Long Weekend in Chicago 

This year for Memorial Day we decided to head north on 65 to Chicago for a long weekend. Since moving to Louisville we made a list of the places we can drive to for quick weekend trips (Chicago is an easy drive now). It’s odd being so close to Chicago but we definitely aren’t complaining. Our trip kicked off Friday and we were off, ready for a fun weekend enjoying Chicago.  

Day one was all about the drive and an awesome dinner. We enjoy eating out and love a fine dining experience. For us, a great restaurant is one of the best things about traveling to a new city. We found a great restaurant in Tru, with its fine dining interior, excellent service and one of a kind prix fix menu. Night one set the tone for the weekend. 

Day two started off with a quick walk around town and then meeting up with friends for brunch at The Gage. The interior of this brunch spot was beautiful and the restaurant was super spacious. Next we took a walk to Millenium Park because what’s a trip to Chicago without seeing “The Bean”?  

For dinner we tried a restaurant I found on Yelp. The restaurant has a varied menu that changes daily.  The Publican was fresh with new fish, seafood, meats, etc. arriving daily. We had the octopus, mussels and the porchetta with pork belly. Yum. 

Day three started off with breakfast at Sunny Side Up then browsing the waterfront with a walk on the river walk. 


One of my favorite meals of the trip was lunch at Bottlefork. I had a delicious burger that was HUGE and simply delicious. After lunch we went to a fun arcade bar and played Tetris, Ninja Turtles and pin ball. A fun and relaxed environment at Headquarters Beercade made the day easy and super relaxed. For dinner we tried Pequods which was recommended to me by a friend. This pizza joint was on the list because we needed to try Chicago style pizza while we were in town but didn’t want to fight the crowds. The food did not disappoint. Deep dish pizza, Chicago style = amazing.

Staying at the The Conrad was wonderful and the perfect location for walking. Connected to Nordstrom, this hotel is in a prime time spot with beautiful rooms and inviting staff. There were a few restaurants and attractions we didn’t get to on this trip so we’ve added it to our agenda for the next trip we make to Chicago. 


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