Vacationing in Chicago

May 18, 2017

Sitting down to write this has me wanting to book a flight back to Chicago right about now. In Chicago there’s always something going on, different events, concerts, sports events, you name it. Along with that, there are so many different neighborhoods to explore, Lincoln Park, Wicker Park, West Loop, Gold Coast, Old Town, the list goes on. I couldn’t wait to plan what we were going to do for our anniversary trip .

365 trips around the sun with you as my husband, thanks for keeping me laughing and always believing in me. Happy 1st Anniversary ❤️

A post shared by Annie • Discovering Your Happy (@anniegpyle) on

The weather while we were there called for rain, but that wasn’t going to stop us. There’s so much to do in Chicago, rain or shine (or snow). And the food options are quite literally endless. So when it came down to picking where we were going to eat it was nearly impossible. But I’ve rounded up all the things we did while in Chicago and where we ate and hopefully when it comes time for you guys to plan a trip this can be helpful. I’ve also jotted down some places that are on my list for next time.

What We Did

Navy Pier – ride the Ferris wheel and enjoy the view of the skyline

Walked the Riverwalk – next time we will definitely do bikes so we can ride along the lakefront as well

Magnificent Mile – so many shops to dip in and out of. And hide from the rain in 😉

Millennium Park/The Bean – snap your must have picture of the bean, but go early, it gets extremely busy

Chicago Athletic Association Hotel/Cindy’s Rooftop/Game Room –  this place is awesome, so many neat little spots to see in the hotel

Restoration Hardware – 3 Arts Club Cafe inside is amazing

Chicago History Museum – save it for something to do on a rainy day

FTW Chicago – fun arcade that also has a full bar and food menu

Where We Ate/Drank

Au Cheval – one of the best burgers in Chicago and yes, we’d have to agree

Parlor Pizza – there are two locations, one in West Loop and one in Wicker Park. Both are great!

Public House – their brunch is amazing, and the Bloody Mary with the loaded skewer added is any Bloody Mary lovers dream

Cindy’s – the rooftop bar at the Chicago Athletic Association Hotel. Great views of Millennium Park

Benchmark – we had some appetizers here and didn’t realize they had a brunch buffet, definitely on the list for next time

Ramen-san – we came here on a whim one night because I was craving a warm bowl of ramen, we were pleasantly surprised with the little spot

Bridgehouse Tavern – right on the Riverwalk and has outdoor seating. Perfect for summer days.

Doughnut Vault – this was one of the very first places to go on my list when we started planning. This little spot it so cute inside and the doughnuts are huge

U.B. Dogs – a last minute stop on our way out of town to grab a couple Chicago dogs, found this spot on Yelp and it was really good with a great lunch special for two

Billy Goat Tavern – made famous from an SNL skit, “Cheezeborger, cheezeborger”, this place is a must just to try the infamous burger

Lottie’s – made famous from one of my very favorite shows, Chicago Fire

Maple & Ash – hands down one of the best steakhouses we’ve been to, from the atmosphere, to the service, to the food, everything was amazing

Goddess & The Baker – a must for a mid-day coffee pick-me-up, great coffee and delicious pastries

Howl at the Moon – probably a huge tourist trap to locals, but it’s such a fun place to listen to live music

Things For Next Time

Architecture Tour

Cubs Game

Rooftop Bars- J. Parker, Soho House, NoMi Garden, GreenRiver, Streeterville Social, Rock Bottom, Wit, Hancock

The Art Institute of Chicago

Blackhawks Game

Restaurants- RM Champagne Salon, Green Street Meats, Hampton Social, Purple Pig, Hub 51, Mindy’s Hot Chocolate, Girl and the Goat, Big Star, Bombobar

Bars- City Winery, Three Dots and a Dash, Green Door Tavern, The Violet Hour, Old Town Ale House, Kingston Mines (we went on our first trip but unfortunately didn’t make it back this time)

You Might Also Like

No Comments

Leave a Reply

%d bloggers like this: