The Ultimate Travel Guide to Chicago


As a lover of all things travel, the list of places I want to visit is quite vast. Something about growing up in smaller towns has always given me an infatuation for cities and the hustle and bustle lifestyle found within. So when the chance came up to visit the Windy City during one of the most iconic times of the year (St. Patrick’s Day) for Chicago, it was a trip I was immediately on board for! It brought together my love for the city and my love to travel with a group of friends to enjoy experiences together, which is exactly where this Chicago travel guide stems from.

Chicago is anything but boring and provides unique places to wander and fully experience. I had such a great time on this trip, and this guide is here to provide you with insight into all the best places to eat and stay, as well as provide simple tips to help you get the full experience during your visit.

There is SO much to this beautiful city, and although I had four full days of exploring the city, I still missed out on a few things I had on my list due to weather conditions. However, if you’re looking for a deeper itinerary or just have general questions, make sure to leave a comment and I’ll provide you with the answers you need.


STAY LondonHouse Chicago

While in Chicago, a great place to stay is LondonHouse Chicago. This hotel resides in a 1923 historic building considered one of the original “Big Four” skyscrapers around the former Michigan Avenue Bridge. Stunning brass details and marble accents can be found throughout the hotel, as well as a rooftop bar offering lunch, dinner and weekend brunch menus.

One of the main reasons we selected this hotel was because of the direct views of the river available in your hotel room. As a St. Paddy’s Day tradition in Chicago, the city dumbs 100lbs of green dye into the Chicago River. I wanted the full St. Patrick’s Day experience and boy, our hotel room with a stunning corner view did not disappoint! The room was super spacious, the king size bed extremely comfortable and the central location super convenient; the Riverwalk is across the street, with Millennium Park and Magnificent Mile Shopping only a short 10-15 minute walk.




Chicago’s food scene is eclectic and oh, so delicious. You’re sure to find a different restaurant option around every corner. I’m certainly no picky eater and I’m always the first to volunteer to try something new, especially when traveling. However, whether you are looking for a place to eat brunch, lunch, dinner, or late night eats, Chicago is a place you’ll be able to find exactly what you are looking for to meet the palettes of those you may be traveling with.


PLACES to Dine in Chicago 

Lou Malnati’s Chicago

You can’t come to Chicago and not get a deep dish pizza, amiright?! Lou Malnati’s is a Chicago staple for deep dish pizza that has been around since the 1940s. There are several locations scattered throughout the city and it does tend to get busy, so consider making reservations. Lou’s deep dish pizzas take 30-45 minutes to bake, so we chose to start with the bruschetta while we waited for the pizza to cook. Service and food were great and extremely filling. We left full and satisfied!

Extra note – If we would’ve had an additional chance to eat pizza, we would have tried Pequod’s who is famous for their caramelized crust edge. Several locals raved to us about their pizza!


Cindy’s Rooftop

One of Chicago’s best rooftop dining locations can be found across the street from The Bean, with atmospheric views of Millenium Park and Lake Michigan. The restaurant is open for lunch and dinner, offering brunch on Saturday and Sundays using locally sourced, North American cuisine. Their cocktail menu is also quite impressive and they get busy, especially for brunch, so make reservations online before you visit.


LondonHouse Tri Level Rooftop Bar

Located inside LondonHouse Chicago Hotel you will find the Rooftop cuisine and cocktail lounge on floor 21, and an additional rooftop bar on floor 22 with views overlooking the Riverwalk. This was a convenient elevator ride away for us when we grabbed brunch on St. Patrick’s Day morning. We started brunch with green mimosas and a crab dip, followed by lobster mac + cheese and chilaquiles. Drinks and food were all great! We even went back around 10pm and the Rooftop lounge had transitioned into a bar, complete with a live DJ.


Ciccio Mio

Y’all! This place is a must when you are in Chicago. They are only open for dinner and reservations are required because of the smaller size of the restaurant, but I promise it is worth it. Superb service, cozy atmosphere, mouthwatering food, and excellent drinks. *Drooling just thinking about it*  When ordering, prepare yourself for a lot of food. Consider sharing entrees with the table so you can try more than one thing. Pro tip: leave room for dessert!!


Andy’s Jazz Club

Looking for entertainment with your meal? This is the place for you! What opened as a lounge in the 1950s has since become one of the most respected jazz venues in Chicago. They currently offer three 75-minute shows nightly, with start times of 6pm, 8:15pm, 10:30pm. I’m a sucker for live music, but outside of the amazing entertainment, the food was also exceptional. I ordered the chicken parmigiana and a bottle of prosecco for the table. The entire experience was unique and one I recommend!


Portillo’s & Barnelli’s Chicago 

What’s another famous food item from Chicago? Why, the Chicago Dog, of course! Now listen, had you asked me 7 years ago if I liked hot dogs, I would’ve told you not no, but heck no. My, my, how the tables have turned. Not a hot dog fan? No worries. Eat like the locals and order an Italian Beef. Feeling brave? Get your sandwich dipped in gravy. Everyone will think you’re from Chicago 😉 I, of course, had to try both. LOL


Ocean Prime

Truth is, we randomly stumbled upon this restaurant wondering in our hotel. I insisted on getting a Chicago dog before we left but I also wanted seafood and we were quickly running out of time in Chicago. How did I manage to get seafood and a Chicago dog for my last meal in the city? We stopped in to grab drinks and an appetizer at Ocean Prime before getting Chicago dogs at Portillo’s. The dirty martini and crab cakes were so good that we came back later in the night for another martini and a butter cake for dessert. In fact, Ocean Prime had the best dirty martini from my entire trip in Chicago. If you’re a martini fan, you’ll want to stop here for a nice meal!





CHICAGO Things to Do

While in Chicago, I highly recommend doing a walking tour if the weather permits. You can get access to a tour guide aka a Chicago Greeter and get a walking tour of specific areas for FREE. Yes, for free. No charge. You can get a customized tour based off of your interests to see architecture, family fun sites, or even a foodie tour. It’s up to you.

The first day we arrived in Chicago was beautiful weather, but it got pretty chilly and even started snowing on our last day in town. Had the weather been nicer I would have gone to the Lincoln Zoo (one of America’s only zoo offering free admission), gone on a architectural boat tour, and rode the Ferris wheel at the Navy Pier. Nonetheless, we made the most of our time in the Windy City and had a blast with other indoor activities.



Explore Millennium Park 

No matter the weather, you should take the time to go see the notorious Chicago bean sculpture and explore Millennium Park. During the warmer months, they have a large fountain, beautiful landscaping, kid’s splash pad, and live music playing in the park. During the winter months you’ll find an ice skating rink.


Explore Local Breweries 

Chicago is full of Irish pubs and endless amounts of local breweries. We ended up popping into a couple that were either on our list or within walk distance. Crushed By Giants Brewing Company has a fun atmosphere and great menu of beer options, as well as wine and cocktails. Banshee Scream Oatmeal Stout was my favorite option from their beer flight. Adam’s Street Brewery is located inside the Chicago loop offering rotating German lagers such as sours, ales, and stouts.



Visit a Chicago Museum

Museum of Contemporary Art Chicago is one to marvel. As a lover of modern art, Chicago’s Contemporary Art Museum was intriguing and eccentric. I should probably mention that I am not one of those people who can stare at art and look at the intricacies or point out certain aspects of an era, but I am a person that can appreciate the work that an artist puts in and the meaning behind it. Going through the different exhibits to see the various cultures displayed was something perplexing.


Attend a Show

One of my favorite things from our Chicago trip was attending the Chicago Magic Lounge show. From the entrance, to your exit, every detail is elegantly thought through to pull you into another world, full of magic. You enter the building through a laundry mat, with washer machines that open to reveal a hidden door. Through the door you’re greeted by a host, rules are explained, and walls fall back as you enter into a large magic lounge with a center stage. Prior to the show you are able to order cocktails and small plates, while card magicians wonder table to table doing close up card magic. The main attraction starts about an hour after the doors open and upon completion you are invited to attend the Magic Lounge bar where they have additional magicians performing magic to keep you entertained after the show. Jan Rose was our host for the night, and this lady has so much spunk and personality! I just loved her and she made the show that much better. If you’re looking for a memorable night in the city of Chicago, make sure you purchase tickets to the Chicago Magic Lounge!

Another fun show available to see in Chicago is the infamous Blue Man Group at the Briar Street Theater. This is a family friendly show that has heavy audience involvement and tons of percussion talent. Truly a dazzling and upbeat experience everyone should get to see.

Pro tip: get tickets close to the stage to be more in the action, or near the aisle if you want a better chance at getting picked to go on stage.



Uncover a Speakeasy

Located below The Hampton Social you will find Chicago’s premier live music venue – The Bassment. Live music, bottle service, swanky cocktails? Yes, please. Entirely designed around music, The Bassment goes above and beyond to provide first-class service and state of the art cocktails. Trust me, you won’t want to leave! Interested in going? Pay ahead for reservations or get there early; this place gets packed!


Phew, looking back at our itinerary, that was a lot of things! There’s just so much to do in Chicago, and we had the best time exploring! I know there are other things that we didn’t get to try, so tell me, what else do I need to hit up next time I’m there?


Happy traveling, friends!