Cheap flights from Calgary to Chicago

Round-trip
1 adult
Economy
From?
To?
Wed 10/20
Wed 10/27

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Calgary to Chicago.
View current United States travel restrictions

Flight information for Calgary to Chicago
(YYC to CHI)

Find info about flight duration, direct flights, and airports for your flight from Calgary to Chicago
Best Price Found$379The best flight deal from Calgary to Chicago found on momondo in the last 72 hours is $379
Fastest flight time5h 56mThe fastest flight from Calgary to Chicago takes 5h 56m
Direct flightsNoneThere are no direct flights from Calgary to Chicago. Popular non-direct routes for this connection are Calgary Airport - Chicago O'Hare Intl Airport and Calgary Airport - Chicago Midway Airport.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Calgary to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

January

The cheapest time of year to fly to Chicago from Calgary is January. Most expensive is December

What is the cheapest day to depart Calgary for Chicago?

Wednesday

The cheapest day of the week is typically Wednesday. The most expensive is typically Friday

When is the cheapest time to fly from Calgary to Chicago?

in the evening

Calgary to Chicago flights are approximately 56% more expensive in the morning than in the evening

What is the cheapest airline that flies to Chicago from Calgary?

American Airlines

American Airlines, United Airlines, and WestJet are the most popular carriers operating from Calgary to Chicago

What is the cheapest Calgary to Chicago flight route?

Calgary - Chicago O'Hare Intl

Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago flight prices

How far in advance should you book Calgary to Chicago flights?

0 days before

The cheapest time to buy a flight from Calgary to Chicago is approximately 0 days to departure


Easily compare round-trip flights from Calgary to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Calgary to Chicago by changing tabs
Multiple Airlines
Nov 22
YYC10:27 amCalgary
13h 39m
2 stops
ORD12:06 amChicago O'Hare Intl
Nov 29
ORD4:12 pmChicago O'Hare Intl
18h 25m
2 stops
YYC10:37 amCalgary
Air Canada
Nov 22
YYC1:15 amCalgary
7h 46m
1 stop
ORD9:01 amChicago O'Hare Intl
Nov 27
ORD3:45 amChicago O'Hare Intl
8h 38m
1 stop
YYC12:23 pmCalgary
American Airlines
Nov 10
YYC7:53 amCalgary
7h 23m
1 stop
ORD3:16 pmChicago O'Hare Intl
Nov 14
ORD12:15 amChicago O'Hare Intl
7h 52m
1 stop
YYC8:07 amCalgary
Delta
Jan 8
YYC3:15 amCalgary
6h 52m
2 stops
MDW10:07 amChicago Midway
Jan 22
MDW1:30 amChicago Midway
7h 38m
1 stop
YYC9:08 amCalgary
Alaska Airlines
Jan 6
YYC5:20 amCalgary
7h 44m
1 stop
ORD1:04 pmChicago O'Hare Intl
Jan 7
ORD8:15 amChicago O'Hare Intl
8h 05m
1 stop
YYC4:20 pmCalgary
United Airlines
Jan 14
YYC1:20 amCalgary
11h 52m
1 stop
ORD1:12 pmChicago O'Hare Intl
Jan 27
ORD4:20 amChicago O'Hare Intl
13h 24m
2 stops
YYC5:44 pmCalgary

Find the cheapest one-way flights from Calgary to Chicago

If you're looking for one-way flights from Calgary to Chicago, view some of our deals below provided by Air Canada and Delta
Multiple Airlines
Jan 4
YYC6:00 amCalgary
11h 33m
1 stop
ORD5:33 pmChicago O'Hare Intl
Air Canada
Nov 4
YYC2:15 amCalgary
7h 46m
1 stop
ORD10:01 amChicago O'Hare Intl
Delta
Nov 6
YYC10:00 amCalgary
7h 03m
1 stop
MDW5:03 pmChicago Midway

Search last-minute flights to Chicago from Calgary

Find and compare flight prices for your last-minute flight from Calgary to Chicago
Multiple Airlines
Oct 20
YYC10:30 amCalgary
8h 04m
1 stop
ORD6:34 pmChicago O'Hare Intl
Oct 27
ORD4:48 pmChicago O'Hare Intl
22h 15m
2 stops
YYC3:03 pmCalgary
Multiple Airlines
Oct 20
YYC7:50 amCalgary
16h 10m
2 stops
ORD12:00 amChicago O'Hare Intl
Oct 27
ORD4:48 pmChicago O'Hare Intl
20h 02m
2 stops
YYC12:50 pmCalgary
Multiple Airlines
Oct 20
YYC10:30 amCalgary
8h 04m
1 stop
ORD6:34 pmChicago O'Hare Intl
Oct 27
ORD4:00 amChicago O'Hare Intl
15h 16m
1 stop
YYC7:16 pmCalgary

Best airlines flying from Calgary to Chicago

Compare and see reviews for airlines that fly from Calgary to Chicago with momondo
AirlineRatingFree CancellationPrice
American Airlines
PriceFrom $147
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10
United Airlines
PriceFrom $194
Free Cancellation
Rating
6.8
7.2

Boarding

6.7

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Not because the flight is going to Africa we can’t get better service on board

1 / 10
WestJet
PriceFrom $313
Free Cancellation
Rating
8.1
8.0

Boarding

7.8

Comfort

8.4

Crew

7.3

Entertainment

6.6

Food

Reviews

The crew all the way from Medicine Hat to Thunder Bay were wonderful! I think Selva was the name of the stewardess on my flight from Medicine Hat to Calgary and she was delightful! It was pretty early in the morning and she was the right amount of pep without being overbearing. She was very organized and professional as well thank you! My flight from Calgary to Toronto was fantastic! I've been on large planes before and the boarding process was very well done by the crew. I was bumped to a window seat (such a blessing) and the selection of entertainment was great. The plane was very clean and modern. Vic the stewardess really stood out and was very kind and professional thank you Vic! I don't remember the names of the ladies on my flight from Toronto to Thunder Bay but they were fantastic as well! Its always a rough time flying into Thunder Bay that late but they made the journey as comfortable as possible, thank you both! All in all thanks Westjet team you did a great job and I look forward to flying with you again!

1 / 10

  • Are airlines flying from Calgary to Chicago offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from Calgary to Chicago, such as United Airlines, American Airlines, and WestJet may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • How far is Calgary to Chicago by plane?

    Chicago is 1397.6 mi away from Calgary. In terms of flight time, this usually takes a little over 4h 25m.


Can I fly to Chicago from Calgary right now?

Information is based on travel restrictions from Calgary to Chicago

Most visitors from Calgary need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Calgary must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Calgary are not required to quarantine after entering Chicago.

Can I fly back to Calgary from Chicago?

Returning to Calgary from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Calgary.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Calgary.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Alternative routes for Calgary to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Edmonton to Chicago Flights
Fastest flight time9h 29m
Cheapest price$277

Similar Calgary to Chicago flights

Flexible with your destination? Broaden your search and find flights similar to your Calgary to Chicago route