Cheap Flights from Toronto to Chicago
Browse current best options from Toronto. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
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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 Toronto to Chicago
Explore current cheapest deals departing from Toronto to Chicago
Round trip
Sort by: Cheapest
September 4 - September 7
YTZ - Chicago
$221
$173
Round trip
September 4 - September 6
YTZ - Chicago
$221
$174
Round trip
October 14 - October 18
YTZ - Chicago
$275
$175
Round trip
September 11 - September 13
YTZ - Chicago
$227
$176
Round trip
October 15 - October 18
YTZ - Chicago
$275
$176
Round trip
September 14 - September 20
YTZ - Chicago
$220
$178
Round trip
September 9 - September 15
YTZ - Chicago
$221
$178
Round trip
September 3 - September 6
YTZ - Chicago
$218
$180
Round trip
September 3 - September 7
YTZ - Chicago
$218
$180
Round trip
September 2 - September 7
YTZ - Chicago
$217
$180
Round trip
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Route Intelligence — 486,190 Searches this Week
Insights for flights from Toronto to Chicago
How much is a round trip from Toronto to Chicago
Regular price: $178 - $360
Prices are currently below the regular range for flights from Toronto to Chicago.
The regular price range for flights from Toronto to Chicago is between $178 and $360. The current lowest deal is $173 with Porter Airlines for travel from Sep 4-Sep 7.
now $173
Low $178
High $360
The cheapest time to fly from Toronto to Chicago
The cheapest month to fly from Toronto to Chicago is November, with a median price of $179. The most expensive month is October, with a median price of $626. Prices are generally lower from January to November.
November
Flights from $179
October
Flights from $626
Direct flights from Toronto to Chicago
Porter Airlines
Last-minute flights going from Toronto to Chicago
Wed, Jul 1
YTZ - Chicago
Toronto (YTZ) - Chicago (MDW)
Porter Airlines
$636
$187
One-way
Wed, Jul 1
YTZ - Chicago
Toronto (YTZ) - Chicago (MDW)
Porter Airlines
$588
$192
One-way
Wed, Jul 1
YTZ - Chicago
Toronto (YTZ) - Chicago (MDW)
Porter Airlines
$588
$193
One-way
Wed, Jul 1
YTZ - Chicago
Toronto (YTZ) - Chicago (MDW)
Porter Airlines
$637
$195
One-way
Wed, Jul 1
YTZ - Chicago
Toronto (YTZ) - Chicago (MDW)
Porter Airlines
$638
$195
One-way
Wed, Jul 1
YTZ - Chicago
Toronto (YTZ) - Chicago (MDW)
Porter Airlines
$600
$195
One-way
Biggest price drops on these dates for flights from Toronto to Chicago
Jul 2 - Jul 6
$637 → $185
71%
Jul 2 - Jul 4
$636 → $185
71%
Jul 1 - Jul 3
$636 → $187
71%
Jul 1 - Jul 4
$638 → $195
69%
Popular Airports to fly from Toronto to Chicago
Toronto - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from YTO to CHI are above the typical level, with 41% good prices.
📅 Best time to fly
November is historically cheapest at $179
Historically, November is the cheapest month to fly from YTO to CHI, with a median price of $179.
⏱️ Flight duration
Direct flights take 3h 50m
The median flight time for this short-haul route is 3 hours 50 minutes.
✈️ Airlines & availability
Mixed availability of direct flights
Around 50.9% of recent deals for this route are direct, with others having 2 stopovers.
🏆 Airline highlight
Porter Airlines offers direct flights
Porter Airlines has recently offered direct flights on the YTO to CHI route.
🎯 Booking tip
Deals are frequent for this route
Deals for flights from YTO to CHI are frequent, with over 1 deal per day.
Toronto main airports to depart from
Billy Bishop Toronto City (YTZ)
Consider Billy Bishop Toronto City for flights to Chicago, offering a convenient departure point.
📍 ~3 km from city center (reachable by car or bus)
💸 Flights from ~$173
Toronto Pearson International (YYZ)
Toronto Pearson International is a major hub for flights to Chicago, providing many options.
📍 ~25 km from city center (reachable by car or train)
💸 Flights from ~$190
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights from Toronto to Chicago.
📍 ~25 km from Chicago (reachable by car)
💸 Flights from ~$173
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient choice for flights from Toronto to Chicago.
📍 ~15 km from Chicago (reachable by car)
💸 Flights from ~$185
Chicago Rockford International (RFD)
Chicago Rockford International Airport offers another arrival option for flights from Toronto to Chicago.
📍 ~100 km from Chicago (reachable by car)
💸 Flights from ~$322
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
Consider Milwaukee for excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$410
South Bend International (SBN)
South Bend is a close alternative to Chicago, offering direct commuter rail links and easier security.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$347
Gerald R. Ford International (GRR)
Grand Rapids is a major regional hub, useful for travelers on the eastern side of the Chicago metro area.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$318
Dane County Regional (MSN)
Madison offers reliable regional service and less congestion compared to major Chicago airports.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$409
Fort Wayne International (FWA)
Fort Wayne provides stable regional service, ideal for travelers in the southeastern Chicago suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$344
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Toronto to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From YTZ
Elite
Sep 14
Chicago, United States
81% AI deal score
$742
$352
Save $390
From YTZ
Elite
Jul 03
Chicago, United States
80% AI deal score
$635
$352
Save $283
From YTZ
Elite
Jul 02
Chicago, United States
80% AI deal score
$635
$352
Save $283
From YTZ
Elite
Sep 01
Chicago, United States
80% AI deal score
$703
$352
Save $351
From YTZ
Elite
Sep 08
Chicago, United States
80% AI deal score
$710
$352
Save $358
From YTZ
Elite
Sep 14
Chicago, United States
80% AI deal score
$715
$352
Save $363
From YTZ
Elite
Sep 07
Chicago, United States
80% AI deal score
$710
$352
Save $358
From YTZ
Elite
Sep 01
Chicago, United States
80% AI deal score
$701
$352
Save $349
From YTZ
Elite
Sep 06
Chicago, United States
80% AI deal score
$696
$352
Save $344
From YTZ
Elite
Sep 06
Chicago, United States
80% AI deal score
$727
$352
Save $375
From YTZ
Elite
Sep 06
Chicago, United States
80% AI deal score
$695
$352
Save $343
From YTZ
Elite
Sep 14
Chicago, United States
80% AI deal score
$730
$352
Save $378
From YTZ
Elite
Sep 01
Chicago, United States
80% AI deal score
$704
$352
Save $352
From YTZ
Elite
Sep 06
Chicago, United States
80% AI deal score
$730
$352
Save $378
From YTZ
Elite
Sep 06
Chicago, United States
80% AI deal score
$692
$352
Save $340
From YTZ
Elite
Sep 13
Chicago, United States
80% AI deal score
$726
$352
Save $374
From YTZ
Elite
Sep 04
Chicago, United States
80% AI deal score
$704
$352
Save $352
From YTZ
Elite
Sep 02
Chicago, United States
80% AI deal score
$698
$352
Save $346
From YTZ
Elite
Sep 07
Chicago, United States
80% AI deal score
$711
$352
Save $359
From YTZ
Elite
Sep 07
Chicago, United States
80% AI deal score
$711
$352
Save $359
From YTZ
Elite
Sep 08
Chicago, United States
80% AI deal score
$711
$352
Save $359
From YTZ
Elite
Sep 06
Chicago, United States
80% AI deal score
$700
$352
Save $348
From YTZ
Elite
Sep 03
Chicago, United States
80% AI deal score
$704
$352
Save $352
From YTZ
Elite
Sep 09
Chicago, United States
80% AI deal score
$704
$352
Save $352
From YTZ
Elite
Sep 07
Chicago, United States
80% AI deal score
$711
$352
Save $359
From YTZ
Elite
Sep 10
Chicago, United States
80% AI deal score
$704
$352
Save $352
From YTZ
Elite
Sep 03
Chicago, United States
80% AI deal score
$701
$352
Save $349
From YTZ
Elite
Sep 12
Chicago, United States
80% AI deal score
$714
$352
Save $362
From YTZ
Elite
Sep 12
Chicago, United States
80% AI deal score
$713
$352
Save $361
From YTZ
Elite
Sep 14
Chicago, United States
80% AI deal score
$727
$360
Save $367
From YTZ
Elite
Aug 11
Chicago, United States
79% AI deal score
$799
$395
Save $404
From YTZ
Elite
Aug 05
Chicago, United States
79% AI deal score
$772
$395
Save $377
From YTZ
Elite
Aug 26
Chicago, United States
79% AI deal score
$774
$402
Save $372
From YTZ
Elite
Aug 31
Chicago, United States
79% AI deal score
$770
$402
Save $368
From YTZ
Elite
Aug 31
Chicago, United States
79% AI deal score
$769
$402
Save $367
From YTZ
Elite
Aug 19
Chicago, United States
79% AI deal score
$775
$402
Save $373
From YTZ
Elite
Aug 31
Chicago, United States
79% AI deal score
$798
$402
Save $396
From YTZ
Elite
Aug 19
Chicago, United States
79% AI deal score
$775
$402
Save $373
From YYZ
Elite
Jul 02
Chicago, United States
78% AI deal score
$1,370
$484
Save $886
From YYZ
Elite
Oct 29
Chicago, United States
77% AI deal score
$1,362
$706
Save $656
From YYZ
Elite
Oct 30
Chicago, United States
77% AI deal score
$1,329
$706
Save $623
From YYZ
Elite
Oct 02
Chicago, United States
77% AI deal score
$1,354
$706
Save $648
From YYZ
Elite
Oct 16
Chicago, United States
77% AI deal score
$1,362
$706
Save $656
From YTZ
Elite
Jul 18
Chicago, United States
77% AI deal score
$656
$395
Save $261
From YTZ
Elite
Jul 18
Chicago, United States
77% AI deal score
$656
$395
Save $261
From YYZ
Elite
Aug 13
Chicago, United States
76% AI deal score
$1,216
$484
Save $732
From YYZ
Elite
Jun 23
Chicago, United States
76% AI deal score
$1,193
$679
Save $514
From YYZ
Elite
Jul 27
Chicago, United States
75% AI deal score
$1,095
$683
Save $412
From YYZ
Elite
Jul 23
Chicago, United States
75% AI deal score
$1,095
$683
Save $412
From YYZ
Elite
Jul 16
Chicago, United States
75% AI deal score
$1,067
$683
Save $384
From YYZ
Elite
Jul 30
Chicago, United States
75% AI deal score
$1,068
$683
Save $385
From YYZ
Elite
Jul 30
Chicago, United States
75% AI deal score
$1,097
$683
Save $414
From YYZ
Elite
Jul 24
Chicago, United States
75% AI deal score
$1,067
$683
Save $384
From YYZ
Elite
Jul 14
Chicago, United States
75% AI deal score
$1,097
$688
Save $409
From YYZ
Elite
Jul 19
Chicago, United States
75% AI deal score
$1,118
$484
Save $634
From YTZ
Elite
Jun 29
Chicago, United States
75% AI deal score
$596
$400
Save $196
From YTZ
Elite
Jun 28
Chicago, United States
75% AI deal score
$617
$400
Save $217
From YYZ
Elite
Jul 21
Chicago, United States
74% AI deal score
$1,022
$683
Save $339
From YYZ
Elite
Jul 17
Chicago, United States
74% AI deal score
$1,054
$683
Save $371
From YYZ
Elite
Jul 11
Chicago, United States
74% AI deal score
$1,031
$683
Save $348
From YYZ
Elite
Jul 23
Chicago, United States
74% AI deal score
$1,067
$687
Save $380
From YYZ
Elite
Aug 15
Chicago, United States
73% AI deal score
$938
$683
Save $255
From YYZ
Elite
Jul 23
Chicago, United States
73% AI deal score
$1,029
$689
Save $340
From YYZ
Elite
Aug 15
Chicago, United States
73% AI deal score
$952
$643
Save $309
From YYZ
Elite
Aug 07
Chicago, United States
72% AI deal score
$925
$683
Save $242
From YYZ
Elite
Aug 15
Chicago, United States
72% AI deal score
$924
$683
Save $241
From YYZ
Elite
Nov 10
Chicago, United States
72% AI deal score
$1,021
$674
Save $347
From YYZ
Elite
Jul 14
Chicago, United States
72% AI deal score
$810
$687
Save $123
From YYZ
Elite
Jul 10
Chicago, United States
71% AI deal score
$1,081
$749
Save $332
From YYZ
Elite
Jul 10
Chicago, United States
70% AI deal score
$1,108
$801
Save $307
From YYZ
Elite
Nov 21
Chicago, United States
69% AI deal score
$1,000
$778
Save $222
From YYZ
Elite
Aug 13
Chicago, United States
68% AI deal score
$879
$683
Save $196
From YYZ
Elite
Aug 14
Chicago, United States
68% AI deal score
$879
$683
Save $196
From YYZ
Elite
Sep 03
Chicago, United States
67% AI deal score
$900
$683
Save $217
From YYZ
Elite
Aug 13
Chicago, United States
67% AI deal score
$857
$683
Save $174
From YYZ
Elite
Aug 12
Chicago, United States
67% AI deal score
$853
$687
Save $166
From YYZ
Elite
Aug 13
Chicago, United States
66% AI deal score
$826
$687
Save $139
From YYZ
Elite
Sep 04
Chicago, United States
66% AI deal score
$880
$694
Save $186
From YYZ
Elite
Jul 16
Chicago, United States
66% AI deal score
$757
$683
Save $74
From YYZ
Elite
Jul 08
Chicago, United States
66% AI deal score
$758
$683
Save $75
From YYZ
Elite
Jul 01
Chicago, United States
49% AI deal score
$1,128
$876
Save $252
From YYZ
Elite
Sep 13
Chicago, United States
48% AI deal score
$966
$778
Save $188
From YYZ
Elite
Jul 25
Chicago, United States
48% AI deal score
$1,100
$884
Save $216
From YYZ
Elite
Jul 23
Chicago, United States
48% AI deal score
$1,297
$1,015
Save $282
From YYZ
Elite
Sep 06
Chicago, United States
47% AI deal score
$961
$801
Save $160
From YYZ
Elite
Sep 04
Chicago, United States
46% AI deal score
$966
$839
Save $127
From YYZ
Elite
Sep 16
Chicago, United States
45% AI deal score
$889
$801
Save $88
From YYZ
Elite
Aug 12
Chicago, United States
44% AI deal score
$683
From YYZ
Elite
Sep 15
Chicago, United States
44% AI deal score
$966
$884
Save $82
From YYZ
Elite
Jun 22
Chicago, United States
42% AI deal score
$920
From YYZ
Elite
Jun 23
Chicago, United States
38% AI deal score
$920
From YYZ
Elite
Jul 10
Chicago, United States
38% AI deal score
$930
From YYZ
Elite
Jun 19
Chicago, United States
38% AI deal score
$1,508
From YYZ
Elite
Jun 25
Chicago, United States
37% AI deal score
$1,038
From YYZ
Elite
Jun 24
Chicago, United States
36% AI deal score
$1,102
From YYZ
Elite
Jul 11
Chicago, United States
35% AI deal score
$1,152
From YYZ
Elite
Jun 24
Chicago, United States
33% AI deal score
$1,508
From YYZ
Elite
Jul 19
Chicago, United States
31% AI deal score
$1,419
From YYZ
Elite
Jun 25
Chicago, United States
31% AI deal score
$1,448
From YYZ
Elite
Jul 30
Chicago, United States
31% AI deal score
$1,470