Chicago doesn’t try too hard.
It doesn’t need to.
It’s confident in its skyline.
Certain in its food.
Warm in ways that surprise you.
If you matched at one of our Chicago events and found yourself wondering where to go next… here’s a little Cheeky guidance.
Because second dates in Chicago deserve character.
🌅 A Riverwalk Golden Hour
Start with a walk along the Chicago Riverwalk just before sunset.
Grab coffee from Café Crèmerie or a casual drink at City Winery, and let the architecture do what it does best — quietly impress.
Chicago glows at dusk.
And walking side by side makes conversation feel easy.
🕯️ West Loop, Elevated but Relaxed
If the mood feels promising, head to the West Loop.
Dinner at Rose Mary or Girl & the Goat brings warmth, flavor, and just enough buzz.
It’s lively without being loud.
Intimate without being intense.
🌊 Lakefront Simplicity
Sometimes the best move is simple.
Meet near North Avenue Beach or along the Lakefront Trail, especially in late afternoon when the skyline feels almost cinematic.
Bring coffee. Walk slowly.
Chicago feels big — until it doesn’t.
🍸 Wicker Park, A Little Playful
If the energy is undeniable, lean into it.
Cocktails at The Violet Hour (still one of the city’s best hidden-feeling rooms) or dinner at Big Star if you want it light and fun.
Second dates should have range.
🌆 Lincoln Park, Soft & Easy
If it rolls into daytime, wander through Lincoln Park Conservatory, then brunch at Summer House Santa Monica.
Light-filled spaces.
No rush.
Just the quiet feeling of wanting to see each other again.
Chicago has edge.
But it also has heart.
And when two people choose each other here — in a city that balances grit and grace — it feels grounded.
We love watching matches turn into second dates.
Chicago does the rest.