CHICAGO 2027
CHICAGO 2027
Experience the Obama Presidential Center & the Best of Chicago!
April 6–9, 2027 (Tuesday–Friday)
Join A-Custom Travel for an unforgettable 4-day trip to Chicago! Explore the city's rich history, culture, and architecture while learning about the inspiring journey of President Barack Obama and First Lady Michelle Obama.
This trip includes visits to the Obama Presidential Center, important locations from the Obamas' lives, and a relaxing Chicago River Architecture Tour featuring some of the city's most famous landmarks.
Hotel
You'll stay for 3 nights at the Embassy Suites Chicago Magnificent Mile, a 4-star hotel located in downtown Chicago.
Hotel features include:
Spacious suites
Complimentary hot breakfast each morning
Walking distance to many popular attractions
Land-Only Package Starting at:$1,575 per person
Deposit: $200 (Due August 15, 2026)
Monthly payment plans available.
Trip Itinerary
Tuesday, April 6 – Arrival
Arrive at Chicago O'Hare (ORD) or Midway (MDW) Airport.
Meet your A-Custom Travel representative in baggage claim.
Transfer to the Embassy Suites Hotel.
Hotel check-in.
Enjoy the rest of the evening at your leisure.
Wednesday, April 7 – Obama Experience Tour
After breakfast, enjoy a guided tour of Chicago featuring:
Millennium Park and Cloud Gate ("The Bean")
The Obama Chicago Tour, including:
Sidley Austin Law Firm (where Barack and Michelle Obama met)
Whitney M. Young Magnet High School (Michelle Obama's high school)
The Obama Family Home
Obama "Kissing Rock" (their first date location)
University of Chicago Law School (where President Obama taught)
Lunch will be on your own at Valois Restaurant, one of President Obama's favorite restaurants.
That afternoon you'll visit the Obama Presidential Center, including:
Museum
Library
Garden Pavilion
Return to the hotel in the evening.
Thursday, April 8 – Chicago Architecture Tour
After breakfast:
Walk to the Chicago River.
Enjoy the famous Chicago River Architecture Boat Tour (approximately 90 minutes).
Spend the remainder of the day exploring Chicago on your own.
Friday, April 9 – Departure
Breakfast at the hotel.
Check out.
Transfer to the airport for your return flight home.
What's Included
3 nights at Embassy Suites Chicago Magnificent Mile
Daily hot breakfast
Round-trip airport transfers in Chicago (with approved flight schedule)
Guided Obama-themed Chicago Tour
Admission to the Obama Presidential Center
Chicago River Architecture Boat Tour
Motorcoach transportation during scheduled tours
Land-Only Package
Airfare is not included.
Booking your own flight allows you to:
Choose your preferred airline
Select your own seats
Earn airline rewards or miles
Check in directly with your airline
Important: Flight information must be submitted at least 60 days before departure to receive included airport transfers.
Not Included
Airfare
Travel insurance (highly recommended)
Tips and gratuities
Personal expenses
Meals not listed in the itinerary
Government taxes or additional fees

