We are traveling from Chicago to Columbus, OH next week and to keep things interesting we'll have our 15-month-old in the back seat. I'm wondering if people who have made this drive have advice in terms of routing, avoiding traffic tie-ups and stopping points. [more inside]
posted by Morydd on Sep 4, 2009 - 6 answers

In September I'm flying to Chicago to meet some friends. We'll be driving a van from Chicago to New York. What are some interesting things to do along the way? Is there anything especially weird that we should stop to see? [more inside]
posted by anoirmarie on Jul 23, 2009 - 9 answers

RoadtripFilter: Where's a cool place to stop for a night between Chicago and Syracuse? [more inside]
posted by mustcatchmooseandsquirrel on Jun 8, 2009 - 7 answers

Quick, interesting stops between Chicago and Dallas (via Memphis) along I57, I55, I30? Quirky, tasty, fun, and beautiful are all invited. [more inside]
posted by brandsilence on Apr 9, 2009 - 10 answers

Chicago to Houston in one week, two lovely gals, one Camry: We're taking a road trip the week before July 4, starting in Chicago and ending in Houston. Any route tips? Things to see? Do? Quirky free attractions to see along the way? [more inside]
posted by melodykramer on May 7, 2008 - 16 answers

Road Trip filter: My girlfriend and I live in Chicago, and we want to take a road trip somewhere for the long weekend. [more inside]
posted by AceRock on Aug 28, 2007 - 28 answers

What amusing rigors can we put the bachelor through as we drive from Chicago to northern Wisconsin? [more inside]
posted by asuprenant on Aug 10, 2007 - 9 answers

What are some fast and fun things to do in Chicago? [more inside]
posted by BradNelson on Jul 5, 2007 - 19 answers

Going on an impromptu road trip to Des Moines. What do we do once we get there? [more inside]
posted by sugarfish on May 17, 2007 - 13 answers

chicagofilter: renting a car - from a dealer (or: where can I find a decently priced mileage-free rental for a roadtrip) ? [more inside]
posted by krautland on Feb 20, 2007 - 9 answers

Starting point: Chicago. Destination: Niagara Falls. Transportation: Honda Civic. Question: Am I nuts? [more inside]
posted by Terminal Verbosity on Jul 24, 2006 - 21 answers

The SO and I live in Chicago and have taken several road trips over the years. We're up for more, the problem is, we seem to have tapped out all the obvious choices. [more inside]
posted by CMichaelCook on Apr 25, 2006 - 31 answers

Chicago-Madison-Milwaukee Bachelor Party Roadtrip ideas... [more inside]
posted by Frank Grimes on Mar 5, 2006 - 17 answers

I'm getting married in October, and our honeymoon is a long leisurely drive up to Massachusetts. We know we'll be stopping at Niagara Falls for one night, but are there any other places we should stop and see, weird roadside attractions, etc? We've already been to the Rock and Roll Hall of Fame in Cleveland...any roads less traveled to consider?
posted by agregoli on Mar 29, 2005 - 33 answers