$39.99and up
MLB Chicago Cubs Wordmark HD Apple Watch Band - 38/40/41mm ShortTarget & 1 more$69.99
Chicago Fire Leather Apple Watch BandFanatics$39.99and up
MLB Chicago White Sox Wordmark Engraved Apple Watch Band - 42/44/45/49mmTarget & 1 more$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 LeatherFanatics$39.99
Chicago White Sox 38/40/41mm Apple Watch Sports BandFanaticsSAVE $10.00
$29.99$39.99
Chicago Cubs 42/44/45mm Logo Silicone Apple Watch BandFanatics$29.95
Chicago White Sox HD Elite Edition Watch Band Compatible with Apple Watch (38/40/41mm Short)AmazonSAVE $10.00
$29.99$39.99
Chicago White Sox 42/44/45mm Logo Silicone Apple Watch 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" WWayfair$58.99
Gametime Chicago Bears Navy Silicone Band fits Apple Watch (42/44mm M/L). Watch not included.JTVSAVE $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 Bears Leather Apple Watch BandOfficial NFL Shop & 2 more$59.99and up
Black Chicago Cubs Leather Apple Watch BandFanatics & 1 moreSAVE $8.75
$26.24$34.99
Youth Timex Chicago Cubs Recruit WatchFanatics$44.95
Timex TWZFBEAYA NFL Recruit Chicago Bears WatchAmazon$99.00
Timex Chicago Leather Strap Watch, 45mm in Silver/White/Tan at NordstromNordstrom$39.99
NFL Chicago Bears Apple Watch Compatible Silicone Band 38/40/41mm - BlueTarget$64.36and up
Timex Men's Chicago 45mm TW2V29000VQ Quartz WatchAmazon & 2 more$94.99
Vintage International Harvester Dual Globe Watch Fob ChicagoEtsy$63.99
Spectators Watching a Baseball Match in a Stadium, Wrigley Field, Chicago, Cook County, Illinois Photographic Print on CanvasWayfair$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$44.99
Game Time Chicago Bears Silicone Watch Band and Case Cover Combo Package Compatible with Apple Watch and AirPods Battery Case (42/44/45mm Navy/Navy)Amazon$59.99and up
Tan Chicago Bears Leather Apple Watch BandFanatics & 1 more$79.99and up
Black Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more$63.99
'Illinois, Chicago, Millennium Park, Pritzker Pavilion, Spectators Watching the Show' Photographic Print on CanvasWayfair$44.95
Timex Tribute TWZHBLAYA NHL Recruit Chicago Blackhawks WatchAmazon$24.99and up
NFL Chicago Bears Wordmark Apple Watch Band - 42/44/45/49mmTarget & 2 more$29.99and up
Navy Chicago Bears Silicone Apple Watch BandOfficial NFL Shop & 1 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 BandFanaticsSAVE $5.50
$16.49$21.99
Purple Chicago Maroons Samsung 22mm Watch BandFanatics