Just stay away from anything from The biggest problem with long meals?
By the time you’re done, you tend to feel groggy and too full to move.
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Instead, mix things up by going to a new spot for every course.
Think: cocktails and appetizers at Sable Kitchen & Bar, dinner at Quartino, and dessert at Pierrot Gourmet.
Finish off with a nightcap at the downstairs Punch House where, conveniently, the punch has already been spiked.
Or other "paint dates" like Soul Impressions or Arts n Spirits, all of which let your creativity flow like BYOB wine.
It's near impossible not to pick up on the sexy vibes in the dimly lit, curtained-off rooms in one of Chicago's top hookah bars.
Also, there’s something about lounging atop pillows on the floor that makes conversation flow easier.
Attend Adler Planetarium's After Dark event (21 ) on the third Thursday of each month to enjoy cocktails and one-of-a-kind views of the Chicago skyline.
Bonus: the lights are likely to go off at some point in the date.
Secret handshakes and last-minute location details -- be a part of one of the many secret supper clubs in and around the city.