Guided Senior Tour Companies from Chicago
Unlike park district and township trips, these companies aren't tied to any one suburb — they run scheduled trips from pickup points across the Chicago area. We list every legitimate operator we can verify, whether or not they have an affiliate program with us, because a good option is a good option. This list will grow as more operators are added.
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Road Scholar
A nonprofit educational travel program for ages 50+. Verified: their programs, including Chicago-area ones, are multi-day (shortest run about 3 days with lodging) — not single-day excursions.
- Typical cost:
- Shorter 3-5 day domestic programs can run under $1,000/person; longer international trips cost more
- Who can join:
- Adults 50+ (and a companion), nationwide
- How to sign up:
- Browse and book directly at roadscholar.org
Verify — Confirmed this is not a day-trip provider — shortest programs are 3 days minimum with lodging included.
Jones Travel
A senior motorcoach service running since 1969, based in Elkhorn, WI, with regular trips into Chicago, Milwaukee, Madison, Wisconsin Dells, and Rockford. Fleet includes handicap-accessible coaches.
- Typical cost:
- Not published — request a quote
- Who can join:
- Open to the public
- How to sign up:
- Call 800-236-3160 or request a quote on their site; current trip lineup is under Popular Trips
Cardinal Buses
A motorcoach company operating since 1923 out of Indiana and Michigan, known locally for Amish-country day tours and popular with senior and retiree groups. Coaches can be lift-equipped and accommodate wheelchairs, scooters, and rollators on request.
- Typical cost:
- Not published — request a quote
- Who can join:
- Open to the public
- How to sign up:
- Call 800-348-7487 or email info@cardinalbuses.com — mention accessibility needs when booking
Mayflower Tours
An Illinois-based tour operator (Downers Grove) running since 1979, with 100+ itineraries including "Motorcoach Holiday" tours and small-ship cruises, each with a professional Tour Manager on board.
- Typical cost:
- Varies by trip — see current offerings
- Who can join:
- Open to the public
- How to sign up:
- Call 800-323-7604 or browse tours at mayflowercruisesandtours.com
Verify — Their branding centers on multi-day 'Motorcoach Holiday' tours rather than single-day excursions — confirm whether any single-day Chicago-area trips are currently offered before assuming so.
Diamond Tours
A national motorcoach operator (38+ years) working with 55+ senior citizen groups, with coaches seating 54+ and most breakfasts/dinners included.
- Typical cost:
- Varies by trip — no fee or deposit required to book, per their site
- Who can join:
- Groups, including 55+ senior citizen groups
- How to sign up:
- Call 800-336-5711 with preferred travel dates
Verify — Confirmed tours to Chicago as a destination; did not confirm they run Chicago-departure day trips specifically for local seniors — likely more relevant as a national group-tour option.