Chicago: Presidential Legacy + Shopping Escape

Join Always On The Go Travel Planning & Concierge for an unforgettable cultural getaway from Kansas City to Chicago. This curated experience combines presidential history, cultural exploration, entertainment, shopping, and leisure—all with the comfort and convenience of luxury group travel.

Whether you're traveling solo, with friends, or as a couple, this all-inclusive experience is designed to create lasting memories while exploring some of the Midwest's most iconic destinations.

Click here to book!

Trip Outline

Day 1 | Kansas City → Springfield → Chicago

Depart Kansas City aboard a luxury motorcoach and travel to Springfield, Illinois, for an inspiring visit to the Abraham Lincoln Presidential Library and Museum. Guests will have time to explore the exhibits and enjoy lunch on their own before continuing to Chicago.

Upon arrival, check into the hotel and enjoy free time to relax, explore the surrounding area, or connect with fellow travelers.

Day 2 | Chicago Cultural Experience

Following breakfast, depart for the Obama Presidential Center for an immersive cultural and educational experience celebrating leadership, community, and civic engagement.

The evening's featured event is a Chicago Dinner Cruise, offering spectacular city views, entertainment, and a memorable dining experience on the water.

After the cruise, return to the hotel and enjoy the remainder of the evening at your leisure.

Day 3 | Shopping & Return to Kansas City

After breakfast and hotel check-out, enjoy time at Chicago Premium Outlets, featuring designer brands and exceptional savings.

Following the shopping experience, depart for Kansas City with scheduled comfort stops along the route. Arrival is anticipated during the late evening hours.

What's Included

✔ Roundtrip luxury motorcoach transportation

✔ Fuel, parking, and transportation-related fees

✔ Three days / two nights hotel accommodations at the Embassy Suites Hotel by Hilton in the downtown Chicago Magnificent Mile area (single or double occupancy)

✔ Daily hotel breakfast and evening reception 

✔ Chicago Dinner Cruise experience

✔ Admission to the Abraham Lincoln Presidential Library and Museum

✔ Admission to the Obama Presidential Center

✔ Premium Outlet Shopping experience

✔ Always On The Go welcome gift

✔ Dedicated AOTG trip hosts throughout the journey

What's Not Included

✘ Travel insurance (strongly recommended)

✘ Meals not specifically listed as included

✘ Personal expenses, shopping, and optional activities

✘ Gratuities for hotel staff, dining staff, or personal services