Visit Chicago on a WIMM – First Timers

September 2016 –  One of my FAVORITE things to do is explore a BRAND NEW city. But it can be overwhelming, where do you start? What do you do? What is actually a tourist trap, and where are the local’s favorites? I’m not going to lie, I didn’t figure out how to do Chicago by myself.  My good friend/tour guide did an incredible job of planning a fabulous Chicago weekend. And now I am here to be that tour guide for you and point you in the right direction to visit Chicago.

In a short 72 hours we did A LOT. But it was all worth it, check out some of the highlights:


Chicago Bagel Authority (Brunch) – Home of the Steamed Sandwich

Chicago Bagel Authority

Wendella Boat Architecture Tour (Afternoon) – Make sure to go on the “Lake & Boat Tour” for views up close and of the Chicago Skyline.

Au Cheval (Dinner) – Be prepared for a 2-3 hour wait for the best burger of your life.  The plus side to this is you get to explore the West Loop in all of its glory. We had beers at Haymarket Pub & Brewery, and cocktails at SoHo House – The Allis, and Lone Wolf.  Once you get in the building, the musical jams are awesome, the single cheeseburger (Which is actually a double cheeseburger) with bacon and a fried egg is life changing.

Au Cheval - Burger


The Bean – Duh.

Cindy’s Rooftop at Chicago Athletic Association Hotel – Views of The Bean, Lake Michigan, and delicious drinks! Looking to do brunch? Reservations are one month out, at least.

Cindy's Rooftop - Chicago

London House Rooftop – Views of the Chicago River, Architecture, Rose, and who doesn’t love rooftops!

LondonHouse Rooftop - Chicago

Eataly Chicago – Welcome to Italy. There are multiple restaurants, and “Life is too short to not eat well”

Eataly - Chicago

Restoration Hardware – I’ve never seen anything like it, they do have them other places then Chicago.

Snow Dragon Shavery – MACARON ICE CREAM SANDWICH. That is enough to visit Chicago.

Cafe Ba-Ba-Reeba! – A pitcher of Sangria plus goat cheese baked in tomato sauce, shrimp with garlic, olive oil, red pepper flake, grilled hanger steak with charred green chili chimichurri & fingerling potatoes

Social 25 – Live band until 12:30am was ALL TIME.  DJ in the basement took the cake.


Barcocina – Brunch. All you can drink, eat at the breakfast bar, and one amazing entree for only $39.95. And it is walking distance to Wrigley Field where we watched the Chicago Cubs play. They just clinched the division so they energy was absolutely incredible.

Barcochina - Brunch - Visit Chicago

Federales – Afternoon margarita back in the Chicago West Loop.  If you are feeling crazy you can take a shot of tequila in an ice shot glass and immediately throw the glass to hit the bell on the wall.

Federales - Visit Chicago

Pequod’s – Last but NOT least, you have to try THIS deep dish pizza.  It is a Chicago staple, and this is the place of locals.  Pizzas take 40-50 minutes to make and ALWAYS ask for extra sauce, it is magnificent.

Pequod's Deep Dish Pizza - Visit Chicago

And that was only 72 hours people. Visit Chicago on a WIMM Facebook Album for more photos. Please let me know if you have any questions or suggestions for my next visit.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.