From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to Chicago O'Hare airport, then subway to Chicago. 6hrs 57min $340. From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to Chicago Midway airport, then subway to Chicago. 9hrs 07min $430. From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to South Bend airport, then bus to Chicago. 10hrs 41min $753. From Halifax, NS bus to Rivière-du-Loup, bus to Gare du Palais, bus to Berri / Place Emile-Gamelin, bus to Montreal, PQ, bus to Toronto, ON, then bus to Chicago, IL. 38hrs 39min $406. From Halifax, NS train to Montréal, QC, train to UNION STATION - NORTHBOUND PLATFORM towards FINCH, subway to Toronto, ON, then bus to Chicago, IL. 42hrs 25min $373. From Halifax bus to Yarmouth NS, Car ferry to Metro Pulse, line 5 bus to Portland, ME, bus to Boston / Logan Airport, bus to South Station, train to Boston - Back Bay, MA, then train to Chicago, IL. 47hrs 03min $395. From Halifax drive to Chicago. 27hrs 38min $347.
Operators: Metro Transit - HRM United Delta Air Lines Air Canada US Airways Chicago Transit (CTA) Porter Airlines Westjet Southwest Greyhound USA Maritimebus Orleans Express STM Megabus CA Greyhound Canada VIA Rail Toronto Transit Greater Portland Metro Bus Concord Coach Lines Boston Express Massachusetts Bay (MBTA) Amtrak