Is there one city that you’ve always dreamed of visiting? For me that was Chicago. It always held the number one spot on my US City Bucket List and I finally had the opportunity to go. And let me tell you, exploring Chicago was really something else. I wandered around the city with Choose Chicago and had the chance to check out several different neighborhoods as well as some tourist hotspots. I dined on some of the most delicious meals and met incredible locals who really love their city.
But, first things first:
Getting To Chicago
I flew over to Chicago with American Airlines. I flew from London and I was able to sit in business class. The experience was remarkable. From the service to the lie-flat beds to the delicious food, my flight was really special. And if you’re flying out of Chicago with American Airlines and you have business class seats, you also have access to their Admiral Club, which is the nicest airport lounge I have ever been in.
Where To Stay
Once you touch down, you’re going to want a comfortable place to base yourself while you’re exploring Chicago. I called The Alise – A StayPineapple Hotel, home for three nights. The view from my room was absolutely gorgeous, the wifi worked well, and the staff was friendly. They even had a cupcake bar every day for guests! The hotel is pet-friendly and in an excellent location!
So, How Do You Spend 72 Hours Exploring Chicago?
Day 1
Instead of hanging in the downtown area, which is referred to as the Loop, why not check out some of the lesser known neighborhoods? Start your day off with a food tour in Chinatown with Chicago Food Planet Tours. They offer several different tours around the city, and I’m so glad we got to do this one.
We dined at four different places in Chinatown and almost everything was delicious. I won’t give all the spots away as I truly believe it’s best to be surprised during a food tour, but the Dim Sum we enjoyed at the first stop was insanely good.
After your food tour, why not see the city from above? The Chicago skyline is pretty magnificent and being able to see all of the buildings and Lake Michigan from the sky is really incredible. Plus, the people over at the Chicago Helicopter Experience were so friendly, that it made my experience that much better. We had an awesome female pilot who took us for an amazing ride. She pointed out landmarks and famous skyscrapers while giving us some more information about the windy city.
The Afternoon:
After you step off the helicopter and on to solid ground again, it’s time for dinner (yes, I promise you’ll be hungry again). Head to Nana for the most amazing meal ever (it was by far my favorite dinner of the trip). Nana is a really cool neighborhood spot in Bridgeport. Do yourself a favor and order the Plantain Sandwich — you won’t be disappointed. Oh, and make sure you also order one of the desserts. Nana, the owner of the restaurant bakes them upstairs in her apartment!
We finished our night off at Friday Night Flights, a special event that Choose Chicago puts on throughout the summer. They invite local breweries to serve up some of their best. You can enjoy up to ten local brews! It’s a lot of fun!
Day 2
Wake up early and head to 360 Chicago to go on Tilt and grab a view of the city from one of the tallest buildings in Chicago. Keep in mind that you can’t control the weather and there may be a chance of zero visibility (as it was for us).
After that, take a stroll down Miracle Mile. It’s filled with shops and department stores, as well as restaurants and cafes. From there, head to brunch (can you tell we did a lot of eating on this trip?).
If you want to dine by the river, River Roast is an excellent choice. Their brunch menu is extensive and features some really interesting choices like rabbit and waffles, an open-faced egg sandwich, and a blues burger. I went for the special that day — it was marinated braised brisket tip that was deep fried and served over a tostada with black bean and crema puree. That was topped with avocado and a cabbage and carrot slaw, and a fried egg. It was incredible.
The Afternoon:
When you’re finished with lunch, it’s time to check in for your architecture river cruise with Chicago First Lady Cruises. You’ll learn so much during the one and a half hour boat ride from a volunteer from the Chicago Architecture Center.
After you finish your cruise, spend some time wandering down the riverwalk.
Later on, it’s time for dinner! Public House serves up some delicious bites, close to the river. Order the mussels as an appetizer and finish your meal off with a freak shake!
Next up on the itinerary are the fireworks at Navy Pier! Head there a bit early so you can take a spin on the Ferris Wheel. And when the fireworks end, make one last stop at London House for a nightcap and for sweeping views of the Chicago skyline lit up!
Day 3
Day three is an easy one, with plenty of free time for you to explore any other places you’re dying to visit in Chicago. But first, start your morning right with a churro and breakfast taco from Bodega. The cute little shop serves up some of the most delicious sweet and savory breakfast foods and you’ll absolutely love them.
When you’re finished, walk to the Art Institute. There’s a reason that this is the number one reviewed museum in the world on Trip Advisor. It holds so many famous pieces of art and has several exhibits to check out. You could probably spend the entire day here and still not even scratch the surface!
Travel Colorfully was invited to Chicago by Choose Chicago and American Airlines.
As always, all opinions are my own!
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