Dressing to the Nines: the best Chicago restaurants for dressing up

Sometimes you just feel like getting dressed up. I'm talking red carpet ready, Golden Globe worthy ensemble dressed up. But when we don't have an occasion for that kind of outfitting, can't we still pretend?


Chicago is home to an abundance of fanciful scenes fit for the lifestyle of the rich and famous. And when us commoners would like a walk in the limelight, these places allow for that to be a reality.

Other than evident go-to venues for luxe living like the Signature Room and Metropolitan Club, AptAmigo has found that these 9 purlieus are the best Chicago restaurants to ensure an enchanted evening and elevate your social status.

Pump Room

Chicago publications has described this Gold Coast venue as "dazzling," "unbelievably delicious," and "sheer perfection." Famous for its history of celebrity sightings, including a whole booth specifically for Frank Sinatra, the stunning atmosphere recaptures the glamour of the 30s' and 40s' with a modern twist. Fun fact: autographs from famous icons fill the hallway walls on the way to the bathroom.

Cape Cod at The Drake

Simply walking past the infamous Drake Hotel off Michigan Avenue in Streeterville will give anyone a charming feeling, but actually dining in at this long-standing restaurant brings a whole other level of sophistication. Serving classic New England seafood and cocktails by quite possibly the most attentive and hospitable waitstaff, this gourmet restaurant is worth every penny.

Bavette's Bar & Boeuf

Dimly lit by white candles and table lamps, this dark, ultra mysterious restaurant is 1920s' era meets upscale urbanite in the heart of River North. Every plate is exquisitely designed and tastes even better. Every expectation you have for a stylish and sensational evening is met at Bavette's.


With panoramic views of the city and Lake Michigan, this elegant dining destination on the edge of Streeterville is an excellent excuse to finally being able to wear your floor-skimming gown. High on the list of fancy outing priorities, the experience you have here is one you won't forget. You will feel on top of the world (and you kind of are) on the 70th floor of the infamous Lake Point Tower.

Pops for Champagne

Have a birthday or anniversary that needs celebrated? No? Just a Wednesday? Pops for Champagne in River North is the answer to your utmost important life achievements in need of some bubbly, but it is also the cure to your midweek struggle. It's impossible to not have the time of your life at this unusually quaint and intimate sparkling bar.


Located atop the Rafaello hotel in Streeterville, this fashionable, speakeasy-esque bar is always a win. Drumbar is best known for its unbelievably delicious crafted cocktails. The bartenders here are much more than your average server. They are highly skilled mixologists who carefully curate the best tasting cocktail you will ever have in your life.


Flapper dresses and fur boas are not only welcome, but encouraged, to adorn when heading to this late-night wonder. Located in the heart of River North, Celeste is one of the most attractive and sought-after lounges the city has to offer.

The Berkshire Room

This snazzy lounge located in the historical ACME Hotel in River North is arguably one of the coolest spots in the city. It somehow manages to pull off an eclectic vibe in a classy setting due to its old time movie feel and black and white decor.

Violet Hour

You literally feel like you are in a dream walking through this heavily disguised destination. As you enter, grand, velvet walls surround you and top to bottom royal curtains enclose behind you. The dark and private ambiance deems this Wicker Park lounge one of the most romantic spots in the city. Similar to Drumbar, Violet Hour also has killer cocktail servers who create outstanding drinks.

Now all you need to do is pick out your outfit!