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

In the trailing 90 days, approximately 29.9% of flights from Calgary to Chicago were non-stop. For flights that include stopovers, travelers typically encounter a median of 2 connections. This indicates that while direct options are available, a significant portion of routes involve at least one stop.

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 has a median duration of 3 hours and 37 minutes. Flights with one stop, however, typically take significantly longer, with a median duration of 8 hours and 57 minutes. Travelers should consider these differences when planning their journey.

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

Historically, cheap flights from Calgary to Chicago are classified as frequent. This suggests that opportunities for finding more affordable fares on this route arise regularly. Travelers can typically expect to see favorable pricing appear with some consistency across the trailing quarter.

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 6 days ago

402 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 19, 2026.)

Today’s best flight deals from Calgary to Chicago

Explore current cheapest deals departing from Calgary to Chicago

Round trip

Sort by: Cheapest

August 28 - August 31

Cheapest

Best

Earliest

YYC - Chicago

CA$421

CA$294

Round trip

August 29 - September 1

YYC - Chicago

CA$416

CA$314

Round trip

October 19 - October 24

Best

YYC - Chicago

CA$446

CA$327

Round trip

October 20 - October 24

Best

YYC - Chicago

CA$446

CA$327

Round trip

October 18 - October 24

Best

YYC - Chicago

CA$439

CA$327

Round trip

October 26 - October 28

YYC - Chicago

CA$363

CA$330

Round trip

September 2 - September 6

YYC - Chicago

CA$342

CA$334

Round trip

October 2 - October 11

YYC - Chicago

CA$325

CA$337

Round trip

September 4 - September 19

YYC - Chicago

CA$383

CA$341

Round trip

September 2 - September 8

YYC - Chicago

CA$327

CA$342

Round trip

Unlock all 500+ flight deals to Chicago and get alerts when great deals appear

Calgary to Chicago: Overview

Insights for flights from Calgary to Chicago

Only 4% of recent fares from Calgary to Chicago were classified as a good price, indicating that finding deals on this route can be challenging. Right now, fares for cheap flights from Calgary to Chicago are above the typical level, with prices typically ranging from $259–$952 and a median of $439. New deals appear almost daily, so setting up a price alert could be beneficial for tracking fare changes.

When is the cheapest time to fly from Calgary to Chicago? The data indicates that February is the most affordable month, with a median fare of just $168. Following closely, January offers a median fare of $203, and November is also a good option with a median fare of $267. These months present the best opportunities for travelers seeking lower prices.

A typical journey from Calgary to Chicago takes approximately 9h 29m, including connections. This duration reflects that most itineraries on this route involve at least one stop. Given that most itineraries connect at least once, travelers should account for this when planning their trip.

The distance between Calgary and Chicago is 2247 km, classifying this as a medium-haul route. This means you can expect a journey that is longer than a short domestic flight but typically shorter than intercontinental travel. Most itineraries 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$341 - CA$640

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

The regular price range for flights from Calgary to Chicago is CAD 341 to CAD 640. The current lowest deal is CAD 280 with WestJet, for travel from Aug 28-Aug 31.

now CA$280

Low CA$341

High CA$640

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, Jul 13

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$715

CA$464

One-way

Tue, Jul 14

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$706

CA$451

One-way

Tue, Jul 14

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

United Airlines

CA$715

CA$463

One-way

Tue, Jul 14

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$711

CA$473

One-way

Thu, Jul 16

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

United Airlines

CA$715

CA$463

One-way

Fri, Jul 17

⌛ Last-Minute

YYC - Chicago

Calgary (YYC) - Chicago (ORD)

CA$665

CA$464

One-way

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

2 nights

Jul 25 - Jul 27

CA$888 → CA$471

47%

5 nights

Dec 9 - Dec 14

CA$712 → CA$366

49%

3 nights

Nov 23 - Nov 26

CA$625 → CA$374

40%

3 nights

Oct 23 - Oct 26

CA$570 → CA$365

36%

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 at a median of $439.

📅 Best time to fly

Fly in February for the best prices

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

⏱️ Flight duration

Typical 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

Only 29.9% of recent flights are direct, with connecting flights typically having 2 stopovers.

🏆 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 are frequent, appearing often in a 30-day window.

Calgary main airports to depart from

Calgary International (YYC)

Cheapest

Calgary International is a great choice for flights from Calgary to Chicago, offering competitive prices.

📍 ~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 many connections from Calgary.

📍 ~25 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$264

Chicago Midway International (MDW)

Chicago Midway International Airport is a convenient option for travelers flying from Calgary to Chicago.

📍 ~15 km from Chicago city center (reachable by car, train, and bus).

💸 Flights from ~$294

Chicago Rockford International (RFD)

Chicago Rockford International Airport serves the wider Chicago area for flights from Calgary.

📍 ~120 km from Chicago city center (reachable by car and bus).

💸 Flights from ~$390

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

📍 ~135 km from Chicago (reachable by rail or car). Requires travel across state lines into Wisconsin.

💸 Flights from ~CA$589

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International is the second largest airport in Michigan with a robust domestic network.

📍 ~220 km from Chicago (reachable by car). Significant driving distance of over 2 hours.

💸 Flights from ~CA$490

Dane County Regional (MSN)

Dane County Regional is a reliable regional hub with efficient operations and good amenities.

📍 ~200 km from Chicago (reachable by car). Travel time from downtown Chicago typically exceeds 2 hours.

💸 Flights from ~CA$632

South Bend International (SBN)

South Bend International is geographically the closest alternative airport to the Chicago metro area.

📍 ~130 km from Chicago (reachable by rail or car).

💸 Flights from ~CA$558

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~230 km from Chicago (reachable by car). One of the furthest recommendations from the origin.

💸 Flights from ~CA$524

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

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From YYC

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Aug 13

Chicago, United States

85% AI deal score

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Sep 02

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Aug 07

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Aug 31

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83% AI deal score

$1,300

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Aug 12

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$1,318

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Aug 28

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Jul 18

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Jun 25

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82% AI deal score

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Oct 09

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Jul 25

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Jul 02

Chicago, United States

81% AI deal score

$1,603

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Jul 09

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80% AI deal score

$1,537

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Sep 02

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79% AI deal score

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Jul 23

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Jul 29

Chicago, United States

79% AI deal score

$1,497

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Sep 03

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$1,056

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Sep 05

Chicago, United States

74% AI deal score

$1,459

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Chicago, United States

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$1,459

$1,088

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Chicago, United States

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$1,561

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74% AI deal score

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Nov 03

Chicago, United States

74% AI deal score

$1,218

$896

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Sep 12

Chicago, United States

74% AI deal score

$1,217

$976

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Nov 08

Chicago, United States

74% AI deal score

$1,288

$1,006

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Dec 01

Chicago, United States

74% AI deal score

$1,364

$1,045

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Chicago, United States

74% AI deal score

$1,364

$1,045

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Sep 22

Chicago, United States

73% AI deal score

$1,545

$1,146

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Sep 05

Chicago, United States

73% AI deal score

$1,640

$1,208

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Sep 25

Chicago, United States

73% AI deal score

$1,660

$1,221

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From YYC

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Nov 12

Chicago, United States

73% AI deal score

$1,748

$1,312

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Jul 30

Chicago, United States

73% AI deal score

$1,263

$976

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Jul 30

Chicago, United States

73% AI deal score

$1,294

$1,003

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From YYC

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Sep 18

Chicago, United States

73% AI deal score

$1,070

$763

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Sep 14

Chicago, United States

73% AI deal score

$1,074

$763

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Sep 15

Chicago, United States

73% AI deal score

$1,099

$763

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Chicago, United States

73% AI deal score

$1,074

$763

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Sep 18

Chicago, United States

73% AI deal score

$1,069

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,069

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Sep 18

Chicago, United States

73% AI deal score

$1,070

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,073

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Sep 14

Chicago, United States

73% AI deal score

$1,092

$763

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Sep 15

Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,073

$763

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From YYC

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Sep 18

Chicago, United States

73% AI deal score

$1,071

$763

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Sep 18

Chicago, United States

73% AI deal score

$1,083

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Chicago, United States

73% AI deal score

$1,070

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,073

$763

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From YYC

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Chicago, United States

73% AI deal score

$1,074

$763

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From YYC

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Sep 14

Chicago, United States

73% AI deal score

$1,070

$763

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From YYC

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Sep 14

Chicago, United States

73% AI deal score

$1,074

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From YYC

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Sep 18

Chicago, United States

73% AI deal score

$1,065

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From YYC

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Sep 05

Chicago, United States

72% AI deal score

$1,459

$1,208

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Chicago, United States

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Sep 05

Chicago, United States

72% AI deal score

$1,503

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From YYC

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Chicago, United States

72% AI deal score

$1,459

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Sep 06

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72% AI deal score

$1,506

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72% AI deal score

$1,459

$1,211

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72% AI deal score

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72% AI deal score

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Sep 15

Chicago, United States

72% AI deal score

$1,487

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Sep 09

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72% AI deal score

$1,487

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72% AI deal score

$1,485

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72% AI deal score

$1,510

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Nov 07

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72% AI deal score

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72% AI deal score

$1,357

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Jun 24

Chicago, United States

72% AI deal score

$1,502

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From YYC

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Aug 23

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72% AI deal score

$959

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72% AI deal score

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72% AI deal score

$959

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72% AI deal score

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72% AI deal score

$959

$756

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72% AI deal score

$959

$756

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Aug 23

Chicago, United States

72% AI deal score

$958

$759

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72% AI deal score

$959

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Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Calgary to Chicago is typically 28-59 days before departure. During this period, the average price for a flight is around $294. Booking within 0-6 days of departure, however, sees prices rise significantly, with an average of $689. Planning your trip within the recommended 28-59 day window can lead to more favorable pricing.

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 historically stands at $439. Prices can go higher, with 75% of observed fares being $952 or less. Travelers aiming for a more economical trip should target prices around or below the good price threshold.

Historically, the cheapest months to fly from Calgary to Chicago are February, with a median price of $168, and January, with a median price of $203. November also offers competitive pricing, with a median of $267. These months typically present opportunities for more affordable travel compared to the annual median price of $439 for this route.

Related routes

Consider alternative routes from Calgary

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