Most Chicago First Dates nights happen in River North, and most of the matches we send out the next morning turn into a first date somewhere within a few blocks of it. That is not an accident. The neighborhood is easy to reach from anywhere on the Brown, Red or Blue Lines, it has a bar or restaurant for every budget, and it stays lively late enough that nobody feels rushed. Here is how we would plan a first date there.
Start with a drink, not a dinner
A first date works best when either of you can wrap it up gracefully after an hour. Pick a cocktail bar on Hubbard or Kinzie where you can sit side by side at the bar rather than face to face across a table – it takes the pressure off and makes the conversation feel like it did at the event. If it is going well, dinner is a two-minute walk in any direction.
Keep the walk short
Suggest a spot that is close to a train stop for both of you. River North sits between the Merchandise Mart, Grand and Chicago stops, and the Clark/Lake hub is a ten-minute walk. Nobody wants a forty-minute rideshare to a second look.
Have a second location in your pocket
The best first dates in this neighborhood move once: a drink, then a walk down to the Riverwalk in summer or a slice on the way to the train in winter. Knowing where you would go next is the difference between an awkward “so…” and an easy “want to keep going?”
What to skip
Skip the loud sports bars on game nights, skip anything with a two-hour wait, and skip the fancy tasting menu on date one. Save the big reservation for date three, when you know it is worth it.
Not matched with anyone yet? See what is coming up on our upcoming speed dating events in Chicago or read about speed dating in River North.