Compare fares, departure times, stops and baggage details for this route, then open the full search when you are ready to check current availability and complete booking.
YWGORDFri, 30 Oct
Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support
Lowest fareC$415American Airlines
Fastest2h 35mgate to gate
Options found102flights on this route
Find your flightYWG → ORD
Available Flights & Fares
Compare fares, timings and baggage. Pick the flight that suits your trip.
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
PublishNDC
0 Pieces 7 KG
C$626
Flight DetailsYWG to ORD - 7H :13 M
Baggage InfoCheck-in 0 Pieces - Cabin 7 KG
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
C$814
Flight DetailsYWG to ORD - 7H :13 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Air Canada
AC-3920
14:15
2026-10-30
Winnipeg (YWG)Winnipeg
2H :35 M
Non Stop
16:50
2026-10-30
CHICAGO (ORD)O Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 1 Pieces
C$660
Flight DetailsYWG to ORD - 2H :35 M
Baggage InfoCheck-in 0 Pieces - Cabin 1 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Type
Non Refundable
Fare Type
PublishNDC
0 Pieces 7 KG
C$660
Flight DetailsYWG to ORD - 2H :35 M
Baggage InfoCheck-in 0 Pieces - Cabin 7 KG
Fare RulesNon-refundable fare. Final rules are verified before booking.
Air Canada
AC-258
07:15
2026-10-30
Winnipeg (YWG)Winnipeg
10H :28 M
1 Stop
YYZ
· 5h 40m Toronto (YYZ), Canada
17:43
2026-10-30
CHICAGO (ORD)O Hare International
Non Refundable 8 Seat Left Economy
Check-in: 0 PiecesCabin: 0 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 0 Pieces
C$660
Flight DetailsYWG to ORD - 10H :28 M
Baggage InfoCheck-in 0 Pieces - Cabin 0 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
Air Canada
AC-258
07:15
2026-10-30
Winnipeg (YWG)Winnipeg
12H :43 M
1 Stop
YYZ
· 8h 05m Toronto (YYZ), Canada
19:58
2026-10-30
CHICAGO (ORD)O Hare International
Non Refundable 9 Seat Left Economy
Check-in: 0 PiecesCabin: 0 Pieces
Type
Non Refundable
Fare Type
Publish
0 Pieces 0 Pieces
C$660
Flight DetailsYWG to ORD - 12H :43 M
Baggage InfoCheck-in 0 Pieces - Cabin 0 Pieces
Fare RulesNon-refundable fare. Final rules are verified before booking.
No flights match the selected filters. Clear filters or open full search.
Airfare Highlights
From flights departing on Fri, 30 Oct 2026.
Lowest fareC$415American Airlines07:00
Earliest departureC$523Air Canada05:15
Shortest durationC$617United Airlines14:15
Night
00:00-05:59
C$523Air Canada at 05:15Morning
06:00-11:59
C$415American Airlines at 07:00Afternoon
12:00-17:59
C$610Delta Air Lines at 17:40Evening
18:00-23:59
C$692Air Canada at 19:05
Departure & Arrival Airport Details
Winnipeg (YWG)
Winnipeg
Canada
Chicago (ORD)
O Hare International
USA
Flights shown for 30 Oct 2026. View all flights opens the complete search result.
Smart travel dates
Holidays and peak dates for Chicago
Fares and hotel rates usually run higher around these dates. Booking earlier or moving your trip by a day or two often costs less.
Busiest periods: Summer travel (15 Jun – 31 Aug), Holiday season (18 Dec – 02 Jan).
12OctColumbus DayMondayPeak
12OctColumbus DayMondayPeak
12OctIndigenous Peoples' DayMondayPeak
11NovVeterans DayWednesdayPeak
26NovThanksgiving DayThursdayPeak
25DecChristmas DayFridayPeak
Fixed-date national holidays. Festivals that follow the lunar calendar shift each year and are not listed here, so check the exact date for your travel year.
Compare your journey
How to travel Winnipeg to Chicago
Ways to make this trip that you can book on FlyX, compared by price and journey time.
OptionFromJourney timeAvailabilityAction
Non-stop flight Fastest₹41,8072h 35m2 flights
Connecting flight₹28,096Longer, includes a stop100 options
5 airlines operate this route.
Road distance and coach duration are approximate estimates from the air distance, not a timetable.
Airlines flying from Winnipeg to Chicago
Compare fares, stops, baggage and refundability across the airlines flying this route.
AI
Air Canada Flights
from C$52361 flights
Fares from
C$523
Non-stop
1 in these results
Departures
61 in the list above
UN
United Airlines Flights
from C$61727 flights
Fares from
C$617
Non-stop
1 in these results
Departures
27 in the list above
DE
Delta Air Lines Flights
from C$61011 flights
Fares from
C$610
Non-stop
None in these results
Departures
11 in the list above
Route Overview & Flight Facts
Fastest flight duration
2h 35m · United Airlines
First departure of the day
05:15 · Air Canada
Last departure of the day
19:05 · Air Canada
Flight options found
102
Direct / non-stop options
2
Airport codes
Winnipeg–YWG, Chicago–ORD
Fares and timings are indicative. The exact price is confirmed with the airline when you search.
Flight Schedule, Timings & Airfare Insights
Daily Flight Schedule & Travel Duration
The search for Fri, 30 Oct found 102 flight options, 2 of them non-stop. The first flight leaves around 05:15 and the last around 19:05. The fastest flight takes about 2h 35m.
Morning vs Evening Departure Fares
Lowest fare by departure window: Morning from C$415, Night from C$523, Afternoon from C$610, Evening from C$692. These observations do not predict the cheapest departure window on other dates.
Cheapest Airfare & Best Time to Book
Search your travel dates to compare current fares. Prices change with airline seat availability.
One-Way vs Round-Trip Fare Comparison
Compare the complete cost and conditions of both options for your dates. A round-trip can have different fare and change rules from two one-way tickets. One booking may contain multiple airline PNRs; confirm baggage transfer and connection protection for separate tickets.
Online Web Check-In & Boarding Pass
Check the operating airline’s opening time and check-in deadline for each sector. Seat charges and availability depend on your fare. Use the airline reference and the links on Web Check-in.
How to Book Cheap Flights on FlyX
1
Enter your travel details
Choose one-way or round-trip, pick your dates and travellers in the search form above.
2
Compare search results
Sort or filter the Winnipeg–Chicago results by price, departure time, stops and airline.
3
Open the fare choices
Check baggage allowance and refundability for each fare type before continuing.
4
Review the final price
Review the refreshed supplier fare, coupon saving and selected payment-method fee before you pay.
5
Pay securely
UPI, cards, net banking and wallets supported; payment and ticket issuance have separate statuses. If issuance is pending, follow the booking status; the confirmed ticket is sent after issuance.
Destination & City Travel Guide
About Chicago
Chicago’s downtown Loop puts Millennium Park, the Art Institute and the Riverwalk within a manageable area. The lakefront creates a second axis for walking, while neighbourhoods farther out need transit time of their own. Passengers landing at O’Hare may be changing flights or visiting relatives in the wider region, so check whether an overnight hotel is near the airport or downtown. The CTA Blue Line runs from the airport into the city and avoids the road congestion that can affect a taxi.
Read more about Chicago
Tips for travellers from India
The Loop is useful for the Art Institute, Millennium Park and central rail links, while a hotel near O’Hare serves an early flight or suburban appointment. These bases are a substantial distance apart. The CTA Blue Line reaches the airport from downtown, but passengers arriving at Terminal 5 first need the airport connection to the main rail-access area. The airport train and an intercity rail departure from Union Station are separate arrangements.
Air India uses Terminal 5. United domestic flights and international departures use Terminal 1, while many international arrivals are processed through Terminal 5, so an onward connection can involve a building change. In the city, pair the Art Institute with Millennium Park rather than crossing to a distant neighbourhood between them. The Riverwalk offers another central route, while the lakefront extends far beyond the downtown section. The Obama Presidential Center opened to the public in June 2026 in Jackson Park, creating a museum outing on the South Side rather than another stop beside the Loop. Plan that visit as its own district trip. A river architecture cruise also has a specific departure dock, which should be matched to the walking route. Choose between a museum-heavy day and a longer lakefront walk before booking several timed attractions.
Best time to visit Chicago
May to June or September to October, about 12–25°C, for river and lake walks.
Places to visit in Chicago
Millennium ParkArt Institute of ChicagoChicago RiverwalkNavy PierMuseum CampusDevon Avenue
How to reach Chicago
By Air: O’Hare International Airport (ORD) is about 27 km northwest of downtown Chicago; the CTA Blue Line takes about 45 minutes to the Loop. Taxis and booked cars also operate.
By Rail: Chicago Union Station serves intercity trains; the CTA Blue Line links O’Hare with downtown.
By Road: Airport taxis and app-based cars use expressways; intercity coaches use downtown stops.
What to do in Chicago
Walk from Millennium Park to the Art Institute.
Follow the Chicago Riverwalk.
Take an architecture cruise on the Chicago River.
Explore the lakefront around Museum Campus.
Chicago airport information
O’Hare International Airport (ORD). Air India operates from O’Hare Terminal 5. United uses Terminal 1 for domestic flights and international departures, while international arrivals without preclearance generally use Terminal 5.
Why Book Your Flight with FlyX?
Compare the available Winnipeg to Chicago options by total price, stops, baggage and fare conditions. Search your dates for current availability, then review traveller details and the final price before paying.
Payment confirmation and ticket issuance are separate steps. If your booking is awaiting a PNR or ticket, follow its status and contact FlyX support when you need help. Your issued ticket contains the airline reference and itinerary. Change and cancellation charges depend on the purchased fare and any separately disclosed service fee.
Fare checked before paymentCoupon eligibility checkedBooking status trackingBooking support
Exclusive Flight Offers & Promo Coupons
Coupon code
Offer
Max saving
FLYX20
Up to 20% Off on Flights
₹1,500
Check coupon eligibility and the final discount on the review page before you pay. View full terms.
Frequently Asked Questions
Is it worth booking Winnipeg to Chicago flights in advance?
There is no guaranteed cheapest booking window. Compare your planned dates early, check nearby dates and consider baggage, connection time and change conditions as well as price. On the Winnipeg to Chicago dates shown on this page, the lowest fare is on a Friday at C$415. This can change from week to week.
How far is Winnipeg from Chicago by air?
The flying distance depends on the routing the airline selects. The flight cards above show duration and stop details for each result.
Are there non-stop flights from YWG to ORD?
Yes. 2 non-stop flights are listed on this page for Winnipeg to Chicago. Use the Stops filter to see only those.
Which airlines fly Winnipeg to Chicago?
Air Canada, United Airlines and Delta Air Lines are listed on this route for the dates shown here. Fares, baggage allowance and refund rules differ by airline and by fare type, so compare the fare conditions and not only the headline price.
How long is the flight from Winnipeg to Chicago?
The quickest non-stop Winnipeg to Chicago flight on this page takes about 2h 35m. Journeys with a stop take longer, since the total includes the layover.
What is the baggage allowance on Winnipeg to Chicago flights?
Allowance is set by the airline and the fare you pick, not by the route. Fares on this page include 2 Pieces. Cabin baggage is counted separately, and the exact allowance for the fare you choose is shown in the fare conditions before payment.
What is the cheapest Winnipeg to Chicago flight fare?
The lowest Winnipeg to Chicago fare on this page is C$415. Fares on the same dates run up to C$2,066, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.
What time do Winnipeg to Chicago flights depart?
On the dates shown here, the first departure is around 05:15 and the last around 19:05, local time at Winnipeg. Use the departure-time filter on the results above to narrow to a morning, afternoon or evening slot.
Why does the price change after clicking Book Now?
Airline seat inventory and fares change continuously. Selecting Book Now runs a live fare verification with the airline so the price you approve is the price you pay. If it has moved, you see the new figure before any payment.
Before you book this route
Check the airport codes YWG–ORD, local departure and arrival dates, and every connecting airport. Connections can have different document and baggage requirements from your final destination.
Where these fares come from
The fares, durations, stops and baggage shown here come from real airline search results for this route. They are examples for the dates on this page, not a full timetable and not a locked price. Run a search to see what is available for your own dates.
Fares shown are for departures on .
Check official travel requirements
Confirm passport, visa and transit rules for your nationality and full itinerary with the relevant government and operating airline. IATA travel-document information explains why requirements vary.
Planning more than the flight? Our Canada guide covers the visa process for Indian passport holders, best time to go, how long to plan for, and which places are worth the days you have. Cities, Rockies and family visits.
The YWG to ORD cards above show selected flight options. Airline prices and seat availability can move quickly, so the final fare is rechecked in the booking flow.
Before you book
Compare nearby dates
The date strip opens the complete search result for the route and selected date.
Use filters
Shortlist by price, stops, departure time and refundable fare preference.
Check fare choices
Continue to Booking opens the verified fare choices, including baggage and refundability, before review.
Lowest Winnipeg to Chicago airfare, in 30 days and in 90 days
Cheapest Fare
Fare
Date
Airline
Departure
Lowest Airfare
C$415
30/10/2026
American Airlines
07:00
Cheapest Airfare Within 30 Days
C$407
07/11/2026
American Airlines
07:00
Cheapest Airfare Within 90 Days
C$394
06/01/2027
American Airlines
07:00
Book Winnipeg to Chicago Flight Tickets on FlyX
FlyX lists each Winnipeg to Chicago flight in these results with its fare, departure time, stops, layover airport and baggage, so you can compare air tickets side by side. To find a cheap ticket, sort by price and check what baggage the fare includes. The fare is checked with the airline again before you pay.
Winnipeg to Chicago Flight Schedule and Timing
The search for these dates returned 102 flight options, 2 of them non-stop. The first departure from Winnipeg is at 05:15 and the last is at 19:05. Flights leave from Winnipeg and land at O Hare International.
Flight Route Details & Analysis
Flight Details
Information
Route
Winnipeg to Chicago
Flight Duration
2h 35m - 30h
Airport Codes
Winnipeg - YWG, Chicago - ORD
Total Flights Available
102 flights2 direct100 with layovers
First Flight Departure
Departs at 05:15
Last Flight Departure
Departs at 19:05
Early Morning Flights (12 AM - 8 AM)
33 flights0 direct33 with layovers
Morning Flights (8 AM - 12 PM)
30 flights0 direct30 with layovers
Afternoon Flights (12 PM - 4 PM)
26 flights2 direct24 with layovers
Evening Flights (4 PM - 8 PM)
13 flights0 direct13 with layovers
Night Flights (8 PM - 12 AM)
No flights in this time slot
Airport Information & Terminals
YWG: Winnipeg International airport. Winnipeg International airport transfer should be matched to the exact hotel, suburb or meeting area. Rail can work well for light luggage, but late arrivals, winter weather and family baggage often make a direct cab or booked transfer easier.
ORD: Chicago airport system. Chicago flights commonly use O'Hare or Midway. O'Hare is a huge hub with rail access; Midway can be easier for some city-side trips. Winter weather and traffic should be part of the booking decision.
✈
Preparing your flight
Please wait while we confirm the live fare and seat availability with the airline.
Winnipeg to Chicago
Loading current fare types...
Try on mobile
Get the FlyX app
Live flight fares, instant e-tickets and trip updates, right on your phone.
Winnipeg
O Hare International
