YWG
2 stops28h 54mPorter Airlines
Deal found 21/1C$ 728
Sun 9/27:30 a.m.YWG - MDW
1 stop7h 23mDelta
Sat 15/26:59 p.m.MDW - YWG
1 stop4h 39mDelta
Deal found 21/1C$ 875
Mon 10/25:37 p.m.YWG - MDW
1 stop19h 05mWestJet
Wed 12/21:26 p.m.MDW - YWG
1 stop22h 25mWestJet
Deal found 20/1C$ 822
Tue 11/25:00 a.m.YWG - ORD
2 stops7h 55mWestJet
Sun 16/26:15 a.m.ORD - YWG
1 stop5h 36mWestJet
Deal found 20/1C$ 695
Wed 19/212:45 p.m.YWG - ORD
2 stops8h 08mDelta
Wed 26/212:15 p.m.ORD - YWG
1 stop4h 28mDelta
Deal found 21/1C$ 676
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 21 January 2025.
Tue 18/37:30 a.m.YWG - MDW
1 stop8h 23mMultiple Airlines
Deal found 21/1C$ 171
Tue 18/37:30 a.m.YWG - ORD
1 stop9h 08mMultiple Airlines
Deal found 20/1C$ 178
Thu 13/26:20 a.m.YWG - ORD
1 stop9h 36mWestJet
Deal found 20/1C$ 226
Tue 11/26:40 a.m.YWG - MDW
2 stops15h 40mDelta
Deal found 20/1C$ 305
Tue 11/212:45 p.m.YWG - ORD
2 stops11h 26mDelta
Deal found 20/1C$ 332
Tue 11/27:30 a.m.YWG - ORD
1 stop5h 41mAir Canada
Deal found 20/1C$ 345
Sat 1/32:15 p.m.YWG - ORD
Nonstop2h 22mUnited Airlines
Deal found 21/1C$ 361
Tue 18/36:00 a.m.YWG - MDW
2 stops32h 15mWestJet
Deal found 21/1C$ 397
Sun 23/311:35 a.m.YWG - MDW
2 stops29h 05mPorter Airlines
Deal found 21/1C$ 425
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 629,999 searches. Data last updated 21 January 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 13/3
6:00 a.m.-3:56 p.m.
2 stops9h 56m
Chicago O'Hare Intl
Mon 17/3
4:45 p.m.-9:08 a.m.
1 stop16h 23m
C$ 476
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 13/3
6:00 a.m.-3:56 p.m.
2 stops9h 56m
Chicago O'Hare Intl
Mon 17/3
7:42 p.m.-12:44 a.m.
3 stops29h 02m
C$ 518
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Sun 9/2
8:15 p.m.-12:10 p.m.
1 stop15h 55m
Chicago Midway
Sun 16/2
1:05 p.m.-11:50 p.m.
1 stop10h 45m
C$ 593
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sun 9/2
7:30 a.m.-1:11 p.m.
1 stop5h 41m
Chicago O'Hare Intl
Sat 15/2
4:00 p.m.-11:23 p.m.
1 stop7h 23m
C$ 617
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Thu 13/3
2:15 p.m.-4:37 p.m.
Nonstop2h 22m
Chicago O'Hare Intl
Mon 17/3
7:10 a.m.-1:27 p.m.
1 stop6h 17m
C$ 630
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 28/3
8:50 a.m.-2:15 p.m.
1 stop5h 25m
Chicago Midway
Tue 1/4
1:16 p.m.-8:15 p.m.
1 stop6h 59m
C$ 643
WinnipegChicago
YWG - ORD
YWGORD
Winnipeg
Sat 29/3
5:43 p.m.-9:45 p.m.
1 stop4h 02m
Chicago O'Hare Intl
Tue 1/4
11:20 a.m.-3:08 p.m.
1 stop27h 48m
C$ 662
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Sun 9/2
11:35 a.m.-12:10 p.m.
2 stops24h 35m
Chicago Midway
Sat 15/2
1:05 p.m.-5:59 p.m.
2 stops28h 54m
C$ 728
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Fri 28/3
8:50 a.m.-6:18 p.m.
1 stop9h 28m
Chicago Midway
Tue 1/4
2:55 p.m.-12:34 a.m.
2 stops9h 39m
C$ 757
WinnipegChicago
YWG - MDW
YWGMDW
Winnipeg
Tue 18/3
7:30 a.m.-3:53 p.m.
1 stop8h 23m
C$ 171
Flights are sorted by cheapest round-trip flights first.
Deals found on 21/1
Showing 1-10 of 18 results
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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.
Travel insights for flights from Winnipeg to Chicago
Get recent, data-driven insights about flights from Winnipeg to Chicago including ideal travel times, pricing trends, and more.
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 17 January 2025.
The best time to book flights from Winnipeg to Chicago is 70 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 21 January 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 evening tend to be the most expensive. A flight in the morning could potentially save you up to 16% 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 Wednesday mornings when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 21 January 2025.
The most flights from YWG to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 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 21 January 2025.
Get a feel of what it's like to fly with WestJet, Air Canada 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.
Delta has consistently been the best U.S. airline for my travels and this flight was no exception
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 3 flights from Winnipeg to Chicago per day from 4 different airlines.
What are the cheapest airlines flying from Winnipeg to Chicago round-trip?
WestJet, at C$ 476, 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 29% lower than the current average price of a flight leaving 3 months from now.
What are the cheapest airlines to fly from Winnipeg to Chicago one-way?
The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 226. However, be on the lookout for offers from Delta and Air Canada, as they are both options that can get you from Winnipeg to Chicago for a low price.
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 (71%), Air Canada (71%), United Airlines( 71%).
What are the cheapest flights from Winnipeg to Chicago?
Looking at all options, your cheapest flight can be booked for C$ 296. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 390 on average our data indicates C$ 709 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, 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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 21 January 2025.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 21 January 2025.
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 21 January 2025.
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.
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