People Cycling Rides

Chicago to St. Louis on Route 66.

This is a Approved Ride
Moderate
Ride Info
Join Us
Ride Leader
Rick Gallo
Tour Dates
5/27/2026–6/5/2026
Start Location
Chicago, IL
End Location
St. Louis, MO
Cost (est.)
$1220 (USD + $100.00 ride fee)
Deposit
$650 (USD
Payment Due
3/20/2026
Avg. Distance
56 mi / 90 km
Avg. Elevation
775 ft / 236 m
Ride Description

From Chicago to St. Louis: Along the first 340 miles of Route 66.

Summary: We will start in the heart of Chicago, staying two days in down town, less than a ¼ mile from Grant Park / Buckingham Fountain. We end in St. Louis, with two days at a hotel that is next door to the Arch (about 0.1 mile away). The miles in between are a combination of bicycle paths (leaving Chicago and entering St. Louis); rural roads (the majority of our pedaling); small cities (McLean, Staunton, Pontiac), as well as the Illinois State Capitol (where you can visit President Lincoln’s home, library, museum, and final resting place). There are more than a dozen iconic Route 66 sites between Chicago and St. Louis, along with a few sites within each of these cities. In addition, there are a few other non-Route 66 historic places to stop at as well.

 

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People Cycling's Ride Rating

People Cycling has four categories for our rides – Easy, Moderate, Difficult, and Challenging. It should be somewhat obvious what these categories mean, but please become familiar with the elevations and distances that define them:

Easy
Easy rides are under 30mi/48km in average distance and 1600ft/500m in average elevation
Moderate
Moderate rides are over the Easy rating but under 50mi/80km and 2460ft/750m
Difficult
Difficult rides are as over the Moderate rating but under 75mi/120km and 3280/1000m
Challenging
Anything over the Difficult rating

NOTE: This is not a strict guideline. There could be rides that have a day or two where the average elevation or distance exceeds the values given above. These anomalies should be outlined in the ride description. It is recommended that you read it carefully.

About People Cycling

People Cycling is a bicycle touring club, which you can join for free. We offer Domestic and International Cycling Tours which are led by volunteer Ride Leaders. Our tours are made up of a small group of participants (typically 15-20 or so) who want to ride an average of 30 to 55 miles a day over a one or two week period in interesting regions of the world. Our tours range in price from frugal getaways to luxurious adventures. We travel road, gravel, or mountain bike styles, and all bicycle types – including e-bikes, recumbents, and tandems are typically allowed.

Our ride leaders are volunteers and do not financially profit on tours they lead. They are also given broad discretion on how to lead their tours, and we consider them our greatest asset.

People Cycling tours are operated at cost or at lower cost (as negotiated by our ride leaders) than individuals can obtain on commercial tours. Within the cost of a tour, there is a nominal fee to support club operations and provide tools to ride leaders to manage their rides.

What are you waiting for? Join today to see what bicycle adventure awaits you in our club.

A lifetime membership in People Cycling is absolutely FREE, so please join us and become one of us – we the people, cycling together.