Chicago Vacation Packages for 2026

It might be called the Windy City, but it will be the attractions, not the wind, that sweeps you off your feet when you visit. Chicago, Illinois, is the hub of the Midwest, and it boasts everything from lakefront beaches to big city skylines. If you've got your eye on a trip there, consider AARP Chicago vacation packages. With vacation packages that include both flights and hotels, cheap Chicago trips for seniors and AARP members are definitely within reach. You can even opt to add on cheap deals on rental cars to complete your entire travel booking experience all at once.

Many tourists gravitate toward The Loop in Chicago, and for good reason. This district is home to the Art Institute of Chicago, Grant Park, Millennium Park, and the iconic Cloud Gate sculpture known affectionately by locals as simply The Bean. You can also find lots of Frank Lloyd Wright architecture throughout Chicago, often just a short distance from a modern skyscraper like the Sears Tower. Other unforgettable ways to spend time in Chicago include attending a Chicago Bulls NBA game, watching a play at the iconic Steppenwolf Theater, or shopping for upscale souvenirs along the Magnificent Mile, a stretch of Michigan Avenue no visitor should miss.

Ditch the booking fees typically associated with airfare, and enjoy the best prices on AARP member and senior vacations in Chicago, IL, by starting your trip planning right here at the AARP Travel Center Powered by Expedia. With a single hotel stay, AARP members can scoop up discounts of 10% on their accommodation. When you bundle accommodation and airfare through our vacation packages, your savings can only grow. We even offer some of the cheapest Chicago car rentals around so that you can plan a trip to the beaches of Lake Michigan or the architectural wonder of nearby Oak Park.