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

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Lowest round trip fares by airline from Chicago and Winnipeg

Cheapest prices ($212 One Way, $428 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Winnipeg

The Marlborough Hotel

The Marlborough Hotel

2 out of 5
331 Smith St, Winnipeg, MB
The price is $60 per night from Sep 20 to Sep 20
Located in Downtown Winnipeg, this hotel is within a 15-minute walk of Canada Life Centre, RBC Convention Centre Winnipeg, and University of Winnipeg. Canadian ...
2/5 (2 reviews)
"No facilities nthng was there crowd was vry bad it was terrible hotel"

Reviewed on Jul 6, 2019

The Marlborough Hotel
Super 8 by Wyndham Winnipeg West

Super 8 by Wyndham Winnipeg West

3 out of 5
3760 Portage Ave, Winnipeg, MB
The price is $70 per night from Oct 15 to Oct 15
Situated in Winnipeg, this hotel is 1 mi (1.6 km) from Assiniboia Downs and 1.3 mi (2.1 km) from Academy Lanes West. Assiniboine Park Zoo and Polo Park are also ...
5/5Exceptional! (1 review)
"Everything was great!!!!! The staff were very friendly, the room was perfectly clean, the breakfast bar was the best I've ever seen!!!!"

Reviewed on May 17, 2018

Super 8 by Wyndham Winnipeg West
Assiniboine Gordon Inn on the Park

Assiniboine Gordon Inn on the Park

3 out of 5
1975 Portage Ave, Winnipeg, MB
The price is $74 per night from Sep 24 to Sep 24
Located in St. James, this motel is within a 15-minute walk of Pavilion Gallery Museum, Assiniboine Park, and Leo Mol Sculputure Garden. Polo Park and Assiniboine ...
Assiniboine Gordon Inn on the Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Winnipeg

Origin Chicago
Destination Winnipeg
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Chicago to Winnipeg

Cheap flights from Chicago to Winnipeg

Sign up for CheapTickets Deals E-mail, so you'll receive late-breaking alerts about airfare sales on cheap flights from Chicago to Winnipeg.

Earn miles, choose seats on cheap flights from Chicago to Winnipeg

Add your frequent flier numbers when you book your cheap flights from Chicago to Winnipeg on CheapTickets and accumulate miles on applicable flights. Also, use our interactive maps to select your seats on flights from Chicago to Winnipeg — aisle or window, front or back. We're not just concerned about finding you cheap flights from Chicago to Winnipeg, we want to ensure you get your airline miles and preferred seats too.

An entire support team for your Chicago to Winnipeg flights

When you book your Chicago to Winnipeg flights on CheapTickets, you get free, real-time trip updates on your mobile phone. CheapTickets has a staff of air traffic analysts and travel experts monitoring events that could delay your Chicago to Winnipeg flights. Choose to have your alerts sent to up to six others, like the person picking you up at the Winnipeg airport.

Need to change your cheap flights from Chicago to Winnipeg?

Change your cheap flights from Chicago to Winnipeg online with CheapTickets. No phone calls, no waiting. We'll let you know if there's part of your airfare that can be put toward a future flights from Chicago to Winnipeg. Travel should be a pleasure, so that's why we strive to get you the best deal on cheap flights from Chicago to Winnipeg and provide the travel support you deserve.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.