Cubs Jersey // Denim Shorts // White Tank Top // Chicago Cubs Baseball Cap

CHI-TOWN– I am such a fangirl of this city. We ate the best food, sat on so many rooftop bars. I met Jordan’s familia and discovered his roots! Did you know Jordan was part German??? We found a pic of one of his ancestors that I swear is Jordan reincarnated lol!

I love me some NYC but I think that Chicago just stole my heart. It was the vest first time here and you betta believe that I’ll be back. Especially for date night in the city at Beatnik. If you haven’t tried it yet, DO IT. Best food ever.

Striped Midi Dress (S) // Jeffrey Campbell Strappy Sandals

We planned a trip for the end of June and the weather was amazing, except for the wind. But HELLOOO it’s the Windy City so I’ll let that slide 😉 Many people warned me the winters in Chicago are tough, so make sure to factor that into your travel plans!

Jordan planned the BEST Chicago itinerary for our trip, and I would do it again. I hope this is helpful for your trip to Chicago! Not headed to Chicago? Sharing more travel guides from across the U.S. and beyond!

*PRO TIP* Download the itinerary image at the end of the post so you can track your Chicago stops!


W Hotel Chicago. Jordan and I stayed at the W Hotel Waterfront for the first few nights of our trip and with his family the other half. We LOVED staying here, in the hub of downtown Chicago. My favorite part was waking up early and running around Millenium Park!

Conrad Hotel. Another great place to stay!


Beatnik. A super chic cocktail bar and the cutest spot for drinks. Inspired by the 1950s, Beatnik has its own unique flair! I loved the natural decor and of course the margaritas!

The Girl and The Goat. Jordan made the family reservations here on our first night after receiving so many great recommendations from our IG fam. We had a great time here!

Free People Black Lace Dress (XS) // Victoria Emerson Wrap Bracelets

LondonHouse Rooftop. HELLOOOO CHICAGO. I loved the Londonhouse rooftop bar! Probably one of the best views of the city and an atmosphere to match. Def check it out if you can!

3 Day Chicago Itinerary Download

*hold down to save to your camera roll if you’re on your phone!*

chicago travel guide

Let me know what your favorite spots are in Chicago in the comments below!