Cheap Flights from Calgary, AB to Chicago, IL from $140
Return flight: Chicago – Calgary
On Cheapflightsplus.com you will find 2 direct and 392 connecting flights from Calgary to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $140, 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: $140 (one-way), $240 (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 $140. The fastest direct flight takes 3h 27m and the fastest connecting – 5h 31m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $308 | 12:41 Calgary Calgary Int. | 17:08 Chicago O'Hare International | 3h 27m | United Airlines | UA1655 |
| from $901 | 12:41 Calgary Calgary Int. | 17:09 Chicago O'Hare International | 3h 28m | Air Canada | AC4026 |
| from $140 | 06:19 Calgary Calgary Int. | 19:31 Chicago O'Hare International | 12h 12m layover 6h 58m - Denver | United Airlines | UA550 UA1495 |
| from $159 | 15:15 Calgary Calgary Int. | 22:02+1 день Chicago Midway | 29h 47m layover 23h 17m - Phoenix | WestJet | WS1492 F91736 |
| from $160 | 19:10 Calgary Calgary Int. | 10:42+1 день Chicago Midway | 14h 32m layover 7h 56m - Phoenix | WestJet | WS1536 F91736 |
| from $160 | 19:10 Calgary Calgary Int. | 19:07+1 день Chicago O'Hare International | 22h 57m layover 16h 14m - Phoenix | WestJet | WS1536 F91410 |
| from $161 | 08:00 Calgary Calgary Int. | 19:45 Chicago O'Hare International | 10h 45m layover 4h 4m - Phoenix | WestJet | WS1394 F91830 |
| from $161 | 19:10 Calgary Calgary Int. | 19:45+1 день Chicago O'Hare International | 23h 35m layover 16h 55m - Phoenix | WestJet | WS1536 F91830 |
| from $164 | 09:55 Calgary Calgary Int. | 23:47 Chicago O'Hare International | 12h 52m layover 6h 12m - Atlanta | WestJet | WS1590 F91441 |
| from $152 | 21:45 Calgary Calgary Int. | 20:49+1 день Chicago Midway | 22h 4m layover 1h 58m - Edmonton 12h 48m - Atlanta | WestJet | WS289 WS1940 F92779 |
| from $152 | 20:00 Calgary Calgary Int. | 23:24+1 день Chicago Midway | 26h 24m layover 3h 41m - Edmonton 15h 17m - Atlanta | WestJet | WS3137 WS1940 F92779 |
| from $160 | 19:10 Calgary Calgary Int. | 17:25+1 день Chicago O'Hare International | 21h 15m layover 11h 0m - Phoenix 1h 58m - Las Vegas | WestJet | WS1536 F93983 F92146 |
| from $160 | 19:10 Calgary Calgary Int. | 00:17+2 дня Chicago Midway | 28h 7m layover 19h 1m - Phoenix 1h 34m - Denver | WestJet | WS1536 F92106 F92210 |
| from $160 | 19:10 Calgary Calgary Int. | 00:30+2 дня Chicago O'Hare International | 28h 20m layover 18h 12m - Phoenix 1h 48m - Houston | WestJet | WS1536 F94182 F93136 |
| from $163 | 20:00 Calgary Calgary Int. | 23:47+1 день Chicago O'Hare International | 26h 47m layover 3h 41m - Edmonton 15h 23m - Atlanta | WestJet | WS3137 WS1940 F91441 |
| from $175 | 00:30 Calgary Calgary Int. | 23:47 Chicago O'Hare International | 22h 17m layover 10h 28m - Atlanta 2h 54m - Philadelphia | WestJet | WS1992 F92298 F92111 |
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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on November 18, 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 |
|---|---|---|---|---|
|
12:41 — 17:08
|
12:41 — 17:08
UA1655
United Airlines
Calgary — Chicago
|
3h 27m |
Find flight
from$308 |
|
|
12:41 — 17:09
|
12:41 — 17:09
AC4026
Air Canada
Calgary — Chicago
|
3h 28m |
Find flight
from$901 |
|
|
00:30 — 21:29
|
00:30 — 06:52
WS1992
WestJet
Calgary — Atlanta
13h 31m stop
20:23 — 21:29
F92779
Frontier Airlines
Atlanta — Chicago
|
19h 59m including layover |
Find flight
from$172 |
|
|
06:19 — 19:31
|
06:19 — 08:57
UA550
United Airlines
Calgary — Denver
6h 58m stop
15:55 — 19:31
UA1495
United Airlines
Denver — Chicago
|
12h 12m including layover |
Find flight
from$140 |
|
|
08:00 — 19:45
|
08:00 — 11:13
WS1394
WestJet
Calgary — Phoenix
4h 4m stop
15:17 — 19:45
F91830
Frontier Airlines
Phoenix — Chicago
|
10h 45m including layover |
Find flight
from$161 |
|
|
09:55 — 23:47
|
09:55 — 16:17
WS1590
WestJet
Calgary — Atlanta
6h 12m stop
22:29 — 23:47
F91441
Frontier Airlines
Atlanta — Chicago
|
12h 52m including layover |
Find flight
from$164 |
|
|
15:15 — 22:02
+1 day
|
15:15 — 18:27
WS1492
WestJet
Calgary — Phoenix
23h 17m stop
17:44 — 22:02
F91736
Frontier Airlines
Phoenix — Chicago
|
29h 47m including layover |
Find flight
from$159 |
|
|
16:35 — 22:02
+1 day
|
16:35 — 19:55
F81502
Freedom Airlines
Calgary — Phoenix
21h 49m stop
17:44 — 22:02
F91736
Frontier Airlines
Phoenix — Chicago
|
28h 27m including layover |
Find flight
from$164 |
|
|
16:35 — 22:22
+1 day
|
16:35 — 19:55
F81502
Freedom Airlines
Calgary — Phoenix
22h 10m stop
18:05 — 22:22
F91738
Frontier Airlines
Phoenix — Chicago
|
28h 47m including layover |
Find flight
from$167 |
|
|
19:10 — 10:42
+1 day
|
19:10 — 22:22
WS1536
WestJet
Calgary — Phoenix
7h 56m stop
16:28 — 20:47
F91736
Frontier Airlines
Phoenix — Chicago
|
14h 32m including layover |
Find flight
from$160 |
|
|
19:10 — 19:07
+1 day
|
19:10 — 22:22
WS1536
WestJet
Calgary — Phoenix
16h 14m stop
14:36 — 19:07
F91410
Frontier Airlines
Phoenix — Chicago
|
22h 57m including layover |
Find flight
from$160 |
|
|
00:30 — 23:47
|
00:30 — 06:52
WS1992
WestJet
Calgary — Atlanta
10h 28m stop
17:20 — 19:25
F92298
Frontier Airlines
Atlanta — Philadelphia
2h 54m stop
22:19 — 23:47
F92111
Frontier Airlines
Philadelphia — Chicago
|
22h 17m including layover |
Find flight
from$175 |
|
|
06:50 — 20:14
|
06:50 — 07:36
WS101
WestJet
Calgary — Vancouver
1h 39m stop
09:15 — 13:22
WS1770
WestJet
Vancouver — Phoenix
2h 33m stop
15:55 — 20:14
F91736
Frontier Airlines
Phoenix — Chicago
|
12h 24m including layover |
Find flight
from$171 |
|
|
07:00 — 18:05
|
07:00 — 08:06
WS3395
WestJet
Calgary — Edmonton
1h 39m stop
09:45 — 13:35
WS1546
WestJet
Edmonton — Minneapolis
2h 52m stop
16:27 — 18:05
SY261
Sun Country Airlines
Minneapolis — Chicago
|
10h 5m including layover |
Find flight
from$185 |
|
|
08:40 — 10:55
+1 day
|
08:40 — 11:09
WS274
WestJet
Calgary — Regina
36m stop
11:45 — 13:44
WS3758
WestJet
Regina — Minneapolis
19h 23m stop
09:07 — 10:55
SY259
Sun Country Airlines
Minneapolis — Chicago
|
25h 15m including layover |
Find flight
from$170 |
|
|
09:55 — 16:06
+1 day
|
09:55 — 16:17
WS1590
WestJet
Calgary — Atlanta
13h 13m stop
05:30 — 07:25
NK3176
Spirit Airlines
Atlanta — Miami
6h 18m stop
13:43 — 16:06
NK157
Spirit Airlines
Miami — Chicago
|
29h 11m including layover |
Find flight
from$166 |
|
|
13:10 — 11:48
+1 day
|
13:10 — 16:22
WS1410
WestJet
Calgary — Phoenix
3h 3m stop
19:25 — 19:40
F94113
Frontier Airlines
Phoenix — Las Vegas
10h 31m stop
06:11 — 11:48
F92330
Frontier Airlines
Las Vegas — Chicago
|
21h 38m including layover |
Find flight
from$165 |
|
|
14:30 — 05:33
+1 day
|
14:30 — 16:52
WS1514
WestJet
Calgary — Los Angeles
4h 29m stop
21:30 — 22:49
F93292
Frontier Airlines
Los Angeles — Las Vegas
1h 19m stop
06:11 — 11:48
F92330
Frontier Airlines
Las Vegas — Chicago
|
14h 3m including layover |
Find flight
from$185 |
|
|
15:15 — 14:46
+1 day
|
15:15 — 18:27
WS1492
WestJet
Calgary — Phoenix
11h 38m stop
06:05 — 09:29
F92532
Frontier Airlines
Phoenix — Dallas
2h 48m stop
12:17 — 14:46
F93242
Frontier Airlines
Dallas — Chicago
|
22h 31m including layover |
Find flight
from$181 |
|
|
20:00 — 23:24
+1 day
|
20:00 — 21:04
WS3137
WestJet
Calgary — Edmonton
3h 41m stop
00:45 — 07:06
WS1940
WestJet
Edmonton — Atlanta
15h 17m stop
22:23 — 23:24
F92779
Frontier Airlines
Atlanta — Chicago
|
26h 24m including layover |
Find flight
from$152 |
|
|
20:00 — 23:47
+1 day
|
20:00 — 21:04
WS3137
WestJet
Calgary — Edmonton
3h 41m stop
00:45 — 07:06
WS1940
WestJet
Edmonton — Atlanta
15h 23m stop
22:29 — 23:47
F91441
Frontier Airlines
Atlanta — Chicago
|
26h 47m including layover |
Find flight
from$163 |
|
|
21:45 — 20:49
+1 day
|
21:45 — 22:49
WS289
WestJet
Calgary — Edmonton
1h 58m stop
00:45 — 07:06
WS1940
WestJet
Edmonton — Atlanta
12h 48m stop
22:28 — 23:29
F92779
Frontier Airlines
Atlanta — Chicago
|
22h 4m including layover |
Find flight
from$152 |
|
|
21:45 — 10:55
+1 day
|
21:45 — 22:49
WS289
WestJet
Calgary — Edmonton
1h 58m stop
00:45 — 07:06
WS1940
WestJet
Edmonton — Atlanta
2h 54m stop
16:12 — 17:12
F92143
Frontier Airlines
Atlanta — Chicago
|
12h 10m including layover |
Find flight
from$161 |
|
|
23:20 — 23:24
+2 days
|
23:20 — 00:01
WS135
WestJet
Calgary — Vancouver
22h 59m stop
23:00 — 06:53
WS1598
WestJet
Vancouver — Atlanta
15h 30m stop
22:23 — 23:24
F92779
Frontier Airlines
Atlanta — Chicago
|
47h 4m including layover |
Find flight
from$175 |
|
|
23:20 — 23:47
+2 days
|
23:20 — 00:01
WS135
WestJet
Calgary — Vancouver
22h 59m stop
23:00 — 06:53
WS1598
WestJet
Vancouver — Atlanta
15h 36m stop
22:29 — 23:47
F91441
Frontier Airlines
Atlanta — Chicago
|
47h 27m including layover |
Find flight
from$186 |
|
*Departure and arrival times - local. Updated on November 18, 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 23:40 from 1 Calgary airport and arrive 00:05 to 23:40 to 7 Chicago airports. Average flight time is 3h 28m.
- The fastest flight 3h 27m
- Average flight time 3h 28m
- The earliest flight 00:05
- The latest flight 23:40
- Distance 1398 ml
The cheapest months to travel to Chicago are february (from 140 $), january (from 152 $), december (from 159 $).
The most expensive months are november (from 166 $), december (from 159 $), january (from 152 $).
What is the lowest airfare Calgary to Chicago?
The cheapest plane ticket found by our users is $140. This airfare is for economy class on one-way UA550 flight by United Airlines for February 1, 2025 which leaves Calgary Int. in Calgary at 06:19 am and arrives at Chicago O'Hare International at 19:31.
Economy class
$140
Business class
?
First class
?
Popular Airlines on the Route
The flight Calgary — Chicago is served by 6 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Air Canada - 30 departures per week at the price of from $ 243 . And the most expensive tickets are offered by WestJet airline - from $ 943.
Direct flights
There are 2 nonstop flights on the route. The fastest direct flight is UA1655 by United Airlines takes 3h 27m and the cheapest is UA550 by United Airlines for $308.
- from $901Find
- from $308Find
See more direct flights
Connecting Flights
There are 392 flights with layovers on the route. The fastest connecting flight is WS6392 by WestJet takes 5h 31m and the cheapest is UA550 by United Airlines for $140.
- from $243Find
- from $258Find
- from $140Find
- from $152Find
- F8 - Freedom Airlinesfrom $164Find
- PD - Porter Airlinesfrom $261Find
See more connecting flights
Airports
You can fly from Calgary to Chicago from 1 airports (Calgary Int.).
Calgary airports
- Calgary Int.-YYCfrom $140Find
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 3 aircraft brands. They range from huge modern airplanes to small-sized.
- Boeing 737-800from $228Find
- Boeing 737 MAX 8from $299Find
- Airbus A320from $347Find
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.
- from $58Find
- from $58Find
- from $70Find
- from $59Find
- from $70Find
- from $61Find
- from $69Find
- from $56Find
- from $77Find
- from $74Find
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.
To find a plane ticket, please select dates.