Cheap flight from Winnipeg to Chicago from PHP 20,087
Here are our top budget-friendly flights, offering flexible one-way or round-trip options. Additional flights with other timings and airlines are also available.
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Flights from Winnipeg to Chicago
Top Airlines Flying from Winnipeg to Chicago
Choose from 1 carriers that fly from Winnipeg to Chicago, including United Airlines,,
Cheap flight deals from Winnipeg to Chicago
Find direct flights from Winnipeg to Chicago within the next three months. Book one-way flights from PHP 10,727 or round-trip tickets from PHP 20,087.
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Round-trip
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One way
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Cheapest nonstop
YWG 7:00 AM2h 31mNonstopORD 9:31 AMWinnipeg - Chicago | Fri, Jul 25 | United Airlines
ORD 7:58 PM2h 35mNonstopYWG 10:33 PMChicago - Winnipeg | Sat, Jul 26 | United AirlinesPHP 20,087 PHP 21,4286% OFF6% OFFPHP 21,428 PHP 20,087 -
YWG 7:00 AM2h 31mNonstopORD 9:31 AMWinnipeg - Chicago | Fri, Jul 18 | United Airlines
ORD 7:58 PM2h 35mNonstopYWG 10:33 PMChicago - Winnipeg | Sun, Jul 20 | United AirlinesPHP 20,142 PHP 21,4286% OFF6% OFFPHP 21,428 PHP 20,142
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YWG 6:15 PM18h 24m1 stopsORD 12:39 PMWinnipeg - Chicago | Sat, Jul 5 | WestJet
ORD 1:40 PM7h 46m1 stopsYWG 9:26 PMChicago - Winnipeg | Sun, Jul 13 | WestJetPHP 11,459 PHP 21,42847% OFF47% OFFPHP 21,428 PHP 11,459 -
YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Tue, Jul 22 | WestJet
ORD 1:40 PM7h 46m1 stopsYWG 9:26 PMChicago - Winnipeg | Sat, Jul 26 | WestJetPHP 12,54541% OFFPHP 21,428 PHP 12,545
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Tue, Aug 12 | WestJet
ORD 1:40 PM8h 16m1 stopsYWG 9:56 PMChicago - Winnipeg | Wed, Aug 13 | WestJetPHP 12,78140% OFFPHP 21,428 PHP 12,781
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Tue, Aug 19 | WestJet
ORD 1:40 PM7h 46m1 stopsYWG 9:26 PMChicago - Winnipeg | Sat, Aug 23 | WestJetPHP 12,78140% OFFPHP 21,428 PHP 12,781
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Thu, Jul 24 | WestJet
ORD 5:30 PM15h 31m1 stopsYWG 9:01 AMChicago - Winnipeg | Wed, Jul 30 | WestJetPHP 14,35433% OFFPHP 21,428 PHP 14,354
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Wed, Aug 6 | WestJet
ORD 5:30 PM18h 11m1 stopsYWG 11:41 AMChicago - Winnipeg | Tue, Aug 12 | WestJetPHP 14,35433% OFFPHP 21,428 PHP 14,354
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Wed, Aug 27 | WestJet
ORD 5:30 PM15h 31m1 stopsYWG 9:01 AMChicago - Winnipeg | Thu, Sep 4 | WestJetPHP 14,35433% OFFPHP 21,428 PHP 14,354
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Wed, Aug 13 | WestJet
ORD 5:30 PM18h 11m1 stopsYWG 11:41 AMChicago - Winnipeg | Mon, Aug 18 | WestJetPHP 14,35433% OFFPHP 21,428 PHP 14,354
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Tue, Aug 26 | WestJet
ORD 5:30 PM15h 31m1 stopsYWG 9:01 AMChicago - Winnipeg | Tue, Sep 2 | WestJetPHP 14,35433% OFFPHP 21,428 PHP 14,354
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Fri, Jul 25 | WestJet
ORD 5:30 PM18h 11m1 stopsYWG 11:41 AMChicago - Winnipeg | Tue, Jul 29 | WestJetPHP 14,69231% OFFPHP 21,428 PHP 14,692
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YWG 1:00 PM17h 25m1 stopsCHI Invalid DateWinnipeg - Chicago | Thu, Jul 3 | Normal Airline
CHI 3:00 PM6hNonstopYWG 4:00 PMChicago - Winnipeg | Sat, Jul 5 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
YWG 7:00 AM2h 31mNonstopORD 9:31 AMWinnipeg - Chicago | Thu, Jul 3 | United AirlinesPHP 10,728 PHP 19,07744% OFF44% OFFPHP 19,077 PHP 10,728
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YWG 7:00 AM2h 31mNonstopORD 9:31 AMWinnipeg - Chicago | Fri, Jul 25 | United AirlinesPHP 11,263 PHP 19,07741% OFF41% OFFPHP 19,077 PHP 11,263
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Fri, Aug 15 | WestJetPHP 7,905 PHP 19,07759% OFF59% OFFPHP 19,077 PHP 7,905
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YWG 12:15 PM24h 24m1 stopsORD 12:39 PMWinnipeg - Chicago | Tue, Jul 1 | WestJetPHP 8,09357% OFFPHP 19,077 PHP 8,093
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YWG 9:00 AM12h 30m1 stopsORD 9:30 PMWinnipeg - Chicago | Fri, Aug 1 | WestJetPHP 8,58955% OFFPHP 19,077 PHP 8,589
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YWG 9:00 AM12h 30m1 stopsORD 9:30 PMWinnipeg - Chicago | Fri, Jul 25 | WestJetPHP 8,78554% OFFPHP 19,077 PHP 8,785
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YWG 9:00 AM14h 17m1 stopsMDW 11:17 PMWinnipeg - Chicago | Thu, Jul 10 | WestJetPHP 9,44650% OFFPHP 19,077 PHP 9,446
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YWG 9:00 AM14h 17m1 stopsMDW 11:17 PMWinnipeg - Chicago | Thu, Jul 31 | WestJetPHP 9,45450% OFFPHP 19,077 PHP 9,454
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YWG 9:00 AM12h 30m1 stopsORD 9:30 PMWinnipeg - Chicago | Fri, Jul 18 | WestJetPHP 9,47050% OFFPHP 19,077 PHP 9,470
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Wed, Jul 2 | WestJetPHP 9,58850% OFFPHP 19,077 PHP 9,588
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YWG 9:00 AM15h 22m1 stopsORD 12:22 AMWinnipeg - Chicago | Thu, Aug 14 | WestJetPHP 9,79249% OFFPHP 19,077 PHP 9,792
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YWG 8:30 AM8h 14m1 stopsORD 4:44 PMWinnipeg - Chicago | Thu, Aug 7 | WestJetPHP 17,9326% OFFPHP 19,077 PHP 17,932
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YWG 1:00 PM17h 25m1 stopsCHI Invalid DateWinnipeg - Chicago | Thu, Jul 3 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Flying from Winnipeg to Chicago
The distance between Winnipeg and Chicago is about 1,154.29 km. It takes around 2 hours 32 minutes on average to fly from Winnipeg to Chicago. The most popular month to Chicago is March. The off-season for travel is April.
| Cheapest one-way flight price | PHP 7,905 |
|---|---|
| Cheapest round-trip ticket price | PHP 11,459 |
| Off-season for travel | April |
| Peak season for travel | March |
| Flight distance | 1,154.29 km |
| Average flight time | 2 hours 32 minutes |
| Popular airline | United Airlines |
When is the cheapest time to fly from Winnipeg to Chicago?
The best time to book the cheapest flights from Winnipeg to Chicago is between Aug 10 and Aug 17. One-way ticket prices start at PHP 7,904 according to our flight calendar.
Cheapest flights
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Winnipeg (YWG) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Winnipeg to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Winnipeg (YWG) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around PHP 24,813. -
How long does it take to fly from Winnipeg (YWG) to Chicago (CHI) and what is the distance?
It takes around 2 hours 32 minutes to fly from Winnipeg (YWG) to Chicago (CHI). -
What are the most popular airlines that fly from Winnipeg (YWG) to Chicago (CHI)?
Airlines with flights from Winnipeg (YWG) to Chicago (CHI): Air Canada, Air New Zealand, United Airlines, avianca and Copa Airlines.
How to find a cheap flight from Winnipeg to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Winnipeg to Chicago. Book your flights at the right time and save more.
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
Compare Flight Prices
Compare prices on travel agency and airline websites.
Look Out for Deals
Check airline and travel agency websites for latest flight deals
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
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