Route 66 Segment 1: Chicago to Springfield

Route 66 Segment 1: Chicago to Springfield

14 Day Epic Bike Tour

Tour Information

Date: 04/28/18 - 05/11/18
Meet: Chicago, IL
Tour Price: $3090
Single Upgrade: $1000

If you're not available to cycle the entire Route 66 cross-country tour this spring, then consider doing just a portion of it with us. We've broken the route up into manageable 2-3 week sections. This segment starts at the beginning of Route 66 in Chicago and ends two weeks later in Springfield, MO.

Almost Sold Out

The tour is guaranteed and has only one or a couple spaces left.



Total of 583 miles with an average of 49 miles per day with two rest days. The terrain is flat and gently rolling.

All lodging, breakfasts, dinners and snacks on riding days, SAG support along the route, detailed maps and cue sheets, one bike maintenance class, mechanical instruction and support, state line crossing party, luggage transfer, send-off banquet and trained guides.


Route 66 Segment 1: Chicago to Springfield

Not available for this epic tour. We will provide you with details on getting your bicycle to and from the tour.

Fly into Chicago, IL and out of Springfield, MO.

Patty Jackson

Patty Jackson
Tour Leader/Chef

Cindi West

Cindi West
Tour Leader

Tour Details

Relatively flat, Route 66 quickly became popular among truck drivers once it was officially established in 1926. Since the Dust Bowl years of the 1930s, it also became popular among families looking for better jobs in California. It became known as the Main Street of America. When interstates started taking over much of its traffic in the 1960s and 1970s, and pieces of it were commandeered for other routes, it was officially decommissioned as a route in 1985.

Since then, Route 66 has experienced a revival. Various sections of the road are now on the National Register of Historic Places and listed as Scenic Byways. Designed to connect the Main Streets of small towns across the country, we will cycle through these small towns and the bigger cities that they’ve become. It is also Adventure Cycling’s newest cross-country route. We’ll follow the expertly designed route, staying in hotels with dry, warm beds and hot showers every night.

There will be two rest days over the course of this section of the trip. We schedule these at scenic and historic stops where there is an opportunity to explore the area. We strongly believe in giving everyone time to see the natural wonders of our country and to relax to keep our bodies healthy and strong.

We offer a reasonable price. You’ll find we have the cheapest per day rate for any hotel cross-country bike touring company.

We carry your luggage, and you, if necessary.

We offer healthy, home-cooked meals prepared by our traveling chef who understands the “performance food” needed to undertake such a challenge. If you require a vegan or gluten-free diet, there will be a small surcharge.

We support the tour with two vehicles equipped with supplies, first aid, food and water.

We limit the group size to around 25 plus staff. You’re neither alone nor anonymous. We guarantee you’ll make some lifelong friends along the way.

Join us to “Get Your Kicks on Route 66!”

TO JOIN: Register on-line or call us at 800-247-1444 to make your registration deposit of $400. The balance of the trip fee is due 75 days before the tour start date. Save 2% if you make your payments by check.

TOUR DETAILS: Help on training, transportation, packing, and an itinerary will be sent upon receipt of your registration fee. We will also mail you periodic Prep Talk newsletters to help you prepare for the trip. For more information, including links to blogs kept by past cross-country participants, contact us and we’d be happy to send you more details. Space is limited so sign up today!

Route 66 Segment 1 Itinerary

Date Location Miles
Apr 28, 2018 Chicago, IL 0
Apr 29, 2018 Matteson, IL 46
Apr 30, 2018 Pontiac, IL 80
May 1, 2018 Bloomington, IL 38
May 2, 2018 Springfield, IL 68
May 3, 2018 Springfield, IL 0
May 4, 2018 Litchfield, IL 50
May 5, 2018 St. Louis, MO 65
May 6, 2018 St. Louis, MO 0
May 7, 2018 Pacific, MO 40
May 8, 2018 Rolla, MO 78
May 9, 2018 Lebanon, MO 65
May 10, 2018 Springfield, MO 55
May 11, 2018 Home 0