Cheap Flights from New York to Chicago
Browse current best options from New York. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
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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 New York to Chicago
Explore current cheapest deals departing from New York to Chicago
Round trip
Sort by: Cheapest
August 5 - August 12
JFK - Chicago
$173
$120
Round trip
November 3 - November 11
JFK - Chicago
$145
$135
Round trip
August 4 - August 5
JFK - Chicago
$187
$136
Round trip
August 18 - August 19
JFK - Chicago
$187
$136
Round trip
August 11 - August 25
JFK - Chicago
$154
$136
Round trip
September 23 - September 30
JFK - Chicago
$155
$136
Round trip
September 1 - September 2
JFK - Chicago
$143
$136
Round trip
September 9 - September 16
JFK - Chicago
$143
$136
Round trip
August 4 - August 12
LGA - Chicago
$127
$137
Round trip
August 25 - August 26
LGA - Chicago
$168
$137
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 New York to Chicago
How much is a round trip from New York to Chicago
Regular price: $119 - $254
Prices for flights from New York to Chicago are currently within the regular range.
Regular prices for flights from New York to Chicago typically range from $119 to $254. The current lowest deal is $120 with JetBlue Airways, for travel from August 5 to August 12.
now $120
Low $119
High $254
The cheapest time to fly from New York to Chicago
The cheapest month to fly from NYC to CHI is December, with a median price of $94. The most expensive month is July, with a median price of $462. Prices are generally lower from January to December.
December
Flights from $94
July
Flights from $462
Direct flights from New York to Chicago
JetBlue Airways
Southwest Airlines
Last-minute flights going from New York to Chicago
Sat, Jun 20
JFK - Chicago
New York (JFK) - Chicago (ORD)
JetBlue Airways
$423
$289
One-way
Sat, Jun 20
JFK - Chicago
New York (JFK) - Chicago (ORD)
JetBlue Airways
$421
$292
One-way
Thu, Jun 25
EWR - Chicago
New York (EWR) - Chicago (MDW)
Frontier Airlines
$402
$240
One-way
Thu, Jun 25
EWR - Chicago
New York (EWR) - Chicago (MDW)
Frontier Airlines
$399
$249
One-way
Mon, Jul 6
JFK - Chicago
New York (JFK) - Chicago (ORD)
$322
$217
One-way
Sat, Jul 11
JFK - Chicago
New York (JFK) - Chicago (MDW)
$301
$187
One-way
Biggest price drops on these dates for flights from New York to Chicago
Jun 25 - Jun 27
$402 → $240
40%
Jun 25 - Jun 29
$399 → $249
38%
Dec 12 - Dec 14
$312 → $169
46%
Aug 12 - Aug 17
$290 → $156
46%
Popular Airports to fly from New York to Chicago
New York - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for New York to Chicago are above the typical level at a median of $334.
📅 Best time to fly
Fly in December for the best prices
Historically, December is the cheapest month to fly, with a median price of $94.
⏱️ Flight duration
9h 6m is the typical flight time
The typical flight duration from New York to Chicago is 9 hours and 6 minutes.
✈️ Airlines & availability
Direct flights are available
42.3% of recent deals are for direct flights, with frequent deals available daily.
🏆 Airline highlight
JetBlue Airways offers direct flights
JetBlue Airways is one of the airlines offering direct flights on this route.
🎯 Booking tip
Deals are frequent for this route
On average, there are over 1 deal per day for flights from New York to Chicago.
New York main airports to depart from
John F. Kennedy International (JFK)
John F. Kennedy International offers flights to Chicago, with prices from $120.
📍 ~20 km from New York city center (reachable by car or train).
💸 Flights from ~$120
LaGuardia (LGA)
LaGuardia offers flights to Chicago, with prices from $137.
📍 ~10 km from New York city center (reachable by car or train).
💸 Flights from ~$137
New York Stewart International Airport (SWF)
New York Stewart International Airport offers flights to Chicago, with prices from $219.
📍 ~70 km from New York city center (reachable by car).
💸 Flights from ~$219
Newark Liberty International (EWR)
Newark Liberty International offers flights to Chicago, with prices from $137.
📍 ~15 km from New York city center (reachable by car or train).
💸 Flights from ~$137
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights to Chicago, offering competitive prices.
📍 ~25 km from Chicago (reachable by car, train)
💸 Flights from ~$120
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient choice for arriving in Chicago.
📍 ~15 km from Chicago (reachable by car, train)
💸 Flights from ~$137
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves the wider Chicago area, providing another arrival option.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$245
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)
💸 Flights from ~$176
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago and connects via commuter rail.
📍 ~125 km from Chicago (reachable by rail)
💸 Flights from ~$227
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, good for travelers on Chicago's eastern side.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$109
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport, less congested than major Chicago or Milwaukee hubs.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$269
Fort Wayne International (FWA)
Fort Wayne International is an alternative for travelers in the southeastern Chicago suburbs, with stable regional service.
📍 ~260 km from Chicago (reachable by car)
💸 Flights from ~$246
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from New York to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From JFK
Elite
Jul 07
Chicago, United States
85% AI deal score
$2,254
$532
Save $1,722
From JFK
Elite
Nov 13
Chicago, United States
85% AI deal score
$2,227
$575
Save $1,652
From JFK
Elite
Jun 18
Chicago, United States
85% AI deal score
$2,602
$691
Save $1,911
From JFK
Elite
Sep 13
Chicago, United States
85% AI deal score
$1,741
$341
Save $1,400
From JFK
Elite
Sep 13
Chicago, United States
85% AI deal score
$1,728
$341
Save $1,387
From JFK
Elite
Sep 13
Chicago, United States
85% AI deal score
$1,708
$347
Save $1,361
From JFK
Elite
Sep 13
Chicago, United States
85% AI deal score
$1,746
$371
Save $1,375
From JFK
Elite
Oct 15
Chicago, United States
84% AI deal score
$1,930
$547
Save $1,383
From JFK
Elite
Sep 11
Chicago, United States
84% AI deal score
$2,112
$560
Save $1,552
From JFK
Elite
Aug 21
Chicago, United States
84% AI deal score
$2,344
$572
Save $1,772
From JFK
Elite
Sep 12
Chicago, United States
84% AI deal score
$2,119
$573
Save $1,546
From JFK
Elite
Jul 09
Chicago, United States
84% AI deal score
$2,184
$597
Save $1,587
From JFK
Elite
Aug 26
Chicago, United States
83% AI deal score
$2,316
$657
Save $1,659
From JFK
Elite
Jun 18
Chicago, United States
83% AI deal score
$2,670
$810
Save $1,860
From JFK
Elite
Jun 24
Chicago, United States
83% AI deal score
$2,845
$836
Save $2,009
From JFK
Elite
Jun 20
Chicago, United States
83% AI deal score
$3,126
$891
Save $2,235
From JFK
Elite
Jun 17
Chicago, United States
83% AI deal score
$3,305
$1,002
Save $2,303
From JFK
Elite
Jun 20
Chicago, United States
83% AI deal score
$1,738
$535
Save $1,203
From JFK
Elite
Sep 01
Chicago, United States
82% AI deal score
$1,901
$573
Save $1,328
From JFK
Elite
Sep 22
Chicago, United States
82% AI deal score
$1,897
$573
Save $1,324
From JFK
Elite
Sep 26
Chicago, United States
82% AI deal score
$1,933
$573
Save $1,360
From JFK
Elite
Sep 19
Chicago, United States
82% AI deal score
$1,922
$583
Save $1,339
From JFK
Elite
Nov 20
Chicago, United States
82% AI deal score
$2,057
$602
Save $1,455
From JFK
Elite
Sep 06
Chicago, United States
82% AI deal score
$2,130
$677
Save $1,453
From JFK
Elite
Aug 14
Chicago, United States
82% AI deal score
$2,327
$684
Save $1,643
From JFK
Elite
Aug 05
Chicago, United States
82% AI deal score
$2,253
$704
Save $1,549
From JFK
Elite
Dec 15
Chicago, United States
82% AI deal score
$2,285
$727
Save $1,558
From JFK
Elite
Jun 18
Chicago, United States
81% AI deal score
$2,174
$611
Save $1,563
From JFK
Elite
Jun 18
Chicago, United States
81% AI deal score
$2,510
$901
Save $1,609
From JFK
Elite
Jun 16
Chicago, United States
81% AI deal score
$2,679
$966
Save $1,713
From JFK
Elite
Aug 05
Chicago, United States
80% AI deal score
$2,058
$770
Save $1,288
From JFK
Elite
Sep 04
Chicago, United States
80% AI deal score
$2,127
$770
Save $1,357
From JFK
Elite
Jul 30
Chicago, United States
80% AI deal score
$2,249
$1,132
Save $1,117
From JFK
Elite
Jul 31
Chicago, United States
80% AI deal score
$2,268
$1,132
Save $1,136
From JFK
Elite
Jun 26
Chicago, United States
80% AI deal score
$2,784
$1,327
Save $1,457
From JFK
Elite
Sep 06
Chicago, United States
80% AI deal score
$1,741
$560
Save $1,181
From JFK
Elite
Nov 05
Chicago, United States
79% AI deal score
$2,065
$770
Save $1,295
From JFK
Elite
Nov 07
Chicago, United States
79% AI deal score
$2,056
$770
Save $1,286
From JFK
Elite
Nov 26
Chicago, United States
79% AI deal score
$2,058
$770
Save $1,288
From JFK
Elite
Aug 19
Chicago, United States
79% AI deal score
$2,289
$845
Save $1,444
From JFK
Elite
Jun 27
Chicago, United States
79% AI deal score
$2,302
$853
Save $1,449
From JFK
Elite
Jun 22
Chicago, United States
79% AI deal score
$2,561
$1,046
Save $1,515
From JFK
Elite
Jul 11
Chicago, United States
79% AI deal score
$2,191
$1,132
Save $1,059
From JFK
Elite
Jul 09
Chicago, United States
79% AI deal score
$2,234
$1,142
Save $1,092
From JFK
Elite
Jun 20
Chicago, United States
79% AI deal score
$3,115
$1,182
Save $1,933
From JFK
Elite
Jul 01
Chicago, United States
79% AI deal score
$1,563
$636
Save $927
From JFK
Elite
Aug 10
Chicago, United States
78% AI deal score
$2,023
$835
Save $1,188
From JFK
Elite
Aug 08
Chicago, United States
78% AI deal score
$1,987
$882
Save $1,105
From JFK
Elite
Aug 01
Chicago, United States
78% AI deal score
$2,566
$967
Save $1,599
From JFK
Elite
Aug 07
Chicago, United States
78% AI deal score
$2,389
$967
Save $1,422
From JFK
Elite
Dec 21
Chicago, United States
78% AI deal score
$2,235
$967
Save $1,268
From JFK
Elite
Jul 04
Chicago, United States
78% AI deal score
$2,369
$997
Save $1,372
From JFK
Elite
Jun 27
Chicago, United States
78% AI deal score
$2,720
$1,022
Save $1,698
From JFK
Elite
Oct 01
Chicago, United States
78% AI deal score
$2,113
$1,205
Save $908
From JFK
Elite
Jun 27
Chicago, United States
78% AI deal score
$2,391
$1,317
Save $1,074
From JFK
Elite
Jul 30
Chicago, United States
77% AI deal score
$2,198
$967
Save $1,231
From JFK
Elite
Jul 31
Chicago, United States
77% AI deal score
$2,253
$967
Save $1,286
From JFK
Elite
Jul 26
Chicago, United States
77% AI deal score
$2,224
$987
Save $1,237
From JFK
Elite
Oct 23
Chicago, United States
77% AI deal score
$2,042
$1,122
Save $920
From JFK
Elite
Jul 18
Chicago, United States
77% AI deal score
$1,942
$1,172
Save $770
From JFK
Elite
Jul 03
Chicago, United States
77% AI deal score
$2,306
$1,402
Save $904
From JFK
Elite
Jul 18
Chicago, United States
77% AI deal score
$593
$325
Save $268
From JFK
Elite
Jun 16
Chicago, United States
77% AI deal score
$841
$475
Save $366
From JFK
Elite
Jul 07
Chicago, United States
77% AI deal score
$1,570
$703
Save $867
From JFK
Elite
Jul 11
Chicago, United States
76% AI deal score
$2,053
$967
Save $1,086
From JFK
Elite
Jul 16
Chicago, United States
76% AI deal score
$1,881
$975
Save $906
From JFK
Elite
Aug 14
Chicago, United States
76% AI deal score
$2,340
$1,402
Save $938
From JFK
Elite
Jun 21
Chicago, United States
76% AI deal score
$3,126
$1,457
Save $1,669
From JFK
Elite
Jun 16
Chicago, United States
76% AI deal score
$2,602
$1,652
Save $950
From JFK
Elite
Sep 12
Chicago, United States
76% AI deal score
$698
$336
Save $362
From JFK
Elite
Sep 14
Chicago, United States
76% AI deal score
$717
$341
Save $376
From JFK
Elite
Sep 14
Chicago, United States
76% AI deal score
$715
$341
Save $374
From JFK
Elite
Sep 12
Chicago, United States
76% AI deal score
$1,727
$754
Save $973
From JFK
Elite
Jun 20
Chicago, United States
76% AI deal score
$1,715
$873
Save $842
From JFK
Elite
Jul 27
Chicago, United States
75% AI deal score
$1,878
$967
Save $911
From JFK
Elite
Nov 20
Chicago, United States
75% AI deal score
$2,069
$967
Save $1,102
From JFK
Elite
Jun 26
Chicago, United States
75% AI deal score
$2,792
$1,307
Save $1,485
From JFK
Elite
Sep 12
Chicago, United States
75% AI deal score
$688
$341
Save $347
From JFK
Elite
Sep 14
Chicago, United States
75% AI deal score
$709
$347
Save $362
From JFK
Elite
Sep 12
Chicago, United States
75% AI deal score
$713
$357
Save $356
From JFK
Elite
Aug 07
Chicago, United States
75% AI deal score
$706
$365
Save $341
From LGA
Elite
Oct 29
Chicago, United States
75% AI deal score
$666
$474
Save $192
From JFK
Elite
Jun 16
Chicago, United States
74% AI deal score
$966
$577
Save $389
From JFK
Elite
Sep 10
Chicago, United States
74% AI deal score
$685
$357
Save $328
From JFK
Elite
Sep 10
Chicago, United States
74% AI deal score
$667
$357
Save $310
From JFK
Elite
Aug 08
Chicago, United States
74% AI deal score
$707
$389
Save $318
From LGA
Elite
Jul 15
Chicago, United States
74% AI deal score
$564
$469
Save $95
From JFK
Elite
Jun 22
Chicago, United States
74% AI deal score
$777
$504
Save $273
From JFK
Elite
Sep 10
Chicago, United States
73% AI deal score
$667
$361
Save $306
From JFK
Elite
Sep 10
Chicago, United States
73% AI deal score
$695
$377
Save $318
From JFK
Elite
Jun 30
Chicago, United States
73% AI deal score
$639
$435
Save $204
From JFK
Elite
Jun 27
Chicago, United States
73% AI deal score
$693
$465
Save $228
From JFK
Elite
Jun 24
Chicago, United States
73% AI deal score
$726
$490
Save $236
From JFK
Elite
Jun 21
Chicago, United States
73% AI deal score
$780
$535
Save $245
From JFK
Elite
Jun 21
Chicago, United States
73% AI deal score
$772
$535
Save $237
From JFK
Elite
Jun 17
Chicago, United States
73% AI deal score
$821
$554
Save $267
From JFK
Elite
Jun 22
Chicago, United States
72% AI deal score
$923
$586
Save $337
From JFK
Elite
Sep 11
Chicago, United States
72% AI deal score
$698
$390
Save $308
From JFK
Elite
Sep 11
Chicago, United States
72% AI deal score
$688
$390
Save $298
From JFK
Elite
Sep 11
Chicago, United States
71% AI deal score
$670
$396
Save $274