Trip.ovh US Road Trip Planner

Overnight Road Trips from Chicago, IL

Routes

30

Avg Distance

291 mi

Avg Drive

5h 35m

Destinations

30

With 30 routes averaging 288 miles, these drives from Chicago, IL are best split across two or more days. Each route includes suggested stop towns and overnight options.

Planning Tips

Book accommodation in the suggested stop town — it breaks the drive naturally and gives you a reason to explore.
Pack an overnight bag that's easy to grab from the car without unpacking everything.
Split long drives so the hardest stretch is the first day when you're freshest.

Frequently Asked Questions

30 routes from Chicago, IL are recommended as multi-day trips — typically 4+ hours of driving with suggested overnight stop towns along the way.

Drive times and distances come from actual road network data via OSRM. Fuel costs use current state-level gas prices. Drive scores factor in elevation profile, road variety, and terrain. All data is recalculated regularly.

Yes. Click any route to see its full trip page with turn-by-turn directions, fuel cost estimates, elevation profile, stop suggestions, weather conditions, and more.

Multi-Day Routes

Chicago, IL → Barr, IL

247.7 mi 5h 5m Score: 8/10

Chicago, IL → Edwardsville, IL

274.5 mi 5h 9m Score: 8/10

Chicago, IL → Holiday Shores, IL

271.7 mi 5h 10m Score: 8/10

Chicago, IL → Bethalto, IL

275.4 mi 5h 13m Score: 8/10

Chicago, IL → Barry, IL

279.4 mi 5h 13m Score: 8/10

Chicago, IL → Rosewood Heights, IL

278.4 mi 5h 20m Score: 8/10

Chicago, IL → Caseyville, IL

286.3 mi 5h 22m Score: 8/10

Chicago, IL → Roxana, IL

280.4 mi 5h 23m Score: 8/10

Chicago, IL → Jackson, IL

243.1 mi 5h 24m Score: 9/10

Chicago, IL → Saint Rose, IL

286 mi 5h 26m Score: 8/10

Chicago, IL → Trenton, IL

287.9 mi 5h 28m Score: 8/10

Chicago, IL → Alton, IL

283.9 mi 5h 28m Score: 8/10

Chicago, IL → East Saint Louis, IL

291.9 mi 5h 29m Score: 8/10

Chicago, IL → Albion, IL

268.7 mi 5h 30m Score: 9/10

Chicago, IL → Brooklyn, IL

293.1 mi 5h 32m Score: 8/10

Chicago, IL → Nashville, IL

299.7 mi 5h 32m Score: 8/10

Chicago, IL → O'Fallon, IL

288.8 mi 5h 32m Score: 8/10

Chicago, IL → Sesser, IL

298.8 mi 5h 34m Score: 8/10

Chicago, IL → Belleville, IL

292.7 mi 5h 34m Score: 8/10

Chicago, IL → Douglas, IL

299.3 mi 5h 44m Score: 8/10

Chicago, IL → Johnston City, IL

311.4 mi 5h 46m Score: 8/10

Chicago, IL → Zeigler, IL

310.7 mi 5h 48m Score: 8/10

Chicago, IL → Marion, IL

317.5 mi 5h 52m Score: 8/10

Chicago, IL → Quincy, IL

309.6 mi 5h 53m Score: 8/10

Chicago, IL → Adams, IL

299.3 mi 5h 54m Score: 8/10

Chicago, IL → Mount Carmel, IL

285.4 mi 5h 55m Score: 9/10

Chicago, IL → Burton, IL

313.7 mi 5h 57m Score: 8/10

Chicago, IL → Crainville, IL

321.6 mi 5h 59m Score: 8/10

Chicago, IL → Cambria, IL

321.7 mi 6h 1m Score: 8/10

Chicago, IL → Norris City, IL

296.8 mi 6h 4m Score: 9/10

Explore More

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