Cheap Flights from Calgary, AB to Chicago, IL from $114
Return flight: Chicago – Calgary
On Cheapflightsplus.com you will find 4 direct and 200 connecting flights from Calgary to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $114, book and save on cheap plane tickets and last minute offers. Also check out YYC-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Calgary to Chicago Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $114 (one-way), $195 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Calgary to Chicago Today
Take a look at the list of non stop flights and flights with layovers from Calgary to Chicago with the lowest price of $114. The fastest direct flight takes 3h 19m and the fastest connecting – 5h 4m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $124 | 08:30 Calgary Calgary Int. | 12:49 Chicago O'Hare International | 3h 19m | Air Canada | AC5240 |
| from $124 | 12:30 Calgary Calgary Int. | 16:50 Chicago O'Hare International | 3h 20m | Air Canada | AC4026 |
| from $124 | 15:15 Calgary Calgary Int. | 19:40 Chicago O'Hare International | 3h 25m | Air Canada | AC4028 |
| from $141 | 12:35 Calgary Calgary Int. | 17:10 Chicago O'Hare International | 3h 35m | United Airlines | UA3552 |
| from $114 | 11:00 Calgary Calgary Int. | 19:20 Chicago O'Hare International | 7h 20m layover 1h 2m - Montreal | Air Canada | AC318 AC7597 |
| from $114 | 10:15 Calgary Calgary Int. | 20:00 Chicago O'Hare International | 8h 45m layover 2h 29m - Ottawa | Air Canada | AC394 AC3553 |
| from $114 | 11:00 Calgary Calgary Int. | 21:26 Chicago O'Hare International | 9h 26m layover 3h 7m - Montreal | Air Canada | AC318 AC7599 |
| from $116 | 07:00 Calgary Calgary Int. | 14:58 Chicago O'Hare International | 6h 58m layover 1h 25m - Toronto | Air Canada | AC134 AC509 |
| from $116 | 13:15 Calgary Calgary Int. | 21:43 Chicago O'Hare International | 7h 28m layover 2h 0m - Toronto | Air Canada | AC146 AC515 |
| from $130 | 10:35 Calgary Calgary Int. | 21:43 Chicago O'Hare International | 10h 8m layover 4h 39m - Toronto | Air Canada | AC142 AC515 |
| from $135 | 15:55 Calgary Calgary Int. | 21:59 Chicago O'Hare International | 5h 4m layover 0h 49m - Minneapolis | WestJet | WS6354 WS7849 |
| from $135 | 07:20 Calgary Calgary Int. | 18:20 Chicago O'Hare International | 10h 0m layover 1h 1m - Toronto 1h 16m - Montreal | Air Canada | AC136 AC414 AC3078 |
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 27, 2024
Flight Schedule Calgary (Alberta) to Chicago (Illinois)
Full flight schedule will help you in detecting at what time planes fly from Calgary to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
08:30 — 12:49
|
08:30 — 12:49
AC5240
Air Canada
Calgary — Chicago
|
3h 19m |
Find flight
from$124 |
|
|
12:30 — 16:50
|
12:30 — 16:50
AC4026
Air Canada
Calgary — Chicago
|
3h 20m |
Find flight
from$124 |
|
|
12:35 — 17:10
|
12:35 — 17:10
UA3552
United Airlines
Calgary — Chicago
|
3h 35m |
Find flight
from$141 |
|
|
15:15 — 19:40
|
15:15 — 19:40
AC4028
Air Canada
Calgary — Chicago
|
3h 25m |
Find flight
from$124 |
|
|
00:30 — 09:20
|
00:30 — 06:06
AC158
Air Canada
Calgary — Toronto
2h 24m stop
08:30 — 09:20
AC7701
Air Canada
Toronto — Chicago
|
7h 50m including layover |
Find flight
from$139 |
|
|
00:50 — 14:58
|
00:50 — 06:31
AC158
Air Canada
Calgary — Toronto
7h 39m stop
14:10 — 14:58
AC509
Air Canada
Toronto — Chicago
|
13h 8m including layover |
Find flight
from$130 |
|
|
07:00 — 14:58
|
07:00 — 12:45
AC134
Air Canada
Calgary — Toronto
1h 25m stop
14:10 — 14:58
AC509
Air Canada
Toronto — Chicago
|
6h 58m including layover |
Find flight
from$116 |
|
|
09:55 — 18:42
|
09:55 — 15:31
AC138
Air Canada
Calgary — Toronto
2h 14m stop
17:45 — 18:42
AC4408
Air Canada
Toronto — Chicago
|
7h 47m including layover |
Find flight
from$139 |
|
|
09:55 — 09:20
+1 day
|
09:55 — 15:31
AC138
Air Canada
Calgary — Toronto
16h 59m stop
08:30 — 09:20
AC7701
Air Canada
Toronto — Chicago
|
22h 25m including layover |
Find flight
from$153 |
|
|
10:15 — 20:00
|
10:15 — 16:02
AC394
Air Canada
Calgary — Ottawa
2h 29m stop
18:31 — 20:00
AC3553
Air Canada
Ottawa — Chicago
|
8h 45m including layover |
Find flight
from$114 |
|
|
10:35 — 21:43
|
10:35 — 16:16
AC142
Air Canada
Calgary — Toronto
4h 39m stop
20:55 — 21:43
AC515
Air Canada
Toronto — Chicago
|
10h 8m including layover |
Find flight
from$130 |
|
|
11:00 — 19:20
|
11:00 — 16:53
AC318
Air Canada
Calgary — Montreal
1h 2m stop
17:55 — 19:20
AC7597
Air Canada
Montreal — Chicago
|
7h 20m including layover |
Find flight
from$114 |
|
|
11:00 — 21:26
|
11:00 — 16:53
AC318
Air Canada
Calgary — Montreal
3h 7m stop
20:00 — 21:26
AC7599
Air Canada
Montreal — Chicago
|
9h 26m including layover |
Find flight
from$114 |
|
|
12:35 — 21:32
|
12:35 — 17:09
AA3695
American Airlines
Calgary — Dallas
1h 51m stop
19:00 — 21:32
AA2585
American Airlines
Dallas — Chicago
|
7h 57m including layover |
Find flight
from$137 |
|
|
13:15 — 21:43
|
13:15 — 18:55
AC146
Air Canada
Calgary — Toronto
2h stop
20:55 — 21:43
AC515
Air Canada
Toronto — Chicago
|
7h 28m including layover |
Find flight
from$116 |
|
|
15:55 — 21:59
|
15:55 — 19:31
WS6354
WestJet
Calgary — Minneapolis
49m stop
20:20 — 21:59
WS7849
WestJet
Minneapolis — Chicago
|
5h 4m including layover |
Find flight
from$135 |
|
|
06:30 — 08:57
+1 day
|
06:30 — 12:28
AC316
Air Canada
Calgary — Montreal
1h 17m stop
13:45 — 15:08
AC7624
Air Canada
Montreal — Boston
15h 52m stop
07:00 — 08:57
NK2855
Spirit Airlines
Boston — Chicago
|
25h 27m including layover |
Find flight
from$143 |
|
|
06:30 — 08:02
+1 day
|
06:30 — 12:28
AC316
Air Canada
Calgary — Montreal
1h 17m stop
13:45 — 15:08
AC7624
Air Canada
Montreal — Boston
15h 22m stop
06:30 — 08:02
UA447
United Airlines
Boston — Chicago
|
24h 32m including layover |
Find flight
from$150 |
|
|
07:20 — 18:20
|
07:20 — 12:59
AC136
Air Canada
Calgary — Toronto
1h 1m stop
14:00 — 15:14
AC414
Air Canada
Toronto — Montreal
1h 16m stop
16:30 — 18:20
AC3078
Air Canada
Montreal — Chicago
|
10h including layover |
Find flight
from$135 |
|
|
13:30 — 18:20
+1 day
|
13:30 — 19:00
AC146
Air Canada
Calgary — Toronto
19h stop
14:00 — 15:14
AC414
Air Canada
Toronto — Montreal
1h 16m stop
16:30 — 18:20
AC3078
Air Canada
Montreal — Chicago
|
27h 50m including layover |
Find flight
from$150 |
|
|
17:15 — 18:20
+1 day
|
17:15 — 22:54
AC152
Air Canada
Calgary — Toronto
15h 6m stop
14:00 — 15:14
AC414
Air Canada
Toronto — Montreal
1h 16m stop
16:30 — 18:20
AC3078
Air Canada
Montreal — Chicago
|
24h 5m including layover |
Find flight
from$150 |
|
|
17:15 — 18:20
+1 day
|
17:15 — 22:54
AC152
Air Canada
Calgary — Toronto
13h 6m stop
12:00 — 13:14
AC410
Air Canada
Toronto — Montreal
3h 16m stop
16:30 — 18:20
AC3078
Air Canada
Montreal — Chicago
|
24h 5m including layover |
Find flight
from$150 |
|
*Departure and arrival times - local. Updated on April 27, 2024
Flight Information
Below we will explain in detail what the flights cost on the destination from Calgary to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Calgary and Chicago is 2249 miles. Time difference between the cities is 1h. Airplanes depart 00:05 to 21:30 from 1 Calgary airport and arrive 00:05 to 21:30 to 7 Chicago airports. Average flight time is 3h 23m.
- The fastest flight 3h 19m
- Average flight time 3h 23m
- The earliest flight 00:05
- The latest flight 21:30
- Distance 1398 ml
What is the lowest airfare Calgary to Chicago?
The cheapest plane ticket found by our users is $114. This airfare is for economy class on one-way AC318 flight by Air Canada for July 18, 2020 which leaves Calgary Int. in Calgary at 11:00 am and arrives at Chicago O'Hare International at 21:26.
Economy class
$114
Business class
?
First class
?
Popular Airlines on the Route
The flight Calgary — Chicago is served by 6 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by American Airlines - 7 departures per week at the price of from $ 137 . And the most expensive tickets are offered by Air Canada airline - from $ 1442.
Direct flights
There are 4 nonstop flights on the route. The fastest direct flight is AC5240 by Air Canada takes 3h 19m and the cheapest is AC318 by Air Canada for $124.
- from $124Find
- from $141Find
See more direct flights
Connecting Flights
There are 200 flights with layovers on the route. The fastest connecting flight is WS6354 by WestJet takes 5h 4m and the cheapest is AC318 by Air Canada for $114.
- from $137Find
- from $114Find
- from $178Find
- from $135Find
- from $142Find
- F8 - Freedom Airlinesfrom $256Find
See more connecting flights
Airports
You can fly from Calgary to Chicago from 1 airports (Calgary Int.).
Calgary airports
- Calgary Int.-YYCfrom $114Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Calgary by 6 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.
- Embraer 190from $114Find
- Airbus A330-300from $114Find
- Boeing 777-300ERfrom $116Find
- Airbus A320-100/200from $116Find
- Boeing 737-800from $124Find
- Airbus A319from $124Find
- Boeing 767-300from $130Find
- Embraer 175from $137Find
- Airbus A321-100/200from $139Find
- Embraer 175 (winglets)from $141Find
Top International Destinations from Calgary
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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