← All destinations

Chicago Price Calendar

Round trip prices from NYC. Click any date to book on Google Flights.

Day trip2 days3 days1 week2 weeks
Cheapest: $259 Most expensive: $597 64 dates Usually: $130–$330
Cheap
Expensive
Nov 1
Sun
$497
Nov 2
Mon
$497
Nov 3
Tue
$497
Nov 4
Wed
$497
Nov 5
Thu
$497
Nov 6
Fri
$493
Nov 7
Sat
$497
Nov 8
Sun
$497
Nov 9
Mon
$497
Nov 10
Tue
$422
Nov 11
Wed
$347
Nov 12
Thu
$347
Nov 13
Fri
$347
Nov 14
Sat
$347
Nov 15
Sun
$347
Nov 16
Mon
$347
Nov 17
Tue
$303
Nov 18
Wed
$259
Nov 19
Thu
$279
Nov 20
Fri
$279
Nov 22
Sun
$293
Nov 23
Mon
$259
Nov 24
Tue
$259
Nov 25
Wed
$259
Nov 26
Thu
$279
Nov 28
Sat
$542
Nov 29
Sun
$597
Nov 30
Mon
$337
Dec 1
Tue
$259
Dec 3
Thu
$279
Dec 4
Fri
$279
Dec 5
Sat
$293
Dec 6
Sun
$293
Dec 7
Mon
$259
Dec 8
Tue
$259
Dec 9
Wed
$259
Dec 10
Thu
$279
Dec 11
Fri
$279
Dec 12
Sat
$293
Dec 14
Mon
$259
Dec 15
Tue
$259
Dec 16
Wed
$259
Dec 17
Thu
$288
Dec 18
Fri
$317
Dec 19
Sat
$322
Dec 20
Sun
$322
Dec 21
Mon
$317
Dec 22
Tue
$371
Dec 23
Wed
$347
Dec 25
Fri
$347
Dec 27
Sun
$352
Dec 28
Mon
$336
Dec 29
Tue
$317
Dec 30
Wed
$317
Dec 31
Thu
$317
Jan 1
Fri
$322
Jan 2
Sat
$327
Jan 3
Sun
$323
Jan 5
Tue
$297
Jan 6
Wed
$297
Jan 7
Thu
$307
Jan 9
Sat
$312
Jan 10
Sun
$312
Jan 11
Mon
$297