New City New Trips and New Adventures – Chicago

My husband and I were lucky enough to take not one but TWO solo non-kid trips this summer. It was so glorious and I am so thankful to have such wonderful family who are willing to keep my children for an extended period of time so we can have our adventures. I have never been to Chicago so when my husband mentioned having a work trip there – I jumped at the chance to join him. Not only did we have a voucher to cover airfare, but we also had a free place to stay. I mean, it was a no-brainer! We got to visit with my husband’s uncle and it was a total blast getting to hang out with him. I didn’t know what to expect about Chicago other than that people love it there – and let me tell you, I drank the Kool-Aid – Chicago is a pretty awesome town. 


{On Our way to the airport}

Day 1 – Travel and Navy Pier

The first day was fast and furious. We arrived in Chicago around 4:30 pm and were picked up by Drew’s Uncle Jeff. We then took the highway down to Navy Pier. It has been a LONG time since I have had to deal with city traffic and let me tell you Chicago has some serious traffic. I HIGHLY recommend giving yourself at least two hours to get to the airport from the city. Also don’t drive… it’s not worth it. That’s what Uber/Lyft is for. 

Once we got down to the pier we went to a new bar called Offshore Rooftop Bar & Grill. I have to say that the ambience, beer and food selections were great. The service, however, was pretty disappointing. We were told to sit wherever but no server ever talked to us (even though one walked by several times). We then were told we were seated at a reserved table (their reserve sign looks like decor) so we moved. But it was pretty frustrating since we were told to go wherever and were never told what to do – the bartender whom we checked with indicated that all tables were first-come, first-serve. I would recommend sitting at the bar and going for a quick drink just for the view. I also understand that they just opened so hopefully they clear up their hiccups soon. 


After the bar we walked the pier and just got some drinks from street vendors as we waited to board The Odyssey for dinner. This was a real treat that Uncle Jeff introduced us too. It was a dinner cruise that took us around Lake Michigan while we dined on some awesome food. It definitely was the best view of Chicago we saw all week. The service was fantastic, the views were spectacular, delicious food, and amazing people watching. I would highly recommend this as a MUST on your trip to Chicago. 


After our boat ride we drove to Uncle Jeff’s apartment in the suburbs of Chicago. I believe my husband and I were so exhausted that we both were dozing on the way home. 

Day 2 – Riverwalk and Magnificent Mile

This day we took the train into Chicago and headed straight for the Riverwalk. It did NOT disappoint. The views were awesome. The drinks were flowing and the path was so CLEAN! I can not stress enough how clean and beautiful this city was. Usually big cities have some kind of trash problem – but this city didn’t and it was impressive. The people watching was also fantastic as well. This is also one of those definite MUST-DOs when in Chicago. 


We then had our Chicago deep dish pizza at Giordano’s. There was a 30 minute wait but we didn’t mind. The pizza takes one hour to cook so this isn’t a place you want to get in and out of quickly anyway. We put in a preorder and waited for our table (this was actually a super nice perk of having to wait). We were able to sit outside which was beautiful and had excellent service. The pizza was great and I would go back again. 


We then went and walked the Magnificent Mile. This is a shoppers’ dream. All of the best shops up and down this street. There is something for everyone. High-end shops as well as businesses everyone can shop at as well. This is also super close to some of the building with the best viewing decks of Chicago. We weren’t able to get into one of these but that is definitely on the bucket list for our next trip. 

Day 3 – Taj Mahal and The Publican 

This day was perfect weather-wise for some time near the water. We went to Uncle Jeff’s hang out spot and it was pretty cool. It was where two of his buddies keep their boats. The Taj Mahal is the name of their hang out and it includes plenty of seating, TV, bar, refrigerator – you name it they have it down to the swing seats. It was the perfect day for some bloodies and apps. Then we went and had lunch at Studio Hotrod Roadhouse which had great bar food at a reasonable price and on the water. It was a great send off by our Uncle Jeff. 


We then went to the hotel at Fairmont in downtown Chicago. It was a fantastic hotel room with great staff and prime location to walk to all the sights. We got an Uber and headed over to The Publican as a recommendation from a friend. They are a family-style restaurant and oh so delicious. Take a look at our fantastic meal below. 


{Our awesome hotel room}

{Our fantastic dinner}

Day 4 – Art Institute, the Bean and FOOD

Today was the only day my husband had to work. So we went to brunch at Wildberry. I had some out-of-this-world crepes and he had biscuits and gravy. They were both so delicious and an easy walk from our hotel. 

We then parted ways and I went back to walk to more of the Magnificent Mile and also do a little bit of work – here is a picture of my office. 


I then went to the Art Institute of Chicago. It was absolutely stunning!! I have been to several Art museums in my life and the Met many times as well and this one is definitely on the top of my list to visit. I walked 6 miles in 3 hours of looking at the museum. I saw everything from Picasso to Warhal to the Byzantine Empire. It was truly inspiring and so fun to do. It is definitely a MUST DO in Chicago. 

I then met up with Drew and we headed to Millenium Park where we saw the Crown Fountain, Chess Promenade, Cloud Gate (the bean), and Jay Pritzker Pavilion. They were all beautiful unique and inspiring. 

For dinner we wanted something simple after all of our travels so we went to a British-style pub called the Elephant & Castle. I had the fish and chips and Drew had the bangers and mash. They were both so delicious. They also had a great selection of beers, views of Trump Tower and entrance to the Riverwalk as well. It was a super neat location and a great recommendation. 

Future Trips – What we missed…  

We definitely did not have enough time in Chicago. There were so many things that we wanted to do that we were not able to – but hopefully this just insures a future trip. Here is the short list of items we would like to do next time we go to Chicago. 

  1. Museum Park on the water
  2. Architecture Boat Ride
  3. Eating spree on Randolph
  4. Eat at one of the many rooftop bars
  5. See the views from 875 N. Michigan Avenue (formerly the Hancock Center) and Willis Tower (formerly Sears Tower)

As you can tell, we had a fantastic time in Chicago. We got to see so many things and spend a lot of great quality time together. I think we got to see a great deal of the city and it definitely left me wanting to come back. I hope that we can get back sooner rather than later. I have definitely fallen in love with Chicago and I plan on researching more things to do on our next trip. 

Lauren Cop is a part-time SAHM (Stay At Home Mom) of Irish Twins and Senior writer/editor ciao_laurencop_sig-01of the Olive Shoe Blog. Currently Lauren and her family live in Tallahassee, FL where she teaches at a local pre-school. A Clemson fanatic, alumni and general sports enthusiast. She loves reading, gardening, food, and traveling. Follow her Twitter, Instagram, and Pinterest.

The Olive Shoe | Paperie & Design | Celebrating Creativity and Creatively Celebrating is designed and run by Lauren {LAC} James © 2015 LAC James All Rights Reserved.

Lauren {LAC} James is a Sr. Designer of Product Graphics for an international manufacturing company by day and a creativity crusader, designer, planner extraordinaire, artist and blogger in her “free” time. Follow her and The Olive Shoe on Facebook, Twitter, Pinterest or Instagram! Pleasesubscribe to receive emails, of course, come back and visit again soon!

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