Cheap flights from Chicago O'Hare Intl Airport to Winnipeg from $176
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Winnipeg departing on 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Not ready to book? to track prices.Porter Airlines flights from Chicago O'Hare Intl Airport to Winnipeg
Our best Porter Airlines deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
Air Canada flights from Chicago O'Hare Intl Airport to Winnipeg
Our best Air Canada deals on Chicago O'Hare Intl Airport to Winnipeg flight tickets
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Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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
Wed 1/13
6:00 am-3:40 pm
1 stop8h 40m
Winnipeg
Fri 1/15
9:35 pm-10:50 am
2 stops14h 15m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 1/13
6:00 am-3:40 pm
1 stop8h 40m
Winnipeg
Fri 1/15
7:00 am-10:23 pm
1 stop16h 23m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 12/14
8:15 am-2:10 am
2 stops16h 55m
Winnipeg
Wed 12/16
7:00 am-5:37 pm
1 stop11h 37m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 11/4
7:03 am-3:49 pm
1 stop7h 46m
Winnipeg
Wed 11/11
6:15 am-10:57 am
1 stop5h 42m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Wed 11/4
3:47 pm-1:44 am
1 stop8h 57m
Winnipeg
Wed 11/11
6:15 am-10:57 am
1 stop5h 42m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Mon 11/2
3:50 pm-12:43 am
1 stop7h 53m
Winnipeg
Tue 11/3
6:15 am-10:57 am
1 stop5h 42m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sun 11/1
5:29 pm-2:44 am
2 stops32h 15m
Winnipeg
Mon 11/9
9:35 pm-4:05 pm
2 stops19h 30m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Tue 11/3
6:20 am-1:48 pm
1 stop6h 28m
Winnipeg
Fri 11/13
6:00 am-5:30 pm
2 stops12h 30m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Sat 12/19
10:00 am-2:52 pm
Nonstop3h 52m
Winnipeg
Sun 1/10
7:00 am-8:45 am
Nonstop2h 45m
ChicagoWinnipeg
ORD Chicago O'Hare Intl - YWG Winnipeg
ORDYWG
Chicago O'Hare Intl
Fri 12/18
10:00 am-2:52 pm
Nonstop3h 52m
Winnipeg
Sat 1/9
8:00 am-8:45 am
Nonstop1h 45m
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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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?
In general, March is the cheapest month to fly from Chicago O'Hare Intl Airport to Winnipeg. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you’re not able to fly to Winnipeg in March, then January is your next best option. Flight prices from Chicago O'Hare Intl Airport to Winnipeg during January average around $0.
What is the cheapest day to depart on your flight to Winnipeg?
The cheapest day to depart on your flight to Winnipeg is on a Saturday when prices can be found for as low as $755. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,150.
What is the cheapest time of day to depart on your flight to Winnipeg?
The cheapest time of day to fly to Winnipeg is in the evening when flights can be purchased for as low as $844. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $914 on average. Flights to Winnipeg from Chicago O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago O'Hare Intl to Winnipeg flight route?
Fly from Chicago O'Hare Intl to Winnipeg for the best Chicago O'Hare Intl - Winnipeg flight prices
What cabin class options are available on Chicago O'Hare Intl Airport to Winnipeg flights?
There is only 1 cabin class available to choose from on Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Winnipeg flights?
You could potentially save up to 50% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Winnipeg flight.
How many flights depart from Chicago O'Hare Intl Airport to Winnipeg on average per day?
6 flights are operational daily from Chicago O'Hare Intl Airport to Winnipeg as of October 2026. The most popular departure time for this route is 7:00PM, with 53% of flights per day taking off in the evening.
How many flights depart from Chicago O'Hare Intl Airport to Winnipeg on average per week?
45 flights are operational weekly from Chicago O'Hare Intl Airport to Winnipeg as of October 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.
When to book flights from Chicago O'Hare Intl Airport to Winnipeg
Cheap Chicago O'Hare Intl Airport to Winnipeg (ORD to YWG) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Winnipeg
Frequently asked questions about flying from Chicago O'Hare Intl Airport to Winnipeg
How far is Chicago O'Hare Intl to Winnipeg by plane?
There are 702.3 mi between Chicago O'Hare Intl and Winnipeg. In terms of flight time, this usually takes a little over 2h 24m.
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Winnipeg Airport?
Prices for flights from Chicago O'Hare Intl Airport to Winnipeg Airport refresh daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Winnipeg Airport?
There are 3 operators available for flights from Chicago O'Hare Intl Airport to Winnipeg Airport as of October 2026.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Winnipeg Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Winnipeg Airport.
What documentation or ID do you need to fly to Winnipeg Airport?
The travel and health documents required for your trip to Winnipeg Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Winnipeg Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago O'Hare Intl Airport to Winnipeg?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Winnipeg, the leading plane model is Embraer 175 (Enhanced Winglets), making up 74.07% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 7.41%, Boeing 777-300ER with 7.41%, and Boeing 777-300 with 7.41%.
What is the most popular airline from Chicago O'Hare Intl Airport to Winnipeg?
momondo data reveals that the most frequently booked airline on the route from Chicago O'Hare Intl Airport to Winnipeg is United Airlines, representing 56% of all bookings. The subsequent popular airlines are WestJet at 28% and Air Canada at 15%.
Best airlines flying from Chicago O'Hare Intl Airport to Winnipeg
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Winnipeg with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $222 | Free Cancellation | Rating 7.2 3,446 reviews | |||
| PriceFrom $322 | Free Cancellation | Rating 7.1 11,764 reviews | |||
| PriceFrom $362 | Free Cancellation | Rating 7.4 10,352 reviews |
United Airlines Flights From Chicago O'Hare Intl Airport to Winnipeg
United Airlines is one of the most popular airlines flying from Chicago O'Hare Intl Airport to Winnipeg, operating 12 flights/week on average for this route. A good United Airlines flight deal for Chicago O'Hare Intl Airport to Winnipeg starts from $362 round-trip, up to an average price of $762. Our users have rated United Airlines at 7.4/10.
Air Canada Flights From Chicago O'Hare Intl Airport to Winnipeg
Across 11,758 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Chicago O'Hare Intl Airport to Winnipeg about 14 times each week, with ticket deals ranging from $322 to $780. Price data is based on momondo searches in the last 72 hours.
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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 allows you to filter the results for Chicago to Winnipeg flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Winnipeg?
Once all potential Chicago to Winnipeg flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Winnipeg right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Winnipeg flights. All you need is a valid email address and we will do the rest; it is that quick and easy.