Ultimate Guide to 3 Days in Chicago, IL

The Windy City!! Writing this as I am just getting back from Chicago and already wishing I was back! With Chicago being the third largest city in America, it is absolutely brimming with fun activities, sounds, sights, and tastes! This midwestern city has a big city feel with local charm. Being able to walk all over the place while being surrounded by so many great food and shops instantly allows you to feel all of the happy vibes.

To help plan your trip to Chicago, or if Chicago has been on your mind for sometime as a place to visit but you just need that little push of convincing, I have the perfect compiled list of everything my bestie and I did on our trip! Let's make the absolute most of your time in Chi-town!

Where to stay:

Hotel St. Clair - Great walking distance to many of the main attractions. Furthest walk we had was 25 minutes to the Navy Pier. Everything else was 15 minutes or less. The only time we had to Lyft somewhere, was to the Cubs baseball game at Wrigley Field. Hotel St. Clair was also one of the more affordable options in downtown Chicago that I could find. Our room was spacious, clean, and very nice!

Transportation:

Walking - Bring some shoes that you are more than comfortable walking 15,000+ steps in because you will be walking A LOT. If you chose to, of course. We walked nearly everywhere. We don't regret it one bit, we actually preferred it and recommend it because this is how you will be able to get a full feel of seeing everything that downtown Chicago has to offer. It may even lead you to fun places and hole in the walls that you would not have known about otherwise.

Uber/Lyft - We only used Uber/Lyft to get to and from the airport and also to get to and from Wrigley Field for the Cubs game. Other than these moments, everything we wanted to see and do was well within walking distance. We did note that Lyft was cheaper than Uber!

Weather:

Our stay was in late September and the highs averaged around 78 degrees and the lows were around 63 degrees. This gives you a good idea on how to pack, if you're choosing similar timeline.

Day 1:

• Giordanos - BEST deep dish pizza! A must to try while in Chicago!

• Starbucks Reserve Roasters - Largest Starbucks! And sooo gorgeous! There are four floors and each one has different options. One being ESPRESSO MARTINIS. Try to go during the week, if your trip allows.

• Wrigley Field - Chicago Cubs game! Try a Chicago style hot dog!

Day 2:

• RoseBud Italian - PASTA, CARBS? YES, YES, YES

• Blue Bottle Coffee - This place was right on the riverwalk and has amazing views. Do note that they do not offer syrup flavors for your coffee.

• Riverwalk - Lots to see and do around here. All within walking distance!

• Michigan Ave Bridge - A great photo op and also neat to walk through.

• Chicago Theatre - Another great photo op! The infamous "chicago" sign!

• Milennium Park - This is where the bean is, but while we were in Chicago, the bean was closed for renovations until Spring 2024. Nonetheless, the park itself is still a staple to walk through.

• Buckingham Fountain - At the entrance of Milennium Park and hard to miss but is so gorgeous and another good photo op!

• Nutella Cafe - Customize your own nutella! This cute cafe also offers Nutella themed/based coffee drinks, pastries, and other items!

• Colores Mexicanos - SO CUTE!!! A ton of handmade items, customized stickers, and cute things! Also some pretty neat mexican themed snacks!

• Signature Room at 95th - A MUST! This is a restaurant on the 95th floor of the 4th tallest building in Chicago! The view is stunning. You are able to get the best foodie pictures from here. Dress code enforced, be sure to bring/wear a cute dress or something not revealing and nothing with holes in it!

Day 3:

• Ralph's Coffee - Did anyone else know that Ralph Lauren has a coffee shop?! And it is connected to his store?! Okay, this is a must just to say you did it. They also have the cutest merch. I tried a maple spice latte and it was yummy! There is usually a line so be ready to wait for a little bit.

• Navy Pier - The furthest walk we had to do from our hotel in downtown Chicago, but well worth it! The pier is so nice to walk through, and lots of photo ops. Be sure to check ahead for any events they may be having on the day/weekend you plan to go. We were able to see LIVE! Chicago all for free here on the pier! You are also able to eat lunch or dinner here as there are many restaurant options offered.

• Coach Store - A random stop on our walk back to the hotel but so glad we stopped! This Coach is considered a flagship store! Meaning, they do custom monogram and also custom purses!

• Michael Jordan's Steakhouse - OKAY THIS PLACE IS 10/10!!!!! They have so many yummy options. The chef comes out and explains the entree to you. Their steak ceasar salad was AMAZING. Their onion soup was the best soup I have had in my LIFE. This place is more on the fancy end and it gorgeous! If you order the jumpman martini, Michael Jordan's infamous Jordan logo will be on it!

Split these activities/eateries up however you see best fit for your schedule but definitely try to do as many of them as you can!

Reach out to me, if you ever plan a trip or have questions on learning more about any of the activities we did! Chicago should definitely be on your list of places to visit and for good reasons!

XOXO,

Tess