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Thursday, April 18th 2019

"I'm a travel junkie who's hooked on deals from YWG." - Chris Myden

Tagged Pages Archive | Chicago

Winnipeg to Chicago - $243 CAD roundtrip including taxes

The Bean in Chicago

Delta is showing flights from Winnipeg to Chicago, Illinois for $243 CAD roundtrip including taxes.

The flights have 1 short stop each way, in Minneapolis.

The flights are in and out of Chicago's Midway airport (MDW) - the airport that's significantly smaller than O'Hare and about 20 minutes closer to downtown.

Availability for travel

late February, March, April, May, June, September, October, November, December 2019

How to find and book this deal

1. Try the following Google Flights search:

Google Flights: Winnipeg to Chicago (ORD)

- Click on the departure date box to open up the calendar view and browse for the cheapest date combinations.

- Look for the dates that are $244 roundtrip.

screenshot from Delta

Join us in the YWG Deals Facebook Group

For live discussion of this deal, or to get some amazing travel advice (about anywhere) from your 11,500 fellow passengers in Winnipeg, join us in the
YWG Deals Facebook Group.
^^^ click the 'Join Group' button when you arrive.

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3-in-1 trip: Winnipeg to Chicago, Puerto Rico, *and* New York City - $435 including taxes

Chicago, Puerto Rico, and New York City

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2-in-1 trip: Winnipeg to Chicago and San Juan, Puerto Rico - $379 CAD roundtrip including taxes

Chicago, Illinois and San Juan, Puerto Rico

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Winnipeg to Chicago, Illinois - $248 CAD roundtrip including taxes | throughout 2017/2018 schedule


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Direct Flights from Winnipeg | the complete list

More and more travelers are getting fed up with the problems and headaches associated with connecting flights and stopovers. Below you will find a comprehensive list of everywhere you can fly to from Winnipeg on a direct flight, along with the best methods for finding direct flights.

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Winnipeg to Chicago - $238 roundtrip after tax

Update: There's also one to Denver for $278 roundtrip after tax. Same dates.

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Winnipeg to Denver - $287 roundtrip after tax

If you've ever tried to fly to Denver from Winnipeg, you know it usually hovers around $650 roundtrip after tax.

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Winnipeg to Chicago - $240 roundtrip after tax

If you've ever tried to fly from Winnipeg to Chicago you know it's expensive. The bottom for fares these days is around $750 roundtrip after tax.

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