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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: $497 64 dates Usually: $105–$310
Cheap
Expensive
Oct 31
Sat
$495
Nov 1
Sun
$497
Nov 2
Mon
$497
Nov 3
Tue
$495
Nov 4
Wed
$421
Nov 5
Thu
$419
Nov 6
Fri
$419
Nov 7
Sat
$421
Nov 8
Sun
$419
Nov 9
Mon
$419
Nov 10
Tue
$421
Nov 11
Wed
$303
Nov 13
Fri
$323
Nov 14
Sat
$303
Nov 15
Sun
$337
Nov 16
Mon
$303
Nov 18
Wed
$259
Nov 19
Thu
$259
Nov 20
Fri
$299
Nov 22
Sun
$428
Nov 23
Mon
$318
Nov 24
Tue
$259
Nov 25
Wed
$259
Nov 26
Thu
$259
Nov 27
Fri
$339
Nov 28
Sat
$398
Nov 29
Sun
$490
Nov 30
Mon
$337
Dec 1
Tue
$259
Dec 2
Wed
$259
Dec 3
Thu
$259
Dec 4
Fri
$299
Dec 5
Sat
$259
Dec 6
Sun
$327
Dec 7
Mon
$259
Dec 8
Tue
$259
Dec 9
Wed
$259
Dec 10
Thu
$259
Dec 11
Fri
$308
Dec 12
Sat
$288
Dec 14
Mon
$288
Dec 16
Wed
$288
Dec 17
Thu
$288
Dec 19
Sat
$347
Dec 20
Sun
$372
Dec 21
Mon
$351
Dec 23
Wed
$347
Dec 24
Thu
$317
Dec 25
Fri
$317
Dec 26
Sat
$327
Dec 27
Sun
$327
Dec 28
Mon
$317
Dec 29
Tue
$307
Dec 31
Thu
$307
Jan 1
Fri
$317
Jan 2
Sat
$312
Jan 3
Sun
$327
Jan 4
Mon
$307
Jan 5
Tue
$297
Jan 6
Wed
$297
Jan 7
Thu
$297
Jan 9
Sat
$297
Jan 10
Sun
$327
Jan 11
Mon
$297