Downtown Chicago Vacation Packages for 2026

Downtown Chicago Vacation Packages

Trying to figure out a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Downtown Chicago trip one to remember. Our Travel Center is a one-stop shop where you can put together the best Downtown Chicago vacation package for you. We have a huge list of accommodations and flight, and Downtown Chicago endeavors to pick from.

Hotel Deals in Downtown Chicago

Our listings include hotels that are close to all the Downtown Chicago points of interest, and some that are just outside the city center for a more restful retreat.

Check out the verified lodging reviews on the AARP Travel Center to help you decide.
• It's easy to choose a terrific hotel, as a number of accommodations in Downtown Chicago have an immaculate overall score of 5 stars
• You should have no issues taking it easy after a busy day, as these hotels have an outstanding 5 star rating for room comfort.
• With a solid 3 rating, you know that you'll be greeted with a clean room when you return from exploring Downtown Chicago
• The immaculate grounds of the area's hotels also got sky-high marks

Thanks to AARP Travel Center's Downtown Chicago hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Downtown Chicago

Downtown Chicago is a big city, which means you probably won't have any problems entertaining yourself. With the city's growing art scene, local attractions, and a rich past that is a beacon for history enthusiasts, you may have a hard time fitting everything into one trip. There are a large number of worthwhile activities in and around Downtown Chicago that will make vacation a bit of an adventure. Not sure where to begin? Here are a several things that the area is known for:

• Grant Park and Buckingham Fountain
• Museum of Science and Industry
• Shedd Aquarium
• Chicago Architecture River Cruise

You can also check out our "Things to Do" tab for more inspiration or to book an activity in Downtown Chicago.

Save with a Downtown Chicago Vacation Package

With so much to see and do in Downtown Chicago, you'll be wanting to focus on your itinerary, not spending time to finding the cheapest hotel. AARP Travel Center allows you to easily reserve everything you wish for, and save money doing it. You can plan your entire trip, including activities in Downtown Chicago from just one place. The hardest packing you'll have to do is for your suitcase. Bundle today and save!