Bars

Rootstock Wine & Beer Bar
They don’t tell you that you can order anything by the glass by the half glass, but its a great way to pair each delicious dish with a wine without getting (over)loaded. Wine list changes seasonally, and the fare feels like being in France.
954 N California Avenue - Humboldt Park
773-292-1616
Webster’s Wine Bar
What a wine list. Merlot from Switzerland? A focus on Portugal? What I like to do is have my server or bartender make me a custom flight with what THEY are excited about, and send it with some cheese or a small plate to enjoy it with. They know their juice and have an obvious love of the job.
1480 West Webster Avenue - Lincoln Park/DePaul
773-868-0608
Bin 36
You can’t drink wine in Chicago without first heading to Bin 36, a monument in quality, affordability, and education for a wine lover. Partially retail, mostly bistro and bar: amazing bar snacks, smiling bartenders, and knowledgeable servers. Warning: if you come for a drink at the bar, you will stay for hours, get a table, eat dinner, get drunk, and then buy bottles of whatever you tasted to bring home. It’s a wonderful atmosphere, a diverse crowd, and my #1 top, all-time favourite.
339 North Dearborn Street - Near North Side
Swirl Wine Bar
Nose. Taste. Swirl. That’s how you start here. Open until 4am, it is the best bet in River North if you want to get out of the ordinary dance club or irish pub. And of course, if you want an ultra-lounge feel with your sparkling flight. There are DJs, lots of regulars, and very many beautiful people. The bartenders remember your face, name, and what you drank last time, and if you sweet talk the owner Rich, he might let you taste something off the menu. And! The price is right- Every wednesday is Industry night: half price wine.
111 West Hubbard Street - River North
312-828-9000