International route
Cheap flights from Winnipeg to Chicago
Winnipeg James Armstrong Richardson International Airport (YWG) to O'Hare International Airport (ORD). 707 miles, 1h 50m nonstop.
YWG to ORD 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
- January 2027over the next six months
- Best day to fly
- Tuesday19% less than Friday
- Time difference
- Same time zone
Winnipeg to Chicago
Round trips from $112
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Jan 5.
Cheapest month: January 2027
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppWinnipeg to Chicago 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 Winnipeg to Chicago
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?
WinnipegChicago has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other arrival 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.
- January 2027 is the cheapest month to fly over the next six months, with round trips from $112; September 2026 is the most expensive at $151 and up, a difference of $39 per traveler.
- Departing on a Tuesday averages 19% less than a Friday 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.
Destination guide
Chicago: Big-shoulders architecture and a lakefront for everyone
Chicago is America's most connected inland hub — O'Hare and Midway between them have nonstops from nearly every US city — so fares are consistently reasonable. The lakefront, the architecture and the food make it a strong long weekend.
Best time to visit: June–September is warm, with festivals almost every weekend (and the highest hotel rates). May and October are cool and cheaper; winter is cold but hotels are a bargain.
Flying the other way? Chicago to WinnipegFares, airlines and tips for ORD to YWG.Ready to compare live fares?
See every airline on YWG–ORD side by side with bags and seat rules spelled out.
Search Winnipeg to ChicagoWinnipeg to Chicago: common questions
How long is the flight from Winnipeg to Chicago?
A nonstop flight from Winnipeg (YWG) to Chicago (ORD) 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 YWG to ORD?
United Airlines operates nonstop flights from Winnipeg (YWG) to Chicago (ORD), 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 Winnipeg to Chicago?
Over the next six months, January 2027 has the lowest round-trip fares from Winnipeg (YWG) to Chicago (ORD), starting at $112 per traveler including taxes and fees. Within any month, Tuesday departures average the lowest prices.
How far in advance should I book Winnipeg to Chicago 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 Winnipeg and Chicago?
Chicago is in the same time zone as Winnipeg, so there is no clock change. YWG is on America/Winnipeg time and ORD on America/Chicago 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.