Labor Day Weekend in Chicago

When it came time to plan our activities for September, we figured we could work around Labor Day and do a small trip somewhere close to Michigan. We bounced a few road trip ideas around and settled on Chicago since I have never been. It’s about a 4 hour drive from Dearborn, Michigan, so not too far but also not too close.

We began our drive on a Saturday morning and arrived in Chicago around 11:30am – we had not accounted for the one hour time difference! Our first stop was Superdawg’s Drive In, which was a recommendation from a coworker. She highly recommended Superdawg’s for a Chicago-style hot dog. It was pretty darn good and I am also highly recommending it!


We hit the Lincoln Park Zoo and Conservatory after a quick lunch since our AirBnB was in the Lincoln Park area. Linking it here for anyone who’s interested because we had such a nice stay there, I feel like I need to tell everyone about it!



The Zoo and Conservatory are both completely free, but you will have to pay for parking if you cannot find street parking. You can probably spend a solid 3-4 hours at the Zoo – there is so much to see!


Our second day in Chicago began with a visit to see the Cloud Gate, or the Bean, in Millennium Park. We tried and failed to take some selfies. Much fun was had.


We then wandered to Grant Park to check out the Buckingham Fountain, which is HUGE! If you’re into fountains, I highly recommend this.


Then we walked some more and got to Museum Campus for a visit to the Shedd Aquarium. Bank of America actually offers free general admission to the Aquarium for the first full weekend of every month, so we took advantage of this. We spent about a solid 3-4 hours in the Aquarium and thoroughly enjoyed our time.


After a brief break, we headed over to the Field Museum, which is a natural history museum. If you’re a fan of totem poles, you’re in for a treat! There is a lot to see at the Field Museum, so plan to spend at least 3-4 hours here.


Dinner that night was one of our only sit-down meals of the trip. We went to The Purple Pig on a recommendation of a friend and had a lovely meal. Definitely get the Uni Toast and the Chocolate Blackout Cake!


Our last day started off with a nice walk along North Avenue Beach, which is a beach along Lake Michigan in the middle of Chicago! The walk was really nice and we wished we had brought our bathing suits!


We ended our trip with lunch at The Little Goat Diner, which was jam packed! We split an order of their Dark Chocolate Crispy Pancakes and a Goat Patty Melt, which were both delicious. Ask for their special condensed milk creamer for your coffee, you won’t regret it!


We had a lovely time in Chicago and I definitely wouldn’t mind going back to check out a whole bunch of other attractions we had missed. Until next time!

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