£158 Cheap Flights from Winnipeg (YWG) to Chicago (CHI)

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Cheap Flights from Winnipeg (YWG) to Chicago (CHI)

Prices were available within the past 7 days and start at £158 for one-way flights and £332 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 13 Jul - Tue, 23 Jul
YWG
Winnipeg
ORD
Chicago
£332 Return, found 2 days ago
£332
Return
found 2 days ago
Select Delta flight, departing Sat, 13 Jul from Winnipeg to Chicago, returning Tue, 23 Jul, priced at £332 found 2 days ago
Delta
Sat, 13 Jul - Tue, 16 Jul
YWG
Winnipeg
ORD
Chicago
£358 Return, found 2 days ago
£358
Return
found 2 days ago
Select Delta flight, departing Sat, 13 Jul from Winnipeg to Chicago, returning Tue, 16 Jul, priced at £358 found 2 days ago
Delta
Mon, 15 Jul - Tue, 23 Jul
YWG
Winnipeg
ORD
Chicago
£367 Return, found 2 days ago
£367
Return
found 2 days ago
Select Delta flight, departing Mon, 15 Jul from Winnipeg to Chicago, returning Tue, 23 Jul, priced at £367 found 2 days ago
Delta
Wed, 17 Jul - Wed, 24 Jul
YWG
Winnipeg
ORD
Chicago
£371 Return, found 2 days ago
£371
Return
found 2 days ago
Select Delta flight, departing Wed, 17 Jul from Winnipeg to Chicago, returning Wed, 24 Jul, priced at £371 found 2 days ago
Delta
Sat, 13 Jul - Mon, 22 Jul
YWG
Winnipeg
ORD
Chicago
£372 Return, found 2 days ago
£372
Return
found 2 days ago
Select Delta flight, departing Sat, 13 Jul from Winnipeg to Chicago, returning Mon, 22 Jul, priced at £372 found 2 days ago
Delta
Wed, 17 Jul - Wed, 24 Jul
YWG
Winnipeg
ORD
Chicago
£375 Return, found 2 days ago
£375
Return
found 2 days ago
Select Delta flight, departing Wed, 17 Jul from Winnipeg to Chicago, returning Wed, 24 Jul, priced at £375 found 2 days ago
United
Fri, 12 Jul - Sat, 20 Jul
YWG
Winnipeg
ORD
Chicago
£380 Return, found 2 days ago
£380
Return
found 2 days ago
Select United flight, departing Fri, 12 Jul from Winnipeg to Chicago, returning Sat, 20 Jul, priced at £380 found 2 days ago
United
Sat, 13 Jul - Sat, 20 Jul
YWG
Winnipeg
ORD
Chicago
£380 Return, found 2 days ago
£380
Return
found 2 days ago
Select United flight, departing Sat, 13 Jul from Winnipeg to Chicago, returning Sat, 20 Jul, priced at £380 found 2 days ago
United
Fri, 12 Jul - Fri, 19 Jul
YWG
Winnipeg
ORD
Chicago
£385 Return, found 2 days ago
£385
Return
found 2 days ago
Select United flight, departing Fri, 12 Jul from Winnipeg to Chicago, returning Fri, 19 Jul, priced at £385 found 2 days ago
Delta
Thu, 11 Jul - Thu, 18 Jul
YWG
Winnipeg
ORD
Chicago
£389 Return, found 2 days ago
£389
Return
found 2 days ago
Select Delta flight, departing Thu, 11 Jul from Winnipeg to Chicago, returning Thu, 18 Jul, priced at £389 found 2 days ago
Flight from Winnipeg to Chicago route information
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
O'Hare Intl.
Return price
£332
Distance
1130 km

Compare flights from Winnipeg to Chicago easily and book in confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Winnipeg to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to CHI-All Airports in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Winnipeg James Armstrong Richardson Intl. to CHI-All Airports.  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Winnipeg James Armstrong Richardson Intl. (YWG) to CHI-All Airports (CHI) 

The easiest way to view the best deals on flights from Winnipeg to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Winnipeg James Armstrong Richardson Intl. to CHI-All Airports start at just £332 and range up to £389.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Winnipeg and Chicago
  • booking your flight during July, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Winnipeg to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Winnipeg James Armstrong Richardson Intl. to CHI-All Airports for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from YWG to Chicago, IL (CHI-All Airports)?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) was £332. Fares this good don’t wait forever, so make sure you book yours ASAP. 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 Chicago, IL (CHI-All Airports)?
We get that life can throw the odd curveball, so we’ve made it as simple as possible for you to cancel your trip online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Winnipeg Airport to Chicago, IL (CHI-All Airports) 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 YWG to Chicago, IL (CHI-All Airports) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Winnipeg Airport to Chicago, IL (CHI-All Airports)?
With a flight distance of 1,100 kilometres, it’s just a short hop from YWG to Chicago, IL (CHI-All Airports). It might be a quick flight, but it’s still worth packing a book to read.
Which airlines fly direct from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports)?
You won’t find any airlines flying directly between Winnipeg James Armstrong Richardson Intl. Airport (YWG) and Chicago, IL (CHI-All Airports), so be prepared to make at least one stop on your journey. A layover can be a good way to break up a trip!
Are Winnipeg Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Chicago, IL (CHI-All Airports) can be hit-or-miss. You may be able to find a bargain, but you could also completely miss out! If you’d prefer to start your trip planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines publish their prices that far in advance. Our suggestion? Check back often as updates are made frequently.
Chicago Airports

Chicago

Winnipeg to O'Hare Intl.
£331.60
*Available to Expedia members.