One Way
Fare Type:
  • Regular
  • Student
    Student Fare

    Only students above 12 years of age are eligible for special fares and/or additional baggage allowances. Carrying valid student ID cards and student visas (where applicable) is mandatory, else the passenger may be denied boarding or asked to pay for extra baggage.

Popular Filters

One Way Price

₹ 24,592 ₹ 82,000

Duration

2 h 35 m 16 h 0 m

Stops From Winnipeg

Departure From Winnipeg

Before 6 am

₹ 28,471

6 am - 12 pm

₹ 24,592

12 pm - 6 pm

₹ 24,592

Arrival at Chicago

Before 6 am

₹ 28,621

6 am - 12 pm

₹ 31,299

12 pm - 6 pm

₹ 24,592

After 6 pm

₹ 24,592

Alliances & Airlines

Oneworld

()

SkyTeam

(5)

Star Alliance

(12)

Layover Airports

Layover Duration

58 m 10 h 30 m
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Ahmedabad to Baku- 4 flights a week!

Limited Period Offers

Winnipeg Airport Contact Info

Winnipeg Intl
Address

Chicago Airport Contact Info


Address

Popular Hotels in Chicago

Premium Hotels Nearby Chicago

Winnipeg to Chicago Flight Schedule

Plan a trip like never before. Keep yourself informed with updated flight schedules for all airlines between Winnipeg - Chicago on Goibibo. Avail yourself with fit to pocket airfares for all major airlines. Also check Chicago Winnipeg Flight Schedule online.

Sorted By:
Departure
Duration
Arrival
Price
Porter Airlines

More Timing Options

₹ 27,582

₹ 24,592

₹ 2,990 Instant Discount

Special Deal Pre-applied for you

Winnipeg to Chicago , 6 Apr

Porter Airlines PD 424

06:00

Mon, 6 Apr 26

Winnipeg, Canada

02 h 32 m

09:32

Mon, 6 Apr 26

Terminal T3

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Porter Airlines PD 6034 | Operated By American Airlines

11:40

Mon, 6 Apr 26

Terminal T3

Toronto, Canada

01 h 55 m

12:35

Mon, 6 Apr 26

Terminal T3

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeatMeal

Fare Option 1

Fare offered by airline.

Not allowed
0 Kg
Non-refundable fare
Not allowed
Chargeable
No Meals

₹ 27,582₹ 24,592

Air Canada

₹ 28,419

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

Air Canada AC 372

08:15

Mon, 6 Apr 26

Winnipeg, Canada

02 h 47 m

12:02

Mon, 6 Apr 26

Montreal, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 8481

13:20

Mon, 6 Apr 26

Montreal, Canada

02 h 35 m

14:55

Mon, 6 Apr 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Basic

Fare offered by airline.

Not allowed
0 Kg
Free cancellation allowed upto 44 days before departure
Not allowed
Chargeable

₹ 28,419

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Date Change Fee starting
₹ 6,640
Chargeable

₹ 30,855

Flex

Fare offered by airline.

1 Piece
1 Piece
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 36,084

Comfort

Fare offered by airline.

1 Piece
2 Pieces
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 40,268

Air Canada

₹ 28,471

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

Air Canada AC 256

05:30

Mon, 6 Apr 26

Winnipeg, Canada

02 h 30 m

09:00

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 406

10:00

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

01 h 21 m

11:21

Mon, 6 Apr 26

Montreal, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 8481

13:20

Mon, 6 Apr 26

Montreal, Canada

02 h 35 m

14:55

Mon, 6 Apr 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Date Change Fee starting
₹ 13,280
Chargeable

₹ 28,471

Flex

Fare offered by airline.

1 Piece
1 Piece
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 36,834

Comfort

Fare offered by airline.

1 Piece
2 Pieces
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 41,018

Latitude

Fare offered by airline.

1 Piece
2 Pieces
Free cancellation allowed upto 44 days before departure
Free date change allowed
Get complimentary meals

₹ 80,745

Delta Air Lines

More Timing Options

₹ 28,621

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

Delta Air Lines DL 3871

11:55

Mon, 6 Apr 26

Winnipeg, Canada

01 h 34 m

13:29

Mon, 6 Apr 26

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL 1306

16:26

Mon, 6 Apr 26

Terminal T1

Minneapolis, United States

01 h 36 m

18:02

Mon, 6 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeatMeal

Delta main basic

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Date Change Fee starting
₹ 6,575
----
Get complimentary meals

₹ 28,621

Delta main classic

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available
Get complimentary meals

₹ 31,057

Delta comfort classic

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available
Get complimentary meals

₹ 32,800

Delta comfort extra

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available
Get complimentary meals

₹ 37,683

United Airlines

₹ 28,621

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

United Airlines UA 5486

08:45

Mon, 6 Apr 26

Winnipeg, Canada

02 h 43 m

10:28

Mon, 6 Apr 26

Denver, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA 2258

19:17

Mon, 6 Apr 26

Denver, United States

02 h 37 m

22:54

Mon, 6 Apr 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

Basic economy

Fare offered by airline.

Not allowed
0 Kg
Non-refundable fare
Date Change Fee starting
₹ 9,895
Chargeable

₹ 28,621

Economy

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Free date change allowed
Free seats available

₹ 31,057

Economy fully refundable

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available

₹ 36,286

Economy plus

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Free date change allowed
Free seats available

₹ 58,152

United Airlines

₹ 28,621

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

United Airlines UA 5486

08:45

Mon, 6 Apr 26

Winnipeg, Canada

02 h 43 m

10:28

Mon, 6 Apr 26

Denver, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA 1488

20:52

Mon, 6 Apr 26

Denver, United States

02 h 37 m

00:29

Tue, 7 Apr 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

Basic economy

Fare offered by airline.

Not allowed
0 Kg
Non-refundable fare
Date Change Fee starting
₹ 9,895
Chargeable

₹ 28,621

Economy

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Free date change allowed
Free seats available

₹ 31,057

Economy fully refundable

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available

₹ 36,286

Economy plus

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Free date change allowed
Free seats available

₹ 61,371

Air Canada

₹ 31,299

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

Air Canada AC 256

05:30

Mon, 6 Apr 26

Winnipeg, Canada

02 h 30 m

09:00

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 3495 | Operated By United Airlines

10:15

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

02 h 03 m

11:18

Mon, 6 Apr 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Date Change Fee starting
₹ 6,640
Chargeable

₹ 31,299

Flex

Fare offered by airline.

1 Piece
1 Piece
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 36,528

Latitude

Fare offered by airline.

1 Piece
2 Pieces
Free cancellation allowed upto 44 days before departure
Free date change allowed
Get complimentary meals

₹ 80,439

United Airlines

₹ 31,299

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

United Airlines UA 8444 | Operated By Air Canada

05:30

Mon, 6 Apr 26

Winnipeg, Canada

02 h 30 m

09:00

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA 3473

10:15

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

02 h 03 m

11:18

Mon, 6 Apr 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

Economy

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Free date change allowed
Free seats available

₹ 31,299

Economy fully refundable

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available

₹ 36,528

Air Canada

₹ 34,439

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

Air Canada AC 264

13:30

Mon, 6 Apr 26

Winnipeg, Canada

02 h 26 m

16:56

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 8913

18:30

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

01 h 55 m

19:25

Mon, 6 Apr 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Basic

Fare offered by airline.

Not allowed
0 Kg
Free cancellation allowed upto 44 days before departure
Not allowed
Chargeable

₹ 34,439

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Date Change Fee starting
₹ 6,640
Chargeable

₹ 36,880

Flex

Fare offered by airline.

1 Piece
1 Piece
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 42,104

Comfort

Fare offered by airline.

1 Piece
2 Pieces
Free cancellation allowed upto 44 days before departure
Free date change allowed
Chargeable

₹ 46,288

United Airlines

₹ 36,880

Get Flat Rs 1350 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Winnipeg to Chicago , 6 Apr

United Airlines UA 8193 | Operated By Air Canada

13:30

Mon, 6 Apr 26

Winnipeg, Canada

02 h 26 m

16:56

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA 8094 | Operated By Air Canada

18:30

Mon, 6 Apr 26

Terminal T1

Toronto, Canada

01 h 55 m

19:25

Mon, 6 Apr 26

Terminal T2

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

Economy

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Free date change allowed
Free seats available

₹ 36,880

Economy fully refundable

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 44 days before departure
Free date change allowed
Free seats available

₹ 42,104

Winnipeg to Chicago Flight Schedule

Planning to fly from Winnipeg to Chicago? Checking the latest Winnipeg to Chicago flight schedule helps you plan your journey with ease. With multiple airlines offering frequent connections between these two cities, passengers can choose flights that best suit their timing, budget, and comfort preferences.

Flights and Duration
Flights between and operate throughout the day, giving travelers flexible options for departure and arrival. The average flight duration typically ranges between one to three hours for most domestic routes, depending on the distance and weather conditions. Morning flights are ideal for business travelers who need to reach Chicago early, while afternoon and evening flights cater to those who prefer a more relaxed schedule.
Many airlines operate daily services on this route, ensuring a seamless and convenient travel experience. You can find both non-stop and connecting flights based on your preferences.

Airlines Operating Between Winnipeg and Chicago
Leading airlines such as IndiGo, Air India, Vistara, SpiceJet, and Akasa Air offer regular flights between Winnipeg and Chicago. Each carrier provides a unique flying experience — from premium cabin options to budget-friendly fares. Depending on your travel needs, you can choose from early morning departures, mid-day flights, or late-night schedules.
If you're looking for the most affordable option, the cheapest fare on this route currently starts at ₹27582 (subject to change). Prices may vary based on travel dates, seat availability, and booking time.

How to Check the Latest Flight Schedule
Flight timings and availability can change due to operational or weather factors. It's always best to verify the Winnipeg to Chicago flight schedule before booking. Most online platforms display live schedules, allowing you to compare airlines, departure times, and ticket prices in one place.
To get the best deals, try booking your flight at least a few weeks in advance. Early reservations often come with lower fares and better seat options, especially during busy travel seasons or weekends.

Travel Tips for a Smooth Journey
  • Arrive early: Reach at least two hours before departure to complete check-in and security formalities.
  • Stay updated: Always recheck your flight status on the day of travel for any delays or gate changes.
  • Compare options: Consider flight duration, layovers, and airline reputation when booking.
  • Pack smart: Follow baggage allowance guidelines to avoid last-minute hassles.
Winnipeg Chicago Cheap Flights Fare Date
Lowest Airfare Today Rs 0
Cheapest Fare Within 30 Days Rs 27582
06 Apr
Cheapest Fare Within 90 Days Rs 27582
06 Apr
Cheapest Fare Within 365 Days Rs 27582
06 Apr
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