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The Best Spots in Chicago for Girls Night (Or Brunch!) Plus, what to wear!

May 8, 2019

The Best Spots in Chicago for Girls Night (Or Brunch!) Plus, what to wear!

Happy Wednesday guys!

I thought it was about time to update my Girls Night Chicago post, because it’s one of the most frequently requested topics I from local and out of town readers alike!

Chicago has no shortage of great spots for girls night–or shortage of spots for ANY occasion for that matter. I’m sharing my giant list of favorites below–(great for girls nights, date nights, whatever!) but first, let’s talk about what to WEAR to girls night–yes? (The short answer: this little midi from Nordstrom–but we’ll get more into that in a second!) 

What to wear to girls night in Chicago:

I always get asked from my gals visiting Chicago–“What do I bring to wear to dinner!?” My answer: Literally anything. ?

Chicago is very laid back, casual place. I can’t think of any restaurant or bar where you’d be out of place wearing flats or jeans. (I mean, I guess if you were going clubbing it might be odd to wear jeans and sneakers…but, even still. I think you’d be fine! ?)

Chicago people are REALLY nice. Nobody is judging you or paying attention to what you’re wearing–so, if you’re visiting from out of town and are stressing over what to pack–you don’t need to worry!

That being said, for girls nights I have a few things that are in the usual rotation:

A pair of straight leg crops (usually Levi’s Wedgie jeans) with a camisole and moto jacket, or a comfortable, feminine dress. The latter of which we’re going to get into today. ?

I recently ordered this linen midi dress from Nordstrom, and it is the PERFECT girls night dress. (Or date night. Or anything night.)  It’s from one of my favorite budget-friendly brands, BP, and it also comes in black. BP is one of Nordstrom’s exclusive in-house brands, much like Treasure and Bond, Caslon, and Halogen, to name a few favorites–I can always count on these brands being quality, versatile, without a crazy price tag! ??

I’ve been getting a lot more into midi length skirts and dresses lately because the length is always appropriate, they’re feminine and on-trend without being “trendy”–and let’s be honest, they’re really comfortable. ?This one also comes in black, but I went for the mustard because I thought it was a great color for Spring and Summer that will also be versatile for fall–especially styled with this purse–I love the tortoise details! ?(This would look so cute with a chunky cardigan and neutral booties come September!)

A note for petite girls: FYI–Nordstrom does free basic alterations for ANY purchase! I often hear from petite gals that midi dresses are too long for them–so I just wanted to share that tip! Yet another reason to love Nordstrom! ?

Here are a few different ways I’d style this dress depending on the setting:

Jess Keys is wearing a little midi dress from Nordstrom | The Golden Girl Blog

Wedges shoes

Midi Dress + Wedges

I love these wedges (you first saw them here!) because they’re comfortable, versatile, dressy but not TOO dressy–making them the perfect heel for pretty much any Chicago girls night dinner scene. (Remember, comfort is key, you know, in case you end up at Howl at the Moon. ?) Run TTS. 

Midi Dress + Polished Flats + Moto jacket:

Jess Keys is wearing a little midi dress from Nordstrom and a jacket | The Golden Girl Blog [one-half-first]Jess Keys is sharing the best spots in Chicago for girls night[/one-half-first][one-half]

Cassie Pointy Toe Slide Sandal


Honestly, I would wear this outfit to any dinner in Chicago. What I love about these slides is that they’re flats, but still polished. So often, flats can be super casual, but these are a little more dressy. Plus, they’re actually comfortable, which is essential for me in the summer because I walk EVERYWHERE! Sandals run TTS. 

If it gets chilly, pull on a neutral colored moto or leather jacket, which adds warmth while still being polished. If you’re going more casual, a jean jacket (I have this one from J.Crew!) would also be adorable here. If you can get away with wearing open toes to work, I think these flats are perfect for the office, again, because they’re more polished than your average flat! 

Midi Dress + Casual Slides (OR sneakers!) + Jean jacket:

Jess Keys is wearing a little midi dress from Nordstrom | The Golden Girl Blog [one-half-first]Miles Slide Sandal TREASURE & BOND[/one-half-first][one-half]

Jess Keys is sharing the best spots in Chicago for girls night


Nylite Plus Sneaker TRETORN featured

For super casual patio nights, you can dress this midi down with casual slides (these are super comfy!) or–of course–my favorite sneakers! (Note: A lot of you always say you don’t know how to pull off sneakers with dresses–you need a classic, minimal sneaker in order to do it–and this pair is perfect, and SO comfortable! These run TTS. The jean jacket is the most casual of layers and pulls the look together perfectly. Runs a teeny bit on the small side, FYI. 


Okay, so, now that you have some thought starters on what to wear–let’s talk about where to GO! Here are a bunch of my favorite restaurants for girls dinner, or honestly, dinner for pretty much any occasion! I’ve categorized them by neighborhood and also linked to their google map location so you can save them for future reference! 

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I can’t believe it took me so long to get to Etta. It’s in my neighborhood! It’s ideal for a girls dinner because the plates are meant to be shared. (Why do men hate sharing? ?

The bucatini cacio e pepe is literally one of the best things I’ve tasted since I left Italy. Don’t miss the homemade focaccia with ricotta too. (Lauren and Mina say not to miss the bubbling shrimp, but I don’t like seafood so I can’t comment on that, haha!) Oh, also, you have to order the Cassanova di Neri “Irroso” wine. It’s the most amazing summer red–slightly chilled–it’s got a tiny bit of effervescence and is so light–you’ll go through multiple bottles with a group. ?


The Robey is one of my absolute favorite spots in the city. Their downstairs cafe has something for everyone–it’s amazing for brunch (although I have not had dinner here, the dinner menu looks great too!) They have a lounge on the second floor which is fun and swanky for cocktails, and a rooftop deck which fills up fast, but worth the wait (you can put your name in and wait in the second floor lounge until a spot is available!) No trip here is complete without a girls pic with the skyline in the back! (Even if it’s cold, they still have an indoor/enclosed portion, so it’s awesome year round!)


I’ve been to this spot twice–it’s so much fun! It’s the most beautiful boho-eclectic decor you’ve ever seen, and  American/fusion will be a hit with your girlfriends. I’ve only had dinner but I believe they also have brunch! 


If you want a fun atmosphere, outdoor seating and super cheap eats–big star is your bet! You’ll have to wait a long time for a table (they don’t take resos) but there are plenty of places around to go and have a drink while you wait! Full disclosure I think their food has gone downhill, but it’s still good for the atmosphere alone! 


Another budget-friendly favorite–amazing cuban food, BYOB, and they make your bottle of wine into the most delicious sangria you’ve ever tasted! This is one of me and Neal’s favorite spots as well–I don’t think there’s anyone who won’t love this place! (They have two locations too!) 


BYOB but it doesn’t feel like a standard BYOB sushi restaurant! It’s really good even for non sushi lovers!

Club Lucky

One spot that I frequent for both girls nights and date nights. You can’t beat this charming Italian American spot that’s been around for decades. It’s basically an Italian diner with really great martinis.

San Soo Korean BBQ:

Speaking of trying new things, if you love Korean BBQ but want a slightly more upscale (re: not divey) setting––you will love this place. We did a big birthday dinner here for Neal for his 31st and it was great. We just went again and took our friend who was visiting––I think it’s perfect for a girls night because it’s really fun (you grill your own meat!) and good for big groups!

Park and Field: 

Ok so I’ve actually never been here BUT have been dying to go–my girlfriends who live in Logan are always at this spot and I always get FOMO. It’s highly instagrammable with an amazing outdoor space! They’ve got a menu of shared plates and craft cocktails with charming vintage decor.

Parsons Chicken + Fish: (Also a new location in Lincoln Park!) 

A Humboldt Park institution, they just opened another location in Lincoln Park, which has a much bigger indoor area, but the biggest draw here is the patio, their frozen boozy Negroni slushies, and of course, delicious fried chicken. Super casual and really fun atmosphere!



The name says it all–it’s summer year round at this spot. You really feel like you’re in Southern California, and the food is really awesome! Great for brunch, lunch or dinner! Their next door spot, Stella Barra, is awesome as well!


I may be biased about this place because I lived across the street for three years, but this has always been one of my favorite restaurants in the city. They have a cute little sidewalk patio in the summer months–the decor is beautiful, and the food and cocktails are ALWAYS good. Get the short rib or steak frites! Both are to die for.


I also recommend this for a date night spot–it’s very dark and candlelit so it’s very romantic, but the portions are huge (perfect for splitting with girlfriends) and it’s BYOB, which makes it very budget-friendly. Your girlfriends will appreciate the cute Argentinian waiters.


One of my favorite places in Lincoln Park, which also has one of the best skyline views in the city. Another great spot to come when its chilly (or nice) because they enclose the rooftop when its cold! They have awesome cocktails–I haven’t eaten here, but I’ve heard it’s great!


Hands down, the best place for the ULTIMATE girls night–it’s a drag queen supper club–the entertainment is phenomenal (shows every half hour) and they have like 50+ different martinis on the menu! They’re also open for brunch, and I’ve heard they have bottomless mimosas!


OK I would not classify this as a “girls night” spot in the typical sense–I would classify it as an “every occasion for everyone” spot. It’s the best greek food (in my opinion) in the city–it’s cheap, and connected to one of my favorite Irish pubs, so you can have a pint and wait for a table! (They don’t serve booze–but their partnership with the pub next door makes it easy!) 

Rickshaw Republic:

This is a new-to-me favorite I just discovered–a few of my girlfriends went here with the boys in tow–it’s Indonesian street food–SO DELICIOUS and a really fun, BYOB, insanely affordable experience. When your girls are getting together wanting to try something new, I highly recommend this cute spot. We did some sort of special menu where you get to try a bit of everything. 

Cafe BaBaReeba: 

A Lincoln Park STAPLE. It’s rare to meet someone who has lived within a 3 mile radius of Lincoln Park ever in their life and never been here. ?It’s a very charming tapas spot that is ideal for girls dinner–they have delicious sangria, and also, fantastic brunch! 



Another one I didn’t get around to trying until recently–Aba is AMAZING. It totally lived up to the hype in both cuisine and ambiance. Not only is the restaurant gorgeous, but the food does not disappoint. This is one “sharable” menu where your husband will actually approve––they have a lot of meat, haha!


This is my #1 most recommended spot for visitors staying downtown. It has the coolest views (of both the skyline and the harbor!) and a great brunch menu. Even if you just go for cocktails, it’s a must-do!


This place is just adorable. Not unlike a lot of restaurants in Chicago, their specialty is Mediterranean small plates–very good food, great drinks, plus they have a rooftop in the summer!  


Chicago’s preppiest restaurant ? It’s so cute, you feel like you’ve been transported straight to the East Coast!


I went here with my college girlfriends for dinner and it was SO amazing. Small plates, all Mediterranean–so it’s actually not terribly unhealthy, either!


Another recco I always give visitors, it’s a swanky asian-fusion/sushi restaurant and it has something for everyone. Their brussels sprouts are out of this world, you can’t not order them. Oh and literally everything else on the menu is divine, too. 


One of my favorite restaurants–plus, it’s actually healthy! (Ish.) They have a few locations, the food is consistently really good and the decor is stunning. You HAVE to get a chocolate chip cookie, too! This is the restaurant that everyone can agree on if there are lot’s of dietary restrictions. Lot’s of options for gluten free, veggie, vegan, etc. 


Top Chef (and now Iron Chef) Stephanie Izard’s upscale take on Chinese. It is probably the best (trendy) Chinese you’ll ever have and the decor and entire experience is so much fun. It’s a great spot for a date or with girlfriends!


You’ve likely seen plenty of brunches or cocktails on Instagram from Soho House. Their downstairs lounge is casual but beautiful–you and the girls can eat all the avocado toast your hearts desire. Plus, they also have high tea, which is fun! For dinner, their food is very *good* but the atmosphere is really what you go here for. (I.E. I don’t think their food competes with all the other West Loop heavy hitters, so if food is your #1–this probably isn’t your spot–but is still a very fun trendy place for dinner!) 


I feel like this West Town gem flies under the radar a lot–which is totally fine with me. Above Roots pizza (another great spot, if you’re looking for a casual pizza joint)–this is a farm to table al-fresco restaurant that grows a lot of their produce right on their roof garden! It’s SO charming and great for dinner with friends or a date! 

Shop more Midi dresses for Girls Night! 

What are your favorite Chicago Girls Night spots!? 

Huge thanks to Nordstrom (where basically 85% of my wardrobe comes from ?) and ShopStyle for sponsoring this post! All opinions are 110% my own! 

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