Chicago-Guide for First Timer’s

On our most recent adventure, we finally made it out to Chicago after 3 years of trying to plan the right time!

I’d never been to the “windy city” and its been on my list for quite some time now. Since I’d been told on multiple occasions not to come during the winter (from locals), we wanted to wait for warmer weather and it was totally worth the wait.

Our primary reason to visit was for pizza and not the deep dish kind either, though we did have one or two.

Check out what to do on your first visit here to Chi-Town


If this is also your first time to Chicago, you’ll want to read on…

Chicago is a decently sized city. I would say, it’s a mini NYC:  much smaller, less skyscrapers per acre and a very well planned city scape. Why does it matter? Granted NYC is extremely walkable, you can walk from central park at 5th ave to Wall Street in less than an hour but you won’t see many parks or green spaces along the way. Chicago is far more pedestrian friendly and has about 3x as many green spaces and parks than NYC.

Millennium Park is less than half the size of Central Park but offers quite a fantastic view and a few extras such as the garden, the bean (cloud gate), an outdoor auditorium, water park space and proximity to the lake. You’ll also find art installations and fountains. It is also connect (by sky walk) to Maggie Daley Park as well you can continue walking into Grant Park.

One of my first missions in Chicago was the architecture cruises. Since I’ve been obsessing about architecture over the last few months after watching a new TV series on the history of it. Visiting the “birthpace of architecture,”  this seemed like a no-brainer. After researching, we opted for Wendella Cruises. I chose this one based on reviews and the option for have beverages available on the boat. More importantly, they offer the most open availability for cruises.

The cruise was about 1-1/2 hrs long. We opted for an earlier cruise (11:30 am) to beat the mid day heat. You’ll go up and down the Chicago River and along the fork toward the North side. There’s a ton of information being rattled out during your cruise, so pay attention! If you’re not super into the info, the just enjoy the ride and scenery.

Immediately following our architecture tour I wanted to visit the “bean.” Since our last name is Bean, it was very obvious that we needed to see it!


First of all, let me just tell you that you should not visit the bean (Cloud gate) during the day time. Just forego that option all together unless it is the only and I mean only option you have. Cloud Gate is extremely crowded and the basic tourist trap. We went back to visit the bean on our last morning in Chicago. I made Brad wake up extremely early to go and was 100% worth it! A total of 5 people were there at the same time as us.


There’s a little stand with two high school/college age boys selling hot dogs (during the day). We took this opportunity to get a “chicago dog.” We left the boys a good tips since their tip jar mentioned something about a college fund. The hot dog was good too!

A short walk away from Cloud Gate is the Art Institute of Chicago. This museum is one of best in the US. On display were some Manet pieces which I had never actually seen in person. Its a fairly large museum and totally worth checking out. Almost everyone I’ve spoken to asked if we were going to visit it! On a hot summer day, this is probably the best spot to be. One of my favorite pieces lives here on a permanent basis: A Sunday Afternoon on the Island of Le Grande Jatte, a pointillism piece by Georges Seurat. Another piece I’d only seen in my art history books that I lost my mind when I saw it in person. It’s so large!!!

If you need some R&R, look no further than AIRE Ancient Bathes. My mother suggested this to us before we left. I rolled my eyes at her over the phone conversation, but when I looked it up I wanted to slap myself for being an ass. This place is so amazing. They do not allow photos inside the bathe areas but you can see inside on their website. Brad and I treated ourselves to massages and the bathe experience. It’s self guided with multiple thermal pools at varying temperatures. There is also the polar pools…enter if you dare. They said it is supposed to be wonderful for your body, all I know is that it’s freezing fucking cold! Dare to dip your entire body in this 3 X 4 foot pool. Brr!

Then there’s the exfoliation salts, oh yeah! You could spend all day in this bathhouse, but I would suggest going during the week when everyone is at work. Less crowds and more relaxing!

83DDD4AB-8E83-49E5-87F7-0A1FD34FD3E0Visit their page here to see inside.

So about that pizza I mentioned…

We booked a pizza tour with a friend of ours. We had the best time. 5 or 6 pizza places all specializing in Chicago cracker thin pizza. Jonathan is usually booked with larger parties, but he made a special booking with just Brad and I today. If you are looking for something different to do here in Chi-Town, go on Jonathan’s Chicago Pizza Tours or even one of his Speakeasy tours. We will definitely go back for the speakeasy tour next visit. He’ll take you to some really cool places that were once visited by the likes of Al Capone himself.

Of course we visited the infamous, Lou Malnati’s. Better than Lou’s, we went out to a dear friend of mine’s place called Spacca Napoli. Yes, it is outside of the city but so totally worth it! Our friend Alberto met up with us for dinner here and we shared 5 pizzas plus dessert.

Along with pizza, we also visited a few other local spots: Stan’s Donuts which was brought to Chicago from Los Angeles and has become the staple donut and favored by locals. We also hit up Garrett’s gourmet popcorn that was highly recommend to us by some of our customers. Get the Garrett mix!

All in all…

Walking the city was quite exhilarating. 3 days was not enough time in Chicago to full emerge ourselves, but we did get to see most of the hot spots and a mini tour of the public library which has a beautiful tiffany stained glass dome. Surprisingly summers can get rather hot, so pack some shorts and a swimsuit. The lake looks so inviting!

If you only have a few days, make sure to capture the essence of Chicago: pizza, art, outdoor spaces and architecture!Where to stay in Chicago:

Along the river is a sought after location for first timers, we stayed at London House with a fantastic river view room. The rooftop bar is one of may favorites. You’ll need to reserve a spot for brunch! The rooftop is not very large, so plan for it to be packed. If you can’t make it up there right away due to crowds, hang out in the bar one floor below. You’ll feel nice a cozy in there with the velvet seating and plush pillows everywhere-dim lighting sets the mood!

Safe Travels!


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