The J. Parker

The panorama of the park, lake, and skyline delivers the best bang for your buck in terms of city views year-round, thanks to the Hotel Lincoln’s brand-new retractable glass dome. For visitors trying to cram lots of Chicago into a single night, this rooftop spot is a no-brainer. What to order: Midwest Mule: Templeton Rye whiskey, lime, and ginger beer. Lincoln Park, 1816 N. Clark St., jparkerchicago.com

Big Star

Guests hoping for a taste of Chicago’s real drinking scene will love the people-watching at this honky-tonk taco joint and all-around “it” bar. Mingle with artsy Wicker Parkers, die-hard foodies, and tequila lovers who’ve downed one too many. What to order: Michelada, a Tecate with salsa and lime in a glass with a salted rim. Wicker Park, 1531 N. Damen Ave., bigstarchicago.com

Green Mill

To impress visiting history buffs, snag Al Capone’s booth at this 108-year-old jazz lounge, once a favorite haunt of the legendary mobster. Most shows start around 9 p.m., but the bar opens at noon—a perfect time to probe in-the-know bartenders about the club’s Prohibition days. What to order: A shot of Malört, as classic Chicago as the bar itself. Uptown, 4802 N. Broadway, greenmilljazz.com

Untitled

Friends from New York or San Fran are used to cramming shoulder to shoulder in bars, so they’ll love the space to breathe—and drink and dance—at this 18,000-square-foot complex with a DJ and the world’s largest selection of American whiskey (507 and counting). What to order: Tennessee Mule: whiskey, amaro, grapefruit juice, and ginger beer. River North, 111 W. Kinzie St., untitledchicago.com