10 Tips for the best 24 hours in the Windy City

Chicago, Illinois is a great city, filled with amazing architecture, culture, and endless quality dining experiences. I normally travel there about twice a year for work and always try to add on a day or two to make sure I can enjoy my favorite Chicago culinary delights. I am just returning from Chicago and was able to enjoy some of my favorite regular spots in addition to a new one. If you come to Chicago and only have 24 hours to see and eat your way through the town, here is my recommended agenda:

1) Start with breakfast at the “Original” Pancake House – There is a reason this place was the first of what would become a nationwide chain, because it does not disappoint. I thought I was going to have a healthy egg white omelet, but from the way they whip up those eggs I had an omelet the size of my plate. Don’t get me wrong… I ate that delicious masterpiece, but I felt a little guilty. My friend ordered the bacon pancakes and still to this day she keeps a picture of that amazing blend of salty and sweet on her phone.
Now that you have a full belly and assuming its not the dead of winter when you make this 24 hour trip…
2) Grab a ticket for the hop on hop off bus tour around the city. You will hear a great summary of the history of the city, including the real reason why it’s called “The Windy City.” It’s not because of the temperature, even though it was (as) windy as could be last week. Here’s a hint: What do people often complain politicians are full of?
Answer: Hot Air (Thank goodness they aren’t asking what today’s politicians are full of, or Chicago could have a very different nickname.)

3) While on the bus tour, hop off at the John Hancock Observatory and head to the top for the amazing view. It’s a little pricy (to me) but if you’re only there once and on a clear day, you need to see the breathtaking view.

4) Lunch must be deep dish pizza: My absolute first stop on every trip to Chicago is to Giordano’s pizza http://www.giordanos.com. This famous restaurant has locations all over downtown Chicago and the suburbs and they deliver nationwide. I know that every resident of Chicago has their own preference as to the best pizza place in town, but for me it’s Giordano’s. This cheesy goodness is consistently a perfect balance of cheese to toppings with fresh tomato sauce. It’s always worth the 45 minute wait for them to cook it and the normal 30 min to an hour wait for a table. Remember it’s deep dish, so ask the waiter what size pizza to order.

5) Take a walk up Michigan avenue towards the Chicago river. You may want to do some window shopping as you walk up what is referred to as the magnificent mile. However, if you want to do some serious shopping, cross the river and go to State Street where the locals shop at similar stores with better pricing.
Once you have walked off some of the pizza, you will want to…
6) Take the architecture boat tour. The tour I normally take leaves from the corner of Michigan avenue right next to the Wrigley building. The company on that corner is Wendella tours http://www.wendellatours.com and their 90 minute architecture tour is always filled with fun facts about the beautiful buildings and the history of the city. If you go on a tour that leaves before sunset you will have some fabulous photo opportunities!
It’s time to eat again and this time its…
7) Dinner at the Purple Pig: I highly recommend a stop at this restaurant the next time you are in Chicago. It’s a foodie haven with a tapas style menu that is sure to delight without completely busting your budget. Their tag line is “cheese, swine and wine” which actually kept me from visiting my past couple of trips since I’m normally looking for a more complete dinner on my short trips. But don’t let the tag line fool you, they have a full compliment of quality food, a range of international wines (no domestic), topped off with great service. This place is packed at all hours, so arrive with about 45 minutes to spare. Trust me its worth the wait. We stopped in around 2pm just to look at the menu and they were at capacity with 20 people waiting outside. We planned to go back around 7pm for dinner, but my brilliant boyfriend decided we should head over around 6, since we would need to wait. We got a lucky break and were seated immediately at the bar directly in front of the chefs. It was like a “mini bar/chefs table” experience, without the heavy price tag because we watched them prepare dishes and made our choices based on what looked good. No need to look at the menu when the food is being made in front of you. Plus the chefs had this great system of calling out items as they came in that was quite entertaining. We had no idea we were going to get dinner and a show. The wait staff and servers are all very knowledgeable about the menu and the wines. Even though they were busy, you never felt neglected or rushed. I am normally not a fan of tapas restaurants because I feel like you pay full size plate prices for a smaller serving. This is not the case at the Purple Pig http://www.thepurplepigchicago.com.
If you are up for a little night cap and maybe chocolate for dessert…
8) Head across the street to Eno. When Eno opened they only sold chocolate, cheese and wine…every woman’s dream, right? I think the Pig has had an impact on their business, because when I stopped in last week they were pretty empty and they mentioned that they also had small plates available. I didn’t try the food, but the chocolate is lovely. I’m allergic to chocolate but its worth taking the allergy drugs for just one piece of their fancy salted carmel chocolate. Plus they offer wine flights that are creatively paired so stop in and enjoy.
If you want to hit the town for a little late night fun…
9) Head toward Hubbard St. There you will find jazz clubs, dance clubs and bars on every corner.
10) If you just want to grab a drink at a bar with great mix of top 40 and dance music, then walk a few blocks over to English http://www.englishchicago.com. If I’m in town on a Friday or Saturday it is always a must hit location with a good crowd.

Well if you made the most of your 24 hours in Chicago, it’s now 2am and you are heading back to your hotel. The next time you’re in town, be sure to see a Cubs game. That is a full day experience on its own, so try that on the second trip to Chicago.

Have fun!