C$ 221 Find Cheap Flights from Calgary to Chicago – Compare and Save

Among airlines operating Calgary to Chicago O'Hare Intl Airport flights:

• United Airlines: offers free seat selection
• WestJet: offers extra legroom; offers free seat selection
• American Airlines: offers extra legroom; offers free seat selection
• Air Canada: offers free seat selection
• Delta: offers extra legroom; offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

3 airlines operate flights between Calgary and Chicago O'Hare Intl Airport. The airlines offering direct flights on this route include:

• United Airlines
• American Airlines
• WestJet

Flights from Calgary to Chicago O'Hare Intl Airport usually depart from Calgary (YYC) and arrive at Chicago O'Hare Intl (ORD).

Here are some options for this route, based on selected ticket types and cabin classes:

• WestJet: a carry-on bag and a checked bag in Economy Class
• American Airlines: a carry-on bag and a checked bag in Economy Class
• Air Canada: a carry-on bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route, and airline, so travellers should check the fare details before booking.

Four cabin classes are available on flights from Calgary to Chicago O'Hare Intl Airport:

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

On this route, layover flights are cheaper than direct options on average. Layover fares average C$ 304 round-trip via Denver Intl (DEN), compared to C$ 462 for direct.

There is no standard. Checked bag policies vary by airline on this route. Most carriers charge C$ 30–C$ 138 for the first checked bag in economy. Premium fares and elite status bookings typically include a free checked bag.

The Boeing 737-800 family is used most often on this route, operated mainly by United Airlines and Air Canada. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

One-stop flights from Calgary to Chicago O'Hare Intl Airport most commonly connect through:

• Toronto Pearson Intl (YYZ) – 60% of one-stop connections
• Salt Lake City (SLC) – 11% of one-stop connections
• Ottawa (YOW) – 11% of one-stop connections
• Denver Intl (DEN) – 7% of one-stop connections

Toronto Pearson Intl (YYZ) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 17% on the Calgary to Chicago O'Hare Intl Airport route. Monday is the cheapest departure day at C$ 404 round-trip on average, while Thursday is the most expensive at C$ 481, a difference of C$ 77. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Afternoon is the busiest departure period on Calgary to Chicago O'Hare Intl Airport flights, with 100% leaving in that window. Morning departures account for 0%, Evening flights for 0%, and Night flights for 0%.

Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, River North, and Grant Park. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

These are the earliest and latest flight times available from Calgary to Chicago O'Hare Intl Airport:

• Earliest: departs at 7:00 am and lands at 10:37 am
• Latest: departs at 1:59 pm and lands at 5:36 pm.

The flight takes about 3h 37m.

Last-minute fares on this route – booked within 2 weeks of departure – run 21% above the route average of C$ 461. Book 22 weeks before departure for the lowest fares.

A direct flight from Calgary to Chicago O'Hare Intl Airport takes 3h 37m, covering 3,577 km.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 349 to C$ 1,820. That means the highest observed fare was about 5x higher than the lowest one.

One-way fares from Calgary to Chicago O'Hare Intl Airport are currently lower than usual. Average one-way flight prices are about C$ 227, which is 20% below the typical average for this route.

Flying via Toronto Pearson Intl (YYZ) gives the shortest average 1-stop total travel time at 8h 08m, compared with 8h 10m via Montreal Pierre Elliott Trudeau Intl (YUL) and 8h 28m via Minneapolis St Paul (MSP).

Chicago O'Hare Intl Airport is 1 hour ahead of Calgary (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around C$ 23 for economy cars. Top options include:
· Routes Car & Truck Rentals
· Europcar
· Hertz
· Dollar
· Ace

Round-trip flights from Calgary to Chicago O'Hare Intl Airport range from C$ 344 to C$ 596, with an average of C$ 461 over the past 12 months. Anything below C$ 344 counts as a good deal.

Two airlines offer in-flight Wi-Fi on Calgary to Chicago O'Hare Intl Airport flights:

• • WestJet
• • American Airlines