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The Art, Architecture & Culture of Chicago

Tour Description

Enjoy comprehensive touring in Chicago, with beautiful lakefront, breathtaking architecture, world-class museums, entertainment, shopping, & dining. You'll cruise the Chicago River on an expertly narrated architectural sightseeing cruise, visit historic Hyde Park, home to National Register of Historic Places landmarks The University of Chicago and the home of current President Obama, and thrill to the awesome view from the Willis (Sears) Tower, for years the tallest building in the world, plus enjoy dining at Lawrys and an entertaining speakeasy dinner show, and luxurious Chicagoland hotel


  • Fully-escorted via deluxe motorcoach with Seniortours escort on board to host complimentary cocktails, soft-drinks, snacks, fun, games & “good times”!
  • 10 delicious meals total—a tasty combination of breakfasts, lunches and dinners — served at some of Chicagoland’s best restaurants, including posh Lawrys The Prime Rib in downtown Chicago.
  • Comprehensive touring in “The Windy City” of Chicago, with beautiful lakefront, breath taking architecture, wonder ful museums, great entertainment, world-class shopping, & fantastic food.
  • Cruise the Chicago River on an expertly narrated architectural history sightseeing cruise.
  • Visit historic Hyde Park, home to 2 landmarks listed on the original 1966 National Register of Historic Places, The University of Chicago, and the longtime home of current President Obama.
  • Thrill to the awesome view from the Willis (Sears) Tower, for years the tallest building in the world.
  • Visit the world-famous Navy Pier, dating back to 1916 and part of famed industrial architect Daniel Burnham’s original Plan of Chicago.
  • Cheer on the Fightin’ Irish when we stop at Notre Dame’s campus and enjoy lunch at Café Navarre in nearby South Bend, IN en route.
  • Wonderful hotel accommodations in the Chicagoland area and en route.
  • Luggage handling, taxes, gratuities to hotel/restaurant staff.
  • Free Any Reason Cancel Protection: No worries about cancel lations for any reason with 100% refunds up to 45 days before departure.
  • Depart from convenient local northeast pickup locations, or fly into Newark, Philadelphia, or Chicago for an easy getaway. Call for specific pricing from your preferred gateway.


B=Breakfast, L=Lunch, D=Dinner, S=Show

Day 1: You’ll enjoy a leisurely ride through the scenic Pennsylvania countryside, with a late afternoon arrival at our hotel amid the rolling hills of eastern Ohio. Enjoy dinner, served after check-in. D

Day 2: The Greater Chicago Metropolitan area know as “Chicagoland” is today’s destination, with deluxe accommodations for the next 3 nights at one of the area’s favorite hotels. B, D Fly-Ride passengers should schedule flights to arrive in Chicago today after 4pm.

Day 3: Today you’ll enjoy a comprehensive city tour of Chicago with an expert local guide. Known internationally as a hub for finance, manufacturing, & technology, Chicago is the 3rd largest city in the US, and the unofficial “capital” of America’s Heartland. Following a devastating fire in 1885, the city experienced what would become the largest building boom in American history, ushering in the era of the skyscraper and the distinctive “Chicago SchooL” architecture, which promoted the use of new building & development technologies. You’ll see firsthand Chicago’s many contributions to American architecture during your tour, in addition to the city’s equally impressive collection of outdoor public art and sculpture, and its many famous landmarks. For lunch on your own, why not explore some real Chicago cuisine with a slice of famous “deep dish” Chicago pizza? Later tonight, you’ll enjoy a delicious dinner at one of Chicago’s favorite restaurants, Lawrys The Prime Rib, right on Chicago’s famous Magnificent Mile. B, D

Day 4: After breakfast, you’ll take a short ride to the “Windy City’s” Navy Pier, where you’ll have a chance to visit the unique Smith Museum of Stained Glass & the famous Ferris wheel before embarking on a narrated cruise on the Chicago River. This evening, we’ll enjoy “speakeasy” entertain ment (subject to availability) and dinner show! B, D

Day 5: After breakfast, bid farewell to the Windy City & head eastward. More fun on the motorcoach today, with a special dining stop & overnight lodging near the Ohio-Pennsylvania border this evening. B, D Fly-Ride passengers should schedule flights to depart Chicago today.

Day 6: After breakfast this morning, we’re homeward bound. With more fun on the coach, we happily ride back to home-sweet-home. B