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

₹ 53,225 ₹ 1,17,000

Duration

2 h 42 m 16 h 30 m

Stops From Chicago

Departure From Chicago

6 am - 12 pm

₹ 64,765

12 pm - 6 pm

₹ 53,225

After 6 pm

₹ 56,083

Arrival at Winnipeg

6 am - 12 pm

₹ 56,083

12 pm - 6 pm

₹ 64,765

After 6 pm

₹ 53,225

Alliances & Airlines

Oneworld

()

SkyTeam

(3)

Star Alliance

(19)

Layover Airports

Layover Duration

55 m 12 h 0 m
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Ahmedabad to Baku- 4 flights a week!

Limited Period Offers

Chicago Airport Contact Info

Chicago Midway Intl
Address

Winnipeg Airport Contact Info

Winnipeg Intl
Address

Popular Hotels in Chicago

Premium Hotels Nearby Chicago

Chicago to Winnipeg Flight Schedule

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

Sorted By:
Departure
Duration
Arrival
Price
United Airlines

₹ 53,225

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

United Airlines UA 8308 | Operated By Air Canada

15:55

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 39 m

18:34

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA 8643 | Operated By Air Canada

20:00

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

21:44

Mon, 23 Feb 26

Winnipeg, Canada

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

₹ 53,225

Economy fully refundable

Fare offered by airline.

1 Piece
0 Kg
No airline cancellation fee
Free date change allowed
Free seats available

₹ 60,930

Air Canada

₹ 53,757

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

Air Canada AC 508

15:55

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 39 m

18:34

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 269

20:00

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

21:44

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 2 days before departure
Date Change Fee starting
₹ 9,075
Chargeable

₹ 53,757

Flex

Fare offered by airline.

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

₹ 61,530

Comfort

Fare offered by airline.

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

₹ 69,899

Latitude

Fare offered by airline.

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

₹ 1,00,116

Air Canada

₹ 56,083

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

Air Canada AC 4048 | Operated By United Airlines

18:00

Mon, 23 Feb 26

Terminal T2

Chicago, United States

02 h 17 m

21:17

Mon, 23 Feb 26

Montreal, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 371

08:05

Tue, 24 Feb 26

Montreal, Canada

03 h 10 m

10:15

Tue, 24 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 2 days before departure
Date Change Fee starting
₹ 9,075
Chargeable

₹ 56,083

Flex

Fare offered by airline.

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

₹ 63,891

Latitude

Fare offered by airline.

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

₹ 1,02,477

United Airlines

₹ 61,544

₹ 59,594

₹ 1,950 Instant Discount

Special Deal Pre-applied for you

Chicago to Winnipeg , 23 Feb

United Airlines UA 8474 | Operated By Air Canada

14:00

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 39 m

16:39

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA 8643 | Operated By Air Canada

20:00

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

21:44

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

Fare Option 1

Fare offered by airline.

1 Piece
0 Kg
Non-refundable fare
Not allowed
----

₹ 61,544₹ 59,594

Economy

Fare offered by airline.

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

₹ 61,849

Economy fully refundable

Fare offered by airline.

1 Piece
0 Kg
No airline cancellation fee
Free date change allowed
Free seats available

₹ 68,756

Air Canada

₹ 62,458

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

Air Canada AC 506

14:00

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 39 m

16:39

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 269

20:00

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

21:44

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 2 days before departure
Date Change Fee starting
₹ 9,075
Chargeable

₹ 62,458

Flex

Fare offered by airline.

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

₹ 69,433

Comfort

Fare offered by airline.

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

₹ 77,802

Latitude

Fare offered by airline.

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

₹ 1,00,116

Air Canada

More Timing Options

₹ 64,765

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

Air Canada AC 8900

08:00

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 40 m

10:40

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 269

20:00

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

21:44

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeMeal

Standard

Fare offered by airline.

1 Piece
0 Kg
Free cancellation allowed upto 2 days before departure
Date Change Fee starting
₹ 9,075
Chargeable

₹ 64,765

Flex

Fare offered by airline.

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

₹ 71,740

Comfort

Fare offered by airline.

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

₹ 80,109

Latitude

Fare offered by airline.

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

₹ 1,02,424

Delta Air Lines

₹ 76,101

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago-Midway to Winnipeg , 23 Feb

Delta Air Lines DL 3799

19:20

Mon, 23 Feb 26

Chicago-Midway, United States

01 h 40 m

21:00

Mon, 23 Feb 26

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL 3656

21:55

Mon, 23 Feb 26

Terminal T1

Minneapolis, United States

01 h 41 m

23:36

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeatMeal

Delta main classic

Fare offered by airline.

1 Piece
0 Kg
No airline cancellation fee
Free date change allowed
Free seats available
Get complimentary meals

₹ 76,101

Delta comfort classic

Fare offered by airline.

1 Piece
0 Kg
No airline cancellation fee
Free date change allowed
Free seats available
Get complimentary meals

₹ 78,427

Delta comfort extra

Fare offered by airline.

1 Piece
0 Kg
No airline cancellation fee
Free date change allowed
Free seats available
Get complimentary meals

₹ 90,512

United Airlines, Air Canada

₹ 86,564

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

United Airlines UA 8308 | Operated By Air Canada

15:55

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 39 m

18:34

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 269

20:00

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

21:44

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate Change

Economy|standard

Fare offered by airlines.

1 Piece
0 Kg
Non-refundable fare
Date Change Fee starting
₹ 6,640

₹ 86,564

Fare Option 1

Fare offered by airlines.

1 Piece
0 Kg
Non-refundable fare
Not allowed

₹ 98,376₹ 91,526

Economy fully refundable|flex

Fare offered by airlines.

1 Piece
0 Kg
Free cancellation allowed upto 2 days before departure
Free date change allowed

₹ 98,810

United Airlines, Air Canada

₹ 98,376

₹ 91,526

₹ 6,850 Instant Discount

Special Deal Pre-applied for you

Chicago to Winnipeg , 23 Feb

United Airlines UA 8474 | Operated By Air Canada

14:00

Mon, 23 Feb 26

Terminal T2

Chicago, United States

01 h 39 m

16:39

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

BAGGAGE : CHECK INCABIN

Information not available

Air Canada AC 267

17:50

Mon, 23 Feb 26

Terminal T1

Toronto, Canada

02 h 44 m

19:34

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate Change

Fare Option 1

Fare offered by airlines.

1 Piece
0 Kg
Non-refundable fare
Not allowed

₹ 98,376₹ 91,526

United Airlines, Delta Air Lines

₹ 97,358

Get Flat Rs 1200 OFF using code GODEALS | Get Flat 8% OFF using Axis Credit cards using GOAXISINTEMI

Chicago to Winnipeg , 23 Feb

United Airlines UA 237

18:10

Mon, 23 Feb 26

Terminal T1

Chicago, United States

01 h 36 m

19:46

Mon, 23 Feb 26

Terminal T1

Minneapolis, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL 3656

21:55

Mon, 23 Feb 26

Terminal T1

Minneapolis, United States

01 h 41 m

23:36

Mon, 23 Feb 26

Winnipeg, Canada

BAGGAGE : CHECK INCABIN

Information not available

FARES
Cabin bagCheck-inCancellationDate ChangeSeat

Economy|delta main classic

Fare offered by airlines.

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

₹ 97,358

Chicago to Winnipeg Flight Schedule

Planning to fly from Chicago to Winnipeg? Checking the latest Chicago to Winnipeg 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 Winnipeg 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 Chicago and Winnipeg
Leading airlines such as IndiGo, Air India, Vistara, SpiceJet, and Akasa Air offer regular flights between Chicago and Winnipeg. 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 ₹null (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 Chicago to Winnipeg 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.
Chicago Winnipeg Cheap Flights Fare Date
Lowest Airfare Today Rs 0
23 Feb
Cheapest Fare Within 30 Days Rs null
23 Feb
Cheapest Fare Within 90 Days Rs null
23 Feb
Cheapest Fare Within 365 Days Rs null
23 Feb
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