Flights from Chicago Midway to Winnipeg

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.

Cheap Chicago Midway - Winnipeg flight offers

Find cheap flight tickets and last-minute flight deals from Chicago Midway to Winnipeg

DELTA
Wed, 11/11 (MDW) Chicago -> (YWG) Winnipeg
DELTA
Thu, 19/11 (YWG) Winnipeg -> (MDW) Chicago
Price found 15 days ago
from $868
DELTA
Tue, 10/11 (MDW) Chicago -> (YWG) Winnipeg
DELTA
Tue, 17/11 (YWG) Winnipeg -> (MDW) Chicago
Price found 2 days ago
from $1,142

Info about flights from Chicago Midway to Winnipeg

Some useful info about flights from Chicago Midway to Winnipeg to help you plan your next trip

Best price last 15 days $868
Average flight duration 3h 24m
Average number of flights per week 1
First flight time 06:00
Last flight time 19:13
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Top airlines on the route Chicago Midway - Winnipeg

Airlines providing flights to Winnipeg from Chicago Midway

DELTA
DELTA
WestJet
WestJet

How much is a ticket from Chicago Midway to Winnipeg?

Flight prices from Chicago to Winnipeg change depending on demand and time of booking.

$868 is the best price recorded in the last 15 days.

Flying at off-peak hours — such as early morning or late evening — can help you save. Also, the best deals tend to appear in the weeks leading up to departure.

Planning flights between Chicago and Winnipeg? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

  • Airports in Chicago: 3 airports are listed in Chicago - Midway, O'Hare, Rockford.
  • Airports in Winnipeg: Only Winnipeg is currently available.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

Flights from Chicago - Midway to Winnipeg

Plan your journey from Chicago Midway to Winnipeg with ease

Use Jetcost to tailor your search — direct or connecting flights, round-trip or one-way, filtered by airline, price, travel time, or agency.

Other popular destinations

Exploring options in Canada? These cities are trending: Calgary, Montreal, Quebec, Toronto, Vancouver.

Flight availability can change quickly — refresh the results if you’ve been away from the page for a while.
Frequently Asked Questions

Frequently asked questions about flights from Chicago Midway to Winnipeg.

How much does an airline ticket from Chicago Midway to Winnipeg cost?

The lowest price recorded in the last 15 days for a flight from Chicago Midway to Winnipeg is $868.

How far is Chicago from Winnipeg?

Chicago is about 1163 km from Winnipeg.

What are the airports in Winnipeg?

Winnipeg has one airport: Winnipeg.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Canada?

The most popular cities in Canada according to our users' searches are: Calgary, Montreal, Quebec, Toronto, Vancouver.

When should I book a flight from Chicago to Winnipeg?

The best time to book a flight from Chicago to Winnipeg is 1 month in advance, while the worst time is 1 week in advance.

What is the cheapest month to fly from Chicago to Winnipeg?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Winnipeg?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Winnipeg?

For flights from Chicago to Winnipeg Sunday is on average the cheapest day to fly, while Tuesday is the most expensive day to fly.