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