- SAVE $50.00$149.99$199.99Chicago Maroons Gold-Tone Stainless Steel Watch with Black LeatherFanatics
- $94.99Vintage International Harvester Dual Globe Watch Fob ChicagoEtsy
- 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
- $24.95NHL Chicago Blackhawks Spirit WatchAmazon
- $44.95Timex TWZFBEAYA NFL Recruit Chicago Bears WatchAmazon
- $50.97and upTimex Men's NHL Citation 42mm Watch – Chicago Blackhawks with Stainless Steel Expansion BandAmazon & 1 more
- SAVE $8.75$26.24$34.99Youth Timex Chicago Cubs Recruit WatchFanatics
- $64.36and upTimex Men's Chicago 45mm TW2V29000VQ Quartz WatchAmazon & 2 more
- $19.992 Brand New in Original Boxes - Watches From Avon 2-Tone Link Watch & Sport Champions Watch-Chicago Bulls Bag No 577Etsy
- $56.24and upMen's Timex Chicago Bears Citation WatchOfficial NFL Shop & 2 more
- $99.00Timex Chicago Leather Strap Watch, 45mm in Silver/White/Tan at NordstromNordstrom
- $44.95Timex Tribute TWZHBLAYA NHL Recruit Chicago Blackhawks WatchAmazon
- $35.09and upSparo Chicago Bears Wood Watch and Phone Wallet Gift SetFanatics & 1 more
- $77.94Timex Tribute Men's NFL Weekender Chrono 40mm Watch – Chicago Bears with Tan Genuine Leather Slip-Thru StrapAmazon
- $44.95Timex Men's TWZFBEAMB NFL Clutch Chicago Bears WatchAmazon
- SAVE $18.75$56.24$74.99Men's Timex Chicago Cubs Citation WatchFanatics
- SAVE $11.25$33.74$44.99Men's Timex Chicago Cubs Clutch WatchFanatics
- $63.74and upMen's Timex Chicago Blackhawks Acclaim WatchFanatics & 4 more
- $63.74and upMen's Timex Chicago Cubs Acclaim WatchFanatics & 1 more
- SAVE $21.21$63.74$84.95Timex Men's TWZFBEAMM NFL Acclaim Chicago Bears WatchAmazon
- $64.95Timex Tribute Men's TWZHBLAMF NHL Gamer Chicago Blackhawks WatchAmazon
- $159.00Men's Chicago Timex Strap Watch - Black WhiteSaks Fifth Avenue
- $99.00and upTimex Men's Chicago Black Leather Watch 45mm - BlackMacy's & 1 more
- $28.50Rico Industries WTSPI5301 MLB Chicago Cubs Spirit Watch, BlackAmazon
- $49.26Game Time Chicago Bears - NFL Watch and Wallet Combo Gift SetAmazon
- $149.00Men's Chicago Stainless Steel Bracelet Watch/45MM - BlackSaks Fifth Avenue
- SAVE $56.25$168.74$224.99Women's Fossil Navy Chicago Maroons Jacqueline Leather WatchFanatics
- $239.99Men's Fossil Brown Chicago Cubs Minimalist Leather WatchFanatics
- SAVE $12.69$77.26$89.95Game Time Chicago Cubs Men's Watch - MLB Fantom SeriesAmazon
- $259.99Women's Black Chicago Cubs Stainless Steel Watch with Leather BandFanatics
- SAVE $23.00$96.00$119.00Timex Men's Chicago Chronograph 45mm Watch – Black Dial & Case with Black Leather StrapAmazon
- $74.95Game Time Chicago Cubs Men's Watch - MLB Sport Steel Series, Officially LicensedAmazon
- $104.95Game Time Chicago Bears Men's Watch - NFL Two-Tone Competitor Series, Officially LicensedAmazon
- $74.95Game Time Chicago Bears Men's Watch - NFL Sport Steel Series, Officially LicensedAmazon
- SAVE $58.75$176.24$234.99Women's Fossil Silver Chicago Maroons Jacqueline Stainless Steel WatchFanatics
- $41.24and upGroove Life Black Chicago Bears Samsung 22mm Short Watch BandFanatics & 1 more
- $239.99Men's Fossil Brown Chicago White Sox Minimalist Leather WatchFanatics
- $259.99Women's Fossil Silver Chicago Cubs Fossil Jacqueline Stainless Steel WatchFanatics
- SAVE $10.00$119.00$129.00Timex Men's Chicago Chronograph 45mm Watch – Silver-Tone Case Black Dial with Stainless Steel BraceletAmazon
- $239.99Women's Fossil Gold/Navy Chicago White Sox Jacqueline Leather WatchFanatics
- $129.00Men's Chicago Stainless Steel & Leather Strap Chronograph Watch/45MM - BrownSaks Fifth Avenue
- $118.90Invicta NHL Chicago Blackhawks Quartz Black Dial Men's Watch 42315Amazon
- SAVE $56.25$168.74$224.99Women's Fossil Pink Chicago Maroons Jacqueline Date Blush Leather WatchFanatics
- $269.99Men's Fossil Black Chicago White Sox Minimalist Stainless Steel WatchFanatics
- $259.99Women's Fossil Silver Chicago White Sox Fossil Jacqueline Stainless Steel WatchFanatics
- SAVE $51.25$153.74$204.99Women's Chicago Maroons Silver-Tone Dial Stainless Steel Quartz WatchFanatics
- SAVE $57.50$172.49$229.99Women's Fossil Silver Chicago Maroons Scarlette Mini Three-Hand Date WatchFanatics
- $269.99Men's Fossil Gray Chicago Cubs Fossil Minimalist Smoke Stainless Steel WatchFanatics
- $279.99Men's Fossil Gray Chicago White Sox Machine Smoke Stainless Steel WatchFanatics
- $269.99Men's Fossil Gray Chicago White Sox Fossil Minimalist Smoke Stainless Steel WatchFanatics
- $259.99Women's Fossil Silver Chicago White Sox Scarlette Two-Tone Stainless Steel WatchFanatics
- $34.0070S Sweda Wrist Watch Genuine Leather Black Band T.p.a. Chicago Chapter #1 in Original Box UnusedEtsy
- $39.99and upNFL Chicago Bears Wordmark HD Apple Watch Band - 38/40/41mm ShortTarget & 2 more
- $39.99and upMLB Chicago Cubs Wordmark HD Apple Watch Band - 38/40/41mm ShortTarget & 1 more
- $69.99Chicago Fire Leather Apple Watch BandFanatics
- $39.99and upChicago White Sox Silicone Apple Watch BandFanatics & 1 more
- $39.99and upMLB Chicago White Sox Wordmark Engraved Apple Watch Band - 42/44/45/49mmTarget & 1 more
- $39.99Chicago Cubs 38/40/41mm Apple Watch Sports BandFanatics