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Image by Leon Wu

Chicago, Illinois

August 18-24,2024

Image by Aveedibya Dey

Tour Highlights

  • 7 Nights Lodging

  • 6 Breakfasts

  • 4 Dinners

  • Guided Tour of Chicago

  • Navy Pier

  • Shedd Aquarium

  • Architectural Cruise of Chicago

  • Water Tower Place Mall

  • "Skydeck Chicago" Observation Deck

  • Federal Reserve Money Museum

  • Gaming at a Chicago-area Casino

  • Luggage Handling

  • All Taxes and Meal Gratuities

Image by Christopher Alvarenga

Day 1-Depart from Florence

Depart from Florence and head to your overnight stop. Dinner is on your own this evening.

Day 2-Chicago

Following breakfast, check out and continue traveling to the “Windy City”. Chicago is one of the most exciting cities in the USA. After checking into your hotel, you will have time to freshen up before departing for dinner at one of Chicago’s popular restaurants.

Image by Neal Kharawala

Day 3-Chicago

Enjoy breakfast, then depart on a tour of Chicago’s highlights. You will also tour Wrigley Field, beloved home of the Chicago Cubs since 1916. After the tour, stop at the historic Navy Pier, and this afternoon you will enjoy a relaxing Architectural Cruise on Lake Michigan with views of Chicago’s skyline. Chicago’s architecture is known worldwide and there’s nothing like seeing it from all three branches of the Chicago River. Over 40 Chicago landmarks, including the Tribune Tower, Wrigley Building, Trump Tower and Marina City, await you on a 75-minute Architecture Tour. After the cruise, return to your hotel to freshen up before departing for a delicious dinner in the area.

Day 4-Chicago

After breakfast, depart for a visit to the Shedd Aquarium. The Aquarium’s exhibits bring you face to face with incredible animals from around the world and from the local area. In the afternoon, enjoy the Untouchables Tour, Chicago’s original gangster tour of infamous sites and hideouts. Later, visit Chicago’s “Magnificent Mile” where you can enjoy some of the city’s fabulous architecture as well as some free time for shopping and sightseeing on your own. A delicious dinner in Greektown will complete your day.

Day 5-Chicago

Following breakfast, visit the Chicago Fed’s Money Museum, followed by a visit to the Lincoln Park Conservatory where you will witness the spectacular displays. Later, head for Chicago’s Skydeck Observation Deck on the 103rd floor at the Willis Tower from which you will enjoy spectacular, breathtaking views spanning up to four states and several interactive displays. Step outside onto the Ledge’s glass balcony that extends 4 feet from the Skydeck and 1,353 feet in the air. After your visit, head for the Water Tower Place Mall which features over 100 stores, spas and restaurants. Afterwards, head to one of the casinos in the Chicago area for some gambling excitement and a chance to win the jackpot. Enjoy dinner at one of the area's popular restaurants.

Day 6-Overnight Stop

Enjoy breakfast, then check out and depart for your last night of lodging where you will check in upon arrival (pack an overnight bag); dinner is on your own this evening.

Day 7-FLorence, SC

After a continental breakfast, check out and prepare for your departure home with lasting memories of your trip to the “Windy City”.


Double occupancy:  $1,239

Single Occupancy: $1,608

TO book this tour please call our office at (843) 656-2450 or fill out a tour inquiry and we will reach out to answer any questions you may have

What Makes Us Special

Local Expert Guides

On each unique tour, learn about the destination from a local perspective.

Handpicked Adventures

All of our tours are catered to senior adults and are recommended by our travelers.

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