As the polar vortex started to settle into Chicago, two friends traveled here to visit for a long weekend. We decided to stay downtown at the Westin. When I walked into the lobby, I was transported back to a birthday celebration several years ago that started at the hotel bar, 320 River Bar. I recall the bill being astronomical (thank you dad).
Fast forward to now. Happy hour specials are now allowed in Chicago, whereas they used to be banned from 1989-2015. To my liking 320 River Bar has $5 glasses of wine daily from 3:20pm - 6:20 pm.
My friends and I engaged in happy hour glasses of wine all four days we were at the hotel, sometimes taking the elevator to the lobby only to return to the room with a glass of wine to enjoy while we lounged around and other times posting up at the bar to enjoy a drink and bar mix snacks before dinner.
The view that weekend was a snowy one, but I look forward to returning in summer as the bar offers a view of the Chicago River.
Find your way with 116 Insider Tips from our Local Spotters
Loved this Spot?Join your international community. Share your favs and become part of our international community!
Monk’s Pub is a cozy, monastery-inspired bar in the Loop serving a wide variety of beers and hearty pub fare — an unexpected escape from the downtown rush.
by
Orso’s in Old Town is a cozy, old-world Italian gem with house-made pasta, live piano, and a charming patio—perfect for date nights or celebrations.
by
I am always stunned by Middlebrow's appetizers, including "the big salad," which includes seasonal vegetables topped with plenty of pepper and shredded cheese.
by
Tavern-style pizza takes the crown at PIZZ'AMICI — thin, crispy crust, cozy vibes, and big local love since they moved from apartment to restaurant in 2024.
by
Vito & Nick's doesn't make typical Chicago pizza: it's the thin crust that reigns supreme here. I drive out of my way to get there, but it's worth it.
by
Reggies Chicago is a grunge bar, concert venue, and shuttle hub with great eats, Sox game packages, a beach bar and unique events like a pancake art show.
by
Luft Balloons in Chicago isn't just a balloon shop – it's a female-operated & owned business that makes balloon sculptures specifically for marches...
by
Little Madrid in Chicago feels so European, it's surprising — trust me, I've spent some time in Madrid myself. Great place for a date or coworker night.
by
Rice'N Bread in Chicago is a special spot for dinner or even pre-gaming a baseball game, a Korean restaurant that always makes my day. Try the bibimbap!
by
I'm not vegan but I do think that "Vegan Plate" in Lincoln Park is one of the best bang-for-your-buck restaurants in Chicago. Try the curry combo plate!
by
"Argyle Street" is Chicago's first shared street. The concept allows cafes to extend outside their doors and provide spaces for the summer night market...
by
116 Insider Tips from our local Spotters
Authentic Stories by Real People
Escape the Crowd & Travel Slow 🐌
✓ 0 Insider Tips from our local Spotters
✓ 116 Insider Tips