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Three miles of lakefront parkland draw people to the Lincoln Park neighborhood—and most hotels here are just blocks away. Room rates are decidedly lower than those downtown, the downside being that you'll invest more in transportation to hit top sites. Parking is easier, but never a snap; plan on using the valet. Wicker Park attracts an artsy mix of young couples and singles who can't walk more than a yard without stumbling into a mom-and-pop-owned fast-food joint or a four-star restaurant.