$176 Find Cheap Flights from Calgary to Chicago - Compare and Save

These are the earliest and latest flight times available from Calgary to Chicago:

• Earliest: departs at 1:37 pm and lands at 5:15 pm
• Latest: departs at 3:19 pm and lands at 6:57 pm.

The flight takes about 3h 38m.

Three cabin classes are available on flights from Calgary to Chicago:

• Economy Class
• Business Class
• First Class

A nonstop flight from Calgary to Chicago takes 3h 38m, covering 1,397 miles.

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.

Round-trip flights from Calgary to Chicago range from $269 to $443, with an average of $350 over the past 12 months. Anything below $269 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 22% above the $350 route average. Book 24 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $223 round-trip via Dallas/Fort Worth (DFW), compared to $352 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $21–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Afternoon is the busiest departure period on Calgary to Chicago flights, with 100% of flights leaving in that window. Morning departures account for 0%, evening flights for 0%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $302 to $1,534. That means the highest observed fare was about 5x higher than the lowest one.

Two airlines offer in-flight Wi-Fi on Calgary to Chicago flights:

• American Airlines
• WestJet

Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

One-way fares from Calgary to Chicago are currently lower than usual. Average one-way flight prices are about $200, which is 8% below the typical average for this route.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Ace
• Dollar

Near Chicago Midway Airport (MDW) — daily rates averaging $84:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Flights from Calgary to Chicago usually depart from Calgary (YYC) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

One-stop flights from Calgary to Chicago most commonly connect through:

• Toronto Pearson Intl (YYZ) - 57% of one-stop connections
• Minneapolis St Paul (MSP) - 14% of one-stop connections
• Salt Lake City (SLC) - 10% of one-stop connections
• Ottawa (YOW) - 10% of one-stop connections

Yes. Flexible dates can save you up to 19% on flights from Calgary to Chicago. Monday is the cheapest departure day at $309 round-trip on average, while Thursday is the most expensive at $381, a difference of $72.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

2 airlines operate flights between Calgary and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 7h 10m, compared with 7h 48m via Minneapolis St Paul (MSP) and 8h 09m via Toronto Pearson Intl (YYZ).

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Among airlines operating Calgary to Chicago flights:

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

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

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

• American Airlines: a cabin bag and a checked bag in Economy Class
• Air Canada: a cabin bag and a checked bag in Economy Class
• WestJet: a cabin bag and a checked bag in Economy Class

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