Chicago in a Weekend – Travel Guide

I am a huge fan of extended weekend trips. Jhonathan and I take them pretty often and love to fit as much as we can into the short time we are in the city. So for me, and extended weekend would consist of Friday (or late Thursday night) to Sunday or Saturday to Monday. And I’d like to add, these trips are always within the U.S. and consist of flights under 4 hours. I find it such a fun challenge to see just how much we can take in from a city in just a few days!

So our most recent trip was to Chicago. This was not my first time visiting the city so we did not hit the most popular tourist attractions as we have already done that. If you haven’t been before you MUST visit the Bean along with these awesome stops I will be sharing with you.

Accommodations

So on this trip I did something a little different and booked our rooms through Hotwire. This ended up being an amazing deal with us spending under $350 for all 3 nights! We stayed at Sofitel and the Freehand. Both hotels are located in great locations, but for me the Freehand was in the better location wise as it was close to everything we had on our list. We had some rain during our trip but so much was close by so it wasn’t an issue.

Shopping

While in Chicago we shopped at Topshop, Louis Vuitton, and Bloomingdale’s. If you are looking for some epic shopping on your trip then all you have to do is head for the Magnificent Mile, it’s Chicago’s version of New York’s 5th Avenue!

Bloomingdale’s was actually right across the street from our hotel and was a huge lifesaver once the rain began. They sell the most perfect travel bag! It is a tote constructed of plastic with a zip top. I was able to safely store my camera, crossbody and around town essentials easily so they could stay totally dry!

When we travel to new cities, Jhonathan and I started to tradition of purchasing a Louis Vuitton travel guide for that particular city. This tradition started after our first time here so we decided to pick the guide up on this trip.

And of course, if you haven’t visited a Top Shop it’s the perfect stop for some sunnies and to get a glimpse at the latest fashion trends. I love the Chicago Mag Mile location!

Entertainment

We decided to head south to check out a White Socks game! The stadium is really beautiful and has such a fun feel to it! One of the coolest touches I noticed was that the vendors carried the snacks and drinks in old wooden soda crates! So cool! We purchased tickets of the club level which is honestly the very best deal! There was even an opportunity for us to visit a suite to play video games and watch the game from a closed in air conditioned space!  – Yes, this is not like the stadiums here in Houston that feature retractable roofs, this space is always open rain or shine.

Jhonathan and I both watch Shameless which is set on the southside of Chicago, so while visiting the southside we had to try Frank’s fav beer, Old Style and ride the L.

Eats

Pizza, cheese curds, and Hotdogs all the way! Oh, and I ate a salad once.

Portillo’s – All I can say is yum, and it’s open late! Jhonathan got a Chicago dog here while I opted for a heaping plate of fettuccine Alfrado with garlic bread. We also both ordered sundaes to enjoy on our walk back to the hotel.

Sugar Factory –  I would like to point out, we didn’t actually eat here. The wait for a table was 2+ hours but the bar was open seating, and since we were just getting a drink that was perfect! So note that if you are going just to get one of their amazing candy filled drinks you don’t have to wait, just head to the bar! We tried a mango themed drink with little penguin gummies and sugar coated orange slices. SO much fun to watch them make the drink and so much fun to enjoy! Also I’d like to mention the interior of this place is beautiful! It have an elegant feel to it, mixed with fun candy and alcohol!

Sights

So on this trip we kept the sights pretty minimal with just a trip to the top 360Chicago. This is a skyscraper that takes you up over 90 stories to panoramic views of the city. There is even a bar atop so you can have a nice drink, or even an ice cream while you take in the breathtaking views of Chicago. I highly recommend this stop as there was virtually no line! I feel like not as many people know of this in comparison to the Willis Tower Skyview so if you are short on time, stop here instead!

Chicago is such a great city, with so much to do and so much to see! I’m sure I will be adding many more travel guides for the city as we will definitely be back!