Chicago 2027 Trip Overview

Get ready to experience the best of Chicago! Explore the city’s iconic landmarks and vibrant neighborhoods, visit the highly anticipated Obama Presidential Center, and enjoy free time to discover Chicago your way.

Travel Your Way

Transportation to Chicago is not included, allowing you to travel your way by plane, train, or car. Flight options, including possible group airfare and transfers, will be reviewed in January 2027 to help determine the most affordable option. Assistance with adding flights to your reservation will be available.

Availability and pricing are subject to change until your deposit is officially made and you receive your officially booked email, so don’t wait too long to lock your spot in

If booking with a roommate, your reservation will not be confirmed until the required deposits from both you and your roommate have been received.

✔️ 4-night stay at Riu Plaza Chicago or Similar
✔️ Deluxe Two Queen Beds 

✔️ Continental breakfast included daily

✔️ Chicago Architecture Boat Tour

✔️ Admission to the Obama Presidential Center

✔️ Chicago’s Iconic Landmarks and Navy Pier
✔️ Transportation to all included experiences
✔️ Convenient payment plan options

✔️ Travel support before, during, and after travel

*Itinerary is subject to change

❌ Round-trip international flights to and from Chicago are not included in the package price.

❌ The RIU Plaza Chicago facility fee of $24 plus local tax PER ROOM PER NIGHT is payable at check-in. This facility fee is subject to change.

❌ Travel insurance is not included. All payments are nonrefundable and final, so travel insurance is highly recommended.

❌ Personal expenses, shopping, souvenirs, snacks, specialty items, and any items or services not specifically listed as included are not included in your package price.

Arrive in Chicago your way and make your way to the hotel for check-in. That evening, join us for a fun Meet & Greet and receive your special welcome gift from Over & Beyond Travel.

After the Meet & Greet, we will make our way to the Chicago Riverwalk, where you will have time to enjoy the views, explore the shops, grab something to eat, and take pictures along the river. Later, we will board the Chicago Architecture Boat Tour for an evening cruise featuring Chicago’s famous skyline and architecture.

After the cruise, dinner is on your own, giving you the freedom to choose from one of Chicago’s many great restaurants before settling in for the night.

View the Chicago Experience Guide

After enjoying breakfast at the hotel, we will visit the main attraction of our trip, the Obama Presidential Center.

Enjoy a free evening to explore Chicago, dine at your leisure, or relax at the hotel.

View the Chicago Experience Guide

Start your morning at your own pace. Enjoy breakfast at the hotel. Then, take an optional short walk to the five-story Starbucks Reserve Roastery, where each floor offers something different. Watch coffee being roasted, learn about the journey from bean to cup, browse exclusive merchandise, and enjoy specialty coffee, freshly baked pastries, or creative cocktails. You can even make your way to the rooftop terrace for beautiful city views.

Later, we will explore several of Chicago’s iconic landmarks, with time to get off and experience select locations along the way. Our final stop will be Navy Pier, where you will have time to explore, take pictures, and enjoy the attractions before the evening is yours to dine, relax, or continue discovering Chicago.

View the Chicago Experience Guide

Enjoy an extra day to experience Chicago at your own pace. Shop, visit more of the city’s sights, explore a museum, try a hands-on experience, enjoy local activities, or simply slow down and take in more of the city.

Additional itinerary suggestions and optional experiences will be shared closer to travel.

View the Chicago Experience Guide

Enjoy one final breakfast at the hotel before checking out and beginning your journey home by plane, train, or car. It has been a wonderful experience exploring Chicago and visiting the new Obama Presidential Center together. Safe travels home, and I hope you will join Over & Beyond Travel as we explore our next destination!

Breakfast & Hotel Check-Out
Safe Travels Until Our Next Adventure