Fun Chicago Travel Guide: Things to do in Chicago

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Chicago Travel Guide | What to Do: The Ledge off the Skydeck Chicago

Chicago Travel Guide

Chicago has been on my bucket list for a while. I’ve visited numerous times before since I grew up less than 2 hours away, but I hardly ventured off Michigan Avenue. This time I made it a point to come and experience more of what Chicago has to offer. After touring around the city, I created this Fun Chicago Travel Guide complete with where to stay, what to do, and where to eat and drink! I hope you enjoy this post, I had so much fun making it!

Where to Stay in Chicago

The Conrad Chicago

I had such an awesome stay at the Conrad Chicago. Let’s start with the location- it’s absolutely perfect! Everything I wanted to do was within walking distance right off Michigan Avenue! I always look for places to stay right in the middle of the action that isn’t too loud.

However, there was so much to do inside the hotel, I hardly wanted to leave. Lounging in the spacious lobby, grabbing a cup of coffee in the hotel restaurant, Baptiste & Bottle, or heading to the awesome rooftop, Noyane, for a glass of wine was a great way to enjoy the beauty and hospitality of the Conrad Chicago.

I stayed in a King Studio which was very spacious for two people! The style of the room and the modern bathroom was so luxurious! I also loved checking out the awesome views from the windows!

The experience as a whole was 5 Star and I would gladly return. Oh, and if you are a coffee lover, you’ll really appreciate your very own Nespresso machine in the rooms!

Conrad Chicago | Chicago Travel Guide: Where to Stay, What to do, Where to Eat and Drink in Chicago Conrad Chicago | Chicago Travel Guide: Where to Stay, What to do, Where to Eat and Drink in Chicago

Conrad Chicago | Chicago Travel Guide: Where to Stay, What to do, Where to Eat and Drink in Chicago

What to Do in Chicago

If you are spending a few days in the windy city and plan on heading to more than one attraction like the Sky Deck, the Shedd Aquarium, or a hop-on bus tour, I would recommend buying the Chicago GO pass. You’ll save 45% on over 25+ Top Chicago Attractions.

Chicago Bean

The actual name of this structure is Cloud Gate, but ask any Chicagoan and they will tell you it’s the Chicago Bean! Nicknamed after its shape, the Bean attracts many visitors for admiration and fun photo opportunities!

Chicago Travel Guide | What to Do: The Bean in Millennium Park

Skydeck Chicago

Face your fears by heading to the Skydeck Chicago. Located on the 103rd floor of the Willis Tower, you’ll have a panoramic view of Chicago’s Skyline! The coolest feature is the Ledge where you can be completely suspended over 1,353 feet on glass balconies!

I’m slightly afraid of heights, but I had to take advantage of this unique opportunity and conquer my fears! Click here to buy skip the line tickets. Highly recommend especially during high season.

Chicago Travel Guide | What to Do: The Ledge off the Skydeck Chicago
Skydeck Chicago

Chicago Architecture River Cruise

Want to relax, rest your feet and learn about Chicago’s skyline? Then Chicago’s First Lady Cruises Architecture River Cruise is right up your alley! On this 90 minute tour, you’ll go all along the Chicago River and learn about all architecture of the city! After touring all day, this was an awesome way to wind down and relax while still sightseeing!

Chicago River

Chicago Theater

Built in 1921, this landmarked theater is a classic icon of the city! Check out their upcoming events and perhaps you’ll catch a show inside!

Chicago Travel Guide | What to Do: Chicago Theater

Find the Chicago Flamingo Wall

After seeing this wall all over Instagram, I had to find it in person! It wasn’t high on my priorities, but I ended up walking by it accidentally! Of course, I had to snap a few photos. I’ll make the mystery easier for you by giving you the address: 601 N Wells St, Chicago, IL 60654.

Chicago Travel Guide | What to Do: Find the Flamingo Wall

Where to Eat in Chicago


I absolutely loved Mercadito! Finding a good Mexican Restaurant is always high on my priorities when traveling and this one did not disappoint. You’ll have to order the guacamole trio that comes with traditional, mango, and tomatillo guacamole, and the mahi-mahi tacos!

If you are a margarita lover you’ll be in heaven with a large tequila-based cocktail menu. My favorite drink was the Little Market which was like a spicy pineapple margarita! And if you are looking for outdoor dining, Mercadito has a small patio!

Mercadito Chicago

The Hampton Social

Rose all day anyone? The Hampton Social is the perfect spot for a fun brunch! After you take your photos under life’s mantra “Rosé all Day” you can enjoy a glass of the Rose of the Day!

I opted for the Frosé which was so tasty, I had to order two. As beautiful and trendy this spot is, I was a bit worried that the food would be sub-par. However, everything we ordered was so delicious, I highly recommend the Tuna Tar Tar and the Fried Chicken Club Sandwich!

Chicago Travel Guide | Where to eat: The Hampton Social Rose All Day

Chicago Travel Guide | Where to eat: The Hampton Social Rose All Day

Portillo’s Chicago Hot Dogs 

It would be wrong to visit Chicago, and not have a Chicago Dog in this Chicago Travel Guide. A Chicago dog is topped with yellow mustard, white onions, green sweet pickle relish, dill pickle, and sport peppers!

Portillo’s Chicago is a classic chain that has been serving hot dogs since 1963! The interior of Portillo’s brings you back in time with the retro design. 

Portillos Chicago

La Bodega del Barrio

If you’re looking for a fun dessert spot look no further than La Bodega Del Barrio! First off, the decor is so cute with many floating piñatas above your head. The churros are so wild with flavors like Fruity Pebbles & Nutella, you better not forget your camera. If you don’t want sweets they also serve tacos, coffee, and tea.

Chicago Travel Guide | Where to eat: Bodega Chicago Travel Guide | Where to eat: Bodega

Where to Drink in Chicago


Situated above the Conrad Chicago Hotel, Noyane has an awesome food and drink menu, as well as amazing views of the city! Catch the sunset and enjoy a glass of wine with good company!

Cindy’s Chicago 

Another rooftop in Chicago, Cindy’s came highly recommended by friends. Unfortunately, I didn’t have the chance to experience it, but I wanted to add it in for a scenic spot to grab cocktails in Chicago!

Broken Shaker Chicago

With various fun locations in the US, I had to check out the Broken Shaker in Chicago. I love the unique cocktails and funky interior design! If you’re looking for a relaxing place to drink with a fun vibe, this place is totally for you!

Tiny Tapp

Located on the Riverwalk, Tiny Tapp is a buzzy spot for after-work drinks with a perfect location right on the Chicago River!

Hope you enjoyed this fun Chicago Travel Guide! I can’t wait to be back to explore more!


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