Cheap flights from Winnipeg to Chicago from $185
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Chicago departing on 10/30. 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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Fly from
Fly to
Route
Depart
Return
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 1/11
9:35 pm-10:50 am
2 stops14h 15m
Chicago O'Hare Intl
Wed 1/27
6:00 am-3:40 pm
1 stop8h 40m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 1/15
9:35 pm-10:50 am
2 stops14h 15m
Chicago O'Hare Intl
Wed 1/27
6:00 am-3:40 pm
1 stop8h 40m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 1/12
9:35 pm-10:50 am
2 stops14h 15m
Chicago O'Hare Intl
Wed 1/27
6:00 am-3:40 pm
1 stop8h 40m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Sat 10/31
6:00 am-6:16 pm
2 stops12h 16m
Chicago O'Hare Intl
Wed 11/4
7:35 pm-2:10 am
2 stops29h 35m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Tue 11/3
9:35 pm-5:30 pm
2 stops20h 55m
Chicago O'Hare Intl
Thu 12/3
6:21 am-12:45 am
1 stop17h 24m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Fri 1/15
7:00 am-10:50 am
1 stop28h 50m
Chicago O'Hare Intl
Tue 1/26
6:00 am-6:25 pm
2 stops35h 25m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Mon 1/11
7:00 am-10:50 am
1 stop28h 50m
Chicago O'Hare Intl
Tue 1/26
6:00 am-2:10 am
2 stops19h 10m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Thu 11/19
4:45 pm-10:18 pm
2 stops30h 33m
Chicago O'Hare Intl
Tue 11/24
5:25 am-6:25 pm
3 stops36h 00m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 12/23
2:15 pm-4:02 pm
Nonstop2h 47m
Chicago O'Hare Intl
Thu 12/24
10:00 am-1:52 pm
Nonstop2h 52m
WinnipegChicago
YWG Winnipeg - ORD Chicago O'Hare Intl
YWGORD
Winnipeg
Wed 12/23
2:15 pm-4:02 pm
Nonstop2h 47m
Chicago O'Hare Intl
Thu 12/24
6:50 am-9:57 pm
1 stop14h 07m
See travel insights to Chicago from
How to get the cheapest flight ticket from Winnipeg to Chicago
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 typical price of a round-trip flight between Winnipeg and Chicago?
Prices are currently low for flights on this route.
Typical prices usually range from $474 to $699.The lowest price recently found on this route was $426.
What is the cheapest month to fly to Chicago?
The month of November is, on average, the cheapest month to fly to Chicago from Winnipeg, with most prices found around $491. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Winnipeg to Chicago during February average around $523.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $612. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Chicago for around $750.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Winnipeg to Chicago during this time can be as low as $665. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $687.
What is the cheapest Winnipeg to Chicago flight route?
Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago flight prices
What cabin class options are available on Winnipeg to Chicago flights?
There are 4 cabin classes available to choose from on Winnipeg to Chicago 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 Winnipeg to Chicago flights?
You could potentially save up to 37% on your flight if you consider stops on a Winnipeg to Chicago flight.
How many flights depart from Winnipeg to Chicago on average per day?
As of October 2026, 7 flights take off from Winnipeg and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 52% of daily flights taking off in the afternoon.
How many flights depart from Winnipeg to Chicago on average per week?
As of October 2026, 54 flights take off from Winnipeg and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.
When to book flights from Winnipeg to Chicago
Cheap Winnipeg to Chicago (YWG to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago
Frequently asked questions about flying from Winnipeg to Chicago
How far is Winnipeg to Chicago by plane?
There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 1h 31m.
When did momondo last update prices for flights from Winnipeg Airport to Chicago?
Prices for flights from Winnipeg Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Winnipeg Airport to Chicago?
The number of operators available for flights from Winnipeg Airport to Chicago is 1 as of October 2026.
How old do you have to be to fly from Winnipeg Airport to Chicago?
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 Winnipeg Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Winnipeg to Chicago?
Based on momondo bookings for flights between Winnipeg and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 84.87% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 6.72%, Boeing 737 MAX 8 with 3.36%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 1.68%.
What is the most popular airline from Winnipeg to Chicago?
Based on momondo bookings for flights between Winnipeg and Chicago, the leading airline is United Airlines, making up 100% of the total bookings.
Best airlines flying from Winnipeg to Chicago
Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $517 | Free Cancellation | Rating 7.4 10,332 reviews | |||
| PriceFrom $563 | Free Cancellation | Rating 7.1 11,748 reviews |
United Airlines Flights From Winnipeg to Chicago
United Airlines flight deals from Winnipeg to Chicago start from $517 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $702 round-trip - but some users have found much cheaper deals with momondo.
Air Canada Flights From Winnipeg to Chicago
Air Canada (7.1/10 from 11,748 reviews) operates around 14 flights from Winnipeg to Chicago in any given week. The average Air Canada airfare for this route is around $1,130, with deals from around $563 rare but found on momondo. Referenced prices are for round-trip Winnipeg to Chicago flight searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Winnipeg to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Winnipeg.
Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Winnipeg which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Winnipeg to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.