A Travel Guide to Chicago: Explore, Indulge & Unwind in the Windy City

After visiting the city three times, I can confidently say Chicago has a special place in my heart. Whether you're returning again for the immaculate river views or visiting for the first time to indulge in its legendary food scene, this itinerary is sure to provide you with tried and true recommendations for experiencing Chicago authentically, including the best things to do, where to eat, where to stay, and how to navigate the city.

I don't always set out in search of new perspectives, but sometimes the right moment finds you unexpectedly, and sometimes from 103 floors above the city. During this trip (which happens to be my very first media trip..ahhhh!), my intention was all about exploring the city’s iconic attractions, relaxing into wellness, and indulging in the local culture and most talked about food scene.

Getting to Chicago

I flew American Airlines direct from Atlanta to O'Hare. Chicago has two major airports, O'Hare, the larger, busier airport and Midway, a smaller airport closer to Downtown. O'Hare to Downtown (The Loop) is about a 30 to 45-minute drive or a 45-minute ride on the Blue Line using CTA, Chicago's transit system, which runs 24/7 and costs only $5.

Best Things to Do in Chicago

SkyDeck Chicago: A New Perspective From the Top

A visit to Skydeck Chicago at the Willis Tower (affectionately still referred to as Sears Tower by Chicago natives) was sure to be on my list to see the city from the top.

We were guided through a museum exhibit beautifully highlighting the history of the Willis Tower and the vibrant, layered story of Chicago itself. From legendary architecture to deep-dish pizza, it was like walking through a tribute to everything that makes this city bold and beloved.

Then came the elevator ride. As we ascended, my ears popped with the altitude—but my anticipation grew stronger with every floor. And then, the doors opened.

It’s hard to explain the feeling when you step out onto the 103rd floor and see the skyline stretch endlessly before you. The city I’d spent days walking through suddenly felt miniature. The cars, the buildings, even the people—all of it seemed to shrink from this vantage point. In that moment, I felt awe. I wasn’t just looking out at Chicago—I was looking down at it, gaining perspective on just how small we all are in this vast, beautiful world.

The Color Factory Chicago: In Living Color

This was my favorite exhibit and definitely worthy of a visit during your time in Chicago. We experienced color in a whole new way at Color Factory Chicago, where every sense was invited in. We saw, smelled, heard, tasted, and even touched color through a series of fun, immersive exhibits. As someone who loves astrology and metaphysics, the Colorscopes room was my favorite — they had different colors and personality attributes based on your birthdate, which felt so aligned with my vibe. Every corner sparked joy and creativity, and it fit perfectly into the theme of my trip: staying present and seeing the world through fresh eyes. Throughout the entire experience, we used personalized QR codes to snap fun photos at all the different photo ops. If you're looking for a playful, one-of-a-kind stop while exploring Chicago, Color Factory needs to be on your list. From celebrating in the confetti room, where every photo felt like a celebration, to the nostalgic ball pit that took us right back to childhood, Color Factory was pure, colorful fun from start to finish.

Koval Distillery: Organic Spirits Forging Ahead

We tasted a variety of organic, handmade spirits after learning about the rich history of Koval, meaning "one who forges ahead." If you’re looking for a unique stop in North Chicago, a visit to KOVAL Distillery is a must. As the first distillery to open in the city since Prohibition, KOVAL lives up to its name — meaning "one who forges ahead." They specialize in organic, handmade spirits, and we got to taste a variety of them, from smooth gin to rich whiskey and bourbon. We received a private tour and tasting, learning about the detailed, high-quality distillation process. After the tasting, we enjoyed the sunny 75-degree weather on their cozy patio. If you go during weekly happy hour (4–6 PM), treat yourself to a cocktail — I had the “Send It to Georgia” made with pear brandy and a kick of Thai chili, while my cousin tried the frozen cranberry negroni. It’s the perfect spot to sip, relax, and learn a little about Chicago’s spirited history.

Of course, no trip to Chicago would be complete without hitting a few more city favorites. Make time for a stroll along the Riverwalk. If you want to get on the water, hop on an architecture boat tour for a beautiful view of the city’s iconic skyline. (Pro tip: if you’re looking for a budget-friendly option, the water taxi gives you a similar view for less than $20.) Millennium Park, Navy Pier, and exploring the historic neighborhoods of Hyde Park and Bronzeville are also top picks to round out your Chicago experience. There's truly something for everyone in this vibrant city!

Where to Stay in Chicago

When choosing a place to stay in Chicago, River North is a top pick. Situated in the Loop district, this area is close to iconic Chicago landmarks like the Magnificent Mile, Millennium Park, and the Chicago Riverwalk, making it an ideal base for exploring the city. If you’re looking for a blend of historic charm and modern luxury, I highly recommend Palmer House Chicago. I was invited for a stay and experience at The Spa at Palmer House during my trip. As the longest-operating hotel in Chicago, it offers a truly elegant and immersive stay. The hotel’s rich history, from surviving the Great Chicago Fire, being the birthplace of the brownie, to becoming a staple of luxury for over 140 years, creates an atmosphere that’s as inspiring as it is relaxing. It's the perfect place to unwind after a day of sightseeing while soaking in the beauty and legacy of this iconic Chicago gem.

West Loop is perfect for the foodies. If your trip revolves around trying great restaurants and bars, you’ll be right at home here. We visited Moneygun/Sunnygun for happy hour and it was incredible — cozy vibes and great drinks. Nearby, you’ll also find Time Out Market, a lively food hall featuring some of the best bites Chicago has to offer, all under one roof.

Lincoln Park is ideal if you're traveling with kids. The neighborhood is home to the beautiful Lincoln Park Zoo (which is free!) and several museums, plus wide green spaces perfect for a family outing or a relaxing stroll.

Wicker Park offers a more eclectic, artsy vibe. It’s a great pick if you love browsing through art galleries, digging through record shops, and hanging out at unique cafés. If you’re looking for a cool night out, check out Dorian’s — a hidden speakeasy tucked behind a record store. They host weekly jazz nights and offer happy hour from 6–8 PM most days, creating the perfect cozy-cool atmosphere for a night in the city.

Wherever you choose to stay, each neighborhood brings its own charm — making it easy to find a home base that matches your travel style.

Where to Eat in Chicago

This might just be my favorite part of the entire trip — because if there's one thing about me, it’s that I LOVE to eat! And let me tell you, I knew I came to the right place. Chicago's food scene is truly unmatched, with flavors for every craving and vibes for every mood.

Let's start with the Chicago staples.We had to make a stop at Portillo’s for the iconic Chicago-style hot dog (no ketchup, of course!) and their dipped Italian beef sandwiches with cheese sauce on the side for the full experience. Another must-try was Giordano’s, famous for their deep dish pizza. While deep dish isn't my absolute favorite, I was surprised by how much I loved their tavern-style pizza — thin, crispy, and honestly, it stole the show for me.

Over in Hyde Park, we explored the soul of the city through food. Virtue serves up elevated soul food that tastes like home but with an upscale twist. Then we popped into Bodega for happy hour, where they serve $5 margaritas and the most delicious-smelling wings I regret not ordering! If you're in the area, don’t make the same mistake — get the wings!

We also had to try Small Cheval, the little sister of the famous Au Cheval, known for serving up one of the most talked-about burgers in Chicago. Simple, classic, and absolutely worth the hype.

Honestly, I need another trip back JUST to eat my way around the city. Chicago’s food scene is truly a journey in itself, one I’d happily take again and again.

Know Before You Go

Do not drive if you don't have to — especially downtown. As someone from Atlanta (with very chaotic drivers), I still wouldn't dare drive in Chicago. I highly recommend relying on public transportation. Download Google Maps before you arrive — it's truly that girl for real-time, detailed transit directions, and it'll make getting around the city a breeze. The trains and buses are reliable, usually on time, and perfect for navigating without getting stuck in downtown traffic.

If you're budget-conscious, definitely opt for the train over Uber or Lyft, especially for trips to and from the airport, where rideshares can get really pricey. You can purchase a CTA pass that works for both trains and buses across the city. On our way out of Chicago, we didn't have time to take the train and ended up grabbing a taxi from the hotel — it cost $65 compared to Lyft, which was surge priced over $100! Public transit will seriously save you money and time.

Wear walkable shoes! Chicago is a very walkable city, and you’ll definitely rack up the steps. Trust me — please don’t be like me and wear heels while hopping between tours and events. I was stylish and cute, but the pain was not worth it.

The Red and Blue Lines run 24/7, but late at night you may encounter some unpredictable characters or homeless individuals on the trains. Just stay mindful of your surroundings — same as you would in any major city.

They don't call it the Windy City for no reason! Dress in layers and don't forget your gloves. Even during the summer, especially downtown between the tall buildings, you might get hit with a strong breeze. Pack a light jacket to layer just in case!

Lastly, if you have a packed schedule with reservations, tours, or events, plan your commute ahead of time. Chicago’s transit is amazing, but you'll want to account for time between transfers and possible delays during peak hours.

I hope this Chicago travel guide gave you all the inspiration (and practical tips) you need for your next adventure to the Windy City! Whether you're a first-time visitor or a returning traveler, Chicago truly has something special to offer at every turn. If you’re looking for even more travel inspiration, be sure to check out my Puerto Vallarta, Mexico travel guide and explore other destinations filled with tips, insights, and real experiences. Thanks for trusting me to help you plan your next getaway — keep traveling, keep shifting, and keep seeing the world in new ways!