Rainy Day in Chicago
Rainy Day in Chicago

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TNT Rooftop Restaurant
Harper Court
City Winery Chicago
30,000-sq.-ft. venue with a winery, Mediterranean eatery, garden courtyard & live entertainment.
Beatnik West Town
A posh space filled with globe-trotting decor is the setting for New American fare & cocktails.
The Empty Bottle
Indie music venue & bar hosting alternative bands in a somewhat small space with cheap drinks.

Harold Washington Library Center, Chicago Public Library
The public library's main branch features a mix of classic & modern architecture & a winter garden.
Intelligentsia
High-end coffee bar chain serving daily roasted brews in a contemporary setting.
Lincoln Hall
Midsize venue for live music performances along with an unpretentious on-site cocktail bar.
Ashland & Roosevelt
Pittsfield Cafe
Familiar breakfast dishes & lunchtime sandwiches served up inside the historic Pittsfield Building.
Color Factory Chicago
900 North Michigan Shops
7 levels of luxury retailers, fashion boutiques & restaurants along Magnificent Mile.
Joffco Square
Radius Chicago
Southgate Market
Cupitol Coffee & Eatery (Streeterville)
Easygoing bar/eatery serving cafe fare such as sandwiches, salads & baked goods, plus coffee & tea.

Stony Island Plaza
Storyville Chicago
Po' boys, gumbo & jambalaya, plus cocktails, in a hip venue with red leather booths & chandeliers.
Marketplace At Six Corners
Bottom Lounge
Venue for underground music, beer & casual American comfort food (including vegetarian options).