“Sugar Daddy” Bachelorette Party Pub Crawl

Sugar Daddy Bachelorette Pub Crawl Chicago

Who isn’t intrigued by the concept of having a sugar daddy? Sure, in practice it’s a little shady, but what’s wrong with having a sugar daddy (or two, or three…) for just one night? For the bachelorette who has a taste for the finer things in life, these swanky Gold Coast hot spots make for the perfect place to flirt for free drinks. They don’t call it the Viagra Triangle for nothing!

Pops for Champagne

601 N State St

Start the night off right with Chicago’s finest selection of champagne – after all, it’s a celebration! Pop some bubbly upstairs, then head to Pops for Champagne’s “speakeasy” downstairs, known as Watershed. This secret bar has a slightly more expansive drink menu than Pop’s for Champagne, for those not excited about champagne or wine in general.

Nico Osteria

1015 N Rush St

After your first round(s) of drinks, you’d be wise to grab a bite to eat before the rest of the night’s festivities. Nico Osteria is one of the Gold Coast’s finest dining establishments, with excellent craft cocktails, homemade pastas, and seafood selections.


201 E Delaware Pl

What better place to meet your sugar daddy for the night than at a rooftop hotel bar? Drumbar is located inside the Raffaello Hotel, and a few floors up. Their cocktail menu changes often, so don’t try to find a new favorite. Besides, it’s worth sampling multiple sips from this menu.

Pump Room

1301 N State Pkwy

Gold Coast hotel bars are more the norm than the exception when it comes to dining and drinking out in this Chicago neighborhood. Pump Room is no exception, though it’s certainly unique in its execution. This hotel bar & restaurant is known for hosting many a celebrity clientele. How’s that for the perfect sugar daddy meet market?

Besides famous faces, Pump Room stands on it’s own thanks to their fantastic dinner and drink offerings. Your crew will feel like stars while drinking at the bar, so make sure not to skip this stop, especially for the photo ops!

Tavern on Rush

1031 N Rush St

If you haven’t found your sugar daddy quite yet, Tavern on Rush is sure to come through for your bachelorette party. Thanks to a regular clientele made up of men with more years and money than sense, Tavern on Rush is the ideal place to get your drinking excursion fully funded. And if you’d rather have fun with just you and your crew, nightly DJs and a beautiful outdoor patio make for the perfect place to retreat from the craziness within.

Redhead Piano Bar

16 W Ontario St

Think of Redhead Piano Bar as the classy version of Howl at the Moon. Instead of dueling pianos, there’s just one, with a classically-trained musician tinkling the ivories. The cocktails cover all your favorite classics, and this spot is open til 4am every day.

Regardless of if you find your sugar daddy or not, this bachelorette party itinerary will take you around the best of Chicago’s Gold Coast. It will certainly be a night to remember–if you can hold your cocktails!

If you buy a copy of our book Historic Bars of Chicago ($12), you can get a Chicago Trolley $45 coupon that is more than 10% off for most rentals, and can help you get around our sugar daddy bachelorette party itinerary in style.

If you have better ideas for a sugar daddy-themed bachelor party, or want help planning an itinerary, email us. We can also help with booking private party rooms if you plan to stay in one location!