How many flights from Calgary to Chicago are non-stop?

In the trailing 90 days, approximately 29.9% of flights from Calgary to Chicago have been non-stop. For flights that include stopovers, the median number of stopovers has been 2. This indicates that while direct options are available, a significant portion of routes involve at least one connection. Travelers should consider this when planning their journey.

How long does it take to fly from Calgary to Chicago?

The typical direct flight from Calgary to Chicago covers a distance of 2247 kilometers and takes approximately 3 hours and 37 minutes. For flights with one stop, the median travel time extends to about 8 hours and 57 minutes. This represents a significant difference in duration. Travelers should factor in the additional time when choosing a connecting flight.

How often do cheap flights from Calgary to Chicago come up?

Historically, cheap flights from Calgary to Chicago come up frequently. This route is classified as offering frequent opportunities for good deals. Travelers can often find competitive prices for this destination. This consistent availability makes it easier to plan a trip to Chicago from Calgary.

Flights From Calgary

To Chicago

Cheap Flights from Calgary to Chicago

Browse current best options from Calgary. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Calgary

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 14 days ago

406 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 2, 2026.)

Today’s best flight deals from Calgary to Chicago

Explore current cheapest deals departing from Calgary to Chicago

2026-10-06 – 2026-10-08
YYC - Chicago
71% AI deal score
CA$346
CA$307
Round trip
2026-09-21 – 2026-09-27
YYC - Chicago
68% AI deal score
CA$325
CA$314
Round trip
2026-09-20 – 2026-09-21
YYC - Chicago
68% AI deal score
CA$342
CA$328
Round trip
2026-09-21 – 2026-09-22
YYC - Chicago
68% AI deal score
CA$342
CA$329
Round trip
2026-10-14 – 2026-10-17
YYC - Chicago
81% AI deal score
CA$441
CA$333
Round trip
2026-09-20 – 2026-09-27
YYC - Chicago
67% AI deal score
CA$325
CA$339
Round trip
2026-10-16 – 2026-10-22
YYC - Chicago
67% AI deal score
CA$341
CA$340
Round trip
2026-12-01 – 2026-12-09
YYC - Chicago
84% AI deal score
CA$519
CA$346
Round trip
2026-09-10 – 2026-09-15
YYC - Chicago
67% AI deal score
CA$339
CA$349
Round trip
2026-10-15 – 2026-10-22
YYC - Chicago
67% AI deal score
CA$342
CA$349
Round trip

Calgary to Chicago: Overview

Insights for flights from Calgary to Chicago

Right now, only 4% of recent fares from Calgary to Chicago are classified as a good price. Fares for this route typically range from $259–$952, with a median price of $439. Current fares are above the typical level, indicating that prices are higher than usual for this route. New deals appear almost daily, suggesting frequent opportunities to find better prices.

When looking for cheap flights from Calgary to Chicago, the data indicates that February is typically the most affordable month to fly, with a median fare of $168. Following closely, January also offers lower prices, with a median fare of $203. Travelers might also find more budget-friendly options in November, where the median fare is $267.

A typical journey from Calgary to Chicago takes approximately 9h 29m, including connections. Most itineraries on this route connect at least once, which contributes to the overall travel time. Given that most flights are not direct, travelers should account for layovers when planning their trip.

The distance between Calgary and Chicago is 2247 km, categorizing this as a medium-haul flight. This distance means you will be traveling a significant but not extremely long distance. Most itineraries on this route connect at least once, with the median number of stopovers for connecting flights being 2.

How much is a round trip from Calgary to Chicago

Regular price: CA$300 - CA$657

Prices are currently below the regular range for flights from Calgary to Chicago.

The regular price range for flights from Calgary to Chicago is between 300 CAD and 657 CAD. The current lowest deal is 291 CAD with WestJet for travel from Oct 6-Oct 8.

now CA$291

Low CA$300

High CA$657

The cheapest time to fly from Calgary to Chicago

The cheapest month to fly from Calgary to Chicago is February, with a median price of $168. The most expensive month is October, with a median price of $746. Prices are generally lower from January to November.

February

Cheapest

Flights from CA$168

October

Most Expensive

Flights from CA$746

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Calgary to Chicago

WestJet

Last-minute flights going from Calgary to Chicago

Mon, Aug 10

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

United Airlines

CA$580

CA$482

One-way

Mon, Aug 10

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$906

CA$492

One-way

Mon, Aug 10

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

United Airlines

CA$764

CA$604

One-way

Mon, Aug 10

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$912

CA$625

One-way

Tue, Aug 11

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$912

CA$484

One-way

Tue, Aug 11

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$806

CA$484

One-way

Biggest price drops on these dates for flights from Calgary to Chicago

3 nights

Aug 11 - Aug 14

CA$912 → CA$484

47%

1 night

Aug 13 - Aug 14

CA$909 → CA$484

47%

2 nights

Aug 12 - Aug 14

CA$906 → CA$484

47%

4 nights

Aug 10 - Aug 14

CA$906 → CA$492

46%

Popular Airports to fly from Calgary to Chicago

Calgary - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Calgary to Chicago are above the typical level over the last 90 days.

📅 Best time to fly

February is historically cheapest at $168

Historically, February is the cheapest month to fly from Calgary to Chicago, with a median price of $168.

⏱️ Flight duration

Total flight time is 9h 29m

The median flight duration from Calgary to Chicago is 9 hours and 29 minutes.

✈️ Airlines & availability

Connecting flights are dominant for this route

Connecting flights make up 70.1% of routes, with a median of 2 stopovers when connecting.

🏆 Airline highlight

WestJet offers direct flights

WestJet is an airline that offers direct flights on the Calgary to Chicago route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Calgary to Chicago appear frequently, typically every 30 days.

Calgary main airports to depart from

Calgary International (YYC)

Cheapest

Calgary International is the most affordable option for flights from Calgary to Chicago.

📍 ~10 km from Calgary city center (reachable by car)

💸 Flights from ~$264

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago, offering a wide range of connections.

📍 ~20 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$264

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago via rail or road.

📍 ~135 km from Chicago (reachable by car or train)

💸 Flights from ~CA$584

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Calgary to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From YYC

Elite

Oct 09

Chicago, United States

79% AI deal score

$1,413

$882

Save $531

From YYC

Elite

Oct 09

Chicago, United States

79% AI deal score

$1,438

$912

Save $526

From YYC

Elite

Sep 25

Chicago, United States

76% AI deal score

$1,297

$877

Save $420

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Calgary to Chicago is typically between 28 and 59 days prior to departure. During this period, the average price for a flight has been around $294. Booking within 7-13 days of travel sees an average price of $329, while waiting until 0-6 days before departure can result in significantly higher average prices, around $689. Planning ahead by at least a month can lead to more favorable fares.

Across the trailing quarter, a good price for a flight from Calgary to Chicago is considered to be $259 or less. The median price for this route has been $439. Prices can vary, with 75% of flights historically costing $952 or less. Travelers aiming for a more budget-friendly trip should target fares around the $259 mark.

Historically, February has been the cheapest month to fly from Calgary to Chicago, with a median price of $168. January also offers competitive fares, with a median price of $203. While November has a median price of $267, the annual median price for this route is $439. Travelers looking for the lowest prices should consider flying in the winter months.

Calgary to Chicago: Overview

Insights for flights from Calgary to Chicago

How much is a round trip from Calgary to Chicago

Regular price: CA$300 - CA$657

Prices are currently below the regular range for flights from Calgary to Chicago.

The regular price range for flights from Calgary to Chicago is between 300 CAD and 657 CAD. The current lowest deal is 291 CAD with WestJet for travel from Oct 6-Oct 8.

now CA$291

Low CA$300

High CA$657

The cheapest time to fly from Calgary to Chicago

February

Cheapest

Flights from CA$168

October

Most Expensive

Flights from CA$746

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec