Last Updated On: August 14, 2017

Summertime is a great time to be in Chicago and it’s one of the best cities in the world, so why not plan a little staycation in your own city.

If you haven’t explored many places downtown and you live in the city or close by then this girl’s guide is perfect for you. If you have never been to Chicago but want to explore Chicago in a not so touristy way then this guide is also for you. I’ve also included links to some of my other girl’s guide within this post so you can add to your staycation if you like. So, take a few days off this summer and plan a little staycation with your girlfriends.

Where to stay

photo credit: Drumbar

There are so many amazing hotels to stay at in Chicago but I’m going to share with you a few of my favorites. Also, try taking a few days off during the week, or use an app like Hotel’s Tonight to get a really great deal. Also, check to make sure there’s not a big event or a conference going on because that will really raise hotel prices.

You might also like A Girl’s Guide to Spending a Relaxing Weekend at The Peninsula Hotel in Chicago

Day #1


Beatrix Chicago

Starting your day with breakfast or brunch at Beatrix in River North. You can sit by the open windows and enjoy a vanilla latte, pastry, or any one of their breakfast or brunch options. My favorite is the egg white omelet. And then, what’s a girls staycation without a little shopping! Head over to Michigan Ave and spend the morning shopping at your favorite stores.

*If don’t want to shop, enjoy the architecture boat tour (check Groupon for discounts).

You might also like  A Girl’s Guide to a Day on Michigan Avenue



Two of my favorite places to go with the girls for lunch are Pierrot Gourmet, the patio is so cute and the shrimp salad is my favorite and so yummy! Or True Food Kitchen, the food is really healthy and really delicious.

After lunch, head to the Riverwalk for an afternoon of relaxing with the girls and enjoy some drinks along the Chicago River. Start at Tiny Hatt and work your way down to Island Party Hut. 320 River Bar also has a great happy hour, located across from City Winery.

You might also like  A Girl’s Guide to Happy Hour in Chicago


photo credit: Andy’s Jazz Club

You can’t go wrong with most restaurants in Chicago for dinner. If you haven’t had deep pizza then head to Lou Malnati’s in the Gold Coast for some ‘za. Or try any restaurant around the Gold Coast like Tavern on Rush, Hugo’s Frogs, etc and request to sit on the patio for some great people watching.

After dinner head with your friends to Andy’s Jazz Club to listen to some live music. Did you know jazz is a huge historical part of Chicago’s history so it a really fun thing to do if you have never been to a jazz club. A perfect way to end the night is to enjoy a cocktail at one of Chicago’s most popular rooftop bars.

Download my checklist: A Girl’s Guide to Chicago Best Rooftop Bars

Day #2


rose' all day at Hampton Soclal
photo credit: The Hampton Social

A great suggestion for breakfast is to go to Stan’s Donuts on Michigan Avenue for the best donuts in the city. If you haven’t been, it’s a must! If you are looking for a fun girl’s brunch similar to Beatrix then you can enjoy a trendy brunch at The Hampton Social. Once you are there you will definitely feel like you are on vacation.

If you haven’t been, head to one of the museums in Chicago. I highly suggest going to either The Art Institute or The Shedd Aquarium. If you and your friends are interested in old historic mansions, a fun tour to do is the Driehaus Museum which is located a few blocks of Michigan Avenue. You can check this website for free admission museum days for Chicago residents.


photo credit: Freds

Head the Gold Coast for lunch at Freds in Barneys and enjoy one of their amazing and huge salads. They are actually not too pricey. You can also enjoy lunch on their balcony which overlooks the Gold Coast. After lunch, depending on what you girls feel like doing you can either grab a coffee and spend the rest of the afternoon taking a walk to explore, or relax and pamper yourself with a free makeup consultant, a spa service, or even a relaxing blowout. My girl’s guide below can help you with how to pamper yourself on a budget.

You might also like A Girl’s Guide to Pampering Yourself in Chicago on a Budget



Every evening during the summer the Jay Pritzker Pavilion host free music and movie events. Here’s the summer schedule so you can check out what’s going on. Before you go to the park stop you and your girlfriends should stop by Eataly to shop your favorite wines and create your own picnic to bring. Relax on the lawn, drink some wine, and listen to some amazing music.

Download my checklist A Girl’s Guide on How to Have Parisian-Inspired Picnic

If you have any questions about this girl’s guide or would like more suggestions about restaurants, bars, etc, send me a tweet or email me!

Download A Girl’s Guide to a Staycation in Chicago (Summer Edition)



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A Girl's Guide to Chicago

Based on the true story of a girl in her twenties who packs her bags and follows her lifelong dream of moving to Chicago. Take a journey with Kelly and discover the hidden gems you never knew about – as she starts a new career, makes new friendships, and even falls into an unexpected romance. Learn more...

  • • Perfect for the girl who loves exploring and living in Chicago.
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Girl's Guide Chicago