International route
Cheap flights from Chicago to Winnipeg
O'Hare International Airport (ORD) to Winnipeg James Armstrong Richardson International Airport (YWG). 707 miles, 1h 50m nonstop.
ORD to YWG at a glance
Computed from airline schedules and the fares we track for this route. Refreshed several times a day.
- Distance
- 707 milesgreat-circle
- Typical flight time
- 1h 50mnonstop, gate to gate
- Nonstop airlines
- UA1 airlineUnited
- Nonstop flights per day
- 1all airlines combined
- Cheapest month
- February 2027over the next six months
- Best day to fly
- Tuesday18% less than Sunday
- Time difference
- Same time zone
Chicago to Winnipeg
Round trips from $115
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Feb 9.
Cheapest month: February 2027
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppChicago to Winnipeg fares by month
Lowest round-trip economy fare per traveler in each of the next six months, taxes and fees included. Select a month to search that date.
Airlines flying Chicago to Winnipeg
1 airline flies nonstop with 1 departures a day combined, plus 3 more with one stop.
- UAUnited AirlinesStar AllianceNonstop · 1 flight a day · first checked bag from $40
- DLDelta Air LinesSkyTeamConnecting via MSP, DTW · first checked bag from $35
- WNSouthwest AirlinesLow-costConnecting via STL · first checked bag from $35
- SYSun Country AirlinesLow-costConnecting via MSP · first checked bag from $45
Connecting options
Hubs where one airline can carry you on both legs, most choices first.
- Minneapolis (MSP)DLSY2 airlines
- Detroit (DTW)DL1 airline
- St. Louis (STL)WN1 airline
Which airport should I use?
Chicago has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other departure airports near Chicago
Tips for this route
- Only United flies this route nonstop, which keeps nonstop fares firm. A one-stop itinerary through MSP or DTW is usually cheaper if you can spare the extra three to five hours.
- February 2027 is the cheapest month to fly over the next six months, with round trips from $115; September 2026 is the most expensive at $147 and up, a difference of $32 per traveler.
- Departing on a Tuesday averages 18% less than a Sunday on this route. If your dates are flexible, shift the outbound by a day or two and check the calendar view before you book.
- Book 6 to 12 weeks ahead; fares climb in the last three weeks and around holidays.
Ready to compare live fares?
See every airline on ORD–YWG side by side with bags and seat rules spelled out.
Search Chicago to WinnipegChicago to Winnipeg: common questions
How long is the flight from Chicago to Winnipeg?
A nonstop flight from Chicago (ORD) to Winnipeg (YWG) takes about 1h 50m gate to gate, covering 707 miles. Connecting itineraries add the layover, typically 2 to 5 hours more in total.
Which airlines fly nonstop from ORD to YWG?
United Airlines operates nonstop flights from Chicago (ORD) to Winnipeg (YWG), with 1 nonstop departure a day between them. One-stop options connect through MSP, DTW and STL.
What is the cheapest month to fly from Chicago to Winnipeg?
Over the next six months, February 2027 has the lowest round-trip fares from Chicago (ORD) to Winnipeg (YWG), starting at $115 per traveler including taxes and fees. Within any month, Tuesday departures average the lowest prices.
How far in advance should I book Chicago to Winnipeg flights?
Book 6 to 12 weeks ahead; fares climb in the last three weeks and around holidays. Air1 Tickets includes free cancellation within 24 hours of booking on every fare, so you can lock in a good price and keep looking.
What is the time difference between Chicago and Winnipeg?
Winnipeg is in the same time zone as Chicago, so there is no clock change. ORD is on America/Chicago time and YWG on America/Winnipeg time. Departure and arrival times in search results are always shown in local time at each airport.
Related routes
Other popular city pairs from the same departure city and to the same destination, with the lowest round-trip fares we found.