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From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to Chicago O'Hare airport, then subway to Chicago. 6hrs 58min $390. From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to Chicago Midway airport, then subway to Chicago. 8hrs 39min $434. From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to South Bend airport, then bus to Chicago. 10hrs 40min $487. From Halifax, Nova Scotia station train to Central Station, train to Union Station, train to Windsor station, taxi to Detroit, MI, bus to Ann Arbor, MI, then train to Chicago, IL. 43hrs 59min $430. From Halifax, Nova Scotia station train to Montreal, bus to Ottawa, ON, bus to Toronto, ON, bus to Detroit, then Bus to Chicago. 47hrs 51min $286. From Halifax, NS bus to Riviere Du Loup, PQ, bus to Quebec, PQ, bus to Montreal, bus to Kirkland, Bus to Toronto, ON, bus to Detroit, MI, bus to Toledo, OH, then bus to Chicago, IL. 42hrs 54min $403. From Halifax drive to Chicago. 27hrs 02min $330.