Chicago | September 9–12, 2027
Get ready to experience the history, culture, food, and energy of Chicago with GEM Travel!
We’re heading to the Windy City for a four-day getaway featuring the Obama Presidential Center, Black history and culture, iconic Chicago sights, great food, and plenty of time to enjoy the city.
Leave the driving and planning to us. Pack your bags, settle into your seat, and enjoy the journey as we travel by motorcoach from the Baltimore area to Chicago.
Whether this is your first visit to Chicago or you’re ready to experience it in a new way, GEM’s Windy City Experience is about more than sightseeing. It’s about discovering the city, sharing experiences, meeting new people, and making memories along the way.
Culture. History. Food. Fun. Chicago.
We’d love to have you join us!
It’s your time to live.
The following are not included in your package price and are the responsibility of each traveler:
Travelers should budget separately for any personal expenses, optional activities, meals, and transportation not specifically listed as included in the package.
Day 1 – Welcome to Chicago!
Arrive in Chicago and at the hotel before 1:00 PM.
1:30 PM – Board group transportation and depart for the DuSable Black History Museum and Education Center.
1:30 PM–5:00 PM – DuSable Museum experience, including transportation to and from the museum.
Evening – GEM Mix & Mingle at the hotel. Meet your fellow travelers, relax, and kick off our Windy City weekend together.
Day 2 – Obama Presidential Center & Group Dinner
11:00 AM–4:00 PM – Experience the Obama Presidential Center. Explore the museum and campus at your own pace.
4:30 PM – Group Dinner at Bronzeville Winery . Enjoy dinner and fellowship with the group before returning to the hotel (https://www.bronzevillewinery.com/).
Day 3 – Chicago, Your Way!
Today is yours!
Enjoy a free day to explore Chicago at your own pace. Book an excursion, shop along the Magnificent Mile, take an architecture cruise, visit Navy Pier, Riverboat Tous, explore local neighborhoods, try some Chicago favorites, or simply relax and enjoy the city. Suggestions and assistance will be provided.

Optional excursions and personal transportation during the free day are not included in the package.
Day 4 – Until Next Time, Chicago!*
Enjoy your final morning in Chicago before checking out of the hotel and departing for home.
Itinerary and scheduled times are subject to change.
*Option to add a pre/post stay to your travels available upon request.
All payments made to GEM Travel, LLC are non-refundable and non-transferable.
GEM Travel, LLC enters into contractual agreements and makes payments to hotels, airlines, cruise lines, tour operators, transportation companies, and other travel suppliers on behalf of our travelers. Many of these payments are non-refundable. This allows us to secure group rates, accommodations, transportation, and other components of your travel package.
Because unexpected circumstances can occur, GEM Travel, LLC strongly recommends purchasing travel insurance to help protect your travel investment.
Travel insurance does not guarantee reimbursement of payments made to GEM Travel, LLC. Coverage, benefits, exclusions, and eligibility for reimbursement are determined solely by the insurance provider and the specific policy purchased. Travelers are responsible for reviewing and understanding the terms of their travel insurance policy.
Unless otherwise specified, all prices are per person based on shared double occupancy.
Prices do not include personal expenses or items not specifically listed as included in the travel package. These may include laundry, alcoholic beverages, bottled water, meals, gratuities, excursions, transportation, or other personal purchases.
Book Now. Pay Over Time (FLEXPay).
GEM Travel, LLC offers payment plans on many of our vacation packages, allowing you to reserve your trip and make scheduled payments toward your balance.
A deposit is required at the time of reservation unless otherwise specified.
All deposits are non-refundable and non-transferable.
The required deposit amount and payment schedule will be provided at the time of booking.
Reservations may be paid in full at the time of booking, provided space is still available.
Payment in full does not change the refund or cancellation terms. All payments remain non-refundable and non-transferable.
A $35 late fee may be assessed for payments received after the scheduled due date.
Failure to make required payments may result in cancellation of the reservation. Any payments previously made will remain non-refundable and non-transferable.
A $45 fee will be assessed for returned or declined payment transactions.
All cancellation requests must be submitted in writing.
Email your cancellation request to francine@mygemtravel.com and include your full name and travel date.
After your email is received, GEM Travel, LLC will send you a cancellation request form. The form must be completed and returned to finalize your cancellation.
If you do not receive acknowledgment of your cancellation request within 48 hours, please call 443-914-3434 to confirm that your request was received.
Cancellation of your reservation does not entitle you to a refund. All payments previously made to GEM Travel, LLC remain non-refundable and non-transferable.
Travelers who purchased travel insurance should contact their insurance provider regarding possible coverage for their cancellation. Approval or denial of an insurance claim is determined solely by the insurance provider according to the terms and conditions of the purchased policy.
GEM Travel, LLC strongly recommends travel insurance for all travelers.
Travel insurance may provide protection for certain unforeseen circumstances, depending upon the plan purchased. Coverage varies by policy and may include benefits related to trip cancellation, interruption, medical emergencies, delays, baggage, or other covered events.
Purchasing travel insurance does not change GEM Travel, LLC's refund policy. Payments made to GEM Travel, LLC remain non-refundable and non-transferable regardless of whether travel insurance is purchased.
Travelers who decline travel insurance accept responsibility for any financial loss resulting from cancellation or interruption of their travel plans.
If you purchased travel insurance for your trip, claims and coverage questions should be handled directly with the insurance provider that issued your policy.
Allianz Travel Insurance
If you purchased travel insurance through the Allianz link on the GEM Travel website, contact Allianz directly for questions regarding your policy, coverage, travel assistance, or claims. Your policy confirmation contains the appropriate contact information and claim instructions.
Important: GEM Travel can provide documentation related to your booking when needed, but insurance providers determine coverage and make all decisions regarding claims and reimbursement.

Enjoy your Chicago stay at the RIU Plaza Chicago, conveniently located near the Magnificent Mile in the heart of the city.
This package includes accommodations in a Deluxe Room with two queen beds, making it a comfortable option for travelers sharing a room.
Room features and hotel amenities include:
Two queen beds
Daily breakfast for up to two guests per room
High-speed Wi-Fi
Two complimentary bottles of water upon arrival
In-room electronic safe
24-hour fitness center access
Access to the hotel’s rooftop bar and city views
Convenient location near shopping, dining, and popular Chicago attractions

Enjoy your Chicago stay at the RIU Plaza Chicago, conveniently located near the Magnificent Mile in the heart of the city.
This package includes accommodations in a Deluxe King Room with one king bed for two travelers sharing the room.
Room features and hotel amenities include:
One king bed
Double occupancy – two travelers sharing one room
Daily breakfast for two guests
High-speed Wi-Fi
Two complimentary bottles of water upon arrival
In-room electronic safe
24-hour fitness center access
Access to the hotel’s rooftop bar and city views
Convenient location near shopping, dining, and popular Chicago attractions
Occupancy: 2 travelers

Enjoy your Chicago stay at the RIU Plaza Chicago, conveniently located near the Magnificent Mile in the heart of the city.
This package includes accommodations in a Deluxe Room with two queen beds for three travelers sharing one room.
Room features and hotel amenities include:
Two queen beds
Triple occupancy – three travelers sharing one room
Daily breakfast
High-speed Wi-Fi
Two complimentary bottles of water upon arrival
In-room electronic safe
24-hour fitness center access
Access to the hotel’s rooftop bar and city views
Convenient location near shopping, dining, and popular Chicago attractions
Occupancy: 3 travelers
Enjoy your Chicago stay at the RIU Plaza Chicago, conveniently located near the Magnificent Mile in the heart of the city.
This package includes accommodations in a Deluxe King Room with one king bed for one traveler—perfect for guests who prefer the privacy and comfort of their own room.
Room features and hotel amenities include:
One king bed
Single occupancy – one traveler per room
Daily breakfast
High-speed Wi-Fi
Two complimentary bottles of water upon arrival
In-room electronic safe
24-hour fitness center access
Access to the hotel’s rooftop bar and city views
Convenient location near shopping, dining, and popular Chicago attractions
Occupancy: 1 traveler
We recommend purchasing travel insurance to help protect your investment in GEM’s Windy City Experience – September 9–12, 2027.
Allianz Travel Insurance offers plans that may include coverage for:
Trip cancellation and interruption
Travel delays
Lost, stolen, or delayed baggage
Emergency medical expenses
Emergency medical transportation
Travel insurance is optional and is not included in your trip package price.
Visit Allianz Travel Insurance to get a personalized quote, review coverage options, and purchase your policy directly online.
We encourage you to purchase coverage early, as certain benefits may have time-sensitive eligibility requirements.
Coverage, exclusions, and limitations vary by plan.
Protect your investment and travel with peace of mind!