$29.99and up
Chicago Bears Silicone Apple Watch BandOfficial NFL Shop & 2 more$29.99and up
Chicago Cubs Silicone Apple Watch BandFanatics & 1 moreSAVE $17.50
$52.49$69.99
Chicago Fire Leather Apple Watch BandFanaticsSAVE $10.00
$29.99$39.99
Chicago White Sox Silicone Apple Watch BandFanaticsSAVE $10.00
$29.99$39.99
Chicago Cubs 42/44/45mm Apple Watch Sports BandFanaticsSAVE $50.00
$149.99$199.99
Chicago Maroons Gold-Tone Stainless Steel Watch with Black LeatherFanaticsSAVE $10.00
$29.99$39.99
Chicago White Sox 42/44/45mm Apple Watch Sports BandFanatics$19.99
Chicago City Flag Printed Watch Strap Compatible with Replacement IWatch Band 38-40mm 42-44mmAmazon$149.99
'Illinois, Chicago, Millennium Park, Pritzker Pavilion, Spectators Watching the Show' Photographic Print on Canvas East Urban Home Size: 20" H x 60" WWayfairSAVE $10.90
$44.09$54.99
Timex Chicago Cubs Rivalry WatchFanatics$119.00
Timex Chicago Chrono Leather WatchBuckle$41.24and up
Timex Chicago Bears Rivalry WatchFanatics & 1 more$24.95
NHL Chicago Blackhawks Spirit WatchAmazon$31.95
MLB Chicago Cubs Charm Watch, SilverAmazon$59.99and up
Black Chicago Cubs Leather Apple Watch BandFanatics & 1 more$79.99
MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - BlackTarget$59.99and up
Black Chicago Bears Leather Apple Watch BandOfficial NFL Shop & 2 moreSAVE $8.75
$26.24$34.99
Youth Timex Chicago Cubs Recruit WatchFanatics$39.99
NFL Chicago Bears Apple Watch Compatible Silicone Band 38/40/41mm - BlueTarget$65.99
Spectators Watching a Baseball Match in a Stadium, Wrigley Field, Chicago, Cook County, Illinois Photographic Print on CanvasWayfairSAVE $7.64
$37.31$44.95
Timex TWZFBEAYA NFL Recruit Chicago Bears WatchAmazon$94.99
Vintage International Harvester Dual Globe Watch Fob ChicagoEtsy$35.09and up
Sparo Chicago Bears Wood Watch and Phone Wallet Gift SetFanatics & 1 more$59.99and up
Tan Chicago White Sox Leather Apple Watch BandFanatics & 1 more$65.99
'Illinois, Chicago, Millennium Park, Pritzker Pavilion, Spectators Watching the Show' Photographic Print on CanvasWayfair$59.99and up
Tan Chicago Bears Leather Apple Watch BandFanatics & 1 more$59.99and up
Black Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more$24.99and up
NFL Chicago Bears Wordmark Apple Watch Band - 42/44/45/49mmTarget & 2 moreSAVE $5.50
$16.49$21.99
Teal Chicago Maroons Samsung 22mm Watch BandFanaticsSAVE $5.50
$16.49$21.99
Black Chicago Maroons Samsung 22mm Watch BandFanatics$44.95
Timex Tribute TWZHBLAYA NHL Recruit Chicago Blackhawks WatchAmazon