Apogee Lounge

Chicago is not your typical destination for a girl’s getaway weekend. But it’s been on our bucket list of American cities that we wanted to visit. We found an amazing deal on Travelocity and booked our tickets right away.

On our way to the hotel, we started to realize that there’s no way we would cover The Windy City in just a weekend but we planned to do our best. Check out this guide on what to do on a girl’s getaway to Chicago.

To Stay

The James Chicago

The James Chicago

The James is located centrally on Magnificent Mile, a popular area in downtown Chicago. The hotel is modern and the rooms are spacious. The staff was amazing and very helpful whenever we needed them. There is a Trader Joes across the street and Walgreens within walking distance. And you can get to many landmarks like the Riverwalk and Millennium Park in less than 15 minutes via Uber. Save money on your full booking with eBates here.


To Do

Apogee Lounge

Apogee Lounge Chicago

The newly opened Apogee Lounge is located atop the Dana Hotel & Spa. It was our first stop after we quickly changed our clothes and headed to the rooftop for a Kentucky Derby party. The views are insane, the decor is chic, and they have two bars for optimal drinking pleasure.

Millennium Park

Cloud Gate

The famous Millennium Park is a must-see on your trip to Chi Town. It’s a beautiful, vibrant park that is also home to Cloud Gate aka The Bean. Yes its touristy but it doesn’t hurt to see landmarks in big cities.


Cindy’s Rooftop

Cindy's Rooftop Chicago

Cindy’s Rooftop directly overlooks Millennium Park – the view is absolutely stunning. You can also dine, drink, and chill out there.


About a 10 minute walk from Millennium Park, you can find the Chicago Riverwalk. The open riverfront spans from Lake Shore Drive to Lake Street. You can take a boat tour to discover information about the surrounding landmarks or visit one of the eateries located on the boardwalk.

To Eat


Quartino Chicago

Quartino is located just a few blocks from The James. They serve authentic Italian cuisine to a local crowd. We ate here twice (I know I know) but the food was just so amazing. Even better they have a $25 three-course lunch special for two – a perfect spread for you and your bestie. Tip: order the smallest size of their sangria pitcher – it actually gives you about two drinks and it’s only $6.

MAD Social

MAD Social Chicago

MAD Social is amazing for brunch! Their bottomless service only runs from 11a-2p, but the food is amazing and their a-la-carte cocktails aren’t half bad.


So technically we didn’t dine here, but this is a great semi-outdoors bar to hang out with friends and grab cheap beers or Micheledas. Federales is lively and I noticed large groups come here. The music is Top 40, but I enjoyed the overall vibe here. I documented the bar briefly in the vlog above.


Pizzeria Due

Pizzeria Due

Now this isn’t a famous deep dish chain, but the locals love it so we decided to give Pizzeria Due a try. I don’t think I like deep dish pizza in general but it was pretty tasty and the place was packed with locals. Plus, it was only a one minute walk from the hotel so that works out if you’re looking to get a bite nearby. Watch the short vlog for the deep dish experience.


Taco Joint 

Taco Joint Chicago

Taco Joint is a Chicago-based Mexican chain. The food is tasty, authentic, and the drinks are amazing.


Unfortunately, we didn’t find much activity for nightlife or even just after dinner drinks. Of course there are bars, but the nightlife only seems to be lively on Saturdays. Many places are closed on Sundays and Mondays (the other two days of our trip). Overall I enjoyed Chicago for it’s laid back pace and beautiful scenery. It was a nice break from NYC but there’s definitely more to explore in Chicago.

Millenium Park


Quartino Chicago

Quartino Chicago

Where will you be heading for your girl’s trip?

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