Chicago Bachelorette & Girls Weekend Guide


For everyone planning a girls trip or bachelorette in Chicago this summer, this is for YOU! I get this question quite a bit (although never in the winter, I might add) but anyway, let’s get right to it.

*I’m making this list assuming that you’re staying downtown, but if you’re doing an Airbnb somewhere else (like Lincoln Park, Wicker Park or Logan Square) send me an email I’ll give you a few other recs.

Don’t forget that Yelp, Uber, Lyft, and public transportation are your friends while you’re in Chicago. 🙂 And always call ahead and make reservations wherever you can.




Summerhouse Santa Monica

Hampton Social



3 Arts Club Cafe


Get a trolley! Schedule a pick up spot and they’ll take you around to fun bars and fun spots to snap photos.

Rent a boat and get on the river. This a MUST. We do this 5-6 times a summer, at least. (Google “Chicago boat rentals” and also check GROUPON before you come!) You can either hire a driver or do it yourself. I suggest a pontoon over the electric boats because they’re easier to drive.

Have drinks at a bar on the river walk.

Go to a Cubs game. (Buy tickets the day of and you can usually get a good deal.)

Crappy weather? Head to Eataly!

*Speaking of weather, expect rain in June (and bring a jacket) but July, August and September are usually hot and humid.*

Enjoy the beach! (Yes, Chicago has a big fun beach with bars and restaurants.)

Spa Day at Soho House or Four Seasons.

Relax at the AIRE Ancient Baths.


Cindy’s Rooftop

The J Parker

Z Bar

The Devereaux



Three Dots and a Dash

The Berkshire Room

The Disco

Broken Shaker

The Aviary

Lone Wolf

Soho House

(Or just go toward Hubbard street and you’ll be fine.)

DIVE BARS: (Aka my faves.)




The Lodge



The Dearborn

Maple & Ash

Joe’s Imports

Beatnik on the River

Gibson’s Italia


Booth One

Girl & The Goat

The Publican


Faves beyond downtown: Big Star, Parson’s, The California Clipper, Park & Field, Dove’s, Longman & Eagle, Bangers & Lace, Clever Rabbit, Violet Hour, Twisted Spoke and Handlebar (my favorite vegetarian spot.)

And that’s my list! If you live in Chicago and have other ideas, tell me below! Would love to know if you end up doing any of these things when you visit, DM or tag me on instagram @thedailytay!

P.S. I suggest snagging this sweatshirt for your travels 😉

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