Chicago Trip Guides

  • Trip Guide

The most epic American road trip

  • 28 Places
  • 191:21
  • 11,212 mi
  • Trip Guide

The coolest retro neon signs along Route 66

  • 17 Places
  • 34:05
  • 2,156 mi
  • Trip Guide

Pun-tastic Restaurants

  • 16 Places

Chicago to New Orleans Road Trip

  • 19 Places
  • 19:28
  • 1,068 mi
  • Trip Guide

Library Lust

  • 7 Places
  • Trip Guide

Get your kicks on Illinois's Route 66

  • 24 Places
  • 07:05
  • 335 mi
  • Trip Guide
  • 2 Weeks

The ultimate road trip guide to I-90, from Boston to Seattle

  • 48 Places
  • 63:53
  • 3,652 mi
  • Trip Guide

U.S. Route 12 Road Trip

  • 51 Places
  • 47:15
  • 2,642 mi
  • Trip Guide

Things to do in ... Chicago

  • 15 Places