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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. 7hrs 10min $383. From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to Chicago Midway airport, then subway to Chicago. 9hrs 04min $383. From dartmouth Bridge Terminal - Bay 10 line 320 bus to Halifax airport, fly to Milwaukee airport, then train to Chicago. 10hrs 32min $475. From Halifax, NS train to Montreal, PQ, bus to Toronto, ON, then bus to Chicago, IL. 42hrs 35min $319. From Halifax, NS bus to Rivière-du-Loup, bus to Montréal-Pierre Elliott Trudeau International Airport, bus to Montreal, PQ, bus to New York, then bus to Chicago, IL. 46hrs 01min $465. From Halifax, NS train to Montréal, QC, train to Brockville, ON, line 5797 bus to Syracuse, NY, then train to Chicago, IL. 47hrs 13min $389. From Halifax drive to Chicago. 27hrs 38min $350.

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