Vacations in Chicago for AARP Members
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.
Top Hotel Deals
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations
All accommodation types in Chicago
More Types of Hotels
- Hotels with Air Conditioning (871)
- Hotels with WiFi (744)
- Hotel with wifi (717)
- Family Hotels (705)
- Smoke Free Hotels (621)
- Hotels with Bars (480)
- Hotels with Complimentary Breakfast (470)
- Hotels with a Pool (458)
- Cheap Hotels (454)
- Luxury Hotels (367)
- Pet-friendly Hotels (324)
- Hotels with an Indoor Pool (308)
- Hotels with Hot Tubs (297)
- Resorts & Hotels with Spas (282)
- Hotel with a Concierge (240)
- Lakefront Hotels (222)
- Beach Hotels (209)
- Hotels with Balconies (172)
- Casinos (121)
- Hotels with Early Check-in (114)
- Hotels with smoking rooms (107)
- Hotels with Fireplaces (86)
- Hotels with Free Airport Shuttle (75)
- Hotels on the River (19)
- Hotels with Tennis Courts (18)
- Gay friendly Hotels (7)
- Oceanfront Hotels (4)
- Hotels with Waterslides (3)
- All-inclusive Hotel (1)