Find the cheapest flights from Chicago to Winnipeg
Cheap round-trip flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customize your resultsTrusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Porter Airlines flights from Chicago to Winnipeg
Our best Porter Airlines deals on Chicago to Winnipeg flight tickets
WestJet flights from Chicago to Winnipeg
Our best WestJet deals on Chicago to Winnipeg flight tickets
momondo Fare Finder
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 10/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Tue 17/11
9:35 p.m.-5:30 p.m.
2 stops20h 55m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 25/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Mon 30/11
8:35 p.m.-6:15 a.m.
2 stops34h 40m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 24/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Mon 30/11
8:35 p.m.-6:15 a.m.
2 stops34h 40m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 13/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Mon 16/11
8:35 p.m.-5:30 p.m.
2 stops21h 55m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 10/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Tue 17/11
9:35 p.m.-4:07 p.m.
3 stops19h 32m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 25/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Mon 30/11
7:55 p.m.-10:40 a.m.
1 stop15h 45m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Thu 5/11
6:20 p.m.-11:15 a.m.
1 stop15h 55m
Winnipeg
Sun 8/11
7:55 p.m.-10:40 a.m.
1 stop15h 45m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 26/10
6:20 p.m.-9:15 a.m.
1 stop14h 55m
Winnipeg
Wed 25/11
8:35 p.m.-12:44 p.m.
2 stops17h 09m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 26/10
6:20 p.m.-9:15 a.m.
1 stop14h 55m
Winnipeg
Wed 25/11
11:00 a.m.-10:40 a.m.
1 stop24h 40m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 2/11
7:50 p.m.-6:25 p.m.
2 stops21h 35m
Winnipeg
Mon 9/11
9:35 p.m.-5:30 p.m.
2 stops20h 55m
See travel insights to Winnipeg from
How to get the cheapest flight ticket from Chicago to Winnipeg
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Winnipeg?
The cheapest month to fly to Winnipeg from Chicago is in September. Flight prices, which tend to average around C$ 730, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of September, then departing from Chicago during the month March is also very affordable. Most momondo users find prices during this month for around C$ 753.
What is the cheapest Chicago to Winnipeg flight route?
Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago - Winnipeg flight prices
What cabin class options are available on Chicago to Winnipeg flights?
There are 2 cabin classes available to choose from on Chicago to Winnipeg flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Winnipeg flights?
You could potentially save up to 41% on your flight if you consider stops on a Chicago to Winnipeg flight.
How many flights depart from Chicago to Winnipeg on average per day?
As of October 2026, there are 6 flights per day flying from Chicago to Winnipeg. The most common time of day flights depart is 7:00p.m., with 53% of flights taking off in the evening.
How many flights depart from Chicago to Winnipeg on average per week?
As of October 2026, 45 flights take off from Chicago and land in Winnipeg each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.
When to book flights from Chicago to Winnipeg
Cheap Chicago to Winnipeg (CHI to YWG) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Winnipeg
Frequently asked questions about flying from Chicago to Winnipeg
How far is Chicago to Winnipeg by plane?
A flight from Chicago to Winnipeg will travel around 1153.0 km. Typically, this will take 2h 37m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Winnipeg Airport?
Prices for flights from Chicago to Winnipeg Airport are updated daily.
How old do you have to be to fly from Chicago to Winnipeg Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The necessary travel and health documents for your Winnipeg Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Winnipeg?
Based on momondo bookings for flights between Chicago and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 72.00% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 8.00%, Boeing 777-300ER with 8.00%, and Boeing 777-300 with 8.00%.
Travelling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Winnipeg?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Winnipeg for you.
Can I find flights from Chicago to Winnipeg with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Winnipeg from Chicago with this policy.
How can momondo help me find flights from Chicago to Winnipeg?
momondo helps you find the best flight between Chicago and Winnipeg by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Winnipeg, momondo offers a useful price alert feature which will track prices for flights to Winnipeg from Chicago and alert you when they change.