Your Guide to a Chicago Summer Bachelorette

Okay, before we get to the hottest must eat & drink bachelorette recommendations for this summer, let’s just do a quick review of what related resources exist in the Chicago itineraries section of Coffee to Cork:

Linked above are my ready-to-go itineraries for a girls’ weekend in Chicago. Although these indicate a certain season, you can use them somewhat interchangeably. These created based on my recommendation to book your hotel or Airbnb in the West Loop, River North or Gold Coast/Old Town.

All three neighborhoods have plenty to do, eat and drink. You cannot go wrong. Create your itinerary first and whichever neighborhood you end up in the most, that’s where you should book your lodging. Being able to walk, especially with a big group, is key to simplicity, getting places on time and having flexibility; however, you don’t need to just stick to just one neighborhood! Venturing out can be fun, as long as you plan for the day and avoid the constant back & forth of ride shares.

NOTE: I live in Chicago, so I am constantly updating my recommendations. Follow me @coffeetocork on Take Me Out of Office (OOO) to stay up-to-date! Here is my affiliate link:

Now, here are your Chicago Bachelorette must eat, drink & do recommendations!



Here are boating options that give you different experiences in various price ranges:

One more idea! – I haven’t gone yet, but The Gwen Chicago is doing a weekly Tipsy Tea event with savory bites, desserts & booze. Looks cute & fun!

Things to note:

  • I recommend making reservations anywhere you plan to go. Or book a private room!
  • Chicago is not the most price-friendly. Especially if you want to have a good time! Plan to splurge a little more than normal.

My itineraries are made with a focus on doing, eating & drinking, which leads to seeing! Make plans easier — the editable excel templates allow you to add in your own personality, interests and adventures. Or simply download the PDF for a ready to go version.

Enjoy! I am eager to hear from you!

xo | Jamie