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Departure City: Chicago

Destination: All Destinations

Dates: All Dates

Change your departure city | Start a new search | All prices are based on double occupancy.

Flight + Hotel

Your dates from C$203

Flight + Car

Your dates from C$196

Hotel + Car

Your dates from C$55

Louisville, KY: Wax Nostalgic on the Banks of the Ohio You won't be able to shrug that deja vu feeling in this historic city where the past is alive. Includes Flight, Hotel, Taxes & Fees	from C$204 per person
Allentown, PA: Liberty's Safehaven Discover the fascinating local legends of Pennsylvania's third largest city Includes Flight, Hotel, Taxes & Fees	from C$217 per person
Philadelphia Vicinity, PA: Venture Like George to Valley Forge and Beyond Trace the steps of George Washington in the pretty country outside of Philadephia, then come back to the present-day like a high roller in Atlantic City. Includes Flight, Hotel, Taxes & Fees	from C$228 per person
Wilmington, DE (via Philadelphia): As Distinguished as a Du Pont, As Winsome as a Wyeth Spend the weekend in the stomping grounds of two of America's most prominent families. Includes Flight, Hotel, Taxes & Fees	from C$234 per person
Kansas City, MO: Bebop 'Till Ya Don't Stop The land of BBQ. The birthplace of Bebop. The City of Fountains. In this city of many hats, there's a lot more to keep you entertained than you might think. Includes Flight, Hotel, Taxes & Fees	from C$242 per person
Omaha, NE: Steaks Are High Birthplace to Fred Astaire, ballyhooed home to the College World Series, and mushrooming with Missouri Riverfront shops--discover why Omaha is much more than a meat-eater's paradise. Includes Flight, Hotel, Taxes & Fees	from C$243 per person
Philadelphia, PA: Declare Your Independence! No longer in the shadow of NYC, the City of Brotherly Love has emerged as an independent center with an outstanding dining scene, charming urban neighborhoods, and high art--with the history. Includes Flight, Hotel, Taxes & Fees	from C$244 per person
Buffalo/Niagara Falls, NY: The Rainbow Connection This honeymoon hotspot is not just for lovers and dreamers. The larger-than-life falls, scenic hiking areas, vineyards, and tasty treats will melt even the coldest of hearts. Includes Flight, Hotel, Taxes & Fees	from C$246 per person
Charlotte, NC: Have a Royal Time in the Queen City History and high-rises go hand in hand in Charlotte, the largest city in North Carolina. Home to lively nightlife, good eats, and pro sports aplenty, you'll be hard-pressed not to have a good time! Includes Flight, Hotel, Taxes & Fees	from C$248 per person
Boston Vicinity, MA: Wicked Smaahrt Look back on days of frivolous collegiate fun around Baahston. Includes Flight, Hotel, Taxes & Fees	from C$248 per person
Jacksonville, FL: Fountain of Youth, of Sorts Relax on the beach while soaking up some southern sunshine, citrus, and seaspray--all nearly as revivifying as a true Fountain of Youth. Includes Flight, Hotel, Taxes & Fees	from C$248 per person