FlyX aircraft connecting destinations across a global flight network

ORD to YWG

Chicago to Winnipeg Flights

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.

Fare checked before payment All fees shown upfront Transparent cancellation policy 24×7 booking support

Lowest fare₹35,067Porter Airlines

Fastest2h 54mgate to gate

Options found106flights on this route

Find your flight ORD YWG

Available Flights & Fares

Compare fares, timings and baggage. Pick the flight that suits your trip.

Mon, 26 Oct 2026 Prices in INR

106 flight options

Fares are checked again before payment.

Bank offer T&C apply

1% cashback

Flipkart Axis Bank Credit Card

Offer terms apply Eligible payments

View Offer & T&C Checked at payment

Flipkart Axis Bank Credit Card

Axis Bank Flipkart Axis Bank Credit Card

Bank offer T&C apply

Up to 10% rewards

Scapia Co-branded Credit Card

Offer terms apply Eligible payments

View Offer & T&C Checked at payment

CRED Bank offer

Bank offer T&C apply

Up to 5% NeuCoins

Tata Neu UPI Payments

Offer terms apply Eligible payments

View Offer & T&C Checked at payment

NeuCard Bank offer

Bank offer T&C apply

Unlimited 1% cashback

Airtel Axis Bank Credit Card

Offer terms apply Eligible payments

View Offer & T&C Checked at payment

Airtel Axis Bank Credit Card

Axis Bank Airtel Axis Bank Credit Card

Bank offer T&C apply

Unlimited 1% cashback

Amazon Pay ICICI Bank Credit Card

Offer terms apply Eligible payments

View Offer & T&C Checked at payment

Amazon Pay ICICI Bank Credit Card

ICICI Bank Amazon Pay ICICI Bank Credit Card

Bank offer T&C apply

5%* Reward Points

Online payments · PhonePe SBI Select Black Card

Offer terms apply Eligible payments

View Offer & T&C Checked at payment

PhonePe SBI Card

SBI Card PhonePe SBI Card

An eligible FlyX coupon saves first. STAY30 is only for eligible hotel bookings. Bank and card offers are additional and checked inside secure payment.

Offers shown here are run by the respective banks and card issuers and are applied by our payment gateway. FlyX is not affiliated with, endorsed by or a partner of these brands, and all names and logos belong to their owners.

Sort by

Porter Airlines

PD-2704

12:20

2026-10-26

CHICAGO (ORD)O Hare International

29H :50 M

2 Stops

YTZ · 21h 09m Toronto (YTZ), Canada

YOW · 2h 56m Ottawa (YOW), Canada

18:10

2026-10-27

Winnipeg (YWG)Winnipeg

Porter Airlines

PD-2706

18:20

2026-10-26

CHICAGO (ORD)O Hare International

23H :50 M

2 Stops

YTZ · 15h 09m Toronto (YTZ), Canada

YOW · 2h 56m Ottawa (YOW), Canada

18:10

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-8908

20:40

2026-10-26

CHICAGO (ORD)O Hare International

15H :09 M

1 Stop

YYZ · 10h 37m Toronto (YYZ), Canada

11:49

2026-10-27

Winnipeg (YWG)Winnipeg

AA

American Airlines

AA-3610

14:50

2026-10-26

CHICAGO (ORD)O Hare International

7H :07 M

1 Stop

YYZ · 2h 26m Toronto (YYZ), Canada

21:57

2026-10-26

Winnipeg (YWG)Winnipeg

Air Canada

AC-4986

07:03

2026-10-26

CHICAGO (ORD)O Hare International

6H :46 M

1 Stop

YYZ · 2h 13m Toronto (YYZ), Canada

13:49

2026-10-26

Winnipeg (YWG)Winnipeg

Air Canada

AC-508

16:30

2026-10-26

CHICAGO (ORD)O Hare International

17H :35 M

2 Stops

YYZ · 3h 50m Toronto (YYZ), Canada

YUL · 7h 30m Montreal (YUL), Canada

10:05

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-4407

11:05

2026-10-26

CHICAGO (ORD)O Hare International

23H :19 M

1 Stop

YYZ · 18h 32m Toronto (YYZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-8904

12:50

2026-10-26

CHICAGO (ORD)O Hare International

22H :59 M

1 Stop

YYZ · 18h 27m Toronto (YYZ), Canada

11:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-8550

13:55

2026-10-26

CHICAGO (ORD)O Hare International

20H :29 M

1 Stop

YTZ · 15h 53m Toronto (YTZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-8550

13:55

2026-10-26

CHICAGO (ORD)O Hare International

21H :54 M

1 Stop

YTZ · 17h 18m Toronto (YTZ), Canada

11:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-8550

13:55

2026-10-26

CHICAGO (ORD)O Hare International

23H :54 M

1 Stop

YTZ · 19h 18m Toronto (YTZ), Canada

13:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-5014

15:47

2026-10-26

CHICAGO (ORD)O Hare International

20H :02 M

1 Stop

YYZ · 15h 15m Toronto (YYZ), Canada

11:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-5014

15:47

2026-10-26

CHICAGO (ORD)O Hare International

22H :02 M

1 Stop

YYZ · 17h 15m Toronto (YYZ), Canada

13:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-508

16:30

2026-10-26

CHICAGO (ORD)O Hare International

19H :19 M

1 Stop

YYZ · 14h 50m Toronto (YYZ), Canada

11:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-508

16:30

2026-10-26

CHICAGO (ORD)O Hare International

21H :19 M

1 Stop

YYZ · 16h 50m Toronto (YYZ), Canada

13:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-4994

18:17

2026-10-26

CHICAGO (ORD)O Hare International

17H :32 M

1 Stop

YYZ · 12h 45m Toronto (YYZ), Canada

11:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-4994

18:17

2026-10-26

CHICAGO (ORD)O Hare International

19H :32 M

1 Stop

YYZ · 14h 45m Toronto (YYZ), Canada

13:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-8908

20:40

2026-10-26

CHICAGO (ORD)O Hare International

17H :09 M

1 Stop

YYZ · 12h 37m Toronto (YYZ), Canada

13:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-5138

21:21

2026-10-26

CHICAGO (ORD)O Hare International

16H :28 M

1 Stop

YYZ · 12h 01m Toronto (YYZ), Canada

13:49

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-5138

21:21

2026-10-26

CHICAGO (ORD)O Hare International

13H :03 M

1 Stop

YYZ · 8h 36m Toronto (YYZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-4986

07:03

2026-10-26

CHICAGO (ORD)O Hare International

14H :11 M

1 Stop

YYZ · 9h 38m Toronto (YYZ), Canada

21:14

2026-10-26

Winnipeg (YWG)Winnipeg

Air Canada

AC-4986

07:03

2026-10-26

CHICAGO (ORD)O Hare International

16H :56 M

1 Stop

YYZ · 12h 23m Toronto (YYZ), Canada

23:59

2026-10-26

Winnipeg (YWG)Winnipeg

Recommended hotels in Winnipeg

Stay options near the arrival city for the same travel date.

No hotel result available

Open hotel search to check current stays for this destination.

Air Canada

AC-8904

12:50

2026-10-26

CHICAGO (ORD)O Hare International

21H :34 M

1 Stop

YYZ · 17h 02m Toronto (YYZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-5014

15:47

2026-10-26

CHICAGO (ORD)O Hare International

18H :37 M

1 Stop

YYZ · 13h 50m Toronto (YYZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-508

16:30

2026-10-26

CHICAGO (ORD)O Hare International

17H :54 M

1 Stop

YYZ · 13h 25m Toronto (YYZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

Air Canada

AC-4994

18:17

2026-10-26

CHICAGO (ORD)O Hare International

16H :07 M

1 Stop

YYZ · 11h 20m Toronto (YYZ), Canada

10:24

2026-10-27

Winnipeg (YWG)Winnipeg

No flights match the selected filters. Clear filters or open full search.

Airfare Highlights

From flights departing on Mon, 26 Oct 2026.

Lowest fare ₹35,067 Porter Airlines 12:20

Earliest departure ₹60,061 Delta Air Lines 06:20

Shortest duration ₹47,272 United Airlines 09:29

Night 00:00-05:59 No option Open full search for more

Morning 06:00-11:59 ₹43,610 Air Canada at 07:03

Afternoon 12:00-17:59 ₹35,067 Porter Airlines at 12:20

Evening 18:00-23:59 ₹35,067 Porter Airlines at 18:20

Departure & Arrival Airport Details

Chicago (ORD)

O Hare International

USA

Winnipeg (YWG)

Winnipeg

Canada

Flights shown for 26 Oct 2026. View all flights opens the complete search result.

Smart travel dates

Holidays and peak dates for Winnipeg

Fares and hotel rates usually run higher around these dates. Booking earlier or moving your trip by a day or two often costs less.

12OctThanksgivingMondayPeak
11NovArmistice DayWednesdayPeak
11NovRemembrance DayWednesdayPeak
25DecChristmas DayFridayPeak
26DecBoxing DaySaturdayPeak
01JanNew Year's 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 Chicago to Winnipeg

Ways to make this trip that you can book on FlyX, compared by price and journey time.

OptionFromJourney timeAvailability

Non-stop flight Fastest₹47,2722h 54m2 flights

Connecting flight₹35,067Longer, includes a stop104 options

5 airlines operate this route.

Road distance and coach duration are approximate estimates from the air distance, not a timetable.

Airlines flying from Chicago to Winnipeg

Compare fares, stops, baggage and refundability across the airlines flying this route.

Air Canada Flights

from ₹37,52972 flights

Fares from: ₹37,529
Non-stop: 1 in these results
Departures: 72 in the list above

United Airlines Flights

from ₹47,07622 flights

Fares from: ₹47,076
Non-stop: 1 in these results
Departures: 22 in the list above

Delta Air Lines Flights

from ₹50,9269 flights

Fares from: ₹50,926
Non-stop: None in these results
Departures: 9 in the list above

Route Overview & Flight Facts

Fastest flight duration	2h 54m · United Airlines
First departure of the day	06:20 · Delta Air Lines
Last departure of the day	21:21 · Air Canada
Flight options found	106
Direct / non-stop options	2
Airport codes	Chicago–ORD, Winnipeg–YWG

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 Mon, 26 Oct found 106 flight options, 2 of them non-stop. The first flight leaves around 06:20 and the last around 21:21. The fastest flight takes about 2h 54m.

Morning vs Evening Departure Fares

Lowest fare by departure window: Afternoon from ₹35,067, Evening from ₹35,067, Morning from ₹43,610. 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 Chicago–Winnipeg 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 Chicago to Winnipeg 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 Chicago to Winnipeg 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 Chicago to Winnipeg dates shown on this page, the lowest fare is on a Monday at ₹35,067. This can change from week to week.

How far is Chicago from Winnipeg 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 ORD to YWG?

Yes. 2 non-stop flights are listed on this page for Chicago to Winnipeg. Use the Stops filter to see only those.

Which airlines fly Chicago to Winnipeg?

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 Chicago to Winnipeg?

The quickest non-stop Chicago to Winnipeg flight on this page takes about 2h 54m. Journeys with a stop take longer, since the total includes the layover.

What is the cheapest Chicago to Winnipeg flight fare?

The lowest Chicago to Winnipeg fare on this page is ₹35,067. Fares on the same dates run up to ₹95,450, depending on airline, timing and fare type. Airline prices change often, so search your dates for the current fare.

What time do Chicago to Winnipeg flights depart?

On the dates shown here, the first departure is around 06:20 and the last around 21:21, local time at Chicago. 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 ORD–YWG, 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 Mon, 26 Oct 2026.

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.

For payment, ticket issuance or a change request, see FlyX support. About FlyX.

Canada travel guide for Indian travellers

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.

Read the Canada travel guide

What to Expect When Booking Your Flight

The ORD to YWG 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 Chicago to Winnipeg airfare, in 30 days and in 90 days

Cheapest Fare	Fare	Date	Airline	Departure
Lowest Airfare	₹35,067	26/10/2026	Porter Airlines	12:20
Cheapest Airfare Within 30 Days	₹34,366	07/11/2026	Porter Airlines	12:20
Cheapest Airfare Within 90 Days	₹33,314	06/01/2027	Porter Airlines	12:20

Book Chicago to Winnipeg Flight Tickets on FlyX

FlyX lists each Chicago to Winnipeg 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.

Chicago to Winnipeg Flight Schedule and Timing

The search for these dates returned 106 flight options, 2 of them non-stop. The first departure from Chicago is at 06:20 and the last is at 21:21. Flights leave from O Hare International and land at Winnipeg.

Flight Route Details & Analysis

Flight Details	Information
Route	Chicago to Winnipeg
Flight Duration	2h 54m - 30h 23m
Airport Codes	Chicago - ORD, Winnipeg - YWG
Total Flights Available	106 flights2 direct104 with layovers
First Flight Departure	Departs at 06:20
Last Flight Departure	Departs at 21:21
Early Morning Flights (12 AM - 8 AM)	12 flights0 direct12 with layovers
Morning Flights (8 AM - 12 PM)	27 flights2 direct25 with layovers
Afternoon Flights (12 PM - 4 PM)	40 flights0 direct40 with layovers
Evening Flights (4 PM - 8 PM)	15 flights0 direct15 with layovers
Night Flights (8 PM - 12 AM)	12 flights0 direct12 with layovers

Airport Information & Terminals

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.

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.