Cheap Flights from Calgary to Chicago
Browse current best options from Calgary. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Calgary
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Calgary to Chicago
Explore current cheapest deals departing from Calgary to Chicago
Round trip
Sort by: Cheapest
September 14 - October 4
YYC - Chicago
$227
$259
Round trip
September 14 - September 20
YYC - Chicago
$254
$259
Round trip
September 15 - September 21
YYC - Chicago
$255
$259
Round trip
September 15 - September 20
YYC - Chicago
$261
$259
Round trip
September 1 - September 19
YYC - Chicago
$283
$264
Round trip
December 1 - December 5
YYC - Chicago
$397
$264
Round trip
December 9 - December 11
YYC - Chicago
$394
$264
Round trip
August 25 - August 27
YYC - Chicago
$366
$265
Round trip
September 3 - September 6
YYC - Chicago
$319
$265
Round trip
August 6 - August 18
YYC - Chicago
$316
$266
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Calgary to Chicago
How much is a round trip from Calgary to Chicago
Regular price: $197 - $415
Prices for flights from Calgary to Chicago are currently within the regular range.
The regular price range for flights from Calgary to Chicago is between $197 and $415. The current lowest deal is $259 with WestJet, for travel from September 14 to October 4.
now $259
Low $197
High $415
The cheapest time to fly from Calgary to Chicago
The cheapest month to fly from Calgary to Chicago is February, with a median price of $168. The most expensive month is October, with a median price of $746. Prices are generally lower from January to November.
February
Flights from $168
October
Flights from $746
Direct flights from Calgary to Chicago
WestJet
Last-minute flights going from Calgary to Chicago
Thu, Aug 6
YYC - Chicago
Calgary (YYC) - Chicago (ORD)
Air Canada
$316
$266
One-way
Wed, Aug 12
YYC - Chicago
Calgary (YYC) - Chicago (ORD)
Deutsche Luft Hansa
$365
$296
One-way
Thu, Aug 20
YYC - Chicago
Calgary (YYC) - Chicago (ORD)
Deutsche Luft Hansa
$356
$309
One-way
Thu, Aug 20
YYC - Chicago
Calgary (YYC) - Chicago (ORD)
Deutsche Luft Hansa
$356
$309
One-way
Tue, Aug 25
YYC - Chicago
Calgary (YYC) - Chicago (ORD)
Deutsche Luft Hansa
$366
$265
One-way
Fri, Aug 28
YYC - Chicago
Calgary (YYC) - Chicago (ORD)
Deutsche Luft Hansa
$363
$308
One-way
Biggest price drops on these dates for flights from Calgary to Chicago
Dec 8 - Dec 17
$496 → $297
40%
Nov 26 - Dec 1
$469 → $296
37%
Nov 26 - Dec 2
$463 → $296
36%
Nov 26 - Dec 3
$463 → $296
36%
Popular Airports to fly from Calgary to Chicago
Calgary - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Calgary to Chicago are above the typical level, with 8% good prices historically.
📅 Best time to fly
February is historically the cheapest month to fly
Historically, February is the cheapest month to fly from Calgary to Chicago, with a median price of $168.
⏱️ Flight duration
Connecting flights take 9h 29m on average
Flights from Calgary to Chicago typically take 9h 29m, with 35.2% of deals being direct.
✈️ Airlines & availability
WestJet offers direct flights
WestJet offers direct flights from Calgary to Chicago. Deals for this route are frequent, with 1.03 deals per day.
🏆 Airline highlight
WestJet has direct flights
WestJet is the only airline with direct flights from Calgary to Chicago, based on recent deals.
🎯 Booking tip
Consider flying in February for better prices
To find better prices, consider flying in February, when the median price is $168.
Calgary main airports to depart from
Calgary International (YYC)
Calgary International is a great choice for flights from Calgary to Chicago, offering competitive prices.
📍 ~10 km from Calgary city center (reachable by car)
💸 Flights from ~$264
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago, offering many connections from Calgary.
📍 ~25 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$264
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient option for travelers flying from Calgary to Chicago.
📍 ~15 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$294
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves the wider Chicago area for flights from Calgary.
📍 ~120 km from Chicago city center (reachable by car and bus).
💸 Flights from ~$390
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic).
💸 Flights from ~$430
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, with direct commuter rail connections.
📍 ~120 km from Chicago (reachable by rail).
💸 Flights from ~$439
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes.
📍 ~205 km from Chicago (reachable by car; requires a significant drive).
💸 Flights from ~$356
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service and less congestion.
📍 ~200 km from Chicago (reachable by car).
💸 Flights from ~$504
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~235 km from Chicago (reachable by car).
💸 Flights from ~$490
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Calgary to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From YYC
Elite
Aug 13
Chicago, United States
85% AI deal score
$1,518
$848
Save $670
From YYC
Elite
Sep 02
Chicago, United States
84% AI deal score
$1,406
$842
Save $564
From YYC
Elite
Aug 07
Chicago, United States
84% AI deal score
$1,352
$854
Save $498
From YYC
Elite
Aug 31
Chicago, United States
83% AI deal score
$1,300
$848
Save $452
From YYC
Elite
Aug 12
Chicago, United States
83% AI deal score
$1,318
$854
Save $464
From YYC
Elite
Aug 28
Chicago, United States
83% AI deal score
$1,498
$914
Save $584
From YYC
Elite
Jul 18
Chicago, United States
83% AI deal score
$1,528
$946
Save $582
From YYC
Elite
Jun 25
Chicago, United States
82% AI deal score
$1,526
$918
Save $608
From YYC
Elite
Oct 09
Chicago, United States
81% AI deal score
$1,410
$802
Save $608
From YYC
Elite
Jul 25
Chicago, United States
81% AI deal score
$1,437
$982
Save $455
From YYC
Elite
Jul 02
Chicago, United States
81% AI deal score
$1,603
$1,040
Save $563
From YYC
Elite
Jul 09
Chicago, United States
80% AI deal score
$1,537
$1,044
Save $493
From YYC
Elite
Sep 02
Chicago, United States
79% AI deal score
$1,152
$842
Save $310
From YYC
Elite
Jul 23
Chicago, United States
79% AI deal score
$1,290
$982
Save $308
From YYC
Elite
Jul 29
Chicago, United States
79% AI deal score
$1,497
$1,078
Save $419
From YYC
Elite
Sep 03
Chicago, United States
79% AI deal score
$1,056
$674
Save $382
From YYC
Elite
Sep 03
Chicago, United States
79% AI deal score
$1,057
$674
Save $383
From YYC
Elite
Sep 05
Chicago, United States
74% AI deal score
$1,459
$1,085
Save $374
From YYC
Elite
Sep 06
Chicago, United States
74% AI deal score
$1,459
$1,088
Save $371
From YYC
Elite
Sep 05
Chicago, United States
74% AI deal score
$1,561
$1,144
Save $417
From YYC
Elite
Sep 06
Chicago, United States
74% AI deal score
$1,588
$1,147
Save $441
From YYC
Elite
Nov 03
Chicago, United States
74% AI deal score
$1,218
$896
Save $322
From YYC
Elite
Sep 12
Chicago, United States
74% AI deal score
$1,217
$976
Save $241
From YYC
Elite
Nov 08
Chicago, United States
74% AI deal score
$1,288
$1,006
Save $282
From YYC
Elite
Dec 01
Chicago, United States
74% AI deal score
$1,364
$1,045
Save $319
From YYC
Elite
Dec 01
Chicago, United States
74% AI deal score
$1,364
$1,045
Save $319
From YYC
Elite
Sep 22
Chicago, United States
73% AI deal score
$1,545
$1,146
Save $399
From YYC
Elite
Sep 05
Chicago, United States
73% AI deal score
$1,640
$1,208
Save $432
From YYC
Elite
Sep 25
Chicago, United States
73% AI deal score
$1,660
$1,221
Save $439
From YYC
Elite
Nov 12
Chicago, United States
73% AI deal score
$1,748
$1,312
Save $436
From YYC
Elite
Jul 30
Chicago, United States
73% AI deal score
$1,263
$976
Save $287
From YYC
Elite
Jul 30
Chicago, United States
73% AI deal score
$1,294
$1,003
Save $291
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,070
$763
Save $307
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,099
$763
Save $336
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,069
$763
Save $306
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,069
$763
Save $306
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,070
$763
Save $307
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,073
$763
Save $310
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,092
$763
Save $329
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,073
$763
Save $310
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,071
$763
Save $308
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,083
$763
Save $320
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,070
$763
Save $307
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,073
$763
Save $310
From YYC
Elite
Sep 15
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,070
$763
Save $307
From YYC
Elite
Sep 14
Chicago, United States
73% AI deal score
$1,074
$763
Save $311
From YYC
Elite
Sep 18
Chicago, United States
73% AI deal score
$1,065
$763
Save $302
From YYC
Elite
Sep 05
Chicago, United States
72% AI deal score
$1,459
$1,208
Save $251
From YYC
Elite
Sep 05
Chicago, United States
72% AI deal score
$1,459
$1,208
Save $251
From YYC
Elite
Sep 05
Chicago, United States
72% AI deal score
$1,503
$1,209
Save $294
From YYC
Elite
Sep 05
Chicago, United States
72% AI deal score
$1,459
$1,209
Save $250
From YYC
Elite
Sep 06
Chicago, United States
72% AI deal score
$1,506
$1,211
Save $295
From YYC
Elite
Sep 06
Chicago, United States
72% AI deal score
$1,459
$1,211
Save $248
From YYC
Elite
Sep 06
Chicago, United States
72% AI deal score
$1,459
$1,211
Save $248
From YYC
Elite
Sep 06
Chicago, United States
72% AI deal score
$1,459
$1,211
Save $248
From YYC
Elite
Sep 15
Chicago, United States
72% AI deal score
$1,487
$1,212
Save $275
From YYC
Elite
Sep 09
Chicago, United States
72% AI deal score
$1,487
$1,220
Save $267
From YYC
Elite
Sep 12
Chicago, United States
72% AI deal score
$1,485
$1,224
Save $261
From YYC
Elite
Sep 21
Chicago, United States
72% AI deal score
$1,510
$1,226
Save $284
From YYC
Elite
Nov 07
Chicago, United States
72% AI deal score
$1,196
$1,000
Save $196
From YYC
Elite
Jul 22
Chicago, United States
72% AI deal score
$1,357
$1,161
Save $196
From YYC
Elite
Jun 24
Chicago, United States
72% AI deal score
$1,502
$1,218
Save $284
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$959
$756
Save $203
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$994
$756
Save $238
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$959
$756
Save $203
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$974
$756
Save $218
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$959
$756
Save $203
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$959
$756
Save $203
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$959
$759
Save $200
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$959
$759
Save $200
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$959
$759
Save $200
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$956
$759
Save $197
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$959
$759
Save $200
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$959
$759
Save $200
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 21
Chicago, United States
72% AI deal score
$958
$759
Save $199
From YYC
Elite
Aug 23
Chicago, United States
72% AI deal score
$963
$759
Save $204
From YYC
Elite
Aug 15
Chicago, United States
72% AI deal score
$978
$771
Save $207
From YYC
Elite
Aug 12
Chicago, United States
72% AI deal score
$978
$771
Save $207
From YYC
Elite
Aug 12
Chicago, United States
72% AI deal score
$965
$771
Save $194
From YYC
Elite
Aug 15
Chicago, United States
72% AI deal score
$965
$771
Save $194
From YYC
Elite
Aug 31
Chicago, United States
72% AI deal score
$984
$771
Save $213
From YYC
Elite
Aug 27
Chicago, United States
71% AI deal score
$1,404
$1,209
Save $195
From YYC
Elite
Aug 18
Chicago, United States
71% AI deal score
$1,389
$1,213
Save $176