Whether you're new to the area and have never been or consider yourself a seasoned visitor to Chicago, you’ll always find something new to discover. Personally, I’ve spent my childhood and young adulthood exploring downtown Chicago, and even after all these years, I still marvel at how much this city has to offer. It’s incredible how one place can hold so many attractions and activities — yet I continually find myself adding new sights to my list.
With several years of experience visiting the Windy City, I want to share a quick guide to help you capture the city’s top attractions in just 24 hours. Join me, and let’s make your weekend trip to Chicago unforgettable!
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Getting downtown:
Getting to downtown Chicago is convenient, with several transportation options depending on how you arrive. If you're flying in from out of town, you’ll likely land at one of the city’s two major airports.
Travelers flying on American, Delta, United, Spirit, or Frontier typically arrive at O'Hare International Airport, home to United Airlines’ headquarters. O'Hare is one of the busiest airports in the world, serving over 40 airlines and accommodating more than 200,000 passengers daily. From O'Hare, you can either take a 40- to 60-minute car ride into the city or opt for a faster and more affordable option—the CTA Blue Line. This train runs 24/7 and will take you directly from the airport to downtown Chicago in just under 40 minutes.
If you’re not flying into O'Hare, your other option is Midway International Airport, located on the city’s southwest side. Midway is smaller and serves around five airlines, including Southwest and Frontier, with over 300,000 passengers traveling through daily. From Midway, you can take the CTA Orange Line, which offers a direct route into the city and is a convenient way to avoid traffic.
If you’re not flying into Chicago and are staying in the suburbs, getting into the city is easy thanks to Chicago’s reliable rail systems. Depending on which direction you're coming from, you can be downtown in about an hour or less.
When traveling from the northern suburbs, I recommend taking the Metra’s North Central Service, which brings you directly to Union Station in downtown Chicago. If you're closer to the inner northern edge of the city, the CTA Red Line is a convenient alternative and runs frequently.
For those arriving from out of town by train, Amtrak is a great option. Several of its routes also arrive at Union Station, making it a central hub for both regional and national travel.
If you're coming from the South Side or nearby southern suburbs, you have a few options. The South Shore Line and the Metra Electric Line will both take you straight into downtown, arriving at Millennium Station. From there, it’s just a short walk to iconic landmarks like Cloud Gate in Millennium Park. For those closer to the inner southern areas of the city, the CTA Red and Green Lines are also efficient ways to reach downtown.
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Im Downtown — NOW WHAT?
Now that I’ve arrived in the heart of Chicago, it’s time to dive into everything this incredible city has to offer.
Chicago is famous for its rich architectural history, especially its iconic Gothic Revival style that emerged after the Great Chicago Fire of 1871, which devastated much of the city. One of the best ways to experience this architectural legacy is along the Chicago Riverwalk. Whether on foot or aboard an architectural river cruise, you’ll get a close-up view of some of the city's most historic and stunning buildings, all while learning the stories behind them.
Another great way to explore the city is by hopping on the Big Bus Chicago tour. It’s a hop-on, hop-off experience that takes you past major landmarks like the Chicago Theatre, Willis Tower (formerly Sears Tower), the John Hancock Center, and the iconic Navy Pier, home to the city’s beloved Centennial Wheel.
If you’re a history lover like me, Chicago won’t disappoint. The city is home to world-class museums such as the Field Museum and the Museum of Science and Industry. However, if you only have one day in town, I’d recommend saving the museums for another visit so you can focus on taking in the sights, sounds, and energy of downtown.
Getting Around the City Without Breaking the Bank
One of the smartest ways to explore a new city is by finding the most cost-effective way to get around—ideally without paying multiple fares throughout the day. A helpful travel tip I always follow is to check if the city offers unlimited day or weekend transit passes. These passes can save both time and money, making it easier to hop from one destination to another without worrying about individual ticket costs.
In Chicago, I highly recommend downloading the Ventra App. It’s the official app for the city’s transit system and lets you purchase CTA (bus and train), Metra, and Pace tickets directly from your phone. It’s incredibly convenient and can sometimes help you save compared to paying per ride.
If public transit isn’t your style or you want a more guided experience, I personally enjoy using the Big Bus Tours. This company operates in most major cities around the world and offers flexible ticket options—usually 24- and 48-hour passes, with add-on excursions like night tours or boat rides. In larger cities like Chicago, you may even find 3- to 5-day packages, which can be a great value if you're planning an extended stay.
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A Scenic Ride Through the Windy City
While most cities offer standard public transit systems—buses, trains, taxis, and even water taxis—some destinations, like Chicago, also feature unique and scenic ways to get around. One of my favorite ways to explore a new city is by combining convenience with sightseeing, and in Chicago, the Big Bus Tour is a perfect way to do just that.
I started my morning downtown along the Chicago Riverwalk, where I hopped on the Big Bus Chicago and headed southbound. The route takes you past some of the city's most iconic landmarks, including the grand Field Museum and the reflective beauty of Cloud Gate in Millennium Park. From there, we continued toward the Museum of Science and Industry, nestled near the Shedd Aquarium and Adler Planetarium on the lakefront’s Museum Campus.
After a quick stop to explore the sea life, vintage trains, planes, and classic automobiles, I boarded the bus again and headed back north toward Navy Pier. The ride itself was a scenic treat—on one side, the shimmering blue waters of Lake Michigan, and on the other, lush green spaces like Grant Park and the impressive Buckingham Fountain. As we cruised further north, I made sure to keep my eyes peeled for the modern wave-like architecture of the famous Aqua Tower.
Before I knew it, we were pulling up to Navy Pier—but the adventure wasn’t over yet. After strolling along the shoreline and soaking up the sun, I couldn’t resist taking a ride on the Centennial Wheel, a modern tribute to the original Ferris Wheel, which made its debut here during the 1893 World’s Fair. The views from the top? Absolutely unforgettable.
💰 Money Saver Tip: When booking your Hop-On, Hop-Off Bus Tour tickets, be sure to look for bundled deals or combo packages. Many tour companies offer discounted rates when you pair your bus ticket with other popular attractions. You can often save anywhere from $20 to $40 per person on must-see experiences like the Chicago Architecture River Cruise, Willis Tower Skydeck, and 360 CHICAGO Observation Deck at the John Hancock Center. It’s a great way to see more while spending less!
As our day in Chicago continues and the sun shines high over the city, we make our way to one of the best spots for million-dollar views and specialty drinks—the John Hancock Tower, now known as 875 North Michigan Avenue. This iconic skyscraper offers a one-of-a-kind experience at 360 CHICAGO, where you can take in panoramic views of the city and Lake Michigan from the 94th floor. Don’t forget to grab a drink at Bar 94, where you can sip cocktails while gazing out over the skyline—an unforgettable way to unwind and take in the moment.
What makes Chicago unique is that it’s home to not just one, but two world-famous observation decks. After the Hancock, we head over to the Willis Tower, formerly known as the Sears Tower, which held the title of the world’s tallest building when it opened in 1973. It was renamed the Willis Tower in 2009, but locals still often call it by its original name.
Here, you can ride the elevator up to the 103rd floor and step out onto The Ledge—a glass balcony that extends out from the side of the building. It’s a thrilling experience and the perfect photo opportunity with the city sprawling out beneath your feet.
Time to Refuel — Chicago Style
After seeing so much of the city, I was definitely starting to feel hungry—and luckily, Chicago offers no shortage of amazing places to eat. Whether you're craving something fast, iconic, or uniquely local, this city has you covered.
Of course, you can’t come to Chicago without trying the legendary deep-dish pizza. There are countless spots to choose from, each with their own loyal fan base. But if you're looking for something quick and nostalgic, head over to the iconic Rock ‘n’ Roll McDonald’s. It’s more than just a fast food joint—this location has a history all its own, and it’s just a short walk from the McDonald’s Headquarters, where you can even experience international menu items from around the world.
If you're in the mood for something truly Chicago, hop off the Big Bus at 614 N. Clark Street, right in front of the Rock ‘n’ Roll McDonald’s, and walk next door to Portillo’s. Here, you can feast on a classic Chicago-style hot dog (hold the ketchup!) or a juicy Italian beef sandwich—two staples every visitor should try. And if you're still hungry or just want something a little different, stop by Bonci nearby for some Roman-style pizza with a modern twist.
Shopping on the Magnificent Mile
After grabbing a bite to eat, I hopped back on the Hop-On, Hop-Off Bus to continue exploring more of Chicago—and the next stop was perfect for a little retail therapy. We rolled into Michigan Avenue, famously known as the Magnificent Mile, one of the premier shopping destinations in the country. I hope you brought your credit card, because between the flagship stores and seasonal sales, it’s almost impossible to leave empty-handed.
As I stepped off the bus, I was immediately surrounded by towering buildings, beautiful window displays, and the buzzing energy of shoppers from all over the world. The Magnificent Mile stretches for about 13 city blocks and is home to over 450 retailers, including high-end luxury boutiques like Saks Fifth Avenue, Neiman Marcus, and Tiffany & Co., as well as more budget-friendly favorites like H&M, Uniqlo, and Nordstrom Rack.
You’ll also find Water Tower Place, a vertical shopping mall with multiple floors of shops, restaurants, and even a theater—perfect for taking a quick break or catching a show. And if you're visiting during the holidays or a major event, the area is beautifully decorated and often hosts seasonal pop-ups and street performers that make the experience even more festive.
Whether you're looking for a fashion upgrade, a souvenir to take home, or just want to do a little people-watching from a sidewalk café, the Magnificent Mile is an essential stop on any Chicago itinerary..
As the afternoon sun casts a golden glow across the city, I hop aboard the Hop-On, Hop-Off Bus one last time to make my way back toward the Chicago Riverwalk. My final stop of the day? A relaxing and unforgettable architecture boat tour—a must-do experience for any visitor to the Windy City. But before we reach the water, there’s still a bit more of Chicago’s magic to soak in.
Our bus winds through a few more city blocks, giving me a chance to admire the rhythm of downtown life—street performers on the corners, people walking briskly between meetings or lingering over coffee on sidewalk patios. We make a memorable stop at one of the city's most iconic landmarks: the Chicago Theatre. Its famous red and gold marquee sign glows like a beacon, and I can’t resist snapping a few photos. Built in 1921, this theater is not only an architectural gem with its French Baroque-style interior, but also a cultural icon that has hosted some of the biggest names in entertainment for over a century. Even if you don’t catch a show, just standing in front of it feels like an experience in itself.
As we continue our route, I begin to notice the city’s vibrant public art scene coming to life. Chicago isn’t just about steel and glass—it’s a living canvas. Murals stretch across building walls, sculptures dot public plazas, and even alleys seem to hold hidden creative gems. We pass by works from celebrated artists like Pablo Picasso (his massive untitled sculpture in Daley Plaza), Marc Chagall, and Jean Dubuffet, as well as contemporary pieces that change with the season. The city takes pride in making art accessible to everyone, and it shows.
Eventually, we arrive at the Chicago Riverwalk, one of the city’s most beloved gathering spots. This beautifully designed, pedestrian-friendly promenade stretches for 1.25 miles along the south bank of the Chicago River, filled with restaurants, wine bars, kayak rentals, and plenty of seating to relax and people-watch. It’s the perfect place to take a breath, cool off by the water, and prepare for one of the most awe-inspiring experiences the city has to offer.
From Land to Water: Exploring Chicago’s Iconic Skyline by Boat
Now that we’ve explored the city by land, it’s time to see it from a whole new perspective—by water. We make our way down to the water’s edge, where we join the waiting line to board one of the many Architecture River Boat CruisesChicago is known for. Several companies, such as Chicago's First Lady Cruises, Wendella Boats, and Mercury Chicago’s Skyline Cruiseline, offer these exceptional tours. As we set off, the cool breeze off the water feels refreshing, and we’re greeted with sweeping views of the Chicago River, lined with some of the city’s most iconic buildings.
The cruise takes us past architectural masterpieces like the Willis Tower (formerly Sears Tower), the stunning Tribune Tower, and the elegant Wrigley Building, each offering a glimpse into Chicago’s rich architectural history. Our knowledgeable guide explains how different styles—Art Deco, Gothic Revival, and sleek modern designs—have shaped the city’s evolution, and how each building tells a unique story of resilience, innovation, and vision. It’s a fascinating experience that brings the city’s history to life, layer by layer.
If you're craving a deeper dive into Chicago’s architectural legacy, head back to Navy Pier and climb aboard the Lake Michigan Lake Architecture Cruise offered by Shoreline Sightseeing or Chicago’s First Lady Cruises. This extended tour will take you around both the northern and southern sections of the city’s stunning skyline, offering an even more expansive view of Chicago’s towering structures. From the John Hancock Center to Aqua Tower, you’ll have ample opportunities to snap breathtaking photos and marvel at how the city has grown over the decades.
The cruise not only provides another stunning angle on the skyline but also enriches your understanding of how lakefront development and architectural innovation have worked hand in hand to shape Chicago into the world-class city it is today.
Personal Travel Tip: Choosing the Best Boat Tour in Chicago
When it comes to Chicago’s famous architecture tours by boat, two of the most popular and reputable tour companies you’ll encounter are Shoreline Sightseeing and Wendella Tours. On average, tickets for these tours will cost around $45.00 for adults and $15.00 - $20.00 for children.
Having experienced both the river tour and the lake shore skyline tour separately, I can tell you that it really comes down to what kind of views you prefer. The river tour provides an in-depth look at the city’s diverse architectural styles, giving you a closer view of the iconic buildings that line the Chicago River. On the other hand, the lake shore cruiseoffers a breathtaking panoramic view of the entire skyline, allowing you to take in the full scope of the city’s towering structures from the water.
If time is a concern and you have to choose just one, Wendella Tours offers a combo cruise that covers both the river and lake shore skyline all in one trip, which is a great option if you're looking for an overview of both perspectives. However, if you have the luxury of time, I highly recommend doing both tours separately. This way, you can truly appreciate the unique features each one offers without feeling rushed.
For more information check out these links below for pricing and booking.
https://shorelinesightseeing.com
https://www.wendellaboats.com/Boat-Tours/chicagos-original-architecture-tour/
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The Guide Book’s Personal Favorite Spots to Shop, Stop, and Eat While Downtown Chicago
Once back on dry land, no trip to downtown Chicago is truly complete without making stops at some of my personal favorite spots—places that offer a little bit of everything: unique shopping, delicious food, and iconic landmarks. If you’re looking to make the most of your time in the Windy City, here are a few must-see destinations that should definitely be on your list.
Fannie May – A Sweet Stop in Chicago
For anyone with a sweet tooth that’s impossible to satisfy, Fannie May is a must-visit. It’s a personal tradition of mine to stop by this iconic Chicago chocolate shop, located just beneath the Chicago Blackhawks Ice Hockey Team Store at the corner of North Michigan Avenue & East Wacker Drive. The moment you step inside, you're welcomed by the rich aroma of handcrafted chocolates, which never fails to make me smile.
Fannie May offers a wide variety of premium chocolates, each crafted with care and attention to detail. Their selection includes everything from classic chocolate bars to luxurious truffles, and they even offer unique treats like caramel-infused chocolates, chocolate-covered nuts, and chocolate-covered fruits. You can choose from their ready-made selections, including their famous Chocolate-Covered Caramels, Pixies® (a delicious blend of caramel, pecans, and milk chocolate), and Mint Meltaways. These items are consistently customer favorites, and once you try them, you’ll understand why.
If you’re craving something more personalized, you can create your own custom chocolate box. Simply choose from a wide variety of fillings, from milk and dark chocolates to creamy pralines, chocolate-covered marshmallows, and even chocolate-dipped pretzels. This is the perfect way to sample a little bit of everything or to create a gift that will impress anyone with a sweet tooth.
For those looking for something a little less traditional, Fannie May also offers seasonal treats, including special holiday-themed chocolates and gift baskets filled with an assortment of their finest offerings. They also sell chocolate-covered strawberries, perfect for a romantic treat or a special celebration.
With chocolates that are as rich in history as they are in flavor, Fannie May is the perfect place to satisfy your cravings and pick up a souvenir that’s truly delicious.
Chicago Architecture Center – A Haven for Architecture Enthusiasts
As someone who has always been fascinated by architecture, I simply can't pass up the opportunity to step inside the Chicago Architecture Center (ACA). If you're like me and have an appreciation for the science and artistry behind how buildings stay standing tall, then this place is an absolute must-see.
The Chicago Architecture Center offers a deep dive into the history, design, and engineering of Chicago's iconic skyline. With exhibits that explore both the historic and modern architecture that define the city, visitors get a comprehensive look at how Chicago became a global architectural hub. Whether you're interested in the innovative techniques that helped shape skyscrapers or curious about the stories behind famous buildings, the ACA has something for everyone.
Inside the ACA, you’ll find a stunning architecture model gallery, featuring intricately detailed scale models of Chicago’s most famous landmarks like the Willis Tower, John Hancock Center, and Aqua Tower. This is a great place to understand how the city evolved architecturally and see the designs up close.
The ACA also offers interactive exhibits that delve into the materials and engineering that make these structures stand tall and endure through time. One of my favorite exhibits is the section dedicated to Chicago’s unique contribution to the world of skyscrapers, especially the Birth of the Skyscraper exhibit that highlights how Chicago led the way in skyscraper innovation.
Architecture Tours:
For those who want to take their exploration to the next level, the ACA offers a variety of architecture tours that will take you into the heart of the city. You can board a Chicago Architecture Foundation River Cruise, where knowledgeable guides point out the various architectural styles along the river while telling the stories behind the city’s most iconic buildings. If you prefer walking tours, the ACA offers those as well, where you can get a more up-close look at the details of the buildings and how Chicago’s history shaped its urban landscape.
Events and Lectures:
Beyond the exhibits, the ACA hosts lectures, workshops, and special events that explore topics ranging from sustainable design practices to the future of urban planning. If you’re in town during a special event or lecture, don’t miss the opportunity to learn from some of the most influential figures in the field of architecture
The McDonald's Headquarters – A Unique Experience in the Heart of Chicago
While nearly every McDonald’s location across the United States offers the same familiar menu, there’s one special spot in Chicago that truly stands out. The McDonald’s Headquarters, located in the heart of downtown, offers a unique experience that goes beyond just grabbing a quick meal.
At the center of it all is Hamburger University, a fascinating training ground where general managers from all over the world come to learn the ins and outs of what it takes to run a McDonald’s restaurant. I had the chance to walk through the campus, and it’s incredible to see how much effort McDonald’s puts into making sure each store operates at its best. The university is not only about teaching operational skills but also about instilling the brand’s values and ensuring the next generation of leaders is ready for success. If you’re lucky enough to see a training session in action, it’s an eye-opening experience!
But the excitement doesn’t end there. The McDonald’s Headquarters is also home to the Global Menu, an exclusive collection of menu items that you can’t find anywhere else in the U.S. This global food offering allows customers the chance to sample a selection of items from around the world. I personally loved trying the McSpicy Chicken from Singapore, and the Poutine from Canada was a hit as well. It's not every day you can get a taste of international McDonald’s innovations, and trust me, they don’t disappoint.
If you’re a fast-food aficionado or simply curious about McDonald’s role in global culture, a visit to their Headquartersin Chicago is an absolute must. It’s a blend of history, food, and fun – all wrapped up in a truly one-of-a-kind experience.
Millennium Park – A Must-See in the Heart of Chicago
No trip to Chicago is truly complete without a stop at Millennium Park, a vibrant space in the heart of the city that’s home to some of its most iconic landmarks. While the park is most famous for the Cloud Gate, affectionately known as "The Bean," it offers so much more to explore.
As you stroll through the park, make sure to stop for a photo op at the Crown Fountain, an interactive display featuring two 50-foot glass towers that project video images of Chicagoans’ faces. The fountain's playful water jets make it a popular spot, especially during the summer months when kids run through the sprays.
Another highlight is the Jay Pritzker Pavilion, an impressive band shell designed by architect Frank Gehry. This architectural marvel hosts free concerts and performances during the warmer months, making it a great place to relax and enjoy some live music.
For those seeking a quieter, more peaceful experience, Lurie Garden offers 3.5 acres of beautifully landscaped trails, lush greenery, and vibrant flowers. It’s the perfect place to unwind and enjoy nature, even in the midst of the bustling city. The garden’s design is inspired by Chicago’s natural landscape, blending modern aesthetics with elements of the city’s historic roots.
Millennium Park truly captures the spirit of Chicago – a place where art, nature, and urban life come together in a stunning display. Whether you're taking in the architecture, snapping photos of the Bean, or simply enjoying the green spaces, this park is a must-visit for any traveler.
Navy Pier – Fun for the Whole Family
For those traveling with young children, Navy Pier is the perfect destination to keep everyone entertained for hours. As you approach the pier, you’ll immediately notice the Chicago Children’s Museum, a fantastic spot filled with interactive exhibits and hands-on activities that will captivate kids of all ages. It’s the perfect place for little ones to learn and play while having fun.
Navy Pier is also home to a variety of restaurants and local shops, so there’s plenty to explore as you stroll along the pier. Here are some of the top spots to eat and shop at while you’re there:
Top Places to Eat:
Riva Crab House – Located right on the water, Riva offers fresh seafood and stunning views of Lake Michigan. Expect to spend around $25 to $50 per person for a meal here.
Giordano’s – Known for its famous Chicago deep-dish pizza, Giordano’s is a must-visit for pizza lovers. A deep-dish pizza typically costs around $20 to $35, depending on the size and toppings.
Sugar Factory – If you have a sweet tooth, don’t miss Sugar Factory, where you can indulge in over-the-top desserts, milkshakes, and candy. Expect to spend around $15 to $25 per person for a treat here.
Navy Pier Beer Garden – For something more relaxed, head to the Beer Garden for craft beers and light bites. A typical beer here costs around $7 to $10, and snacks range from $5 to $15.
Top Places to Shop:
The Pepsi Wave Swinger – Not just a ride, but also a great spot to shop nearby. As you walk around Navy Pier, you’ll find a variety of charming local boutiques selling unique souvenirs, artwork, and Chicago-themed products. Most souvenirs range from $5 to $50.
Navy Pier Mercantile – This shop offers a range of gifts, from Chicago memorabilia to jewelry and apparel. Expect to spend around $10 to $50 for a souvenir.
The Pier Park Store – Located near the Ferris wheel, this shop features an assortment of trendy apparel and accessories, perfect for those wanting to take home a stylish keepsake. Prices typically range from $20 to $60 for apparel and accessories.
One of the biggest attractions at Navy Pier is the Outdoor Pier Park, where you’ll find the 300-foot-tall Ferris wheel. This iconic ride offers stunning bird's-eye views of the city, Lake Michigan, and beyond. Tickets for the Ferris wheel are typically around $20 per person.
If you're planning to spend a day at Navy Pier, expect to spend anywhere from $100 to $300, depending on the activities you choose. In addition to the Ferris wheel, there are plenty of other fun attractions, including the Chicago Shakespeare Theater, the Crystal Gardens, and the Family Funhouse. Whether you’re riding the Ferris wheel, enjoying some entertainment, or simply taking in the sights, Navy Pier offers a fun-filled day for the whole family.
Where to Stay:
The London House Hotel - Chicago, IL
For a truly immersive experience, consider staying at Sable at Navy Pier, the only hotel located directly on the pier. Room rates typically start around $200 to $300 per night for a standard room, depending on the season and availability. This modern hotel offers stunning views of Lake Michigan and the Chicago skyline from every guest room. Each room is equipped with floor-to-ceiling windows, 55” LG Smart TVs, and a mini-fridge. Guests can enjoy in-room dining from the on-site Lírica Restaurant, which serves Latin-inspired cuisine, with entrée prices ranging from $15 to $30. Alternatively, grab a drink at Offshore, the world’s largest rooftop bar. Cocktails here typically cost around $12 to $18.
Amenities include a fitness center with Peloton bikes, free Wi-Fi, and concierge services. The hotel is within walking distance of all Navy Pier attractions, making it a convenient base for your adventures.
Navy Pier Chicago, IL
Finding the Perfect Slice of Chicago Pie
Growing up between the Midwest and the southern part of the United States, I’ve had my fair share of pizza styles, from New York’s thin crust to the thick, hearty layers of Chicago’s deep dish and stuffed crust pizzas. While many claim that New York pizza reigns supreme (and I’ll admit, it does have its merits), there’s something undeniably special about a slice of Chicago deep dish pizza. Packed with layers of gooey cheese, savory toppings, and rich tomato sauce, it’s an experience every pizza lover should have.
If you're visiting Chicago, there are two places I highly recommend for an unforgettable deep dish pizza experience: Giordano's and Lou Malnati’s Pizzeria. These two iconic spots have been serving up perfectly crafted deep dish pies for years, and they never disappoint.
Giordano's – Located at multiple locations around the city, including a popular spot at 730 N Rush St, Chicago, IL, Giordano’s is famed for its stuffed deep dish pizza, which has become synonymous with Chicago-style pizza. Expect to pay around $18 to $30 for a medium-sized pizza (feeds 2-3 people), depending on the toppings you choose. The buttery crust, layered cheese, and savory sauce make this a must-try while you're in town. Keep in mind, it can take around 45 minutes to an hour to cook, but it's definitely worth the wait.
Lou Malnati’s – Another legendary deep dish pizzeria, Lou Malnati’s has locations throughout the city, including one at 1121 N State St, Chicago, IL. Famous for its buttery, flaky crust and flavorful sausage, a Lou Malnati’s deep dish pizzatypically costs between $20 and $35 for a medium pizza. If you’re really hungry or dining with a group, go for the large, which can run you between $30 and $40. I recommend trying their Malnati Chicago Classic, which is packed with fresh mozzarella, vine-ripened tomatoes, and a special blend of sausage.
Both Giordano's and Lou Malnati’s offer delivery and carryout options, but nothing beats sitting down in one of their welcoming locations and enjoying a fresh, hot slice. Whether you’re a first-timer or a seasoned pizza lover, Chicago’s deep dish pizza will change your perception of what pizza can be. Just don’t be surprised if you end up ordering more than one slice—you won’t be able to resist!
Portillos Chicago, IL
Local Top Places to Wine & Dine
While downtown in the city, if pizza and hotdogs aren’t your thing, here are a few other eateries to try out.
Ocean Prime Chicago
For those craving a fine dining experience by the Riverwalk, Ocean Prime is a standout choice. Located on the first floor of the LondonHouse Hotel at 87 E Wacker Dr, this upscale steak and seafood restaurant combines modern elegance with fresh, expertly prepared dishes. Ocean Prime offers an extensive menu, including fresh seafood selections like Chilean Sea Bass ($60), Lobster Linguine ($59), and a variety of steaks such as the 8 oz Filet Mignon ($62) and 16 oz Ribeye ($70). If you're looking to indulge in both steak and seafood, expect to spend about $150 for a full meal with both options, or anywhere from $30 to $70 per person depending on your choices.
Ocean Prime also has a fantastic selection of sides like Parmesan Truffle Fries ($15), Black Truffle Mac & Cheese ($18), and a range of seafood appetizers. For those looking to enjoy a drink with their meal, the wine list is diverse, with options such as Chardonnay, Far Niente, Napa Valley, 2022 ($43) or Cabernet Sauvignon, Chimney Rock, Stag’s Leap District, 2019 ($65 per 3 oz pour).
Estimated cost per person: Around $130 for a complete meal (appetizer, entrée, side, and drink).
If you're in the mood for a refined dining experience with stunning river views, Ocean Prime offers just that. It's a great option for those looking to enjoy a sophisticated atmosphere paired with delicious food.
For more details, visit Ocean Prime Chicago.
https://ocean-prime.com/locations-menus/chicago/menus/
ADDRESS: 87 E Wacker Dr, Chicago, IL 60601
Burgers, Sports, & Beer: Doc B’s
Located at 55 E Grand Ave, Chicago, IL 60611 in the vibrant River North neighborhood, Doc B’s is the perfect blend of casual dining and elevated flavors. Known for its relaxed yet lively atmosphere, this spot is a go-to for anyone craving a hearty meal, craft cocktails, and a great beer selection. Whether you're a sports fan catching a game or someone simply looking to enjoy good food in a welcoming environment, Doc B’s delivers.
Their extensive menu features a variety of options, ensuring there’s something for everyone. Some standouts include their Classic Cheeseburger ($16), which is always juicy and perfectly cooked, and the Grilled BBQ Chicken Sandwich($17) that’s packed with flavor. For those seeking a lighter option, the Kale & Quinoa Salad ($14) or Ahi Tuna Poke Bowl ($18) offer fresh and healthy alternatives. If you’re in the mood for something more indulgent, their Lobster & Shrimp Roll ($22) is an absolute must-try, bursting with rich flavors and perfectly seasoned seafood.
But the appeal of Doc B’s isn’t just the food—it’s also their selection of craft cocktails and beers. With an extensive list of local and international brews, alongside signature cocktails like the Strawberry Basil Smash ($14) and Peach Mule($12), you’ll always find something to complement your meal. Whether you’re there for a casual night out or an afternoon hangout, the atmosphere makes it easy to sit back, relax, and enjoy the game on one of their multiple screens.
Estimated cost per person: Expect to spend around $50.00 - $60.00 per person, including tip, for a satisfying meal and drinks. For a group outing or a casual gathering, Doc B’s is a great choice, especially if you’re in the mood to indulge in some classic American comfort food with a twist.
Rooftops and Views: Cindy’s Rooftop
Saving the best for last, Cindy’s Rooftop is a must-visit spot for those looking to experience Chicago from above. Located at 12 S Michigan Ave, Chicago, IL 60603, this rooftop restaurant offers breathtaking views of Lake Michiganand Millennium Park, including the iconic Cloud Gate (The Bean). Whether you’re there for brunch, lunch, or dinner, Cindy’s provides an elevated experience with views that will leave you speechless.
The ambiance at Cindy’s is perfect for a relaxing meal while taking in the stunning skyline and lake views. The space is chic and modern, yet inviting, making it ideal for a special night out or a laid-back afternoon. Their menu offers a range of elevated American dishes, with fresh, seasonal ingredients. You can enjoy dishes like the Avocado Toast ($16), Lobster Roll ($26), or the hearty Buttermilk Fried Chicken ($24). For brunch, you might indulge in their Cindy’s Pancakes($14) or a Brunch Burger ($18).
Cindy’s offers a full bar with a fantastic selection of cocktails, craft beers, and fine wines, so it’s a perfect spot to unwind. Whether you're savoring the food, sipping a refreshing cocktail, or just soaking in the views, it’s a place you’ll want to make sure to check off your Chicago itinerary.
Estimated cost per person: Expect to spend around $40.00 - $60.00 per person, depending on what you order and if you opt for drinks as well. The combination of delicious food, outstanding service, and incredible views makes it a spot worth the investment.
For more information, visit Cindy’s Rooftop.
cindysrooftop.com
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Chicago is one of those cities that can feel completely different depending on how you choose to experience it. From the rumble of the ‘L’ overhead and the glass-and-steel canyon of the Riverwalk to deep-dish pizza, Lake Michigan and one of the greatest skylines in the country, you could spend a week here and still barely scratch the surface. But if you've only got 48 hours, you can see an incredible amount — and hopefully this guide gives you a place to start.