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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 14 dates Usually: $130–$330
Cheap
Expensive
Oct 31
Sat
$495
Nov 4
Wed
$495
Nov 5
Thu
$497
Nov 6
Fri
$491
Nov 9
Mon
$422
Nov 21
Sat
$259
Nov 28
Sat
$398
Nov 30
Mon
$337
Dec 2
Wed
$259
Dec 3
Thu
$293
Dec 19
Sat
$317
Dec 26
Sat
$322
Dec 28
Mon
$317
Jan 5
Tue
$307