On the Road to Woodstock – from the Midwest

Woodstock's 50th Anniversary - with travel thru Chicago

5 Days  |  August 14-18, 2019

Starting At $995.00
This package includes a pre-Woodstock Anniversary stay in Chicago, just as they did in 1969 people came from across America to be at Woodstock. This tour is planned for mid-western groups, who can't drive all the way at once. It features several unique Musical Events in Chicago so that "By the time you get to Woodstock, you'll be rockin' strong, and everywhere is a song and a celebration."

On the Road to Woodstock – from the Midwest

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Chicago Blues Highlights:

  • Dinner at Buddy Guy’s Blues Club
  • Guided Chicago Sightseeing
  • Tour of Original Chess Records
  • Meet the Blues Brothers
  • Free Time at Navy Pier
  • Folk Music Concert


50th Anniversary Tributes to:

  • The Woodstock Music Festival
  • Neil Armstrong’s Walk on the Moon
  • The song “Age of Aquarius” is a #1 Hit



Cleveland Woodstock Highlights:

  • Moon Rock Evening at Rock and Roll Hall
  • Woodstock Rock Gala with Dinner, Music & Dancing
  • Optional Tours in Cleveland
    • Walking with Neil Armstrong . . . . . $39
    • Lunching on The Nautica Queen . . $39
    • Shopping for Bell Bottoms . . . . . . . $49

Full Tour Package Includes:

  • Two Nights Embassy Suites, Chicago Magnificent Mile
  • Two Nights Intercontinental Hotel Cleveland
  • Four Hotel Breakfasts
  • Two Dinners + Snacks at Rock Hall Party
  • All Taxes & Tips
  • One Free Double with Every 16 Paid


Prices Per Person

$995 Double

$895 Triple…$845 Quad…$1,395

Special Event Policies:

  1. $10 Per Person due 1 year prior (refundable at 90 days)
  2. $100 Per Person due at 90 days prior (Non-Refundable)
  3. Final Payment at 45 days prior  (Non-Refundable)
  4. Hotel Assignments are made on receipt of second deposit.
  5. Seating assignments are made on receipt of final payment.
  6. Space is limited to 1500 people.

If you need motorcoach transportation, check out our travel affiliate Buster.com for the best prices.

Day 1 – Arrive Chicago – Buddy Guy’s Blue Club

You should plan on an afternoon arrival at the Embassy Suites Chicago Magnificent Mile, within walking distance of Navy Pier. You will have two nights in this 4 Star Hotel. Make sure you arrive in time to get settled in before the Hotel Manager’s Reception at 5:00pm.

Then at 6:00pm, you are off to Buddy Guys Legends, the world’s premier Blue Club owned and operated by Grammy Award Winning Blue’s Musician, Buddy Guy. He is a Rock and Roll Hall of Famer himself and has had a major influence on rock titans like Jimi Hendrix, Eric Clapton, and Stevie Ray Vaughan.  Tonight here, in our private party area; you enjoy a dinner menu of Louisiana-style cajun and soul food – served while a Blues combo makes a little music. (D) 

Day 2 – Chess Records – Blues Brothers – Folk Music Concert

Morning sightseeing will have three features, but not necessarily in this order, final itineraries will be juggled a bit so we can accommodate all groups.

First you will have a local guide for the morning who will point out the major sights such as Grant Park, Buckingham Fountain, Soldier Field, the Museum Campus, and Navy etc.

Then you will tour the original Chess Records where so many Rock and Blues artists created their hits. Muddy Waters, Howlin’ Wolf, Etta James, Chuck Berry and the Rolling Stones all recorded here. You’ll see the original recording studios, the offices of Leonard & Phil Chess and plenty of memorabilia from the era. Coincidentally, Chess was sold in 1969, and Leonard dies two months after Woodstock.

Also during your morning tour, the Blues Brothers will hijack your bus for 30 minutes. They’re “putting the band back together” and you’ll find yourself “on a Mission from God” with Jake & Elwood Blues. “They’ve got a full tank of gas, half a pack of cigarettes, its dark out and they’re wearing sunglasses.”

At lunch time, you have two hours free time at Navy Pier for shopping and noshing. Then you visit the brand new Chicago Blues Experience– an interactive museum opening in the spring of 2019 the exhibits here cover the complete history of the Blues.

After the Blues Experience all groups come together at The Old Town School of Folk Music, a vibrant part of Chicago’s music scene. The school was started in a rundown storefront when music “sharing” meant singing together and playing by ear! Early performers included Pete Seeger, Studs Terkel and Mahalia Jackson. Today the school occupies two buildings in the bustling neighborhood near Lincoln Square and teaches 1000s of students every week.

Here you have a matinee, a concert with folk tunes from the Woodstock era, featuring the songs of Peter, Paul & Mary, Joan Baez and Bob Dylan. Sing along with your favorites from silly to serious – this music is meant for you and me!  There will also be a blues and harmonica lesson where everyone is involved in the fun, and everyone gets a free harmonica.  Your group will return to the hotel in time for the Embassy Suites’ Manager’s reception, and you are on your own for dinner and evening pursuits. (B)

Day 3 – Cleveland – Rock and Roll Hall of Fame

After breakfast this morning, your group of Old Hippies and 60’s Music Lovers will depart for Cleveland, OH.  It’s time pull on those Tie- Dyed Shirts and Bell Bottoms, put flowers in your hair, grab your Love beads and join us in Cleveland as we kick off the Woodstock 50th Anniversary weekend. Dinner is on your own this evening after hotel check-in. Featured hotels for our Midwestern Groups is the luxurious Intercontinental Hotel in Cleveland.

Tonight, the doors of the Rock and Roll Hall of Fame open at 7:00 pm for an exclusive four hours among the exhibits. It’s been said that visiting the Rock & Roll Hall of Fame is like taking a peek into your favorite musician’s closet. The Hall’s permanent collection contains thousands of one-of-a-kind items ranging from musical instruments and song lyrics to quirky stage props and colorful costumes.

The ever-changing exhibits here feature such topics as The Roots of Rock & Roll, Cities & Sounds, and The British Invasion. While nothing had been announced at the time this itinerary was published, we fully expect the Rock Hall will have a have a major exhibit on what is one of the greatest happenings and, perhaps the most pivotal moment in music history – Woodstock.

You will also find exhibits with film & video, interactive kiosks, reading material and, of course, plenty of music. We have hired a number of extra docents this evening to help as you enjoy Rock History. There will be cash bars should you want to rest a moment with a cocktail, hors d’oeurves and desserts.

A second unique feature of this evening is the Moon Rock Party starting at 9:00 pm on the Rock Hall Plaza. Just 26 days before Woodstock began, Neil Armstrong walked upon the moon, both of these events happened in the year “The Age of Aquarius” hit No. 1 on the charts. So, to the event planners at U.S. Tours that’s like a time “when the Moon is in the Seventh House and Jupiter aligns with Mars.” Come and join us on a night when there’s a full moon over Cleveland at 9:22 pm, and “when Peace will guide the Planets and Love will steer the Stars.”(B)

Day 4 – Cleveland Optional Tours – Woodstock Concert

Today’s activities are to be scheduled as each group planner desires, it’s an opportunity to put your own personal touch on the trip.  There are optional sightseeing tours available that we can add to your tour package.

1. Walking with Neil Armstrong

This tour visits the Observatory Park Planetarium, where see the sky as it appeared on July 21, 1969 as Neil Armstrong gazed out at the heavens from his unique vantage point!  The Astro-Nat (Astronomy-Naturalist) will also make ‘Jupiter align with Mars.’ You will also visit the Great Lakes Science to see an authentic Space Capsule and other NASA displays. A gourmet boxed lunch is included.  $39.00pp

2.  Lunch with the Queen

The Nautica Queen’s Luncheon Cruise is a unique adventure combining the best of dining and sightseeing in Cleveland. There’s a lavish buffet and musical entertainment while cruising under historic bridges and along the lake and riverfront.  $39.00pp

3.  Shopping for Bell Bottoms

Grab your pocket book we’re shopping for Bell Bottoms and Peace Beads.  This tour includes a visit to two different Vintage Clothing Shops.   Flower Child is the regions premier vintage shop and museum, while Sweet Lorain is an award winning vintage department store with racks of 60’s clothes organized by year and type    Also included is a special Rock n’ Roll Luncheon at the Music Box Supper Club produced exclusively for you Woodstock Fans, it includes a “Peace, Love & Music” Sing-a-Long.    $49.00


The Second night’s event coincides with the Opening of Woodstock 50 years ago. It is a Rock Gala, at the Cleveland Auditorium. It’s a dinner dance and a musical stage production, a Woodstock Tribute Band, an audience in bell bottoms and tie-died shirts. It’s an evening of music and dancing, dining and remembering.

We encourage everyone to dress for the event. Once you cross the doorway it is again the year 1969, cast away those conservative clothes and thoughts that came with maturity and enjoy the memories of your youth, celebrate “Peace & Music,” Rock on.

This evening is for all of your customers who were teenagers in 1969. But especially for those who were either too young, or not allowed to go to Woodstock. It’s also a modern, comfortable version of that rowdy concert, which you can sell by asking two simple questions: “Are you old enough now”? “Will your Mom let you go now”? It’s time they “got to Woodstock.”

Should you have customers who actually attended the 1969 Woodstock Event, we want to publish their memories in an anniversary booklet to be placed on the dinner table. Ask them to hold their comments to 500 words, and submit to us 60 days in advance. Each contributor will be recognized at the event and awarded a special “Peace & Love” necklace. (B,D)

Day 5 – Departure

Time to go home.

                          “We are stardust, we are golden, we are caught in the devil’s bargain,

                           And we got to get ourselves back to the garden.”

Center map