Anniversary trip to Chicago the third week in January — romantic spots needed

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As we are approaching 50, we are not really into the nightclub scene but do enjoy a nice romantic restaurant restaurant followed by a dimly lit speakeasy bar.

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Hogsalt restaurants will fit what you're looking for. You have Bavette's, but also look into Trivoli Tavern and Armitage Alehouse. Unfortunately, reservations are unlikely and you'll just need to put your name in with hostess on the earlier side of the evening. Few other ideas are Carino, Valhalla, Obelix, Osteria Langhe, and Monteverde. Have plenty more, obviously, but don't want to overwhelm with too many options.

Best cocktail bar neighborhood in the city is Logan Square - The Meadowlark, Billy Sunday, Scofflaw, Best Intentions, and Cara Cara Club just to name a few. Conveniently, aforementioned Osteria Langhe is in Logan, as well.

ETA: My Chicago thread guide has a pretty extensive list of cocktail bars if you'd like to run through that.

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We are staying in downtown at the La Salle but be willing to take an Uber somewhere if it was worth it

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The Loop? Yes, you'll want to... leave Very much 9-5 and can seem pretty desolate at night because everyone lives in the neighborhoods and many spots close shop early. No issue taking the train on your way to dinner and cocktails but Lyft/Uber back would probably be the move.

I’d recommend staying in River North. Better spot to get out and walk. As Hoops said, the loop is 9-5 and I wouldn’t walk around after dark.

If you’re looking for another Marriott property, I’d recommend The Gwen or The Ritz.

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I’d recommend staying in River North

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I may actually change the hotel to river north. Any bars you would recommend in river north?

Logan Square bars mentioned above seem cool but appears to be a good ways from downtown.

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Logan Square bars mentioned above seem cool but appears to be a good ways from downtown.

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Eh, it's somewhere around 12-15 minutes on the Blue Line from Clark/Lake in The Loop. It's a worthwhile go if cocktail bars are your thing. In general, the best cocktail bars in Chicago aren't going to be in the immediate downtown area. They'll be in neighborhoods like Logan Square, Pilsen, etc.

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I may actually change the hotel to river north. Any bars you would recommend in river north?

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Gilt Bar (The Library is their basement cocktail lounge), Arbella, Dearly Beloved, Gus' Sip & Dip (might be a tough one), Three Dots (probably the most popular/touristy recommendation), and The Drifter (a classic under Green Door Tavern). Of these, Gilt Bar and Arbella likely what you most may be looking for.

You've picked great place to eat in Bavette! We sat downstairs in the basement. Very cool.

Thanks !

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Gilt Bar (The Library is their basement cocktail lounge), Arbella, Dearly Beloved, Gus' Sip & Dip (might be a tough one), Three Dots (probably the most popular/touristy recommendation), and The Drifter (a classic under Green Door Tavern). Of these, Gilt Bar and Arbella likely what you most may be looking for.

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I would add Sparrow to the list. I've tried to get into Gus' twice now and have given up due to having to stand in the cold.