all that jazz: a chicago city guide

Way back in May I spent the weekend in Chicago celebrating my BFF's upcoming nuptials. Seeing as she got married last week- I figured I should probably get around to showing you some (not all) of the fun we had at her bachlorette weekend. Beth wanted to get away and visit a big city, so she picked Chicago as our destination. As the Matron of Honor, I planned the festivities and centered it all around the gangster era of old Chicago. We partied like Gatsby at night and did tourist stuff during the day. So. Much. Fun.

There were five of us. Some flew in from Florida, others from NC. I really wanted us all to stay together and after a bunch of research (and texts to check with the bride) I settled on a one bedroom rental through Airbnb. The apartment was in a newly built high-rise right off of Michigan Avenue. It had floor to ceiling windows, a living room that fit three air mattresses (think slumber party), and a huge bathroom (imagine 5 girls all getting ready at the same time). The location alone was worth it! I highly recommend looking into Airbnb. We all agreed it was much cooler than a generic hotel.

So... breakfast. We girls love to eat and this place was such a hit. We became regulars. We ate at Waffles Cafe (the E Ohio location) every morning. The Intelligentsia coffee is spectacular as well as everything on the menu. Most of the girls stuck with omelets with side of waffles and waffle hash browns. Oh, those waffle hash browns.

Helen and I tried the eggs benedict made with, you guessed it, a waffle and pulled pork. Needless to say, we didn't really eat lunch the whole trip. These late breakfasts filled us for the day.

We spent most of the daytime walking around the city. We shopped the Magnificent mile and walked all the way out to the Planetarium. The walk along the lake was gorgeous! We caught a water taxi back into the city- so we got to ride in a boat on the lake and the river.  

We saw the bean. It's so bright and cute and a tad smaller than I imagined it- still awesome though. 

Now for the really hip spots. I did a lot of research into the best places to spend the late night hours in Chicago and these stops were our favorites. The Berkshire Room, inside the Acme hotel, was a place I merely bookmarked on my Yelp in case we happened to be in the area. Lucky for us, we were close by. This craft cocktail lounge is pretty new, we were able to get a private corner right away. The menu is out of this world. We had candies peanuts and almonds, bacon dusted popcorn, tobacco onion dip, a cheese plate, a bread (6 different types) plate, and cookies with coffee milk. The flavors and service were incredible. My favorite aspect is the Dealer's choice drink option. You choose a spirit, a flavor (smoky, fruity, herbaceous, etc) and a glass and the expert bartenders just make something up. This place was so chill and the Acme hotel looked really cool! I will be returning!

Jimmy at the James is another hotel bar. Although, it's more like a door around the corner from the hotel that leads to a mysterious curtained room that then leads into a lounge that is part 20's speakeasy and part Mad Men. This is the kind of place that celebrities would go if they wanted privacy. The lounge is small and intimate with spectacular service and inventive food and drink. The music and general vibe was just too cool.

We mostly stuck to cocktail lounge type hangouts on our nights out. However, we got a recommendation from a waiter for Three Dots and a Dash, an old school Tiki Bar. It was rowdy and crowded, luckily we were able to get a table and relax as our waitress got the drinks. The menu is large with awesome pictures and all the drinks are served in different tiki glasses. I chose the Dead Reckoning just because of the mug. This place, while loud and more bar-like, had a great atmosphere of vintage island fun. If you are gonna go- get there early!

For our big 20's night out we went to dinner at Untitled. This was the perfect place to go all dressed up as we were. Untitled is a speakeasy supper club restaurant. You enter through a black door next to a CVS and walk underground into a gorgeously lit lounge, whiskey library and restaurant. We arrived a bit before our reservation to explore and visit the library. Once we were seated we felt like celebrities. We had a fantastic table overlooking the dining area with a direct view of the stage. Oh yeah, there was a live band playing and at one point during dinner a burlesque dancer preformed. That's just the kind of thing that happens at Untitled. The whole place oozed the speakeasy atmosphere and had some of the best food and drinks ever. I has the Mucho Humo and it literally tasted like smoke and the past. Unlike anything else, ever. The menu is all small plates and meant to be shared. My favorites were the scallops. Their menu has changed since we were there, but everything we tasted was absolutely incredible. This would be a wonderful place for a date night- I hope take Byron soon. Just make sure you get a reservation ahead of time.

Other notes on Chigaco.
Call and make reservations at least a week ahead of time for all bars and restaurants. This saved us so much time. Ask waiters, store clerks, really anyone where they like to go. People in Chicago are so nice, that midwest vibe I guess. Our service, everywhere, was impeccable! For a great view of the city visit the Hancock building- skip the tour and visit the Signature Lounge instead. The cost of a drink is cheaper than the tour and the views are the same. For a late night city view visit the Terrace at Trump. The drinks are expensive (share a cider for a deal), but the menu is cool and the views over the river are amazing. Also, some of these pics were taken by the girls. We created a shared album on the icloud so we could have 5 times the pics of everything.
We had such a great weekend and I really miss all the girls. Cheers!


  1. this was the most fun vacation i think i've ever been on! i literally enjoyed every single place we stopped at. thank you so much for organizing the world's best bachelorette party! can we please do this again... soon?!?!?

    1. It was pretty epic! I miss all the girls so much! We seriously need to do it again!