What To Do With One Night in Chicago, Illinois

Once a year I fly to Chicago for Pampered Chef’s National Conference. PC’s home office is just outside of Chicago in Addison, Illinois, so it makes sense for them to host 3,000+ consultants in their neck of the woods. Next year I’ll explore the Windy City more (mark my word), but this time I took advantage of what free time we had and enjoyed one night in Chicago.

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What We Did: One Night in Chicago

With the exception of visiting Illinois for about five minutes when I was around 12, this was the first time I ventured outside of the convention center walls, and I’m so glad I did.

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Since this was my first outing out, and we only had a few hours to spare, my friends and I set our sights on downtown Chicago for an Architecture Boat Tour, and it let me tell you…it was FANTASTIC.

Architecture Tour with Shoreline Sightseeing

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I’m not going to lie to you: I wasn’t all that thrilled about the idea of an architecture boat tour. It just didn’t sound all that riveting.

But it was seriously wonderful, and I’m glad I joined my friend (and then pulled a few other friends along with us). In fact, it was so good that I would absolutely go again next year.

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We went with Shoreline Sightseeing for our 75-minute tour, and here’s what I was expecting: a boring history lesson. Here’s what we got: an entertaining, jaw-dropping tour of downtown Chicago from literally the heart of Chicago.

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The weather was unbelievably perfect, the Shoreline staff was helpful, incredibly knowledgeable, and funny, and it was the best way I can think of to actually see Chicago.

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Looking up at these massive skyscrapers towering above you from a river boat was simply breathtaking.

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It was fun to pick out which decade each building was built, and even more astonishing to see it from the Chicago River.

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I would absolutely go on this tour again (and plan on it next year when I’m back in town).

Where We Ate

Oh, Chicago. It’s probably a good thing I don’t live near you. Pizza is my weakness, and your deep dish pie is pretty darn delicious. And by the way, I’m absolutely taking recommendations for next year, so leave your favorites in the comments.

Lou Malnati’s

Known for the classic and famous deep-dish pizza, we went out of our way to eat this on our first night in town. We had several local Chicagians (Chicagoites?) recommend Lou Malnati’s, so we made sure we tried it first. It turns out that we stayed in the one teeny tiny little area where they don’t deliver to, so a friend Ubered over, picked it up, (somehow didn’t sneak a slice for herself on the car ride back), and brought it to our hotel.

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The sausage pie, is one giant sausage patty that cooks while the whole pizza is baking!

We also got a Spinach pizza, and oh my word. It was amazing and so flavorful. We bought a salad (to give the appearance that we were healthy, but we barely made a dent in it.

I’d show you more pictures of the pizza…but we ate it too fast.

Also, quick fun fact about Lou Malnati’s: you can only find it in Chicagoland…or three places in Arizona. Looks like I don’t have to travel too far to get me some deep-dish pizza now! Actually, they ship their pies, so it can come right to my doorstep if I ever really need some!

Portillo’s

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Another Chicago institute local friends insisted we visit Portillo’s…so we did, and it was awesome. We went to the Harwood Heights location, and the second we stepped inside I was in love. Any place that goes all out with their decorations is a-okay in my book.

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This spot had a retro vibe going on, and it was so much fun.

My friends got a classic Chicago dog, while I got “hot meat in a pouch,” aka an Italian Beef Sandwich. I went with hot peppers, and whoa boy! Those packed a punch, but it was absolutely delicious. Mouth-watering flavorful meat, a soggy bun that actually held up the whole time (purposefully soggy since I ordered it dipped in gravy), and those hot peppers tied the entire thing together.

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I knew I was having more pizza later that night, so I strayed from ordering their famous cheese fries and lemon cake, but oh how I wish I didn’t have so much will power and tried them. A friend got their Strawberry Shortcake and ate it next to me a few hours later, and it smelled divine.

Next time I’m saving room for dessert. …or I can just have it shipped to me.

Public House

After our boat tour we made a mad dash to find some dinner…only it was a Friday night and we didn’t have a clue where we were, and we didn’t make reservations anywhere.

Long story short: we were on the verge of getting hangry, so we picked the first place we could find that didn’t have an hour-long wait or prices that would make us want to jump in the Chicago river.

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Thankfully, we landed at a great place that filled our bellies and let us relax: Public House Chicago.

The menu at Public House was classic, simple American favorites, but in a fun atmosphere. And when I say, “fun,” I mean there’s a live DJ playing tunes, and you can even sit at tables that have taps built into them!

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My rose sangria hit the spot, and my friends downed their cocktails, so I know they’d say the same about theirs. I got the BLT with an egg on it, and enjoyed every single bite.

If I went back I’d totally get one of their flat breads; I had a few bites of my friends, and it was delicious. Then again, I have a thing for pizza!

Giordano’s

If you stay near the convention center you’ll see a Giordano’s delivery car driving around no less than probably five times every hour. They hit the jackpot since they deliver in the area, there are literally thousands of hungry foodies ready to devour some pizza.

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We had it one night with the leaders on our team, and while their deep dish was good, a friend ordered the thin crust veggie, and oh my word. The flavors just exploded in your mouth and tasted so great. I had to seriously hold myself back from eating all the slices of that one.

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If you’re craving some classic Chicago pizza now, Giordano’s has several locations in several cities around America; I’ve eaten at the one in Vegas before! Oh, and if you reallyyou can ship it right to your doorstep want some deep dish pie, , too!

Where to Sleep

If you’re going to Chicago and staying near the Convention Center, the only place you need to look at is Embassy Suites near O’Hare Rosemont.

It’s seriously your best option because it’s literally just steps across the street from where you’ll be spending your day(s), it has free breakfast with a made-to-order omelette station; there’s a cocktail reception every night (hello, free drinks); the rooms are large and have fridges so you can hold all your leftover pizza.

Until Next Time, Chicago

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So that was my quick jaunt to Chicago. I’m already planning on hopefully going out for an extra day next year so I can see a little bit more of the city (if it’s okay with the husband since he’ll be watching all three kiddos again).

If you only had a few hours in Chicago, what do you recommend I do next time? Also, share your favorite places to eat (especially downtown)!

16 Comments

  1. You had me at city skyscrapers and pizza. I went through Chicago once and that was in year 1999. I never went outside of the airport but I remember being stuck inside due to a snow storm. I always wondered what it would be like actually exploring the city. Thank you for sharing your little adventure.

    1. I hope you’ll have a chance to go back and visit sometime. It’s always a bummer being so close to a new place, but not being able to explore it quite yet.

  2. Chicagoans! And at Lou Malnati’s you need to eat the Malnati salad! You really missed out on the lemon cake because this is only the second time they have brought it back in about 10 years.

    1. NOOOOOOOOO!!!!!! I mean, they said the famous lemon cake was back, but had I known that I totally would’ve splurged. SHOOT! And we did get that salad!!! The dressing was SO good. (Lol we all had a few bites to make us feel better about having some greens after scarfing down all of that pizza)

  3. Hubby and I went to Chicago and our favorite outing was Chicago Pizza Tours for 3.5 hours of pizza, history and fun! It was incredible. The guide and driver took us a various neighborhoods to sample many different kinds of pizza. We had a wonderful time and were so full – but happy.

  4. Oh my pizza! That sounds and looks amazing! We are planning a trip back to Chicago soon and I now have some great recommendations for food and pizza!

  5. i agree that the architecture tour probably wouldn’t have been on the top of my list either, but it looks like a great way to see all of the sights, especially in one day! & i’ve heard great things about giordano’s & portillos from illinois friends! definitely would love to try those!

    -cassy @ blissfullyher.com

  6. This looks like such an amazing little getaway! Looks like Chicago has a lot to offer.

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