First Time Visit to Beautiful Chicago: Chicago Travel Guide
Langham Chicago
Chicago Travel Guide
My uncle lived near Chicago and had always talked about the beautiful city and its incredible food when I was growing up. I believe I was about 8 years old when I first felt the deep desire to go to Chicago. In 2021, I finally had the privilege of traveling to one of my dream cities - Chicago, and it remains one of my favorite destinations.
As to why it took me this long to get here? Not sure, but you best believe we are always planning our next Chicago trip! Chicago definitely hits the top of my list of must-travel places in the United States. It’s unique and incredibly beautiful, and the food is insanely good!
I always have such a great time in Chicago, and I am happy to be sharing this guide with you. It’s perfect for a first-time traveler to Chicago, but has plenty of unique options for seasoned travelers too. We love to visit with Husdon, so I’ve made special mention of where you can and cannot bring your pets in the city in case you also want to travel with your dog.
Disclosure: This post contains recommended products I have personally used and all opinions expressed here are my own. This post may contain affiliate links and I may earn a small commission when you click the link at no cost to you. Read my disclaimer here.
Spring: Chilly
We live for Spring in Chicago. The sun is out and the flowers are blooming. For a California gal, it was still pretty chilly running about high 50s to low 60s throughout the day, but the weather is perfect for walking around and enjoying the beautiful streets of Chicago!
Winter: Best for Avoiding Crowds
Windy City is VERY cold during the winter months. However, if you are doing more indoor activities, I highly recommend visiting during this time to avoid crowds and get better prices with your hotel stays.
Fall: For a Holiday Spectacular
Fall is beautiful in Chicago. The weather does get pretty chilly (low 60s to mid 50s) but Chicago goes all out when it comes to the holidays so you will feel every bit of joy experiencing Chicago-level Holiday production as you walk up and down the streets!
Summer: Beautiful, but Busy
This is PRIME season for Chicago with the weather at low 70s to about mid 80s. However, since it is prime weather in Chicago, there are plenty of outdoor events and festivals that may cause prices to hike up and an influx of crowds everywhere you go.
My Recommendation
My personal favorite time to visit Chicago is late September. The crowds are not too bad, the weather is warm in the morning and just the right amount of chill at night. This is the perfect time to get some lake time in the morning and hit a rooftop bar at night!
Visiting Chicago: Where To Stay
Chicago is a pretty large city, but if you plan it well, it’s also very walkable! If that’s important to you, pay close attention to where your accommodations are to make sure you are centrally-located to the attractions and restaurants you want to visit. Otherwise, it’s easy to get around with a rideshare app, or even with public transportation.
21c Chicago
VIP Gifts
21c museum chicago hotel
We stayed at 21c Museum Chicago Hotel and it was outstanding! There are quite a few things that make this hotel unique, number one being that the first two floors of this boutique hotel are a museum. Not just any museum, the art is very controversial - which makes it incredibly eccentric and worth visiting.
We stayed in one of their corner suites, and this massive room was more beautiful than we could ever imagine. It definitely has a luxurious and modern vibe without the high costs. It’s very clean and the entire hotel is well thought out. The corner room is simply divine. It’s spacious and the view of the city is insane. I love that it has a lot of room to hang out, do work, and enjoy your time.
Best of all, there’s so much room for Hudson to run around and play. This hotel is pet friendly, and they actually have a VIP (Very Important Pup - cute right?!?) special that gives a little gift to your best friend during your stay!
The staff is seriously amazing, and the location is perfect. It’s walking distance from various experiences and restaurants but distant enough that you don’t hear the bustle of the main road. It’s also super easy to access public transportation as well as ride-share if you do need to go further out.
Overall, I am so glad we found 21c Museum Hotel. It was such a neat place to “go home” to every night. It exceeded our expectations and truly felt comfortable during our long stay!
Kimpton Monaco
Kimpton Gray Chicago
This stunning hotel is located at the heart of Downtown Chicago. It is one of Chicago’s historical buildings and you can feel it staying here. I love the sophisticated modern design and the gorgeous architecture. They also house Vol.39, a beautiful and unique bar that serves delicious drinks. I highly recommend checking them out!
Kimpton Hotel Monaco Chicago
Located across the street from the Riverwalk and endless restaurants and museums, the Kimpton Monaco Chicago by far has the best location out of all the hotels that we’ve stayed at. The views are incredible, so I HIGHLY recommend booking a corner suite. The room has window seating by each window and that itself blows you away. They are also VERY pet friendly!
Langham Chicago
Langham Chicago
This hotel is as luxurious as it gets! Located at the heart of Downtown Chicago, Langham Chicago checks all the boxes. The rooms are spacious, elegant, and very comfortable. If you are thinking of a work trip, consider booking a room at Langham Chicago for its stunning views that will inspire you and get your creative juices flowing.
They are also VERY pet friendly and the staff is incredible. If your budget allows, I recommend getting a Club Room so you can access the lounge where they serve breakfast, lunch, and happy hour. The Club is intimate, beautiful, and is the home of the unlimited candy cart!
Best Things To Do in Chicago - Tourist Destinations You Shouldn't Miss
Filled with tourist destinations, museums, restaurants, and so much more, one trip is not enough to truly explore Chicago. There’s so much to do and each experience takes time to appreciate and explore. My advice to you is to create an itinerary and give yourself time for every experience. Don’t hurry because you’ll miss out. Enjoy what you scheduled and look forward to coming back for the rest! These are my top recommendations for which tourist destinations you should try to prioritize for your first trip.
The Most Recognizable Windy City Location - Millenium Park
Right outside the doors of the Art Institute of Chicago is Millennium Park, which houses many of Chicago’s famous attractions. You’ll find Cloud Gate here, commonly called “The Bean.” Laurie Garden is also here as well as the Crown Fountain. It’s a beautiful place to spend a couple of hours walking and enjoying the scenery. Side note: Although it’s a park, dogs are prohibited on the property. We made the mistake of taking Hudson on the first day and were asked to leave.
See Chicago From Above - Skydeck + Ledge
Located in the tallest building in Chicago, this experience will knock your socks off. The Willis Tower is 1,450 ft. tall allowing you to see thousands of miles of beauty from all directions.
You first enter through their newly revamped attraction emphasizing what Chicago is all about. Then you get on an elevator to the 103rd floor of the tower where you can witness the incredible views and experience the Ledge. The Ledge is a thrilling glass balcony extending from the tower. In my opinion, it’s quite scary but it’s an experience I will never forget.
Skydeck Chicago
An Experience You Won't Forget - 360 Chicago + Tilt
Another observation deck located in the heart of Magnificent Mile, 360 Chicago is a must-visit. The deck is located 90 floors up from the John Hancock tower, and I must say - the views are different here vs. the Skydeck. One is not better than the other, but rather different. 360 Chicago offers a bar at the observation deck that allows you to take in the gorgeous views while sipping a cocktail.
It is also the home of the thrilling attraction, Tilt. This is where you stand in a glass column that tilts over the city 1,030 feet up. Not going to lie, I was pretty scared, but it was a memory that will last a lifetime!
Entertainment & Education: Interactive, Immersive Experiences in Chicago
I know they call New York the city that never sleeps, but I think Chicago might have a one-up on the big apple. Not only are there a million things to do here, the variety of options for entertainment and education are pretty overwhelming. Here are some of our favorite interactive experiences in Chicago.
Shoreline Sightseeing Architecture River Tour
This is easily one of the most educational yet entertaining experiences I’ve ever had in my life. It’s a 75-minute tour on the beautiful Chicago River with the most incredible tour guide that explains each and every significant building and neighborhood that lines up the river.
This experience teaches you a whole lot about Chicago but also gives you an insight into how architects come up with their ideas and inspiration. Being able to understand the architecture, passion, and excellence that went behind building most of Chicago makes you love the city even more.
HQ Beer Arcade
Chicago has hundreds of breweries in the city and suburbs, and you really can't go wrong with any of them, but one of the coolest places to visit in Chicago is HQ Beer Arcade. Home of vintage arcade games, this place was a great little date night experience. They have a wide variety of old-school arcade games including pinball machines, Tekken, and so much more! The food + drink selections are out of this world and the aesthetic is unreal.
Chicago Magic Lounge
A night of magic - literally! But in all seriousness, our night spent at Chicago Magic Lounge was one of the best nights of my life. Every second of being in the vicinity made your eyes open wide, jaw drop, and laugh hysterically. The talent was incredible, as well as the staff and the food.
You definitely don't want to miss this one! You won’t believe your eyes
Urban Kayak Historic Chicago
This tour is great exercise while being entertained and educated about the beautiful city of Chicago. For approx. 2 hours, you get to kayak along the Chicago River and learn about snippets of the history of Chicago that only the locals know about.
Urban Kayaks also offers other tour options as well as paddle boarding. Located right on Riverwalk, I highly recommend booking with them!
Winter’s Jazz Club
This was our favorite way to end our night. Conveniently located in the heart of Downtown Chicago, this intimate and beautiful listening room hosts very talented musicians 6 nights a week. I do love that they play different variations of Jazz music, some I’ve never even heard before. I love that they also serve drinks to complete your night. Their schedule varies so I recommend checking it out ahead of time.
Must-See Art and Museums in Chicago
Chicago is a mecca of arts and culture. If you know me, you know that I LOVE museums and Chicago is full of them. You could spend months here and not have enough time to see them all, so consider picking one or two from this list that really interests you and start planning your return visit for the others.
Immersive Van Gogh
Immersive is an understatement. This experience truly envelopes your mind, your senses, and your soul. Not everyone understands art easily, but your mind accepts Van Gogh’s art from this amazing experience. The music, the environment - EVERYTHING about this experience was outstanding. Each “show” runs about 20-25 minutes. I recommend experiencing it from the first floor as well as the second floor. It feels a little different from the first floor than the second because the first allows you to feel like you’re in the art while the second feels as if you’re spectating the entire thing. The way this experience makes you feel will stay with you forever.
The Art Institute of Chicago
I enjoyed opening up my imagination and stepping into a different mind that made each piece of art in this museum whole. The collection of art is unique and truly, not one I’ve ever encountered before. From the Thorne Miniature Rooms to the Ambiguous Standards Institute - the variation of art found in every corner of this building was unique and astounding to explore.
WNDR Museum
The WNDR Museum was such an incredibly fun, immersive experience! The collection of interactive exhibits pulled out your inner child while keeping you intrigued. We had such a great time here! It’s adult and kid-friendly.
Places To Eat In Chicago
This modern Mexican restaurant is definitely one of my favs! Not only do they have a dog-friendly patio, but the aesthetic and vibe of the restaurant were also amazing. Food-wise, everything was very delicious. We had a great variety of food, but they have hands down some of the best fresh guacamoles I’ve ever had in my life. I also highly recommend the Adobo Fried Rice - my favorite dish during our entire trip!
Gorgeous would be an understatement when describing this restaurant. Located in Lincoln Park, which is a very trendy neighborhood. FYI, you would have to take the train or Uber if you stay downtown, but it's definitely worth it. I love that they welcomed Hudson in their covered back patio. Food-wise, they had incredible options. It was really difficult choosing just one dish, but what we ended up ordering was amazing! I definitely recommend the burrata and the tuna tartare.
Located in Wicker Park, Daisies is quite a ways away from Downtown Chicago but absolutely worth the trip. We went for lunch and had some quick and easy sandwiches, and my goodness - it was some of the best sandwiches we’ve ever had! I ordered the Wagyu Beef Sandwich and Gary ordered the Lamb Sandwich, which was delicious. I personally don’t like lamb, but I scarfed down Gary’s sandwich like no joke lol. They also have a backyard patio so Hudson was able to join us.
This hole-in-the-wall sushi spot is my FAVORITE sushi spot ever. The unique offerings and different takes on traditional dishes blew my mind. The restaurant itself was very intimate, with a total city vibe, but the food will truly knock your socks off. The katsu is a MUST!
When we got dropped off, our Uber driver immediately said, you’re in for an amazing treat, and he was not kidding! The restaurant overall is beautiful. I loved how intimate yet open it was, and the staff was incredible. I ordered the Poke Salad which is basically a Poke Bowl and it was delish. Gary got the surf and turf, and he kept talking about how great the steak was. I loved everything about this place, and if you are there on a Monday night, make sure to call and see if they are still holding their Ladies' Night where they give away a designer item to a lucky lady!
Although Chicago is known for their deep-dish pizza, we just had to try the famous Robert’s Pizza, which isn’t a deep dish. However, it definitely exceeded our expectations. What we were told was that Robert himself has spent years perfecting the crust of his pizza, and my goodness, it is beyond perfect. Every bite hits the spot, and the atmosphere is amazing. They also have a really awesome outdoor patio right by the river for a one-of-a-kind experience!
Hampton Social will always have my heart. I’ve been dying to visit this restaurant for years. So you must know my excitement when I discovered we were dining with them on one of our evenings! The vibe, the staff, the restaurant setup, the food, and the drinks were all five stars. This is a restaurant that I will go back to again and again and again. I HIGHLY recommend you take the time to check it out!
Located in probably my favorite area in Chicago, Carmine’s was amazing. We had a quick lunch here and everything we had was delicious. If you like calamari, I highly recommend checking out their grilled calamari - which is something I had never had before but have eaten again and again since. They also have a very beautiful outdoor patio that sits right on the street which I can personally say is an amazing vibe.
Located at the beautiful Navy Pier, Lirica is a newer restaurant with all the views. I recommend visiting on a Saturday night, as the pier sets up fireworks around 9 pm. The food was phenomenal. They took a modern and artistic twist to traditional Latin dishes, and I could have not been happier. From apps to dessert, every bite was beyond amazing.
More Places to Eat in Chicago
[Click to go to my IG Reel Reviews]
City Winery Riverwalk | Sapori Trattoria | Little Goat Diner | Osteria Del Pastaio
Tips for Planning your Trip to Chicago
We had a great time in Chicago and truly enjoyed each of the restaurants and experiences on this list, but of course, these are just ideas to get you started on planning your itinerary. Depending on the time of year you visit, where you're staying in the city, or your budget, you might want to prioritize different things than we did.
Here are some of my tips for making the most of your trip to Chicago!
Choose the best time to visit based on your preferences and priorities, considering factors such as weather, events, and crowds.
Research and decide on the neighborhoods you want to visit and stay in based on your interests and budget.
Create an itinerary of the attractions, activities, and restaurants you want to experience and prioritize them based on your interests and the time available.
Consider purchasing a CityPASS or other attraction pass to save money and skip lines at popular attractions.
Use public transportation or walk to get around the city, and download a transportation app to help navigate the routes.
Prepare for the weather by checking the forecast and packing appropriate clothing and gear.
Bring comfortable shoes for walking and exploring the city.
Try the local food specialties, such as Chicago-style pizza, hot dogs, and Italian beef sandwiches.
Discover Chicago
Chicago is definitely on my list of favorite cities EVER. It’s beautiful and clean, and there is always so much to do! The people are nice, the art and architecture are breathtaking, and the food scene is AMAZING. Honestly, I would go back again and again and probably (hopefully) live there at some point in my life.
Sincerely,
Reneze
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