Cheap flights from Calgary to Chicago Midway

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.
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

How to get the best price from Calgary to Chicago Midway?

Depending on when you travel and how far in advance you book, fares between Calgary and Chicago can differ a lot.

Pick a travel date to see today’s available fares.

Search engines like Jetcost can highlight price changes in just seconds. For example, some users find better prices by flying on one day of the week over another — try several searches to spot the cheapest day.

Which airports near Calgary or Chicago offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

  • Airports in Calgary: Only Calgary is currently operating.
  • Airports in Chicago: 3 options available in Chicago - Midway, O'Hare, Rockford.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Flights from Calgary to Chicago - Midway

Plan smarter: flights from Calgary to Chicago Midway

Find the flight that fits your plans with Jetcost. You can filter results by stops, agencies, budget, time of day, and airline — all in one search.

Other popular destinations

Travelers flying to United States also checked out: Atlanta, Los Angeles, Miami, New York City, Orlando.

Comparing offers from multiple agencies helps you find the best price for the same route. You can also spot exclusive deals from individual airlines right in the results list.
Frequently Asked Questions

Frequently asked questions about flights from Calgary to Chicago Midway.

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

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Calgary to Chicago Midway.

How far is Calgary from Chicago?

Calgary is about 1396 mi from Chicago.

What are the airports in Chicago?

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

What are the airports in Calgary?

Calgary has one airport: Calgary.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Atlanta, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Calgary to Chicago?

The best time to book a flight from Calgary to Chicago is 2 months in advance, while the worst time is 9 weeks in advance.

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

This information is not available at the moment.

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

This information is not available at the moment.

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

This information is not available at the moment.