Our guide to the best road trips from Chicago, including several you haven’t considered before.
Illinois
U.S. Route 20 Road Trip: Your Guide for Driving the Longest Road in America!
U.S. Route 20 is the longest road in America. Perfect for a summer road trip!
The Most Fun Things To Do In Chicago At Night
From museums to karaoke bars to restaurants, Chicago has a number of cool things to do at night.
Quirky Attraction: International Museum of Surgical Science (Chicago)
Chicago’s International Surgical Science Museum is the place to find vintage wheelchairs, surgery-themed artwork, and medical artifacts.
The White Squirrels Are (Almost) Everywhere in Olney, Illinois
Olney is a quirky small town known for its large population of albino squirrels. I set out to find them.
How to live in Chicago (or nearly any major American city) on $1000 a month
If you’re forced to live on a pauper budget due to circumstance, you can still get by in most cities.
A Short Midwest Road Trip in the Chevrolet Trax (And How to Open the Gas Tank!)
The Trax was an ideal vehicle for getting around Chicago and taking a short road trip.
Quirky Attraction: The Leaning Tower of Niles in Niles, Illinois (Chicago)
The Leaning Tower of Niles just outside Chicago is half the size of the famous Pisa attraction.
Food Challenge: Portillo’s Chocolate Cake Shake vs. Philly’s Tastykake Shake
The battle is on between two cake-laden milkshakes, one chocolate and one butterscotch.
Four Cool Chicago Attractions: Oz Park, Christkindlmarket, Doughnut Vault, the Bloomingdale (606) Trail
Find statues of Dorothy, Toto, the Scarecrow, Tin Man, and Cowardly Lion in Chicago’s Oz Park.