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Chicago — 3 Days, Solo, Under $700 Chicago is the best-value major US city for a solo weekend trip — and one that consistently surprises people who expect it to be just a smaller New York. This three-day itinerary makes the most of the Windy City's best: an Architecture Foundation River Cruise (the highest-rated tourist activity in the city, and genuinely one of the finest city tours in America), a morning at the Art Institute with its extraordinary Impressionist collection, an afternoon walk along the Lake Michigan shoreline that makes you understand why Chicago has always felt like a coastal city despite being a thousand miles from any ocean, and an evening on 6th Street listening to jazz in a bar that has been running since Prohibition. The deep-dish pizza versus thin-crust debate gets settled over a full individual pie at Lou Malnati's. Three hotels are included, every booking link is beneath its activity, and the full budget — including flights — lands between $528 and $786.
Chicago — 3 Days, Solo, Under $700 Chicago is the best-value major US city for a solo weekend trip — and one that consistently surprises people who expect it to be just a smaller New York. This three-day itinerary makes the most of the Windy City's best: an Architecture Foundation River Cruise (the highest-rated tourist activity in the city, and genuinely one of the finest city tours in America), a morning at the Art Institute with its extraordinary Impressionist collection, an afternoon walk along the Lake Michigan shoreline that makes you understand why Chicago has always felt like a coastal city despite being a thousand miles from any ocean, and an evening on 6th Street listening to jazz in a bar that has been running since Prohibition. The deep-dish pizza versus thin-crust debate gets settled over a full individual pie at Lou Malnati's. Three hotels are included, every booking link is beneath its activity, and the full budget — including flights — lands between $528 and $786.