- Regular
- StudentStudent 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
+ 1 more
One Way Price
Duration
Stops From Winnipeg
Departure From Winnipeg
₹ 29,260
₹ 26,176
₹ 26,972
₹ 31,469
Arrival at Chicago
₹ 26,972
₹ 26,176
₹ 27,469
Alliances & Airlines
Oneworld
()
SkyTeam
(15)
Star Alliance
(31)
Layover Airports
+ 1 more
Layover Duration
Further Flights From Winnipeg (YWG)
Further Flights From Chicago (CHI)
Top International Routes
Top International Cities

Grab Up to 20% OFF* on Flights!
18th Oct'25
Popular Hotels in Winnipeg
Hotels in Winnipeg
Premium Hotels Nearby Winnipeg
Popular Hotels in Chicago
Hotels in Chicago
Premium Hotels Nearby Chicago
Winnipeg to Chicago Flights, Fares @ ₹26176 + Flat Rs 1500 OFF
₹ 27,176
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
Air Canada AC 8331
06:15
Sat, 25 Oct 25
Winnipeg, Canada
02 h 12 m
07:27
Sat, 25 Oct 25
Calgary, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 4026 | Operated By United Airlines
12:38
Sat, 25 Oct 25
Calgary, Canada
03 h 32 m
17:10
Sat, 25 Oct 25
Terminal T1
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Standard
Fare offered by airline.
₹ 12,730
₹ 27,176₹ 26,176
Flex
Fare offered by airline.
₹ 36,381₹ 35,381
Latitude
Fare offered by airline.
₹ 84,247₹ 83,247
₹ 27,972
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
United Airlines UA 5389
07:00
Sat, 25 Oct 25
Winnipeg, Canada
02 h 31 m
09:31
Sat, 25 Oct 25
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic economy
Fare offered by airline.
₹ 9,480
₹ 27,972₹ 26,972
Economy
Fare offered by airline.
₹ 30,313₹ 29,313
Economy fully refundable
Fare offered by airline.
₹ 35,322₹ 34,322
Economy plus
Fare offered by airline.
₹ 35,925₹ 34,925
₹ 28,469
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
United Airlines UA 5623
16:25
Sat, 25 Oct 25
Winnipeg, Canada
02 h 35 m
18:00
Sat, 25 Oct 25
Denver, United States
BAGGAGE : CHECK INCABIN
Information not available
United Airlines UA 377
20:28
Sat, 25 Oct 25
Denver, United States
02 h 31 m
23:59
Sat, 25 Oct 25
Terminal T1
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic economy
Fare offered by airline.
₹ 9,480
₹ 28,469₹ 27,469
Economy
Fare offered by airline.
₹ 30,810₹ 29,810
Economy fully refundable
Fare offered by airline.
₹ 35,819₹ 34,819
Economy plus
Fare offered by airline.
₹ 54,320₹ 53,320
₹ 29,650
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
Delta Air Lines DL 6936 | Operated By WestJet
08:30
Sat, 25 Oct 25
Winnipeg, Canada
02 h 14 m
09:44
Sat, 25 Oct 25
Calgary, Canada
BAGGAGE : CHECK INCABIN
Information not available
Delta Air Lines DL 7137 | Operated By WestJet
12:15
Sat, 25 Oct 25
Calgary, Canada
03 h 28 m
16:43
Sat, 25 Oct 25
Terminal T5
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Delta main classic
Fare offered by airline.
₹ 29,650₹ 28,650
Delta main extra
Fare offered by airline.
₹ 33,901₹ 32,901
₹ 29,650
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
Air Canada AC 374
11:15
Sat, 25 Oct 25
Winnipeg, Canada
02 h 45 m
15:00
Sat, 25 Oct 25
Montreal, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 8965
18:35
Sat, 25 Oct 25
Montreal, Canada
02 h 31 m
20:06
Sat, 25 Oct 25
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic
Fare offered by airline.
₹ 29,650₹ 28,650
Standard
Fare offered by airline.
₹ 6,365
₹ 32,131₹ 31,131
Flex
Fare offered by airline.
₹ 37,441₹ 36,441
Comfort
Fare offered by airline.
₹ 41,686₹ 40,686
₹ 30,177
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago-Midway , 25 Oct
Delta Air Lines DL 3660
06:40
Sat, 25 Oct 25
Winnipeg, Canada
01 h 35 m
08:15
Sat, 25 Oct 25
Terminal T1
Minneapolis, United States
BAGGAGE : CHECK INCABIN
Information not available
Delta Air Lines DL 3543
08:50
Sat, 25 Oct 25
Terminal T1
Minneapolis, United States
01 h 40 m
10:30
Sat, 25 Oct 25
Chicago-Midway, United States
BAGGAGE : CHECK INCABIN
Information not available
Delta main classic
Fare offered by airline.
₹ 30,177₹ 29,177
Delta comfort classic
Fare offered by airline.
₹ 31,951₹ 30,951
Delta comfort extra
Fare offered by airline.
₹ 37,611₹ 36,611
₹ 30,260
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
Air Canada AC 256
05:00
Sat, 25 Oct 25
Winnipeg, Canada
02 h 25 m
08:25
Sat, 25 Oct 25
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 505
12:20
Sat, 25 Oct 25
Terminal T1
Toronto, Canada
01 h 54 m
13:14
Sat, 25 Oct 25
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic
Fare offered by airline.
₹ 30,260₹ 29,260
Standard
Fare offered by airline.
₹ 6,365
₹ 32,742₹ 31,742
Flex
Fare offered by airline.
₹ 38,051₹ 37,051
Comfort
Fare offered by airline.
₹ 42,297₹ 41,297
₹ 30,889
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
United Airlines UA 8444 | Operated By Air Canada
05:00
Sat, 25 Oct 25
Winnipeg, Canada
02 h 25 m
08:25
Sat, 25 Oct 25
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
United Airlines UA 8694 | Operated By Air Canada
12:20
Sat, 25 Oct 25
Terminal T1
Toronto, Canada
01 h 54 m
13:14
Sat, 25 Oct 25
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Economy
Fare offered by airline.
₹ 30,889₹ 29,889
Economy fully refundable
Fare offered by airline.
₹ 35,898₹ 34,898
₹ 32,131
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
Air Canada AC 4135 | Operated By United Airlines
07:00
Sat, 25 Oct 25
Winnipeg, Canada
02 h 31 m
09:31
Sat, 25 Oct 25
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Standard
Fare offered by airline.
₹ 6,365
₹ 32,131₹ 31,131
Flex
Fare offered by airline.
₹ 37,441₹ 36,441
Latitude
Fare offered by airline.
₹ 81,657₹ 80,657
₹ 32,469
₹ 1,000 Instant Discount
Use code GODEALS and get Rs 1310 discount per pax
Winnipeg to Chicago , 25 Oct
Air Canada AC 256
05:00
Sat, 25 Oct 25
Winnipeg, Canada
02 h 25 m
08:25
Sat, 25 Oct 25
Terminal T1
Toronto, Canada
BAGGAGE : CHECK INCABIN
Information not available
Air Canada AC 507
14:10
Sat, 25 Oct 25
Terminal T1
Toronto, Canada
01 h 54 m
15:04
Sat, 25 Oct 25
Terminal T2
Chicago, United States
BAGGAGE : CHECK INCABIN
Information not available
Basic
Fare offered by airline.
₹ 32,469₹ 31,469
Standard
Fare offered by airline.
₹ 6,365
₹ 34,951₹ 33,951
Flex
Fare offered by airline.
₹ 40,260₹ 39,260
Comfort
Fare offered by airline.
₹ 44,506₹ 43,506
Winnipeg Chicago Cheap Flights | Fare | Date |
---|---|---|
Lowest Airfare Today | Rs 0 | |
Cheapest Fare Within 30 Days | Rs 25638 |
25 Oct
|
Cheapest Fare Within 90 Days | Rs 25638 |
25 Oct
|
Cheapest Fare Within 365 Days | Rs 25638 |
25 Oct
|
Get cheap flights from Winnipeg to Chicago with Goibibo India
Q: Why choose Goibibo for your flight booking from Winnipeg to Chicago?
A: Goibibo lets you search and compare flight tickets to various destinations with just a click. There is a huge inventory of airlines for you to choose from, and exciting deals and discounts so that you can book your flight tickets at reasonable prices. You can always reach out to Goibibo customer care for any help.
Q: How to get a cheap flight ticket from Winnipeg to Chicago?
A: At Goibibio, it’s very simple to find cheap flights. • After entering the source and destination on the home page, you will get a list of flights. Click on the ‘Cheapest’ filter below to see the cheapest flights first. • You can also grab a cheap flight booking by setting up an alert for Winnipeg to Chicago flights. Goibibo will let you know whenever there is a price drop for your flight. What’s the best time to book a flight from Winnipeg to Chicago? • For a cheap domestic flight, try booking 3-4 weeks in advance. • For an international flight, you must book at least 7-8 weeks ahead for a better price. • You can also check the calendar view while booking to compare the prices for various dates. • Set up a price alert to get notified about the best prices for your flight from Winnipeg to Chicago.
Q: What should you keep in mind while booking a flight from Winnipeg to Chicago?
A: At Goibibo, you can compare flights from all major airlines at one go. Always keep an eye out for the best offers on your Winnipeg to Chicago flight. Plus, there are no hidden charges when you book a Winnipeg to Chicago flight on Goibibo.
Q: Is there any discount on a flight booking from Winnipeg to Chicago?
A: Goibibo always has discount offers running on flights. You can find many coupons on the website and app for your Winnipeg to Chicago booking. While booking, you can choose the best coupon from the list for an instant discount on your tickets.
Winnipeg to Chicago Flights
Searching for Winnipeg to Chicago cheap flights? Then, Goibibo is your one-stop destination to book Winnipeg to Chicago flight in a hassle-free manner. It is one such platform that brings forth all the options for you at one place and lets you book the most suitable flight with the best deals and offers.
There is no dearth of options when it comes to Winnipeg to Chicago Flight booking. Several budget and premium airlines fly on this route. You can easily check the Winnipeg to Chicago flight schedule on Goibibo. There are approximately 45 flights flying daily between Winnipeg and Chicago from early morning to late at night. Out of these Winnipeg to Chicago flight, 4 are non stop flights 41 are connecting flights. Air Canada, Delta Air Lines, United Airlines, WestJet are some major airlines that fly between Winnipeg and Chicago.
The lowest airfare of Winnipeg to Chicago flight is ₹26176 and the average airfare is 31752 depending on the airline, timings and availability. So, it is advisable to book domestic flights 2-3 weeks well in advance to avail minimum airfare. You can also book Winnipeg to Chicago cheap flights if you are flexible with your dates and timings.
You will board your Winnipeg to Chicago flight from the Winnipeg Intl and deboard it at .
You cannot only book Winnipeg to Chicago cheap flight tickets through Goibibo but can also do web check-in and track your flight status.
How to book a Winnipeg to Chicago flight ticket on Goibibo?
Booking flight tickets on Goibibo is very simple. For a Winnipeg to Chicago flight, check below:
How can I check the flight schedule for a Winnipeg to Chicago flight?
To check the Winnipeg to Chicago flight schedule,
How much baggage can I carry on my Winnipeg to Chicago flight?
Baggage allowance depends on the class of travel and airline. In the Winnipeg to Chicago Air India flight, 25 kg of checked baggage is allowed, while 8 kg of hand luggage is permitted. On the other hand, in all domestic IndiGo flights, a passenger can carry 7 kg of hand luggage and 15 kg of checked baggage.
Where will I board my flight at Winnipeg and deboard at Chicago?
When you have booked a Winnipeg to Chicago flight, you will board the flight at and de-board at .
How can I do web check-in for my upcoming Winnipeg at Chicago flight?
To avail the web check-in service and avoid queues at airports, you have to visit the official airline websites. Commonly, you have to fill the cities of departure and arrival, PNR number and last name to select your preferred seats and meals.
About Chicago
Chicago is a magnificent city located on Lake Michigan in Illinois in the United States. The city is known for its picturesque skyscrapers, sandy beaches, colourful art, jazz and pop music, happening downtown, and a thriving nightlife. The action does not stop here, Chicago is filled with iconic landmarks, neighbourhoods, world-class museums and giant parks that host several art and music festivals. The party culture of Chicago is known to everybody; from street fests to frenzy music parties, you can experience everything here.
Best Time to Visit
April to August and September to November is the best time to visit when the temperature is good and a variety of festivals take place. Book hotels in Chicago now for the early discounts.
Places to Visit
The Millenium Park is a giant park and overlooks the city’s magnificent skyline, Lincoln Park Conservatory and Zoo, Willis Tower, The Art Institute of Chicago, The Field Museum, the National Museum of Mexican Art, the Museum of Science and Industry and 360 Chicago Observation Deck are good places of interest to visit with children. Chicago is a sports fanatic. Head down to Wrigley Field to book tickets for a baseball match or plop down to a local bar to enjoy a pint of beer while watching the game. If you are interested in enjoying a sunny water ride and the sky-high buildings, then you can take a Shoreline Architecture River Cruise from the area of Navy Pier. Love swimming? Then head down to North Avenue Beach and Oak Street Beach to enjoy sandy beaches, volleyball sports and nearby restaurants. CityPass and GoChicago Card offer free admission to many attractions and discounts on shopping and restaurants.
Food and Restaurants
Chicago offers you a wide range of continental dishes that you might never have seen anywhere. You can either dine at Michelin five-star restaurants or chop down local dishes at small cafes and fast-food joints. The Magnificent Mile is a great place to shop and eat out. Lincoln Square Chinatown, Greektown, Uptown and Wicker Park has many cafes and restaurants. Chicago’s curated hot dogs, Italian Beef, thin-crust and deep dish pizza and pork chop sandwiches are iconic foods that you must try when in the city. The city has a reputation for its thriving music scene, be it jazz or symphony orchestra. Half Acre Beer Company, Metropolitan Brewing and Goose Island Brewpub are popular breweries to visit while Spy Bar and Blue Chicago and Primary lighten the mood with drinks and music.
Transportation
O’Hare International Airport (ORD) and Midway International Airport (MDW) are two airports that serve the city. While O’Hare is connected to several international and domestic flights, Midway serves mostly to Southwest and Delta flights and is closer to downtown. Cheap flight tickets from here to other popular cities can be booked online on Goibibo. Also, flight status & other details related to flight booking & air tickets can be easily accessed on it. So for the cheapest air tickets, it is recommended to book flights online. CTA trains, taxis and shuttle services are great options to reach the city centre from both the airports. Rail and road transport systems are excellently maintained and are great options to travel from far-away cities to Chicago. Amtrak operates on many routes in the US including routes in Chicago.
For getting around the city, the Chicago Transit Authority operates buses and trains for convenient travel. L train, taxis, rental cars, ride-sharing apps and water taxis are also other options to travel. Metra commuter trains is an easy and good option if you are travelling to the suburbs.
About Winnipeg
Frequently Asked Questions - Winnipeg to Chicago Flights
Q: What are the name and codes for Winnipeg and Chicago airports?
A: The name of Winnipeg airport is Winnipeg Intl and its code is YWG and name of Chicago Airport is , its code is .
Q: When does the first flight leave from Winnipeg to Chicago?
A: The first flight from Winnipeg to Chicago is Air Canada at 05:00.
Q: Which is the last flight on Winnipeg to Chicago route?
A: The last flight from Winnipeg to Chicago route is Air Canada at 18:30.
Q: What is today’s cheapest fare from Winnipeg to Chicago?
A: Today lowest airfare on Winnipeg to Chicago flight route is 0.
Q: How many flights fly from Winnipeg to Chicago on the daily basis?
A: Around 45 flights are flying daily from Winnipeg to Chicago. Out of which 4 are direct and 41 are connecting flights on this route. Some major airlines between this route are Air Canada, Delta Air Lines, United Airlines, WestJet.
Q: Which airline has maximum number for flights between Winnipeg to Chicago?
A: Out of 45 daily flights between Winnipeg to Chicago Air Canada has maximum 18 flights. After that Delta Air Lines has 15, United Airlines has 13, WestJet has 12 flights between Winnipeg to Chicago.
Q: Which is the cheapest flight from Winnipeg to Chicago in next 7 and next 30 days?
A: Cheapest flight in next 7 days on Winnipeg to Chicago route is at ₹25638. And in next 30 days lowest price on Winnipeg to Chicago route is ₹25638.
Q: Which are the most preferred airlines from Winnipeg to Chicago ?
A: Air Canada, Delta Air Lines, United Airlines, WestJet are the most preferred airlines on Winnipeg to Chicago flight route.
