The Most Perfect 2 Day Chicago Itinerary

What fun! Tory Burch's Pineapple Mira Beach Shirt

Home sweet home Chicago!

Did you know the pineapple symbolizes hospitality? It’s true. I love hosting out of town guests and constantly asked for suggestions. Chicago dwellers even reach out to me for advice on where to take their out of towners! Sure the local spots are the best (and always will be), but sometimes we need to show off what The Windy City is all about. And it’s not The Hockey Pockey.

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Just like the pineapple, a warm welcome always sets the tone for the perfect trip. Lucky for you, I have designed TWO PERFECT DAYS IN CHICAGO. These are timed to a “T”, strategic in location and hit all the highlights. These well balanced agendas include relaxation, cocktails, architecture, history, food and downtime. And not to mention just as fun for you as they are your guests! How do I know? This isn’t my first rodeo kids. My mom and I have done it a million times!

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P.S. Feel free to send me a thank you note after your visitors love you forever. So let’s get to it shall we?

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DAY ONE

4:00 – 4:15 PM
The Chicago Cultural Center
A quick look at the world’s largest Tiffany dome. FREE

4:30 – 5:15 PM
Millenium Park
A selfie at “The Bean” is a must. FREE

5:30 – 7:00 PM
The Art Institute
Just rated the #1 museum in the WORLD by TripAdvisor. The feature is always amazing and I personally love the miniature dollhouse rooms in the lower level. You could easily spend all day here but this is a great little taste. $$$

7:00 – 8:00 PM
Dinner at Terzo Piano Outdoor Rooftop (Inside if Cold)
This is attached to The Art Institute and captures one of the most beautiful views of the city. Be sure to make a reservation in advance and request a window seat if eating indoors! Closes at 8:00 PM $$$$

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DAY TWO

12:30 – 1:30 PM
Lunch at The Purple Pig
Located right off Michigan Avenue and the Chicago River, this wine and cheese spot has been rated #1 in the USA. Side note: the stair river access to the next adventure are right here. $$$$

2:00 PM
Architectural River Cruise
One of the most beautiful ways to see the city and the stories behind every building are surprisingly fascinating. One of the best things to do in Chicago! $$$

3:30 PM
Cocktail at the Trump Tower Outdoor Terrace (16th floor)
Skip the Sears Tower – this is the most spectacular view in all of Chicago! The skyline, the Wrigley building, clock tower and the river. You can see it all. Cocktails are $20 – $30 and 100% worth it. $$$$$

7:00 PM
Power Hour Happy Hour at Morton’s Steakhouse
One of the classic steak houses in Chicago and the BEST happy hour deal in all of the city. $5 filet mignon sliders and $5 wines will make up for that visit to the Trump. Weekdays only and so yummy! Seriously a steal. Sun – Fri only. $$

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HUNGRY FOR MORE? 

Chicago Food Planet Food Tour
Explore the Goldcoast, Wickerpark or China Town one bite at a time. Come hungry and learn an incredible amount of history and fun facts. I lived in Goldcoast for 7 years and was shocked at how much I learned on the Goldcoast tour. One of my other favorite To Do’s. $$$

Tea
The Drake is a classic traditional tea. Princess Di stayed here! Tiffen at The Langham is modern and luxurious. I’ll let you be the judge though. Both are fantastic! $$$$

Brunch at Barney’s and Mag Mile Shopping
Fred’s, a popular dining destination, sits on the top floor of Barney’s in the heart of Chicago’s shopping mecca. Hit up Rush St., Oak St. and Michigan Ave. in one blow. Bonus: I highly recommend grabbing a cupcake out of the nearby Sprinkles ATM. $$$

Lincoln Park Zoo + J. Parker Cocktails
The last remaining free zoo in the United States. Grab a cocktail at The J. Parker rooftop (top floor of The Lincoln Hotel) for an aerial view of Lincoln Park. Stunning! FREE + $$$

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So speaking of rooftops and warm weather. Do you like my pineapple tunic from Tory Burch? It is secretly a dress and makes for the perfect swimsuit coverup. Unfortunately we aren’t quite there yet weather wise, so I paired it with denim in the meantime. I was quite inspired by this look actually! Oh and Arin and I took these photos a couple weeks back when it was 70! Wasn’t that the best treat ever?!

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So where are you favorite touristy spots in Chicago? I could always use a few more tricks up my sleeve. Share below if you have some goodies!

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And if you are new to Chicago…welcome to one of the most wonderful cities in the world!

Shop The Post:
Tory Burch Pineapple Mira Beach Shirt c/o ShopBop || Tory Burch Lucite Cuff (old but love this one) || Panama Hat from my honeymoon (love this affordable one) || Mudpie Monogrammed Pouch || Kate Spade sunglasses (old) || Zara heels (old but any of these would do just fine!) || 7 For All Mankind White Bootcut Jeans

  • Love this post!! I had no plans today and your post and the beautiful weather inspired me to get out and be a tourist in my own city today!

    • I hope you had the BEST day yesterday!!! It was so beautiful 🙂

  • SarahLagen

    This is great!! I love all of your suggestions for out of town guests!! I’ll have to come back to this next time I have a friend in town!! 🙂

    • Thank you Sarah! It is always a big hit for me. Even if you take portions of the itinerary it works out great! Summer, are you here yet?

  • Lindsey Burton

    Love the outfit and this post 🙂 Can’t wait to visit so I have an excuse to do all of these things!

    • Me too Lindsey! I’ll see you in Nantucket first 🙂

  • Nicole you are positively stunning in these photos — that “hospitality” pineapple print is adorable!! I love your itineraries for Chicago visitors! The Art Institute is an absolute must!!!

    Sed Bona

    • Thanks Ashley! Pineapples just make me oh so happy.

  • Tomissa Porath

    I need to get on this Morton’s action, STAT!

  • Jocelyn Anderson

    Just this past weekend my daughter and I met up with a good friend in Chicago. We did many of these things on the list! I would definitely recommend the river cruise, as it gives you a lot of insight into the history of the skyscraper and the buildings making up Chicago! Additionally, we even figured out the best times to hit up the Willis Tower and even Shedd Aquarium without having to fight the crowds! 🙂 If you would like a peek at an outsiders point of view of Chicago check out the other fun activities we did in our two days there [jocelynlouise.com].