4 Best Bars in Illinois, USA

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We've compiled the best of the best in Illinois - browse our top choices for the top things to see or do during your stay.

404 Wine Bar

Lakeview

Next door to the rowdy Diag Bar & Grill you'll find the serene 404 Wine Bar, a romantic spot filled with cozy nooks. The librarylike back room has ornate chandeliers, shelves lined with books, and dramatic oxblood walls. Grab a spot on the patio or near one of two fireplaces and enjoy a glass, flight, or bottle of wine accompanied by a cheese plate.

2852 N. Southport Ave., Chicago, IL, 60687-4128, USA
773-404–8400

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Le Midi Wine

Wicker Park

Done up in pretty Prussian blue with warm walnut accents, this wine bar/bottle shop channels calm vibes—and if you're still feeling keyed up, a pour or two from the Eurocentric wine list should do the job. Standard wine bar fare like cheese and charcuterie plus a few Spanish-inspired pintxos make up the small food menu. 

2108 W. Division St., Chicago, IL, 60622, USA
773-303–4884
Nightlife Details
Closed Mon.

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Stonecliff Winery

Along the Mississippi River and housed in the historic Dubuque Star Brewery building, Stonecliff offers five tastings of its local wines and a commemorative take-home glass. On Friday and Saturday evenings, the nightlife scene picks up here with live music or karaoke in the piano bar. One Friday of every month features a party with food and drink specials on the deck.

600 Star Brewery Dr., Dubuque, IA, 52001, USA
563-583-6100
Nightlife Details
Tasting room and wine garden Sun.-Thu. 12-7; Fri. and Sat. 12-11; winter closed Mon.

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Webster's Wine Bar

Logan Square

This long-running cozy, candlelit bar is a romantic place for a date. It stocks more than 500 bottles of wine (at least 20 are available by the glass) plus ports, sherries, single-malt Scotches, a few microbrews, and a menu of small tasting entrées at reasonable prices. At $20 for 3 pours, the Monday evening self-guided blind tastings are a hit with neighborhood oenophiles.

2601 N. Milwaukee Ave., Chicago, IL, 60647, USA
773-292--9463
Nightlife Details
Closed Sun.

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