Chicago may not always take the lead when stacked against other big cities. Its bistros, for one, are no match for those clustered on a Parisian street side and its vineyards will never conquer the grapes of the West Coast. But when stripped down to its gritty jazz roots, Chicago comes in second to none. Vocalists, bassists and trumpeters from all over the map flock to these neighborhood hot-spots to find inspiration in the city. Lucky for you, these places require little more than leaving the house.
Best for Foodies: Katerina's
The crowd at Katerina's is a hungry one, and rightfully so, after such energetic sets of bopping, scatting and dancing. Fortunately, Katerina knows how to please her music-lovin' guests with carefully-crafted Mediterranean fare. The menu's list of orektika (greek for appetizers) has just the thing to curb your appetite before the next round of drinks and beats. Small plates include baked eggplant, grilled calamari and tiropitakia, a flakey phillo shell filled with ricotta, feta and goat cheese and served with amaretto-cinnamon oranges. Food is served until 1 a.m. and cover charge varies, typically between $5 and $10. Check the restaurant's website for upcoming shows.
Best With a Date: Pops for Champagne
This Parisian-themed jazz club will have you swooning for more than just your date with its exposed stone walls and intimate lounge seating. Start the evening with a little bubbly on the bar's main level, where champagne-inspired chandeliers and an onyx bar provide an elegant atmosphere. Pop's drink list boasts over 160 varieties of champagne and sparkling wine; order up a few flutes and it won't take much to lure your date downstairs for some sultry tunes. Past acts have included pianist Dan Trudell, vocalist Tammy McCann and saxophonist Chris Greene. Check the bar's website for upcoming shows. Music starts at 9 p.m. Keep it cheap Tuesday through Thursday with no cover, or spoil your date on the weekend for $15 per person.
Best for Jazz Novices: Checkerboard Lounge
Newcomers to the jazz scene will love this unpretentious South Side spot. In collaboration with the Hyde Park Jazz Society, the Checkerboard Lounge hosts Checker Jazz every Sunday from 7:30-11:30 p.m. Themed nights like "Sax in the City" have highlighted Chicago's contemporary saxophone players, while other artists have included multi-reedist Ari Brown, trumpeter Pharez Whitted and bassist Frank Russell. The Hyde Park Jazz Society will also be hosting their second annual jazz fest this year on Sept. 27. Checkerboard Lounge offers a full bar and welcomes outside food. Admission is $10, and $5 for students with IDs.
Best Downtown Beats: Andy's
The jazz at this downtown spot only ceases when the staff needs some shut-eye. In a single week you can catch 15 different acts at Andy's. Be sure to pick the appropriate time slot though: Stopping in during rush hour will find you in the throes of downtown's post-work boozin' crowd, while the later hours are reserved for a more subdued, sultry-eyed group. Whether the sun is rising or setting outside Andy's, the stellar beats are always belting inside. Most of the acts here lean toward mainstream jazz with an emphasis on bebop and swing. Cover prices vary and there’s typically a two-drink minimum.
Best for Seasoned Cats: Green Mill
OK, so we're stating the obvious here. But you try to find a jazz club that trumps the Mill and then we'll talk. There's a reason this speakeasy spot has been home away from home for many serious artists and enthusiasts. The hip locale was, after all, once frequented by Capone and his henchman. Even Sinatra checked out the spot after catching wind of its mobster appeal. You might not find any gangsters lurking about the bar these days, but you'll certainly be in the company of some of Chicago's finest jazz musicians.
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