Last Updated On: February 23, 2018

As I write this girl’s guide, it is actually a somewhat warm day in Chicago for the end of February. Although it is currently pouring. I have my fingers crossed that spring is just around the corner for us. However, for those of us who live in Chicago, the last few weeks of winter can be especially tough and can also be rather draining. Whenever I’m feeling like I have a little bit of the winter blues I try to go to a few fun places in the city that I know will cheer me up. A place that gives me that vacation vibe. So if you are feeling like me, in a little bit of a winter funk, you can use this guide and enjoy some of these fun spots with the girls.

Head to one of these places if you are looking for a place that is glamorous, pretty, and cheery

3 Arts Club Cafè

If you are looking for a place that is somewhat fancy, a gorgeous place to go with the girls is 3 Arts Club Cafè. Located inside RH (Restoration Hardware), you can enjoy a glass of wine in the beautiful garden-inspired atrium restaurant. You definitely won’t feel like you are in the city during the middle of winter. Afterwards, you can explore floors of beautiful Restoration Hardware furniture. What’s even better is that you can even take your wine and walk around and relax anywhere you like within the store.

Location: 1300 N. Dearborn

The Cafe at The Ritz- Carlton

This is my new favorite hidden gem. If the wait is too long over at 3 Arts Club Cafè you can enjoy a cocktail and relax in similar style at The Cafe at the newly renovated Ritz- Carlton. The space is really pretty, really cheery, and really cozy. It also has an atrium, has plenty of cozy couches, even an outdoor patio for warmer days.

Location: 160 E. Pearson Street


For stunningly gorgeous and funky bohemian vibes, Beatnik is a must for cocktails. It’s bright, eclectic space can’t help but put you in a better mood. Enjoy a few fun cocktails with the girls and forget all about how miserable it is outside.

Location: 1604 W. Chicago Avenue

3 Arts Club Cafe

Head to one of these places if you are looking for a coastal or beachy vibe

The Hampton Social

If you love an East Coast beachy vibe and want to feel like you are spending the afternoon in The Hamptons, then The Hampton Social is a must. I love the decor and how bright and airy their space is. It’s the perfect spot to enjoy a glass of rosè with the girls. Head to The Hampton Socal for happy hour after work with 1/2 price glasses of rosè from 3 pm to 6 pm on weekdays.

Location: 353 W. Hubbard Street

Summer House Santa Monica

Summer House is always giving me fun California vibes. You can feel like you are on vacay, even if it’s just for a few hours. Whenever I’ve felt like I’m in a winter funk, Summer House is a great spot for fresh summer-ish cocktails. The food is also good and it’s hard to leave without getting one of their delicious cookies.

Location: 1954 N. Halsted Street

Lowcountry South Loop

This is perfect for a group of girlfriends who are ok with getting a little messy. Enjoy an east coast seafood boil with a summer on the East Coast backyard picnic table vibe to match. Their cocktail menu includes refreshing highball drinks and a signature rum punch.

Location: 1132 S. Wabash Avenue

Blue Door Kitchen

Once you walk inside Blue Door Kitchen you feel like you are instantly in the South. It definitely reminds me of a restaurant you would find somewhere in Savannah or in the Carolina’s. It’s small, cozy, and cute and the food is really good too. Not the best place for a group of girls but perfect for a cute lunch date or with a small group for dinner.

Location: 52 W. Elm St


The Lakefront Restaurant

Enjoy beautiful views of the Lake Michigan and the city skyline at this newly opened restaurant. On a warmer day take a stroll along the lakefront to this restaurant to enjoy some cocktail right next to the water. I don’t know what it is but being by the water does so much for my body and mood. I instantly feel refreshed. Once the warmer days are here you can sit outside and enjoy some drinks on their dog-friendly patio.

Location: 2401 N. Lake Shore Drive

Head to one of these places if you are looking for a tropical and exotic vibe

Lost Lake

If you love a good tiki bar with a little bit of dive bar feel then this is the place for you and your girlfriends. It’s over the top decorated and it’s such a fun vibe. The drinks are really delicious and also decorated with typical tropical umbrellas and flowers and even some drinks arrive at your table with flames. Be careful, the drinks are also pretty strong too.

Location: 3154 W. Diversey Parkway

Three Dots and a Dash

Walk through an alley in Chicago and end up in Hawaii. Ok, not really but you get the point. If you can’t make it up north to Lost Lake you can always head to Three Dots and a Dash. This place is perfect if you like strong drinks in crazy fun tiki type mugs in a speakeasy type bar.

Location: 435 N. Clark Street (back alley on Hubbard Street)

The Flamingo Rum Club

If you want to go out dancing with your girls head to The Flamingo Rum Club for a fun night of watching and dancing to live entertainment. Just pretend for one night you are in a tropical place far away.

Location: 601 N. Wells Street

Have you been to any of these places? Do you have a favorite? Did I miss any that should have been on the list?

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