Before heading to Europe for a month this summer, my mom and I spent 4 days together in Chicago to have a joint early birthday celebration and to see Elton John on his farewell tour.
Here’s our best things from that time that could make a great girl’s weekend for anyone!
1) Thompson Chicago
The Thompson Chicago in the Gold Coast neighborhood was incredible. It’s in a great location (10 min walk to the waterfront, 10 mins to The Magnificent Mile and 2 minutes to Tavern on Rush – more on that later), has great service and if you have Globalist status with Hyatt, you’ll get great perks including free breakfast, free parking and the possibility for a suite upgrade – we used free night certificates and got upgraded to a Junior Suite with a great view.



2) Tavern On Rush
The Tavern on Rush had incredible food and cocktails. Our server, Luis, was amazing and if you can sit in his section you should. He took great care of us but also wasn’t afraid to help us explore new things like this pear martini drink that was life changing.


His service, and the drinks, were so good we took my aunt and cousin back when they joined us a few days later.

3) Girl & The Goat
Girl & The Goat was a place we’d not “herd” (baaa-haha!) of, but when we were in the elevator at the Thompson Chicago a fellow guest said it was the best food in Chicago. Two others said the same thing later that day, so it was clearly a sign. Having eaten all over the US and the world I was like “sure ok”… He was absolutely correct. I’d say one of my favorite meals of all time! The food is flavorful and is just *POW* in your mouth.



The Popcorn Situation for dessert is a can’t-miss.


4) Caffe Oliva
Caffe Oliva was where we ended up for snacks and drinks a few times. The food was very good, the drinks reasonable, but the service was average. If you want good food and drinks with a nice view and don’t mind that the service isn’t over the top amazing like with Luis at Tavern on Rush, then it’s still worth a visit. It has fun cabanas for larger parties and it’s dog-friendly too!



5) Bobby’s Bike Hike
We mostly did a bit of walking along the shore and we were in town for the Elton John concert, but there’s one can’t-miss activity that can make any visit amazing – a bike tour with Bobby’s Bike Hike.

We had Lou take us around on the Lakefront Neighborhood tour. We chose to ride a tandem bike together and it was a blast.

It’s not for everyone – I heard on RAGBRAI that “wherever your relationship is going it’ll get there faster on a tandem” and that’s completely correct. Thankfully, after 40 years together, mom and I have a very solid relationship so it was no problem at all. But even if you each have your own bicycle it’s worth it for the tour. You see neat places, off the beaten path spots and fun parts of Chicago history like Streeterville and the original Playboy Mansion.


6) Candle Making At Reggie Hathorn
The other thing we did which we can’t say enough good things about is the Candle Therapy experience at Reggie Hathorn. We ended up being guided through the process by Reggie himself. There’s wine, candles and creativity – what’s not to love?!


We talked, laughed, relaxed and enjoyed our candle making class. We also purchased his book, which he signed for us both, and left feeling connected to one another, ourselves and Reggie’s vision by the end.


Of course you may not be able to see an icon like Elton John, but if you get a chance to go to a concert at Soldier Field – I highly recommend it. The venue itself presented a few challenges, so we didn’t get to our seats until 45 minutes into the concert due to the poor layout and communication issue from the staff there. But the experience of the concert was incredible.

We’ve been to Chicago on the road trip so check out those posts too to add other great ideas to your girl’s weekend in Chicago, IL for maximum fun!
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