Cheap Flights from New York to Chicago (NYC to CHI)

Discover more affordable routes and cheaper dates from New York to Chicago (NYC to CHI) within a date range.

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USD 82
6:30pm - 8:00pm
Wed Jul 23rd
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 82
6:30pm - 8:00pm
Tue Jul 15th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 82
6:30pm - 8:00pm
Wed Jul 16th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 16th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 82
6:30pm - 8:00pm
Tue Jul 22nd
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 82
6:30pm - 8:00pm
Sat Jul 26th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 26th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 82
6:30pm - 8:00pm
Fri Jul 25th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Fri Jul 25th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 82
6:30pm - 8:00pm
Sat Jul 19th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 19th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 86
5:00am - 6:37am
Tue Jul 8th
2h 37m
New York (EWR) → Chicago (ORD)
Direct
Tue Jul 8th 2025 Spirit Airlines · NK 2543 Depart at 5:00am from New York (EWR) Fly for 2h 37m Arrive at 6:37am in Chicago (ORD)
USD 87
5:23pm - 11:53pm
Sat Jul 12th
7h 30m
New York (EWR) → Chicago (ORD)
1 Stop
Sat Jul 12th 2025 Spirit Airlines · NK 1218 Depart at 5:23pm from New York (EWR) Fly for 3h 12m Arrive at 8:35pm in Fort Lauderdale (FLL)
Layover in Fort Lauderdale for 0h 55m
Sat Jul 12th 2025 Spirit Airlines · NK 1219 Depart at 9:30pm from Fort Lauderdale (FLL) Fly for 3h 23m Arrive at 11:53pm in Chicago (ORD)
USD 89
6:59am - 3:31pm
Wed Jul 16th
9h 32m
New York (LGA) → Chicago (ORD)
1 Stop
Wed Jul 16th 2025 Spirit Airlines · NK 1571 Depart at 6:59am from New York (LGA) Fly for 2h 51m Arrive at 9:50am in Orlando (MCO)
Layover in Orlando for 3h 33m
Wed Jul 16th 2025 Spirit Airlines · NK 1369 Depart at 1:23pm from Orlando (MCO) Fly for 3h 8m Arrive at 3:31pm in Chicago (ORD)
USD 95
10:30pm - 11:59pm
Sat Jul 19th
2h 29m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 19th 2025 United Airlines · UA 2084 Depart at 10:30pm from New York (EWR) Fly for 2h 29m Arrive at 11:59pm in Chicago (ORD)
USD 95
10:30pm - 11:59pm
Sat Jul 26th
2h 29m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 26th 2025 United Airlines · UA 2084 Depart at 10:30pm from New York (EWR) Fly for 2h 29m Arrive at 11:59pm in Chicago (ORD)
USD 95
7:20am - 8:57am
Wed Jul 23rd
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 95
2:20pm - 3:57pm
Tue Jul 22nd
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2360 Depart at 2:20pm from New York (LGA) Fly for 2h 37m Arrive at 3:57pm in Chicago (ORD)
USD 95
7:20am - 8:57am
Tue Jul 22nd
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 95
8:25am - 10:03am
Tue Jul 22nd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2479 Depart at 8:25am from New York (LGA) Fly for 2h 38m Arrive at 10:03am in Chicago (ORD)
USD 95
1:17pm - 2:55pm
Tue Jul 22nd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2199 Depart at 1:17pm from New York (LGA) Fly for 2h 38m Arrive at 2:55pm in Chicago (ORD)
USD 95
6:00am - 7:38am
Tue Jul 22nd
2h 38m
New York (EWR) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2164 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
USD 95
8:25am - 10:03am
Wed Jul 23rd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 2479 Depart at 8:25am from New York (LGA) Fly for 2h 38m Arrive at 10:03am in Chicago (ORD)
USD 95
11:25am - 1:03pm
Tue Jul 22nd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 1941 Depart at 11:25am from New York (LGA) Fly for 2h 38m Arrive at 1:03pm in Chicago (ORD)
USD 95
9:15am - 10:53am
Tue Jul 22nd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 623 Depart at 9:15am from New York (LGA) Fly for 2h 38m Arrive at 10:53am in Chicago (ORD)
USD 95
10:25am - 12:03pm
Tue Jul 22nd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 1310 Depart at 10:25am from New York (LGA) Fly for 2h 38m Arrive at 12:03pm in Chicago (ORD)
USD 95
9:30pm - 11:09pm
Mon Jul 21st
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Mon Jul 21st 2025 United Airlines · UA 393 Depart at 9:30pm from New York (LGA) Fly for 2h 39m Arrive at 11:09pm in Chicago (ORD)
USD 95
7:30pm - 9:09pm
Tue Jul 22nd
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 1819 Depart at 7:30pm from New York (LGA) Fly for 2h 39m Arrive at 9:09pm in Chicago (ORD)
USD 95
9:30pm - 11:09pm
Wed Jul 23rd
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 393 Depart at 9:30pm from New York (LGA) Fly for 2h 39m Arrive at 11:09pm in Chicago (ORD)
USD 95
6:25am - 8:04am
Wed Jul 23rd
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 2389 Depart at 6:25am from New York (LGA) Fly for 2h 39m Arrive at 8:04am in Chicago (ORD)
USD 95
8:30pm - 10:09pm
Tue Jul 22nd
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2181 Depart at 8:30pm from New York (LGA) Fly for 2h 39m Arrive at 10:09pm in Chicago (ORD)
USD 95
6:25am - 8:04am
Tue Jul 22nd
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2389 Depart at 6:25am from New York (LGA) Fly for 2h 39m Arrive at 8:04am in Chicago (ORD)
USD 95
9:30pm - 11:09pm
Tue Jul 22nd
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 393 Depart at 9:30pm from New York (LGA) Fly for 2h 39m Arrive at 11:09pm in Chicago (ORD)
USD 95
4:25pm - 6:05pm
Tue Jul 22nd
2h 40m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 1842 Depart at 4:25pm from New York (LGA) Fly for 2h 40m Arrive at 6:05pm in Chicago (ORD)
USD 95
3:25pm - 5:05pm
Tue Jul 22nd
2h 40m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 1504 Depart at 3:25pm from New York (LGA) Fly for 2h 40m Arrive at 5:05pm in Chicago (ORD)
USD 95
6:30pm - 8:10pm
Tue Jul 22nd
2h 40m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 598 Depart at 6:30pm from New York (LGA) Fly for 2h 40m Arrive at 8:10pm in Chicago (ORD)
USD 95
7:59pm - 9:41pm
Sat Jul 19th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 19th 2025 United Airlines · UA 353 Depart at 7:59pm from New York (EWR) Fly for 2h 42m Arrive at 9:41pm in Chicago (ORD)
USD 95
9:55pm - 11:37pm
Sat Jul 26th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 26th 2025 United Airlines · UA 1308 Depart at 9:55pm from New York (EWR) Fly for 2h 42m Arrive at 11:37pm in Chicago (ORD)
USD 95
9:59pm - 11:41pm
Tue Jul 22nd
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
USD 95
9:59pm - 11:41pm
Thu Jul 24th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Thu Jul 24th 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
USD 95
9:55pm - 11:37pm
Sat Jul 19th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 19th 2025 United Airlines · UA 1308 Depart at 9:55pm from New York (EWR) Fly for 2h 42m Arrive at 11:37pm in Chicago (ORD)
USD 98
6:30pm - 8:00pm
Fri Jul 18th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Fri Jul 18th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 98
6:30pm - 8:05pm
Tue Jul 8th
2h 35m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 8th 2025 Spirit Airlines · NK 2178 Depart at 6:30pm from New York (LGA) Fly for 2h 35m Arrive at 8:05pm in Chicago (ORD)
USD 110
1:17pm - 2:55pm
Wed Jul 23rd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 2199 Depart at 1:17pm from New York (LGA) Fly for 2h 38m Arrive at 2:55pm in Chicago (ORD)
USD 110
9:15am - 10:53am
Wed Jul 23rd
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 623 Depart at 9:15am from New York (LGA) Fly for 2h 38m Arrive at 10:53am in Chicago (ORD)
USD 110
6:05am - 7:44am
Sat Jul 19th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 19th 2025 United Airlines · UA 2389 Depart at 6:05am from New York (LGA) Fly for 2h 39m Arrive at 7:44am in Chicago (ORD)
USD 110
5:25pm - 7:05pm
Tue Jul 22nd
2h 40m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2005 Depart at 5:25pm from New York (LGA) Fly for 2h 40m Arrive at 7:05pm in Chicago (ORD)
USD 112
5:00am - 6:37am
Mon Jul 7th
2h 37m
New York (EWR) → Chicago (ORD)
Direct
Mon Jul 7th 2025 Spirit Airlines · NK 2543 Depart at 5:00am from New York (EWR) Fly for 2h 37m Arrive at 6:37am in Chicago (ORD)
USD 112
6:00am - 7:38am
Sun Jul 20th
2h 38m
New York (EWR) → Chicago (ORD)
Direct
Sun Jul 20th 2025 United Airlines · UA 2164 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
USD 112
9:30pm - 11:09pm
Fri Jul 25th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Fri Jul 25th 2025 United Airlines · UA 393 Depart at 9:30pm from New York (LGA) Fly for 2h 39m Arrive at 11:09pm in Chicago (ORD)
USD 112
10:00pm - 11:42pm
Sun Jul 20th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Sun Jul 20th 2025 United Airlines · UA 1308 Depart at 10:00pm from New York (EWR) Fly for 2h 42m Arrive at 11:42pm in Chicago (ORD)
USD 113
6:05am - 7:44am
Sat Jul 26th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 26th 2025 United Airlines · UA 2389 Depart at 6:05am from New York (LGA) Fly for 2h 39m Arrive at 7:44am in Chicago (ORD)
USD 115
6:00am - 7:38am
Wed Jul 23rd
2h 38m
New York (EWR) → Chicago (ORD)
Direct
Wed Jul 23rd 2025 United Airlines · UA 2164 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
USD 115
6:00am - 7:38am
Sat Jul 26th
2h 38m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 26th 2025 United Airlines · UA 2164 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
USD 115
7:54pm - 9:36pm
Tue Jul 22nd
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 353 Depart at 7:54pm from New York (EWR) Fly for 2h 42m Arrive at 9:36pm in Chicago (ORD)
USD 116
6:30pm - 8:00pm
Thu Jul 10th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Thu Jul 10th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 116
6:30pm - 8:00pm
Thu Jul 24th
2h 30m
New York (LGA) → Chicago (ORD)
Direct
Thu Jul 24th 2025 Spirit Airlines · NK 1179 Depart at 6:30pm from New York (LGA) Fly for 2h 30m Arrive at 8:00pm in Chicago (ORD)
USD 121
9:59pm - 11:41pm
Mon Jul 21st
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Mon Jul 21st 2025 United Airlines · UA 1308 Depart at 9:59pm from New York (EWR) Fly for 2h 42m Arrive at 11:41pm in Chicago (ORD)
USD 121
7:20am - 8:57am
Sat Jul 26th
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 26th 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 121
7:20am - 8:57am
Sat Jul 19th
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 19th 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 121
8:00am - 9:39am
Tue Jul 22nd
2h 39m
New York (EWR) → Chicago (ORD)
Direct
Tue Jul 22nd 2025 United Airlines · UA 2100 Depart at 8:00am from New York (EWR) Fly for 2h 39m Arrive at 9:39am in Chicago (ORD)
USD 121
7:00am - 8:39am
Sat Jul 19th
2h 39m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 19th 2025 United Airlines · UA 2050 Depart at 7:00am from New York (EWR) Fly for 2h 39m Arrive at 8:39am in Chicago (ORD)
USD 121
8:30pm - 10:09pm
Mon Jul 21st
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Mon Jul 21st 2025 United Airlines · UA 2181 Depart at 8:30pm from New York (LGA) Fly for 2h 39m Arrive at 10:09pm in Chicago (ORD)
USD 121
7:30pm - 9:09pm
Mon Jul 21st
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Mon Jul 21st 2025 United Airlines · UA 1819 Depart at 7:30pm from New York (LGA) Fly for 2h 39m Arrive at 9:09pm in Chicago (ORD)
USD 121
7:59pm - 9:41pm
Sat Jul 26th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 26th 2025 United Airlines · UA 353 Depart at 7:59pm from New York (EWR) Fly for 2h 42m Arrive at 9:41pm in Chicago (ORD)
USD 123
8:30pm - 10:09pm
Fri Jul 25th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Fri Jul 25th 2025 United Airlines · UA 2181 Depart at 8:30pm from New York (LGA) Fly for 2h 39m Arrive at 10:09pm in Chicago (ORD)
USD 127
7:00am - 8:39am
Sun Jul 20th
2h 39m
New York (EWR) → Chicago (ORD)
Direct
Sun Jul 20th 2025 United Airlines · UA 2050 Depart at 7:00am from New York (EWR) Fly for 2h 39m Arrive at 8:39am in Chicago (ORD)
USD 131
10:30pm - 11:59pm
Sat Jul 12th
2h 29m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 12th 2025 United Airlines · UA 2084 Depart at 10:30pm from New York (EWR) Fly for 2h 29m Arrive at 11:59pm in Chicago (ORD)
USD 131
7:20am - 8:57am
Sat Jul 12th
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 12th 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 131
2:20pm - 3:57pm
Tue Jul 15th
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 2360 Depart at 2:20pm from New York (LGA) Fly for 2h 37m Arrive at 3:57pm in Chicago (ORD)
USD 131
7:20am - 8:57am
Tue Jul 15th
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 131
7:20am - 8:57am
Wed Jul 16th
2h 37m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 16th 2025 United Airlines · UA 561 Depart at 7:20am from New York (LGA) Fly for 2h 37m Arrive at 8:57am in Chicago (ORD)
USD 131
6:00am - 7:38am
Wed Jul 16th
2h 38m
New York (EWR) → Chicago (ORD)
Direct
Wed Jul 16th 2025 United Airlines · UA 2164 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
USD 131
9:15am - 10:53am
Wed Jul 16th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 16th 2025 United Airlines · UA 623 Depart at 9:15am from New York (LGA) Fly for 2h 38m Arrive at 10:53am in Chicago (ORD)
USD 131
1:17pm - 2:55pm
Tue Jul 15th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 2199 Depart at 1:17pm from New York (LGA) Fly for 2h 38m Arrive at 2:55pm in Chicago (ORD)
USD 131
9:15am - 10:53am
Tue Jul 15th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 623 Depart at 9:15am from New York (LGA) Fly for 2h 38m Arrive at 10:53am in Chicago (ORD)
USD 131
6:00am - 7:38am
Sat Jul 12th
2h 38m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 12th 2025 United Airlines · UA 2164 Depart at 6:00am from New York (EWR) Fly for 2h 38m Arrive at 7:38am in Chicago (ORD)
USD 131
8:25am - 10:03am
Wed Jul 16th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 16th 2025 United Airlines · UA 2479 Depart at 8:25am from New York (LGA) Fly for 2h 38m Arrive at 10:03am in Chicago (ORD)
USD 131
10:25am - 12:03pm
Tue Jul 15th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 1310 Depart at 10:25am from New York (LGA) Fly for 2h 38m Arrive at 12:03pm in Chicago (ORD)
USD 131
11:25am - 1:03pm
Tue Jul 15th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 1941 Depart at 11:25am from New York (LGA) Fly for 2h 38m Arrive at 1:03pm in Chicago (ORD)
USD 131
8:25am - 10:03am
Tue Jul 15th
2h 38m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 2479 Depart at 8:25am from New York (LGA) Fly for 2h 38m Arrive at 10:03am in Chicago (ORD)
USD 131
6:20am - 7:59am
Sun Jul 27th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Sun Jul 27th 2025 United Airlines · UA 2389 Depart at 6:20am from New York (LGA) Fly for 2h 39m Arrive at 7:59am in Chicago (ORD)
USD 131
6:25am - 8:04am
Wed Jul 16th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 16th 2025 United Airlines · UA 2389 Depart at 6:25am from New York (LGA) Fly for 2h 39m Arrive at 8:04am in Chicago (ORD)
USD 131
6:05am - 7:44am
Sat Jul 12th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Sat Jul 12th 2025 United Airlines · UA 2389 Depart at 6:05am from New York (LGA) Fly for 2h 39m Arrive at 7:44am in Chicago (ORD)
USD 131
8:30pm - 10:09pm
Tue Jul 15th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 2181 Depart at 8:30pm from New York (LGA) Fly for 2h 39m Arrive at 10:09pm in Chicago (ORD)
USD 131
6:25am - 8:04am
Tue Jul 15th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 2389 Depart at 6:25am from New York (LGA) Fly for 2h 39m Arrive at 8:04am in Chicago (ORD)
USD 131
9:30pm - 11:09pm
Tue Jul 15th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 393 Depart at 9:30pm from New York (LGA) Fly for 2h 39m Arrive at 11:09pm in Chicago (ORD)
USD 131
7:00am - 8:39am
Sat Jul 12th
2h 39m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 12th 2025 United Airlines · UA 2050 Depart at 7:00am from New York (EWR) Fly for 2h 39m Arrive at 8:39am in Chicago (ORD)
USD 131
9:30pm - 11:09pm
Wed Jul 16th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Wed Jul 16th 2025 United Airlines · UA 393 Depart at 9:30pm from New York (LGA) Fly for 2h 39m Arrive at 11:09pm in Chicago (ORD)
USD 131
7:30pm - 9:09pm
Tue Jul 15th
2h 39m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 1819 Depart at 7:30pm from New York (LGA) Fly for 2h 39m Arrive at 9:09pm in Chicago (ORD)
USD 131
4:25pm - 6:05pm
Tue Jul 15th
2h 40m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 1842 Depart at 4:25pm from New York (LGA) Fly for 2h 40m Arrive at 6:05pm in Chicago (ORD)
USD 131
3:25pm - 5:05pm
Tue Jul 15th
2h 40m
New York (LGA) → Chicago (ORD)
Direct
Tue Jul 15th 2025 United Airlines · UA 1504 Depart at 3:25pm from New York (LGA) Fly for 2h 40m Arrive at 5:05pm in Chicago (ORD)
USD 131
9:55pm - 11:37pm
Sat Jul 12th
2h 42m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 12th 2025 United Airlines · UA 1308 Depart at 9:55pm from New York (EWR) Fly for 2h 42m Arrive at 11:37pm in Chicago (ORD)
USD 319
10:30pm - 11:59pm
Sat Jul 5th
2h 29m
New York (EWR) → Chicago (ORD)
Direct
Sat Jul 5th 2025 United Airlines · UA 2084 Depart at 10:30pm from New York (EWR) Fly for 2h 29m Arrive at 11:59pm in Chicago (ORD)
USD 1201
6:45am - 9:40am
Sat Jul 12th
27h 55m
New York (JFK) → Chicago (ORD)
1 Stop
Sat Jul 12th 2025 Turkish Airlines · TK 112 Depart at 6:45am from New York (JFK) Fly for 9h 40m Arrive at 11:25pm in Istanbul (IST)
Layover in Istanbul for 7h 5m
Sun Jul 13th 2025 Turkish Airlines · TK 185 Depart at 6:30am from Istanbul (IST) Fly for 11h 10m Arrive at 9:40am in Chicago (ORD)
USD 1695
12:50pm - 9:40am
Sat Jul 12th
21h 50m
New York (JFK) → Chicago (ORD)
1 Stop
Sat Jul 12th 2025 Turkish Airlines · TK 4 Depart at 12:50pm from New York (JFK) Fly for 9h 40m Arrive at 5:30am in Istanbul (IST)
Layover in Istanbul for 1h 0m
Sun Jul 13th 2025 Turkish Airlines · TK 185 Depart at 6:30am from Istanbul (IST) Fly for 11h 10m Arrive at 9:40am in Chicago (ORD)
USD 1702
5:35pm - 4:30pm
Fri Jul 25th
23h 55m
New York (EWR) → Chicago (ORD)
1 Stop
Fri Jul 25th 2025 TAP Portugal · TP 202 Depart at 5:35pm from New York (EWR) Fly for 6h 55m Arrive at 5:30am in Lisbon (LIS)
Layover in Lisbon for 7h 45m
Sat Jul 26th 2025 TAP Portugal · TP 243 Depart at 1:15pm from Lisbon (LIS) Fly for 9h 15m Arrive at 4:30pm in Chicago (ORD)
USD 1801
12:50pm - 9:40am
Mon Jul 14th
21h 50m
New York (JFK) → Chicago (ORD)
1 Stop
Mon Jul 14th 2025 Turkish Airlines · TK 4 Depart at 12:50pm from New York (JFK) Fly for 9h 40m Arrive at 5:30am in Istanbul (IST)
Layover in Istanbul for 1h 0m
Tue Jul 15th 2025 Turkish Airlines · TK 185 Depart at 6:30am from Istanbul (IST) Fly for 11h 10m Arrive at 9:40am in Chicago (ORD)
USD 1801
12:50pm - 9:40am
Tue Jul 15th
21h 50m
New York (JFK) → Chicago (ORD)
1 Stop
Tue Jul 15th 2025 Turkish Airlines · TK 4 Depart at 12:50pm from New York (JFK) Fly for 9h 40m Arrive at 5:30am in Istanbul (IST)
Layover in Istanbul for 1h 0m
Wed Jul 16th 2025 Turkish Airlines · TK 185 Depart at 6:30am from Istanbul (IST) Fly for 11h 10m Arrive at 9:40am in Chicago (ORD)
USD 1833
7:50pm - 10:00pm
Tue Jul 15th
27h 10m
New York (JFK) → Chicago (ORD)
1 Stop
Tue Jul 15th 2025 Turkish Airlines · TK 2 Depart at 7:50pm from New York (JFK) Fly for 10h 5m Arrive at 12:55pm in Istanbul (IST)
Layover in Istanbul for 5h 50m
Wed Jul 16th 2025 Turkish Airlines · TK 155 Depart at 6:45pm from Istanbul (IST) Fly for 11h 15m Arrive at 10:00pm in Chicago (ORD)
USD 1838
7:50pm - 5:55pm
Sat Jul 12th
23h 5m
New York (JFK) → Chicago (ORD)
1 Stop
Sat Jul 12th 2025 Turkish Airlines · TK 2 Depart at 7:50pm from New York (JFK) Fly for 10h 5m Arrive at 12:55pm in Istanbul (IST)
Layover in Istanbul for 1h 30m
Sun Jul 13th 2025 Turkish Airlines · TK 5 Depart at 2:25pm from Istanbul (IST) Fly for 11h 30m Arrive at 5:55pm in Chicago (ORD)
USD 1865
12:50pm - 9:40am
Sun Jul 13th
21h 50m
New York (JFK) → Chicago (ORD)
1 Stop
Sun Jul 13th 2025 Turkish Airlines · TK 4 Depart at 12:50pm from New York (JFK) Fly for 9h 40m Arrive at 5:30am in Istanbul (IST)
Layover in Istanbul for 1h 0m
Mon Jul 14th 2025 Turkish Airlines · TK 185 Depart at 6:30am from Istanbul (IST) Fly for 11h 10m Arrive at 9:40am in Chicago (ORD)
USD 1886
7:50pm - 5:55pm
Tue Jul 15th
23h 5m
New York (JFK) → Chicago (ORD)
1 Stop
Tue Jul 15th 2025 Turkish Airlines · TK 2 Depart at 7:50pm from New York (JFK) Fly for 10h 5m Arrive at 12:55pm in Istanbul (IST)
Layover in Istanbul for 1h 30m
Wed Jul 16th 2025 Turkish Airlines · TK 5 Depart at 2:25pm from Istanbul (IST) Fly for 11h 30m Arrive at 5:55pm in Chicago (ORD)
USD 2132
12:50pm - 9:40am
Sat Jul 5th
21h 50m
New York (JFK) → Chicago (ORD)
1 Stop
Sat Jul 5th 2025 Turkish Airlines · TK 4 Depart at 12:50pm from New York (JFK) Fly for 9h 40m Arrive at 5:30am in Istanbul (IST)
Layover in Istanbul for 1h 0m
Sun Jul 6th 2025 Turkish Airlines · TK 185 Depart at 6:30am from Istanbul (IST) Fly for 11h 10m Arrive at 9:40am in Chicago (ORD)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality. It's designed for remote workers, backpackers, and people living abroad.

Read Sonaa's 7 Amazing Skyscanner Alternatives for Booking Travel

ANDY TRAVELS

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Read Josh's Ultimate Guide To Find Cheap One Way Flights

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Read Wesley's My Best Cheap Flight Hacks (Why Pay More?)

Cheap Flights from New York to Chicago (NYC to CHI)

Sarah Belizaire

John Ford

Roaming Sonaa

ANDY TRAVELS

Travel With Bender

Wesley Mergard

Latest Cheap Flight Searches

FlightList Blog

Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights

Why I Built FlightList & Solved My Own Problem

About FlightList