Cheap Flights from Montreal to Chicago
Browse current best options from Montreal. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Montreal
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
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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 Montreal to Chicago
Explore current cheapest deals departing from Montreal to Chicago
Round trip
Sort by: Cheapest
September 24 - September 30
YUL - Chicago
$449
$236
Round trip
September 15 - September 18
YUL - Chicago
$455
$237
Round trip
September 13 - September 20
YUL - Chicago
$447
$237
Round trip
October 2 - October 4
YUL - Chicago
$511
$237
Round trip
October 15 - October 24
YUL - Chicago
$512
$237
Round trip
October 10 - October 18
YUL - Chicago
$512
$239
Round trip
September 22 - September 29
YUL - Chicago
$449
$242
Round trip
September 16 - September 23
YUL - Chicago
$448
$242
Round trip
September 18 - September 27
YUL - Chicago
$430
$242
Round trip
September 18 - September 20
YUL - Chicago
$456
$242
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 Montreal to Chicago
How much is a round trip from Montreal to Chicago
Regular price: $329 - $471
Prices are currently below the regular range.
The regular price range for flights from Montreal to Chicago is between $329 and $471. The current lowest deal is $236 with Porter Airlines, for travel from Sep 24-Sep 30.
now $236
Low $329
High $471
The cheapest time to fly from Montreal to Chicago
The cheapest month to fly from Montreal to Chicago is December, with a median price of $245. The most expensive month is July, with a median price of $545. Prices are generally lower from February to December.
December
Flights from $245
July
Flights from $545
Direct flights from Montreal to Chicago
Air Canada
Last-minute flights going from Montreal to Chicago
Wed, Jul 1
YHU - Chicago
Montreal (YHU) - Chicago (MDW)
Porter Airlines
$605
$291
One-way
Fri, Jul 3
YHU - Chicago
Montreal (YHU) - Chicago (MDW)
Porter Airlines
$590
$287
One-way
Fri, Jul 3
YHU - Chicago
Montreal (YHU) - Chicago (MDW)
Porter Airlines
$587
$291
One-way
Sat, Aug 1
YUL - Chicago
Montreal (YUL) - Chicago (MDW)
Deutsche Luft Hansa
$744
$347
One-way
Wed, Aug 5
YUL - Chicago
Montreal (YUL) - Chicago (MDW)
Porter Airlines
$830
$252
One-way
Wed, Aug 5
YUL - Chicago
Montreal (YUL) - Chicago (MDW)
Porter Airlines
$828
$260
One-way
Biggest price drops on these dates for flights from Montreal to Chicago
Aug 7 - Aug 9
$880 → $257
71%
Aug 7 - Aug 10
$879 → $257
71%
Aug 14 - Aug 18
$863 → $251
71%
Oct 8 - Oct 14
$929 → $318
66%
Popular Airports to fly from Montreal to Chicago
Montreal - Chicago route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares for Montreal to Chicago are above the typical level, with a median price of $370.
📅 Best time to fly
December is historically the cheapest month to fly.
Historically, December is the cheapest month to fly from Montreal to Chicago, with a median price of $245.
⏱️ Flight duration
Flights are typically 5h 54m long.
The median flight duration from Montreal to Chicago is 5 hours and 54 minutes.
✈️ Airlines & availability
Direct flights are available with Air Canada.
Air Canada offers direct flights on this route, with a mix of direct and connecting options available.
🏆 Airline highlight
Porter Airlines offers a recent deal for $236.
A recent deal from Porter Airlines for $236 was found for travel from September 24-September 30.
🎯 Booking tip
Deals appear frequently, about once a day.
Deals for flights from Montreal to Chicago are frequent, appearing about once per day.
Montreal main airports to depart from
Montréal–Pierre Elliott Trudeau International (YUL)
Montréal–Pierre Elliott Trudeau International Airport (YUL) is a convenient option for flights from Montreal to Chicago.
📍 ~15 km from Montreal city center (reachable by car or bus).
💸 Flights from ~$236
Montreal Saint-Hubert Longueuil (YHU)
Montreal Saint-Hubert Longueuil Airport (YHU) offers an alternative departure point for your trip to Chicago.
📍 ~10 km from Montreal city center (reachable by car or bus).
💸 Flights from ~$278
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 Montreal.
📍 ~20 km from Chicago city center (reachable by car, train, and bus)
💸 Flights from ~$236
Chicago Midway International (MDW)
Chicago Midway International Airport provides a convenient option for travelers arriving in Chicago from Montreal.
📍 ~15 km from Chicago city center (reachable by car, train, and bus)
💸 Flights from ~$250
Chicago Rockford International (RFD)
Chicago Rockford International Airport is an alternative for reaching the wider Chicago area from Montreal.
📍 ~120 km from Chicago city center (reachable by car and bus)
💸 Flights from ~$401
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options.
📍 ~135 km from Chicago (reachable by car, direct rail via Amtrak Hiawatha service from Chicago Union Station)
💸 Flights from ~$382
South Bend International (SBN)
South Bend International is geographically the closest alternative to the Chicago area with easier security and parking.
📍 ~120 km from Chicago (reachable by car, directly connected to downtown Chicago via the South Shore Line commuter rail)
💸 Flights from ~$434
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub offering a wide range of cabin classes.
📍 ~225 km from Chicago (reachable by car)
💸 Flights from ~$401
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 ~$454
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$444
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Montreal to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From YUL
Elite
Oct 21
Chicago, United States
84% AI deal score
$909
$424
Save $485
From YUL
Elite
Jul 07
Chicago, United States
84% AI deal score
$1,114
$552
Save $562
From YUL
Elite
Jul 28
Chicago, United States
84% AI deal score
$1,114
$552
Save $562
From YUL
Elite
Jul 08
Chicago, United States
84% AI deal score
$1,117
$554
Save $563
From YUL
Elite
Jul 17
Chicago, United States
84% AI deal score
$1,117
$558
Save $559
From YUL
Elite
Jul 17
Chicago, United States
84% AI deal score
$1,123
$558
Save $565
From YUL
Elite
Jul 28
Chicago, United States
84% AI deal score
$1,131
$564
Save $567
From YUL
Elite
Jul 21
Chicago, United States
83% AI deal score
$901
$434
Save $467
From YUL
Elite
Jul 14
Chicago, United States
83% AI deal score
$907
$434
Save $473
From YUL
Elite
Jul 13
Chicago, United States
83% AI deal score
$907
$434
Save $473
From YUL
Elite
Jul 10
Chicago, United States
83% AI deal score
$913
$434
Save $479
From YUL
Elite
Jul 30
Chicago, United States
83% AI deal score
$942
$446
Save $496
From YUL
Elite
Aug 14
Chicago, United States
83% AI deal score
$916
$451
Save $465
From YUL
Elite
Jul 16
Chicago, United States
83% AI deal score
$941
$455
Save $486
From YUL
Elite
Aug 20
Chicago, United States
83% AI deal score
$898
$455
Save $443
From YUL
Elite
Jul 21
Chicago, United States
83% AI deal score
$941
$455
Save $486
From YUL
Elite
Aug 28
Chicago, United States
83% AI deal score
$963
$465
Save $498
From YUL
Elite
Sep 24
Chicago, United States
83% AI deal score
$975
$465
Save $510
From YUL
Elite
Jul 24
Chicago, United States
83% AI deal score
$955
$466
Save $489
From YUL
Elite
Sep 24
Chicago, United States
83% AI deal score
$934
$497
Save $437
From YUL
Elite
Oct 21
Chicago, United States
83% AI deal score
$978
$524
Save $454
From YUL
Elite
Jul 28
Chicago, United States
83% AI deal score
$1,106
$552
Save $554
From YUL
Elite
Aug 12
Chicago, United States
83% AI deal score
$1,159
$554
Save $605
From YUL
Elite
Jul 17
Chicago, United States
83% AI deal score
$1,113
$558
Save $555
From YUL
Elite
Jul 07
Chicago, United States
83% AI deal score
$1,119
$561
Save $558
From YUL
Elite
Jul 07
Chicago, United States
83% AI deal score
$1,119
$561
Save $558
From YUL
Elite
Jul 07
Chicago, United States
83% AI deal score
$1,118
$561
Save $557
From YUL
Elite
Jul 09
Chicago, United States
83% AI deal score
$1,119
$561
Save $558
From YUL
Elite
Jul 09
Chicago, United States
83% AI deal score
$1,119
$561
Save $558
From YUL
Elite
Jul 09
Chicago, United States
83% AI deal score
$1,117
$561
Save $556
From YUL
Elite
Aug 11
Chicago, United States
83% AI deal score
$1,151
$561
Save $590
From YUL
Elite
Jul 09
Chicago, United States
83% AI deal score
$1,118
$561
Save $557
From YUL
Elite
Jul 07
Chicago, United States
83% AI deal score
$1,118
$561
Save $557
From YUL
Elite
Jul 28
Chicago, United States
83% AI deal score
$1,118
$562
Save $556
From YUL
Elite
Jul 28
Chicago, United States
83% AI deal score
$1,114
$562
Save $552
From YUL
Elite
Aug 06
Chicago, United States
83% AI deal score
$1,150
$567
Save $583
From YUL
Elite
Jul 17
Chicago, United States
83% AI deal score
$1,117
$567
Save $550
From YUL
Elite
Jul 17
Chicago, United States
83% AI deal score
$1,118
$567
Save $551
From YUL
Elite
Jul 17
Chicago, United States
83% AI deal score
$1,117
$570
Save $547
From YUL
Elite
Jul 08
Chicago, United States
83% AI deal score
$1,123
$580
Save $543
From YUL
Elite
Jul 08
Chicago, United States
83% AI deal score
$1,113
$580
Save $533
From YUL
Elite
Jul 15
Chicago, United States
82% AI deal score
$907
$455
Save $452
From YUL
Elite
Sep 15
Chicago, United States
82% AI deal score
$929
$455
Save $474
From YUL
Elite
Jul 15
Chicago, United States
82% AI deal score
$946
$465
Save $481
From YUL
Elite
Sep 18
Chicago, United States
82% AI deal score
$924
$465
Save $459
From YUL
Elite
Aug 20
Chicago, United States
82% AI deal score
$909
$466
Save $443
From YUL
Elite
Jul 11
Chicago, United States
82% AI deal score
$950
$469
Save $481
From YUL
Elite
Jul 23
Chicago, United States
82% AI deal score
$751
$446
Save $305
From YHU
Elite
Sep 14
Chicago, United States
82% AI deal score
$1,657
$584
Save $1,073
From YUL
Elite
Jul 08
Chicago, United States
82% AI deal score
$1,118
$593
Save $525
From YUL
Elite
Jul 07
Chicago, United States
82% AI deal score
$1,135
$599
Save $536
From YUL
Elite
Nov 02
Chicago, United States
80% AI deal score
$885
$487
Save $398
From YUL
Elite
Nov 07
Chicago, United States
80% AI deal score
$887
$498
Save $389
From YUL
Elite
Jul 04
Chicago, United States
80% AI deal score
$840
$542
Save $298
From YUL
Elite
Aug 28
Chicago, United States
80% AI deal score
$1,190
$491
Save $699
From YUL
Elite
Oct 03
Chicago, United States
79% AI deal score
$956
$424
Save $532
From YUL
Elite
Aug 06
Chicago, United States
79% AI deal score
$980
$434
Save $546
From YUL
Elite
Jul 23
Chicago, United States
79% AI deal score
$941
$545
Save $396
From YUL
Elite
Jul 02
Chicago, United States
79% AI deal score
$825
$547
Save $278
From YUL
Elite
Jul 01
Chicago, United States
79% AI deal score
$854
$574
Save $280
From YUL
Elite
Jul 01
Chicago, United States
79% AI deal score
$843
$575
Save $268
From YUL
Elite
Jul 28
Chicago, United States
79% AI deal score
$1,118
$517
Save $601
From YUL
Elite
Jul 28
Chicago, United States
79% AI deal score
$1,120
$517
Save $603
From YUL
Elite
Aug 06
Chicago, United States
79% AI deal score
$1,156
$523
Save $633
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,117
$523
Save $594
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,114
$523
Save $591
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,117
$523
Save $594
From YUL
Elite
Aug 06
Chicago, United States
79% AI deal score
$1,150
$523
Save $627
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,108
$523
Save $585
From YUL
Elite
Jul 28
Chicago, United States
79% AI deal score
$1,115
$526
Save $589
From YUL
Elite
Jul 28
Chicago, United States
79% AI deal score
$1,115
$526
Save $589
From YUL
Elite
Jul 28
Chicago, United States
79% AI deal score
$1,127
$526
Save $601
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,117
$532
Save $585
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,117
$532
Save $585
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,130
$532
Save $598
From YUL
Elite
Aug 06
Chicago, United States
79% AI deal score
$1,169
$532
Save $637
From YUL
Elite
Aug 13
Chicago, United States
79% AI deal score
$1,173
$532
Save $641
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,117
$532
Save $585
From YUL
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,117
$532
Save $585
From YUL
Elite
Jul 16
Chicago, United States
78% AI deal score
$955
$434
Save $521
From YUL
Elite
Aug 15
Chicago, United States
78% AI deal score
$916
$434
Save $482
From YUL
Elite
Aug 24
Chicago, United States
78% AI deal score
$912
$565
Save $347
From YUL
Elite
Sep 03
Chicago, United States
78% AI deal score
$983
$572
Save $411
From YUL
Elite
Jul 24
Chicago, United States
78% AI deal score
$762
$539
Save $223
From YUL
Elite
Jul 25
Chicago, United States
78% AI deal score
$774
$539
Save $235
From YUL
Elite
Jul 11
Chicago, United States
78% AI deal score
$763
$548
Save $215
From YUL
Elite
Aug 06
Chicago, United States
78% AI deal score
$1,152
$532
Save $620
From YUL
Elite
Jul 08
Chicago, United States
78% AI deal score
$1,121
$545
Save $576
From YUL
Elite
Jul 08
Chicago, United States
78% AI deal score
$1,113
$545
Save $568
From YUL
Elite
Jul 08
Chicago, United States
78% AI deal score
$1,117
$545
Save $572
From YUL
Elite
Jul 07
Chicago, United States
78% AI deal score
$1,124
$552
Save $572
From YUL
Elite
Jul 09
Chicago, United States
78% AI deal score
$1,117
$552
Save $565
From YUL
Elite
Aug 11
Chicago, United States
78% AI deal score
$1,196
$552
Save $644
From YUL
Elite
Jul 09
Chicago, United States
78% AI deal score
$1,114
$552
Save $562
From YUL
Elite
Jul 09
Chicago, United States
78% AI deal score
$1,117
$552
Save $565
From YUL
Elite
Jul 07
Chicago, United States
78% AI deal score
$1,122
$552
Save $570
From YUL
Elite
Jul 08
Chicago, United States
78% AI deal score
$1,119
$554
Save $565
From YUL
Elite
Jul 08
Chicago, United States
78% AI deal score
$1,118
$554
Save $564
From YUL
Elite
Jul 08
Chicago, United States
78% AI deal score
$1,117
$554
Save $563
From YUL
Elite
Aug 06
Chicago, United States
78% AI deal score
$1,190
$558
Save $632