| ID | ROUTE | LOCALITY | COUNTRY | CREATED | USED FOR | DISTANCE (km) | ASCENT (m) | TERRAIN | VIEWS |
|---|---|---|---|---|---|---|---|---|---|
| 1864324 | C&D: Streeterville + Beach | Near North Side | US | 4 years ago | Running | 7.268 | 14 | Mixed | 112 |
| 2335104 | Gold Coast - Charlie/Olivia 2024 | Near North Side | US | 3 years ago | Walking | 2.573 | 3 | Road | 106 |
| 2923599 | SAt Route 03/28 | Near North Side | US | 1 year ago | Cycling | 64.713 | 223 | Road | 74 |
| 621965 | 10 SC | Near North Side | US | 8 years ago | Running | 16.277 | 18 | Road | 74 |
| 910548 | 10.010 Miles | Near North Side | US | 7 years ago | Running | 16.110 | 44 | Road | 71 |
| 2022814 | Dreihaus | Near North Side | US | 4 years ago | Walking | 1.244 | 0 | Road | 70 |
| 1913623 | Chicago 15km Run | Near North Side | US | 4 years ago | Running | 15.222 | 63 | Mixed | 67 |
| 1223286 | LP 6.96 (Larabee/Lincoln/Lakeshore/North/Clybourn) | Near North Side | US | 6 years ago | Running | 11.198 | 7 | Road | 67 |
| 904291 | 17.125 | Near North Side | US | 7 years ago | Running | 27.559 | 92 | Road | 65 |
| 922643 | Chicago - Art Galleries Tour | Near North Side | US | 7 years ago | Walking | 2.992 | 7 | Mixed | 63 |
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| 3419666 | Chasing Emma | Near North Side | US | 2 months ago | Running | 9.796 | 30 | Road | 61 |
| 837261 | 3.198 (North/Lake/Division/Orleans/Cleveland) | Near North Side | US | 7 years ago | Running | 5.147 | 8 | Road | 60 |
| 1201642 | 4.00 (run LP Up Clark) | Near North Side | US | 6 years ago | Running | 6.445 | 6 | Road | 59 |
| 3097358 | Gold Coast 2025 | Near North Side | US | 1 year ago | Walking | 2.535 | 4 | Road | 59 |
| 2231076 | 9 Miles Wolf Point Lincoln Park. | Near North Side | US | 3 years ago | Running | 14.115 | 51 | Mixed | 58 |
| 1908941 | Biking South 5/16/22 | Near North Side | US | 4 years ago | Cycling | 49.693 | 112 | Mixed | 58 |
| 850542 | 5.078 Miles (Division/Fountain/Division/Hill | Near North Side | US | 7 years ago | Running | 8.172 | 18 | Road | 58 |
| 880658 | 1.019 (Circle) | Near North Side | US | 7 years ago | Running | 1.640 | 1 | Road | 58 |
| 846987 | 2.945 (Division/Chicago/Division) | Near North Side | US | 7 years ago | Running | 4.740 | 14 | Road | 57 |
| 830465 | 6.15 Mile(North,Lake To Fountain,Chicago,Division) | Near North Side | US | 7 years ago | Running | 9.899 | 24 | Road | 57 |
| 3010055 | Navy Pier Shakeout | Near North Side | US | 1 year ago | Running | 2.578 | 9 | Mixed | 57 |
| 2905399 | Chicago | Near North Side | US | 1 year ago | Walking | 4.325 | 12 | Road | 56 |
| 841917 | 6.974 (See About) | Near North Side | US | 7 years ago | Running | 11.224 | 24 | Road | 56 |
| 1108739 | Quarantine 5K + | Near North Side | US | 6 years ago | Running | 5.161 | 4 | Road | 56 |
| 2963435 | Mari | Near North Side | US | 1 year ago | Running | 10.957 | 39 | Mixed | 55 |
| 3259129 | 5k | Near North Side | US | 7 months ago | Walking | 5.739 | 13 | Mixed | 54 |
| 1280386 | 11.16 (LP To Montrose) | Near North Side | US | 6 years ago | Running | 17.961 | 9 | Road | 54 |
| 3023498 | Pequod's | Near North Side | US | 1 year ago | Running | 6.839 | 19 | Mixed | 52 |
| 2940418 | City 6 | Near North Side | US | 1 year ago | Running | 9.745 | 30 | Road | 52 |
| 1322623 | 6.05 (LP To Diversey) | Near North Side | US | 6 years ago | Running | 9.741 | 6 | Road | 51 |