- $29.99and upChicago Bears Silicone Apple Watch BandFanatics & 2 more
- SAVE $17.50$52.49$69.99Chicago Fire Leather Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago Cubs Silicone Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago White Sox Silicone Apple Watch BandFanatics
- SAVE $10.00$29.99$39.99Chicago Cubs 38/40/41mm 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
- $19.99Chicago 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
- $146.99Spectators Watching a Baseball Match in a Stadium, Wrigley Field, Chicago, Cook County, Illinois Photographic Print on Canvas Ebern Designs Size: 16"Wayfair
- SAVE $10.90$44.09$54.99Timex Chicago Cubs Rivalry WatchFanatics
- $119.00Timex Chicago Chrono Leather WatchBuckle
- $41.24and upTimex Chicago Bears Rivalry WatchFanatics & 1 more
- $31.95MLB Chicago Cubs Charm Watch, SilverAmazon
- $24.95NHL Chicago Blackhawks Spirit WatchAmazon
- $59.99and upBlack Chicago Bears Leather Apple Watch BandOfficial NFL Shop & 2 more
- $59.99and upTan Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $79.99MLS Chicago Fire Apple Watch Compatible Leather Band 42/44/45/49mm - TanTarget
- $59.99and upBrown Chicago Cubs Leather Apple Watch BandFanatics & 1 more
- $59.99and upTan Chicago Bears Leather Apple Watch BandOfficial NFL Shop & 2 more
- SAVE $8.75$26.24$34.99Youth Timex Chicago Cubs Recruit WatchFanatics
- SAVE $7.64$37.31$44.95Timex TWZFBEAYA NFL Recruit Chicago Bears WatchAmazon
- $39.99NFL Chicago Bears Apple Watch Compatible Silicone Band 38/40/41mm - BlueTarget