How to Chicago in 3 Days
Updated: Jan 24
I'm extremely happy to have people in my life who are just as spontaneous as I am. My trip to Chicago didn't necessary start with a lot of planning. I literally just messaged my friend from Miami, Danny asking if he was free from the 7th to the 10th of August to come to Chi-Town with me and without hesitation he said yes and we literally booked our flights a couple days after this conversation happened. I booked my flights with Spirit Airlines ( pretty much the American Ryanair ), and yes, got the Spirit Experience. My flight was supposed to leave on Tuesday evening at 9:45PM from LaGuardia Airport, but since there was a huge storm in NY a couple hours before, all the flights got delayed, so did mine. I finally got on the plane at 1:00AM and met Danny at O'Hare International Airport at 3:00AM. We were planning on going out on the first night, but since we got to the city super late, we went straight to the AirBnB and passed out.
The first actual day was a success. We woke up, got ready and headed to one of the most amazing vegan restaurants I've ever been to. The Handlebar has the most amazing vegan dishes. Danny had a vegan chimichanga and I had vegan french toast. I'm drooling even just thinking about it. Here's what it looked like :
I was so full after eating all of this, but of course we shared.
Here's their website: Handlebar Chicago
Have a look at their menu and drool.
Navy Pier was our next destination, where we hopped on the Architecture Boat Tour.
Chicago is known around the world for its architectural feats, both inside and outside of the buildings. From the 100-year-old Art Deco, Neo-Classical, and Gothic Towers, to some of the tallest modern-day skyscrapers, Chicago is where old meets futuristic architectural endeavors. It has something for everyone in a way that no other city replicates today. The 90 minute boat tour was amazing, our tour guide exceptional, she explained everything about the buildings, history, legends. I can only recommend it to everyone who is visiting Chicago, it's one of the easiest way to learn about the history and architecture of the city, plus they serve alcoholic drinks on the boat haha, it's almost like a booze cruise with professors and student on it.
You can get your tickets for the cruise here: Shoreline Sightseeing
After getting educated on the booze cruise we visited Navy Pier and hopped on the Centennial Wheel to get the best view of the pier. Tickets were on sale online, so if you can, get them online and you can just show them the barcode on your phone. Save money and paper! Tickets are sold here: Centennial Wheel
After all the awesome views we walked around the city, more exactly on Michigan Ave, which is basically the 5th Ave or Oxford Street of Chi-Town. I could've spent all my money there.
Later that night my friend surprised me with a ticket to the 360 Chicago Observatory Deck, and boy, oh boy! watching the sunset from up there, yes, nothing compares to that. Plus, their gin & tonic was awesome. I recommend that you get a drink when you're up there, it definitely sets the mood.
Here are some pictures from the top of Chicago:
If you get a chance, I highly recommend that you pop in to the John Hancock Center, where you can check out the breathtaking chandelier they have just above the water fountain.
That was only the start of our night in Chicago, we kind of went on an adventure, starting with the awesome rooftop bar & lounge, The Devereaux, which doesn't only has to offer awesome cocktails, but has a pool. Just take a look at this, it's perfection:
After finishing our cocktails we went to have dinner at Hugo's Frog Bar and Fish House, where we had a couple sides dishes, such as broccoli, baked potato, sweet potato fries as our meal. The staff was super friendly and we actually met one of my manager's old friends here, an old, sweet Irish gentlemen. Cheers to new friends in Chicago!
After dinner, we decided it was time to dance off the calories, so we headed to Studio Paris Nightclub and danced the night away to some awesome tunes.
The 2nd day we started with a magnificent breakfast at the 3 Arts Club Cafe, which is a must if you want insta-worthy pictures on your feed. Not only the interior design, but the food and the mimosas were delicious too. Just take a look at this place, it's everything a basic white girl needs in her life:
I honestly had an awesome experience at this cafe, the staff was very nice, but we've been advised that taking pictures with a professional camera inside the main dining hall is prohibited, so just keep that in mind.
Another place you need to visit is Stan's Donut Shop, if you're in Chicago. They have the best cronut, you know, a cross between a croissant and a donut. Try it!
Next stop was the Millennium Park, where The Bean or Cloud Gateis. This incredible sculpture is made up of 168 stainless steel plates welded together, its highly polished exterior has no visible seams. It's just breathtaking!
I recommend you walk around in Millennium Park and Lurie Garden as it has some hidden little gems, like this little artificial river, where you can cool down on a hot day.
Walking down on S Columbus Dr from here will take you to the beautiful Buckingham Fountain in Grant Park. It's one of the largest fountains of the world and it was built in a Rocky rococo wedding cake style and inspired by the Latona Fountain at the Palace of Versailles, it is meant to allegorically represent Lake Michigan.
The same day we've heard on the radio in our Uber that Bazzi (yes, the guy who sings 'Mine') has his last concert of his tour in the Chicago House of Blues,so we decided to get our tickets and go to his concert.
One of the best night's of my life! The concert was amazing, I definitely recommend you check out if there are any events in the Chicago House of Blues while you're there, because it's worth it.
After the concert we visited a couple of extraordinary bars and lounges, such as the LondonHouse Chicago, which has an amazing rooftop with even better views.
Have a look at it :
The next one we visited was the Gwen Chicago. The craziest drinks and best bartenders I've ever came around! Seriously, if you like interesting cocktails, go there! I had a "Mayan Friendly" cocktail and boy, it was out of this world. It had tequila, pineapple, lemon, cinnamon and agave nectar in it.
The night didn't stop there. My favourite club in Chicago, which I have actually recommended to other friends before and they loved it as well, was Celeste, which is the "Sexiest 5AM bar" according to Chicago Magazine. This is seriously a MUST in Chicago!
Day 3, last day started off pretty late since we were out dancing all night the night before.
Our first stop was Beatnik on the River, which is all of your instagram dreams, it's a bohemian, extravagant restaurant, located on the Chicago River. The servers, the food, the drinks were all top notch.
My other favourite place in Chicago was La Bodega, an incredible coffee shop on the corner of Clark & Kinzie St. with ornate mosaic floor tiles, another insta-worthy location, and food, of course, what else could I possibly interested in?
Not only the churro cone ice cream, but the interior design was stunning as well.
Our last stop was Cindy's Rooftop Bar, where you can get the best view of The Bean and the whole Millennium Park. Drinks are pricey, but if you're like us, you can sneak up for the picture only. There's usually a long wait, but it's worth it!
I'd definitely go back to Chicago anytime, it's such a friendly and vibrant city, full of art and good vibes.
There are some other places that I didn't have time to visit, but they're worth checking out:
If you have a car while you're there, you should definitely drive down to Starved Rock State Park, for a beautiful hike. It's only a 1:30 h drive!
Now go on and explore Chi-Town!