I had been to the windy city once before, but that was almost 10 years ago. Clearly, things had changed. The more I read about the food and museums the more excited I got! I couldn’t wait to get there. Here are my tips for Chicago for what to avoid doing when you visit.

Don’t reserve anything the day of your flight

This is really more a “anywhere travel” tip, not just Chicago. We arrived at the airport at 5am only to find out our 7am flight was delayed by 3 hours. Typically I don’t plan anything that requires a reservation to close to landing time because you never know how long it will take to arrive at your destination. I figured four hours after we landed should be plenty of time…I was wrong. Luckily I was able to get in touch with groupon very early in the morning and explain the situation and they helped rework our plans. I would have called the company, but they didn’t open up until we would be on the plane, which does not help.

Skip the Shedd Aquarium

I am normally totally fine with kids at tourist attractions (hello I have an entire section of this site dedicated to all things Disney), but this place was horrible. This place had no idea how to run a tourist attraction or handle the volume of people that were there. Which makes zero sense considering they have been open for years. We had a CityPass for Chicago which supposedly gave us access to an express line – this is the biggest lie (more about CityPass here). It took us over 30 minutes to get inside. Once inside it became shockingly apparent they were well over capacity. You could barely get up to an exhibit to see anything without a stroller appearing from every side. The dolphin showing was included in our tickets, but we were never told we had to pick a show time until all of them had been booked. We went to see a 4D show and they forgot to close the doors so the next showing started walking in.

If you absolutely must go to the aquarium pay attention to after hours events. We spoke with a former worker who said it is the only time of day he recommends people going without kids. You get the time to really enjoy the exhibits and are not being shoved from window to window. Plus cocktails are usually involved so you can’t beat that! Added bonus – the view from the Planetarium and Aquarium is probably the best view in the city. If you are looking to see the skyline at night, you will not find a better place.

Do the Architecture River Tour

Anytime I go on vacation I immediately ask anyone I know who has already visited that city for suggestions. The first hand recommendations are always a great starting point. Most of these people know me well enough to know what I would enjoy or what is something I could skip. The #1 thing I heard from everyone is go on an architecture river tour. This was not just because architecture fascinates me, but because it is that awesome. Chicago’s unique river layout gives you the opportunity to see the city from the river and learn all about its history and culture. There are quite a few tour options to pick from. You cannot go wrong with any them.

There is food everywhere

Living in Philadelphia I have accustomed accustom to delicious food. Whether it is something as simple as a burger and fries or something a bit more upscale, I expect it to be delicious. Chicago did not disappoint in the food category. Yes, you clearly need to get deep dish pizza (c’mon skipping pizza in Chicago is like skipping cheesesteaks in Philadelphia), but beyond that there is amazing food at every corner. Whether you are looking for classic Italian with a truly unique ambiance at Italian Village, a deliciously inexpensive hot dog and chocolate cake batter milkshake (yes you read that correctly) at Portillo’s, or maybe you want to go a bit fancier and check out one of Chef Izard’s many locations like Girl and the Goat – whatever you desire you can find it there. It is one of the few places you’d be happy with pretty much any restaurant you turned into.

There is far too much to see

I realized this during the planning phase. Chicago is a city that is perfect for a long weekend, but you will not see everything you want in that time frame. Personally, I love that about it. It gives me plenty of excuses to continue to return and keep being surprised by the city. I work multiple jobs and one of them is in baseball. So when we took this trip it was after a long homestand. I did not take into account just how exhausted I would be after it was over. This led to calling it a night much quicker than normal. The silver lining is even if we had stayed out longer or hustled a little faster to see more things. There was still zero chance of us seeing the entire city.

I can’t wait to visit the windy city again and am already daydreaming about that pizza. What are some of your favorite things to do in Chicago?