- SAVE $10.00$29.99$39.99Chicago Cubs Silicone Apple Watch BandFanatics
- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 2 more
- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 1 more
- $29.99and upChicago Cubs Silicone Apple Watch BandFanatics & 1 more
- SAVE $10.00$29.99$39.99Chicago Cubs Silicone Apple Watch BandFanatics
- $69.99Chicago Fire Leather Apple Watch BandFanatics
- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 1 more
- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 2 more
- $29.99and upChicago Cubs Silicone Apple Watch BandFanatics & 1 more
- $29.99and upChicago White Sox Silicone Apple Watch BandFanatics & 1 more
- SAVE $10.00$29.99$39.99Chicago White Sox Silicone Apple Watch BandFanatics
- $29.99and upChicago Cubs Debossed Silicone Apple Watch BandFanatics & 1 more
- $29.99and upChicago White Sox Silicone Apple Watch BandFanatics & 1 more
- SAVE $10.00$29.99$39.99Chicago White Sox Debossed Silicone Apple Watch BandFanatics
- $29.99and upChicago White Sox Debossed Silicone Apple Watch BandFanatics & 1 more
- SAVE $10.00$29.99$39.99Chicago Cubs 38/40/41mm Apple Watch Sports BandFanatics
- SAVE $10.00$29.99$39.99Chicago Cubs 42/44/45mm Apple Watch Sports BandFanatics
- SAVE $50.00$149.99$199.99Chicago Maroons Gold-Tone Stainless Steel Watch with Black LeatherFanatics
- SAVE $10.00$29.99$39.99Chicago White Sox 42/44/45mm Apple Watch Sports BandFanatics
- SAVE $10.00$29.99$39.99Chicago White Sox 38/40/41mm Apple Watch Sports BandFanatics
- $37.12and upChicago Bears 42/44/45mm Personalized Silicone Apple Watch BandFanatics & 1 more
- SAVE $10.00$29.99$39.99Chicago Cubs 42/44/45mm Logo Silicone Apple Watch BandFanatics
- $37.12and upChicago Bears 38/40/41mm Personalized Silicone Apple Watch BandFanatics & 1 more
- $37.12and upChicago Bears 42/44/45mm Personalized Silicone Apple Watch BandFanatics & 1 more
- $37.12and upChicago Bears 38/40/41mm Personalized Silicone Apple Watch BandOfficial NFL Shop & 1 more
- SAVE $10.00$29.99$39.99Chicago White Sox 38/40/41mm Logo Silicone Apple Watch BandFanatics
- $19.99Chicago City Flag Printed Watch Strap Compatible with Replacement IWatch Band 38-40mm 42-44mmAmazon
- $34.0070S Sweda Wrist Watch Genuine Leather Black Band T.p.a. Chicago Chapter #1 in Original Box UnusedEtsy
- $111.99Gametime Chicago Bears Leather Band fits Apple Watch (38/40mm M/L Black). Watch not included.JTV
- $41.24and upTimex Chicago Bears Rivalry WatchFanatics & 1 more
- $24.95NHL Chicago Blackhawks Spirit WatchAmazon
- $31.95MLB Chicago Cubs Charm Watch, SilverAmazon
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- $59.99and upBrown Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $59.99and upTan Chicago Bears Leather Apple Watch BandFanatics & 2 more
- $59.99and upTan Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $59.99and upBlack Chicago Bears Leather Apple Watch BandFanatics & 2 more
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - BrownTarget
- $59.99and upBlack Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - BlackTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - TanTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 38/40/41mm - TanTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 38/40/41mm - BlackTarget
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 38/40/41mm - BrownTarget
- $39.99NFL Chicago Bears Apple Watch Compatible Silicone Band 38/40/41mm - BlueTarget
- SAVE $8.09$36.86$44.95Timex TWZFBEAYA NFL Recruit Chicago Bears WatchAmazon
- $94.99Vintage International Harvester Dual Globe Watch Fob ChicagoEtsy
- $59.99and upBlack Chicago White Sox Leather Apple Watch BandFanatics & 1 more
- $59.99and upTan Chicago White Sox Leather Apple Watch BandFanatics & 1 more
- $59.99and upBlack Chicago Blackhawks Leather Apple Watch BandNHL Shop & 1 more
- $59.99and upBrown Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more
- $59.99and upTan Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more
- SAVE $5.50$16.49$21.99Gray Chicago Maroons Samsung 22mm Watch BandFanatics
- $59.99and upBlack Chicago Blackhawks Leather Apple Watch BandFanatics & 1 more
- $56.24and upMen's Timex Chicago Bears Citation WatchOfficial NFL Shop & 1 more
- $59.99and upBrown Chicago Bears Leather Apple Watch BandFanatics & 1 more
- $59.99and upBlack Chicago Bears Leather Apple Watch BandFanatics & 1 more
- SAVE $5.50$16.49$21.99Blue Chicago Maroons Samsung 22mm Watch BandFanatics
- $59.99and upTan Chicago Bears Leather Apple Watch BandFanatics & 1 more
- $24.99and upNFL Chicago Bears Wordmark Apple Watch Band - 42/44/45/49mmTarget & 2 more