Cheap Flights from Chicago to Winnipeg starting at S$ 172
Book one-way or return flights from Chicago to Winnipeg from as little as S$ 172. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- MDW07:008h 25m1 stopYWG15:25Wed, May 1|Chicago - Winnipeg|Frontier AirlinesS$ 172S$ 31044% OFF44% OFFS$ 310S$ 172
- MDW07:008h 25m1 stopYWG15:25Wed, May 15|Chicago - Winnipeg|Frontier AirlinesS$ 175S$ 31043% OFF43% OFFS$ 310S$ 175
- ORD06:009h 25m1 stopYWG15:25Thu, May 2|Chicago - Winnipeg|Frontier AirlinesS$ 195S$ 31037% OFF37% OFFS$ 310S$ 195
- MDW07:277h 58m1 stopYWG15:25Wed, Jun 5|Chicago - Winnipeg|Frontier AirlinesS$ 209S$ 209
- MDW21:1218h 13m1 stopYWG15:25Thu, May 16|Chicago - Winnipeg|Frontier AirlinesS$ 213S$ 213
- MDW07:277h 58m1 stopYWG15:25Mon, Jun 10|Chicago - Winnipeg|Frontier AirlinesS$ 232S$ 232
- MDW07:277h 58m1 stopYWG15:25Mon, Jun 3|Chicago - Winnipeg|Frontier AirlinesS$ 240S$ 240
- MDW07:277h 55m1 stopYWG15:22Wed, Jul 3|Chicago - Winnipeg|Frontier AirlinesS$ 243S$ 243
- ORD07:008h 25m1 stopYWG15:25Wed, May 15|Chicago - Winnipeg|WestjetS$ 243S$ 243
- ORD12:3412h 10m1 stopYWG00:44Mon, May 13|Chicago - Winnipeg|Frontier AirlinesS$ 248S$ 248
- CHI13:003h 5mDirectYWG14:00Sat, May 4|Chicago - Winnipeg|Frontier AirlinesFind 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 Chicago to Winnipeg? Find one-way or return flights that are affordable and fit your itinerary.
Trip.com monitors the ticket fares of flights from Chicago to Winnipeg. Stay updated on price trends and snag the best deals for your upcoming trip.
View airlines operating flights from Chicago to Winnipeg. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Find more flights and airlines
Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Winnipeg.
- CheapestMDW07:008h 25m1 transferYWG15:25Midway International Airport - Winnipeg James Armstrong Richardson International AirportWed, May 1Frontier AirlinesS$ 172
- ORD06:009h 25m1 transferYWG15:25O'Hare International Airport - Winnipeg James Armstrong Richardson International AirportThu, May 2Frontier AirlinesS$ 195
- ORD06:009h 25m1 transferYWG15:25O'Hare International Airport - Winnipeg James Armstrong Richardson International AirportThu, May 2Frontier AirlinesS$ 195Find More Flights
Frequently Asked Questions
How to find a cheap flight from Chicago to Winnipeg
Cheapest direct flight price | S$ 172 |
---|---|
Cheapest return ticket price | S$ 511 |
Cheapest month | March |
Peak season for travel | October |
Flight distance | 1,154.29km |
Popular airline | United Airlines |
Plan Your Trip Around Winnipeg
Find Cheap Flights & Deals on Trip.com
Popular Flights from Chicago
- Flights Chicago to Taipei
- Flights Chicago to Hong Kong
- Flights Chicago to Shanghai
- Flights Chicago to Seoul
- Flights Chicago to Tokyo
- Flights Chicago to Bangkok
- Flights Chicago to New York
- Flights Chicago to Manila
- Flights Chicago to Beijing
- Flights Chicago to Atlanta
- Flights Chicago to Orlando
- Flights Chicago to Dallas
- Flights from O'Hare International Airport to Singapore
- Flights from Midway International Airport to Singapore
- Flights from Chicago to Beihai Fucheng Airport
- Flights from Chicago to Changde Taohuayuan Airport
- Flights from Chicago to Zhengzhou Xinzheng International Airport
- Flights from Chicago to Chiayi Airport
- Flights from Chicago to DDG Airport
- Flights from Chicago to Ordos Ejin Horo Airport
- Flights from Midway International Airport to Singapore Changi Airport
- Flights from O'Hare International Airport to Singapore Changi Airport
Recommended Hotels in Winnipeg
- Hotels near Bunn's Creek Parkway
- Hotels near Gary Hobson Memorial Park
- Hotels near Benjaminson Park
- Hotels near Foot Locker
- Hotels near Tom Chester Park
- Hotels near Parc Trottier
- Hotels near African Foodways Market
- Hotels near The Wave Church - Winnipeg
- Hotels near Antiques & Funk
- Hotels near St James Civic Centre
- Hotels near Outlet Collection Winnipeg
- Hotels near Westwood Centre
- Hotels near St. Andrew Bobola
- Hotels near Harte Trail
- Hotels near Riel House National Historic Site
- Hotels near Laverendrye Park
- Hotels near Vermillion Park
- Hotels near Aurora Farm
- Hotels near The Happy Tree Kindness Rock Garden
- Hotels near Cordova Park
- Hotels near Government House of Manitoba
- Hotels near Muriel Street Park
- Hotels near Seven Oaks Memorial
- Hotels near St. Ann Church
- Hotels near SmartCentres Kenaston Common
- Hotels near Mulvey Market
- Hotels near Peoples Jewellers
- Hotels near Winnipeg Public Library Administration Office
- Hotels near Flying J Travel Center
- Hotels near St. John's Park
Popular Flights to Winnipeg
- Flights Toronto to Winnipeg
- Flights Calgary to Winnipeg
- Flights Edmonton to Winnipeg
- Flights Vancouver to Winnipeg
- Flights Los Angeles to Winnipeg
- Flights Abbotsford to Winnipeg
- Flights London to Winnipeg
- Flights Ottawa to Winnipeg
- Flights New Delhi to Winnipeg
- Flights Victoria to Winnipeg
- Flights Atlanta to Winnipeg
- Flights Orlando to Winnipeg
- Flights from Singapore Changi Airport to Winnipeg
- Flights from London to Winnipeg James Armstrong Richardson International Airport
- Flights from Tokyo to Winnipeg James Armstrong Richardson International Airport
- Flights from Sapporo to Winnipeg James Armstrong Richardson International Airport
- Flights from Osaka to Winnipeg James Armstrong Richardson International Airport
- Flights from Dubai to Winnipeg James Armstrong Richardson International Airport
- Flights from San Francisco to Winnipeg James Armstrong Richardson International Airport
- Flights from Singapore Changi Airport to Winnipeg James Armstrong Richardson International Airport
Recommended Routes
- Flights Los Angeles to Toronto
- Flights Los Angeles to Vancouver
- Flights New York to Toronto
- Flights Orlando to Toronto
- Flights Los Angeles to Calgary
- Flights Las Vegas to Toronto
- Flights Honolulu to Vancouver
- Flights Fort Lauderdale to Toronto
- Flights New York to Vancouver
- Flights San Francisco to Vancouver
- Flights Las Vegas to Vancouver
- Flights Las Vegas to Calgary
- Flights from Paine Field Airport to Montreal
- Flights from Melbourne International Airport to Victoria
- Flights from Concord-Padgett Regional Airport to Ottawa
- Flights from San Francisco to Brandon Airport
- Flights from San Francisco to Sault Ste. Marie Airport
- Flights from San Francisco to Greater Moncton International Airport
- Flights from San Francisco to St. John'S International Airport
- Flights from San Francisco to Campbell River Airport
- Flights from San Francisco to Powell River Airport
Site Operator: Trip.com Travel Singapore Pte. Ltd. Travel License No. 02943