The only thing you’ll miss about starting your night alfresco at Graham Elliot Bowles’s eatery is hearing what’s on the chef’s iPod, which blasts through the dining-room speakers. (Depending on your musical taste, this could be a blessing.) What you’ll get in exchange is a pretty sidewalk patio where you can dine on whimsical Parmesan clouds dusted with bacon powder or lavender marshmallow floating in split-pea bisque, all under the shade of Huron’s towering trees. 217 W Huron St (312-624-9975).
Keep the creativity (and the cocktails) flowing with a stop at the Dana Hotel’s rooftop patio, where sunsets are met with summery drinks like the Verao Batida, a cool concoction of ripe stone fruit, cachaça, citrus honey and fresh mint. Yes, you will need to don oversized sunglasses (and rock lots of hair product) to fit in at this sceney, 26th-floor meetup, but you might just lure a sugar daddy (or mama) to cover next month’s rent. 660 N State St (312-202-6060).
Now that you’re properly fed and leaning more toward buzzed than belligerent, be nice and indulge the sports fan in the group with a stop at this LCD-outfitted sidewalk patio. While your friend is pounding beers to ESPN baseball highlights, you can relax within the flower-lined partition with daily cocktail deals and watch the hodgepodge of tourists, bros and local ladies stumbling in stilettos. 9 W Hubbard St (312-644-0004).
Make like the Spaniards and follow drinks with more drinks and a bit of a snack to pad the stomach. Only, don’t do it with Spanish food (tepid tapas may induce a snooze fest instead of keeping the party going). Instead, head for this new pan-Asian hot spot, snag a rattan chair on the sidewalk setup, and use those spiffy new teak tables to balance Sunda’s crisp, custom-brewed wheat beers and suds-soakers like pork-belly buns and oxtail pot stickers. Slated to open mid-May. 110 W Illinois St (312-644-0500).
Bull & Bear
If you still have your credit card on you by this point, bravo! Now is the time to use it. Start a tab at this virtual urban oasis where comfy, espresso-colored seating for nearly 100 is flanked by wooden planters, and bottle service gets a summer spin via ice-cold pitchers of white sangria or blackberry mojitos. Just be sure to close out your tab before someone in the gang discovers the serve-yourself beer taps inside. 431 N Wells St (312-527-5973).