Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Convenient & reliable booking and payment system
Latest Flight Deals from Winnipeg to Chicago
Book one-way or return flights from Winnipeg to Chicago from as little as NZD 222. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- YWG08:009h 27m1 stopORD17:27Wed, May 8|Winnipeg - Chicago|WestJetNZD 222NZD 33434% OFF34% OFFNZD 334NZD 222
- YWG17:0026h 58m1 stopORD19:58Fri, May 17|Winnipeg - Chicago|WestJetNZD 240NZD 33428% OFF28% OFFNZD 334NZD 240
- YWG08:006h 39m1 stopMDW14:39Wed, May 15|Winnipeg - Chicago|WestJetNZD 240NZD 33428% OFF28% OFFNZD 334NZD 240
- YWG17:0018h 29m1 stopORD11:29Fri, May 10|Winnipeg - Chicago|WestJetNZD 243NZD 243
- YWG08:006h 41m1 stopMDW14:41Wed, May 29|Winnipeg - Chicago|WestJetNZD 246NZD 246
- YWG08:009h 17m1 stopMDW17:17Thu, May 30|Winnipeg - Chicago|WestJetNZD 264NZD 264
- YWG17:009h1 stopORD02:00Fri, May 31|Winnipeg - Chicago|WestJetNZD 264NZD 264
- YWG08:0014h 3m1 stopORD22:03Mon, May 20|Winnipeg - Chicago|WestJetNZD 267NZD 267
- YWG08:008h 37m1 stopORD16:37Wed, May 22|Winnipeg - Chicago|WestJetNZD 275NZD 275
- YWG08:0010h 34m1 stopORD18:34Thu, Jul 11|Winnipeg - Chicago|WestJetNZD 275NZD 275
- YWG13:003h 5mDirectCHI14:00Sun, May 12|Winnipeg - Chicago|WestJetFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Searching for the best last minute flight from Winnipeg to Chicago? Find one-way or return flights that are affordable and fit your itinerary.
Trip.com monitors the ticket fares of flights from Winnipeg to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Winnipeg to Chicago
View airlines operating flights from Winnipeg to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
WestJet
From NZD 222
United Airlines
From NZD 289
Flair Airlines
From NZD 298
Delta Air Lines
From NZD 321
Air Canada
From NZD 322
Porter Airlines
From NZD 334
ANA airlines
Find more flights and airlines
Alternative Routes from Winnipeg to Chicago
Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Winnipeg to Chicago.
- CheapestYWG08:009h 27m1 transferORD17:27Winnipeg James Armstrong Richardson International Airport - O'Hare International AirportWed, May 8WestJetNZD 222
- YWG08:006h 39m1 transferMDW14:39Winnipeg James Armstrong Richardson International Airport - Midway International AirportWed, May 8WestJetNZD 224
- YWG08:006h 39m1 transferMDW14:39Winnipeg James Armstrong Richardson International Airport - Midway International AirportWed, May 8WestJetNZD 224Find More Flights
How do I find the cheapest flights?
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
Flight Information from Winnipeg to Chicago
Cheapest nonstop flight price | NZD 221 |
---|---|
Cheapest round-trip ticket price | NZD 552 |
Off-season for travel | February |
Peak season for travel | July |
Flight distance | 1,154.29km |
Popular airline | United Airlines |
Payment Methods
Our Partners
Copyright © 2024 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.
Site Operator: Trip.com Travel Singapore Pte. Ltd.