The Windy City stole my heart when I traveled there last year for Lollapalooza. Luckily I had a bestie that resides there to show me around- so you know you’re getting the inside scoop on America’s one and only Chi-town.

Pittstop’s Picks

6. The Hampton Social

I watched the famous “Rose all day” wall pop up on my Instagram feed time and time again. I needed to get the aesthetic of that wall on my feed too. I finally pinpointed the famous wall at a hip restaurant called The Hampton Social. A nautical themed brunch spot that’s ever so pleasing to the eye—and the tummy! Stop in for mimosas before hitting up the Mag Mile.

5. The Navy Pier

This Chicago staple could take up an entire day. Unfortunately, I only had a couple hours at this sweet spot. The Navy Pier is full of beer gardens, restaurants, sweets, shopping and… a greenhouse? It also features some unique views of the city and the water. This experience is a must!

 

4. Yolk.

If you’re balling on a budget and in need of a greasy hang-over cure from your night out head to Yolk. In the heart of the city within walking distance to the River Walk, this affordable breakfast place was delicious. We felt like locals on their outdoor patio!

3. The Riverfront

One of the coolest parts of this city by far is its River Walk. Enjoy a sunny day at restaurants and bars right on the water. You can even try out a boat tour for a different experience altogether!

2. The John Hancock Observatory

This view is just as sweet as the Willis Tower and has a unique 360-degree experience. Try out this one instead for a shorter wait!

1. Millennium Park and Grant Park

I hold these parks so dear to my heart because it’s where I witnessed 18 of my favorite musicians perform in one place. These parks have a uniqueness about them that you will never forget. If you ever get the opportunity to travel to this great City for Lollapalooza I can promise that you won’t regret it.

P.S. While you’re there get a lobster corndog and a Chicago-style deep dish slice. We kept going back for them! **see photo below and cue drooling**

 

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Comment below or e-mail us some of your favorite Windy City spots that didn’t make our list. We’re going back next year, and we want some tips from your travel experiences!