Cheap Flights from Winnipeg (YWG) to Chicago (ORD) from HK$1,582~

View HK$1,582 flight on Wed, 8 Oct 2025Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago O'Hare Intl. Airport (ORD)

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Find Cheap Flights from Winnipeg (YWG) to Chicago (ORD)

Prices were available within the past 7 days and start at HK$1,582 for one-way flights and HK$2,776 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$2,776 Return, found 4 days ago
HK$2,776
Return
found 4 days ago
Select United flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$2,776 found 4 days ago
United
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,072 Return, found 4 days ago
HK$3,072
Return
found 4 days ago
Select United flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,072 found 4 days ago
United
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,124 Return, found 4 days ago
HK$3,124
Return
found 4 days ago
Select United flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,124 found 4 days ago
Air Canada
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,196 Return, found 4 days ago
HK$3,196
Return
found 4 days ago
Select Air Canada flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,196 found 4 days ago
Air Canada
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,282 Return, found 4 days ago
HK$3,282
Return
found 4 days ago
Select Air Canada flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,282 found 4 days ago
Delta
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,294 Return, found 4 days ago
HK$3,294
Return
found 4 days ago
Select Delta flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,294 found 4 days ago
United
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,311 Return, found 4 days ago
HK$3,311
Return
found 4 days ago
Select United flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,311 found 4 days ago
United
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,334 Return, found 4 days ago
HK$3,334
Return
found 4 days ago
Select United flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,334 found 4 days ago
United
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,342 Return, found 4 days ago
HK$3,342
Return
found 4 days ago
Select United flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,342 found 4 days ago
Delta
Sun, 28 Sep - Sun, 12 Oct
YWG
Winnipeg
ORD
Chicago
HK$3,346 Return, found 4 days ago
HK$3,346
Return
found 4 days ago
Select Delta flight, departing Sun, 28 Sep from Winnipeg to Chicago, returning Sun, 12 Oct, priced at HK$3,346 found 4 days ago

Find the cheapest month to fly from Winnipeg (YWG) to Chicago (ORD)

June is typically the cheapest month to fly

From HK$1,888 - HK$3,811 per traveller.

Graph displaying average flight prices per month

Winnipeg to Chicago route information
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Return price
HK$2,776
Distance
1130 km
Average flight time
2 hours 31 mins

Flights from Winnipeg to Chicago

Book cheap flights from Winnipeg (YWG) to Chicago (ORD) on Expedia.com.hk. Find the best flight deals to destinations around the world for your next leisure or business travel on Expedia.com.hk.

Search for flights from Winnipeg (YWG) to Chicago (ORD) to find great flight deals suitable to your travel date and time. Expedia.com.hk flight booking search engine is simple to use and looking for cheap flights is as easy as a click of a mouse or on your mobile devices.

Be assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Winnipeg (YWG) to Chicago (ORD) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

Save more when combine your Chicago flight with a hotel for a package deal! Discover additional savings by booking in advance. Now you can find activities in Chicago and things to do in Chicago for your perfect vacation with Expedia Thing to Do.

If you would like to book flights to Chicago more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is HK$1,582 now!

 

Frequently asked questions

How much is a flight from Winnipeg Airport to ORD?
Round-trip flights from Winnipeg Airport to ORD start from HK$2,776. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book today so you don't miss out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from YWG to O'Hare Airport?
Each air carrier has its own set of terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from YWG to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Winnipeg Airport to O'Hare Airport?
With a flight distance of 1,150 kilometers, it's just a hop from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport. It might be a quick journey, but it's still worth bringing a book to read.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport?
If you want to fly straight from Winnipeg Airport to O'Hare Airport, you'll need to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly on this route.
Are Winnipeg James Armstrong Richardson Intl. Airport (YWG) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices are constantly going up and down, so not always. While last-minute deals between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and ORD are of course possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some carriers release their prices up to a year ahead of the departure date. Expedia is constantly updating the biggest airfare bargains around, so keep checking and be ready to pounce when the price is low.

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