This blog may contain affiliate links. Read our disclosure policy for more info.
Planning a trip to Chicago? You’re in the right place!
We’ve spent plenty of time in the Windy City and can confidently say it’s one of the best U.S. cities to explore. With its legendary food scene, iconic architecture, buzzing neighborhoods, and rich history, Chicago offers a little something for everyone. But with so many amazing experiences to choose from, it can be tough to narrow things down!
That’s why we created this detailed 3-day itinerary to help you see the very best of Chicago. From deep-dish pizza and skyline cruises to famous museums and hidden gems, this guide is packed with can’t-miss moments. Let’s dive into the ultimate 3-day Chicago adventure!
Don’t Miss Out On Our Top Choice!
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did was this food and walking tour of Chicago! Not only did we learn about the city’s most famous sights, but we also found the best hot dogs, deep dish pizza, and sweets.
Check out the 1,400+ 5-star reviews and book this tour here!
Itinerary Overview
Three days in Chicago might fly by, but we guarantee the itinerary below will pack in iconic sights, unforgettable eats, and nonstop fun. From deep-dish pizza and skyline cruises to world-class art and mobster history, this itinerary is the perfect mix of classic and cool. Here’s a quick look at what’s in store for your time in the Windy City.
Note: Traffic in Chicago is not great. And while ride shares like Uber are available, it can often take you a long time (and a lot of money) to get around the city. Luckily, Chicago has a great public transit system called the “L” that can get you almost anywhere. While Chicago is safe during the day, we also think it’s smart to bite the bullet and pay for ride shares after dark instead of walking around or using public transportation.
Day 1: Your first day in Chicago starts with this famous sights and food walking tour. Afterwards, you’ll cruise down the river and learn all about the city’s revolutionary architecture on an architecture cruise with over 13,000 5-star reviews. And you still have Wicker Park, dinner, and a comedy show!
Day 2: Start day 2 by visiting the Art Institute of Chicago, then follow it up with incredible views of the city at the Willis Tower SkyDeck. To top it all off, you’ll end the day on a sunset cruise of Lake Michigan.
Day 3: On the final day, you will learn all about Chicago’s notorious gangs on a mobster history tour. Then you get to spend the afternoon biking around or kayaking on Chicago’s Lake Michigan before heading to the Fulton Market District for dinner and drinks.
Day 1
Breakfast – Ralph’s Coffee
We recommend starting your first morning in Chicago with a stroll down the iconic Magnificent Mile, one of the most famous streets in the city. Since you have a food tour coming up later, skip breakfast and just grab a quick coffee at Ralph’s Coffee, which is tucked inside the Ralph Lauren store. With coffee in hand, make your way down the Magnificent Mile towards the Plaza of the Americas (where the tour begins at 11:30 am) and get a great first glimpse of Chicago’s incredible architecture.
Morning – Experience Chicago’s best sights and foods on a walking and tasting tour
Chicago is a city that knows how to eat—and how to impress with its architecture—and this food tour is proof of that! There’s a good reason it’s our top pick activity in the city.
We loved visiting local hotspots to indulge in the city’s most iconic dishes, while soaking up some of its most legendary landmarks. As we wandered from bite to bite, we passed architectural gems like the historic Chicago Theatre, the elegant Palmer House, and the striking modern skyline that lines the river. It felt like the perfect mix of foodie adventure and sightseeing tour in one.
Honestly, the pizza alone is worth booking this tour for! I know that Chicago pizza divides opinions, but I loved it. For me, the thick, buttery crust and layers of gooey cheese really hit the spot. You’ve got to try it while you’re here and see what you think!
I also enjoyed re-strolling down the city’s Magnificent Mile, where we visited a classic hot dog stand and got to taste a true Chicago-style dog—beef frankfurter, loads of pickled toppings, and absolutely no ketchup (Chicagoans are serious about that!).
What surprised us most was how many iconic sights we saw along the way. From Millennium Park and the famous Bean to charming downtown streets and historic hotels, the tour doubles as a sightseeing walk through some of the city’s most beloved landmarks. We even stepped inside the gorgeous Palmer House Hilton, where we sampled their famous brownie—a recipe that’s been delighting guests since the 1890s.
As a bonus, the tour includes a free two-hour kayak or bike rental that you can use within three days. We planned ahead and scheduled ours for later in the trip, which was such a fun perk. And of course, a big shoutout to our guide Jeff—he was charismatic, engaging, and clearly loves sharing Chicago with visitors.
Reserve this popular tour here and get FREE cancellation 24 hours before you go!
Afternoon – Learn about Chicago’s top sights on an architecture cruise
After that incredible food tour, you’ll need to walk off some of that hot dog and pizza so you don’t fall into a food coma (I would know). Fortunately, our next activity, this architecture cruise, starts about a 20-minute walk from where the food tour ends. Just make sure you put down that you want to be picked up at the Michigan Ave meeting point since there are several options. Book the 3:15 pm option so you have time to walk there.
As for the tour? Let’s just say it was really difficult not to put this as our top choice, so we decided to just sneak it in after. It takes a subject some might dare call boring and makes it absolutely fascinating. This is an essential experience for anyone interested in the city’s rich architectural history.
As we went along the river, our expert guide Kevin narrated the evolution of Chicago’s skyline, highlighting over 40 notable buildings, including the Wrigley Building, John Hancock Center, and the Willis Tower. The tour covers all three branches of the Chicago River, offering a comprehensive view of the city’s architectural diversity.
Beyond the impressive structures, the cruise dives into pivotal moments that shaped Chicago’s architectural identity. You’ll learn about the Great Chicago Fire of 1871 and how it led to innovative building techniques, like balloon-frame construction, propelling the city to become a cradle of modern American architecture. The unique perspective from the river allows for an appreciation of details often missed at street level.
Whether you know nothing about architecture or came to Chicago exclusively for it, everyone will love this cruise as it offers a captivating blend of history, design, and storytelling. And with tens of thousands of 5-star reviews were not the only ones that feel this way!
Check availability and book this cruise here!
Late Afternoon – Head to Wicker Park
After your river cruise wraps up on Michigan Avenue, it’s the perfect time to explore one of Chicago’s coolest neighborhoods: Wicker Park. From the tour drop-off point, just walk to Grand Station and hop on the Red Line L—Wicker Park is only a short ride away. This artsy, bohemian area is known for its colorful street art, art galleries, and a great mix of vintage shops and trendy boutiques. It’s the kind of place where you can sip craft coffee, stumble across a pop-up art show, or catch a live music performance all in the same afternoon.
Here are some notable things you can find in the area:
- Myopic Books – This iconic used bookstore is a maze of shelves stacked floor to ceiling with everything from rare finds to popular fiction. It’s cozy, quirky, and perfect for book lovers who could easily lose an hour (or three) browsing.
- The Flatiron Arts Building – This eclectic and inventive art center is a prime example of Wicker Park’s trendy vibes. It’s open until 10 pm, so we loved exploring the local art galleries and seeing what live performance was taking place. There’s always something happening here!
- Milwaukee Avenue – This bustling strip is the heart of Wicker Park’s charm. You’ll find record shops, thrift stores, coffeehouses, and stylish boutiques tucked along the street—ideal for casual exploring and people-watching.
- Murals – There is plenty of street art around, so you can take a self-guided tour to see some of the best! The Vivian Maier Mural is one of the most famous, and the Greetings from Chicago mural is iconic (although, technically outside of Wicker Park – it’s worth a detour!).
Dinner – Antique Taco Wicker Park
For dinner, head to Antique Taco Wicker Park, a casual and eclectic taco spot that’s a local favorite. With its laid-back vibe, outdoor patio, and delicious tacos (don’t miss the al pastor), it’s the perfect way to wrap up your time at Wicker Park. Pair your meal with one of their signature margaritas or a cold beer for the ultimate chill evening.
Evening – Catch a comedy show at The Den Theatre
After dinner at Antique Taco, walk just around the corner to The Den Theatre. This venue hosts a diverse lineup of performances, including stand-up comedy, plays, and live music. It’s a fantastic way to experience Chicago’s vibrant arts scene and discover local talent. To see what’s playing and purchase tickets, visit their official website.
Day 2
Morning – Visit the Art Institute of Chicago
Today, you get to experience some incredible art, but that’s not until 10 am. So start your morning however you’d like before making your way to the Art Institute of Chicago for this amazing guided tour of its best works. This tour only runs until 12:30 pm, which means you’ll have plenty more time to explore the city afterwards.
What we love the most about this tour is that it includes skip-the-line entry to the museum. We would have been waiting for well over an hour otherwise! Plus, our guide, Heath, made the experience ten times more interesting. He weaved fascinating stories into every masterpiece we saw.
Some of the highlights in the museum include Seurat’s Sunday on La Grande Jatte, Hopper’s Nighthawks, and Picasso’s The Old Guitarist. Seeing these paintings in person makes them so much more interesting.
One of my favorite stops was definitely Marc Chagall’s America Windows, which is a vibrant blue stained-glass piece. I also loved getting a glimpse into the surreal world of Salvador Dali with Inventions of Monsters.
Whether you’re an art novice or a seasoned museum-goer, this tour is the best way to experience the Art Institute. It turned what could have been an overwhelming visit into an unforgettable journey through some of the world’s greatest masterpieces. And don’t just take our word for it because you can read hundreds of 5-star reviews here.
Reserve this tour now and pay later when you book it in advance here!
Lunch – Imee’s Kitchen
After exploring the Art Institute, take a short 15-minute walk toward the Willis Tower and stop for lunch at Imee’s Kitchen along the way. This casual spot serves delicious multicultural comfort food, featuring hearty rice bowls, flavorful meats, and plenty of vegetarian options. It’s a quick, satisfying meal that’ll fuel you up before heading to one of Chicago’s most iconic landmarks.
Afternoon – Willis Tower SkyDeck
Next up is a visit to the iconic Willis Tower, formerly known as the Sears Tower, and one of Chicago’s most iconic architectural landmarks. The main attraction here is the Skydeck, which gives you jaw-dropping views from the 103rd floor. If you have the stomach for it, you can step out onto The Ledge—a glass box extending over 4 feet (1.2 meters) from the building’s edge. It’s a thrilling way to see the city from above, and your admission also includes access to the Chicago Museum exhibit on the lower floors.
Plan to spend around two hours here to fully enjoy the experience. Tickets start at $32 USD and must be booked in advance with a reserved time slot. If you are going to stop for lunch before I suggest booking your spot for 2 pm so you have enough time to walk there and stop for lunch.
Evening – Sunset cruise on Lake Michigan
Let’s end your day with another standout experience. This sunset cruise on Lake Michigan is a fantastic way to get a new perspective on Chicago and enjoy the sunset. Departure times vary depending on the time of year, ranging from 5:15 pm in the fall to 7:30 pm in the summer, but regardless of when you visit, this is absolutely worth your time.
The meeting point is about a 30-minute walk or a quick 15-minute train ride from Willis Tower. You’ll have a bit of downtime before the cruise, which makes it the perfect opportunity to stroll back through Millennium Park, visit Cloud Gate, or simply relax and explore the waterfront near where the cruise starts.
The cruise itself started on the Chicago River, winding past some of the city’s most famous buildings, such as the Hancock Center and the Aqua Tower. Our guide was full of interesting facts, pointing out details we wouldn’t have noticed on our own. But the real magic happened when we passed through the locks and entered Lake Michigan!
From out on the lake, the city looked just like a postcard. We grabbed drinks (not included), found a perfect spot on the open deck, and watched as the sky turned pink and orange before fading into deep blue.
Just when I thought it couldn’t get any better, the city skyline began to light up, which was absolutely breathtaking. I think that this is the most magical thing you can do in Chicago!
Check out the 1,000+ 5-star reviews and book this cruise here!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
Dinner – Volare Ristorante Italiano
After the cruise, head to Volare Ristorante Italiano, just a quick six-minute walk from the tour’s endpoint. This welcoming spot serves up classic Italian dishes with rich flavors and generous portions, perfect after a full day of sightseeing. Whether you’re craving homemade pasta, fresh seafood, or a hearty risotto, you can’t go wrong with anything on the menu.
Day 3
Breakfast – Tempo Cafe
Let’s start the final day in Chicago with breakfast at Tempo Café, a local diner just a 10-minute walk from this morning’s tour meeting point. This beloved spot serves hearty portions of all your favorite American breakfast staples. It opens at 6:30 am, and the tour doesn’t start until 10 am, so you’ll have plenty of time to enjoy the morning and get ready for the day.
Morning – Discover Chicago’s infamous crime and mob history
If you love true crime, history, or just a good story, this Chicago gangster tour is an absolute must. It’s one thing to hear about Al Capone, John Dillinger, and the St. Valentine’s Day Massacre, but it’s quite another to stand where it all happened.
For two hours, we were chauffeured around the city in a comfy, air-conditioned coach, but in reality, it felt like we were being transported back in time to Prohibition-era Chicago. Our guide, Jay, was a talented storyteller who had us laughing as she wove tales about the Windy City’s infamous mobsters. We even saw the courthouse where many of them were prosecuted!
One of the most chilling stops was the Biograph Theatre, where the notorious gangster John Dillinger was gunned down by the FBI. I actually got goosebumps while hearing the story of his final moments.
We also visited Holy Name Cathedral and learned about the brutal assassination of Hymie Weiss right outside its doors. But I think visiting the site of the St. Valentine’s Day Massacre in Lincoln Park was the most eerie of all, especially once we were filled in on the violent events that unfolded there.
The tour had the perfect mix of bus time and opportunities to hop off, stretch our legs, and take pictures. It’s definitely not your run-of-the-mill sightseeing tour, and it’s a super unique and engaging way to get to know Chicago’s history. True crime fans can’t miss this one!
Book this top-rated tour here, before it sells out!
Lunch – Portillo’s
Since today’s timeline is more relaxed, take a small detour after the mob tour ends and walk 15 minutes to Portillo’s for lunch, a true Chicago locals’ favorite. This retro-style eatery is famous for its Chicago-style hot dogs, Italian beef sandwiches, and crinkle-cut fries, all served in a fun, fast-paced setting. It’s a must-try spot for classic local flavors.
After lunch, it’s just another easy 15-minute walk to the bike shop (or 25 minutes if you want to kayak) to your afternoon adventure.
Afternoon – Bike or Kayak
Remember that your free two-hour bike or kayak rental from the food tour on day one is still valid, and this afternoon is the perfect time to use it! If you’re in the mood to cycle, head to Bobby’s Bike Hike, just a short walk from Portillo’s, and explore Chicago’s scenic lakefront trails at your own pace. Prefer to get out on the water? Then make your way to Bobby’s Kayak at Ohio Street Beach for a peaceful paddle with skyline views.
Either option offers a fun, active way to enjoy the city at your own pace on your final day.
Evening – Head to Fulton Market District
Wrap up your final evening in Chicago by heading to the Fulton Market District, one of the city’s hottest neighborhoods for food, drinks, and nightlife. Once an industrial warehouse zone, it’s been transformed into a stylish, upscale area full of energy and character. Whether you’re in the mood for gourmet dining, craft cocktails, or something playful and fun, this neighborhood has it all.
We recommend starting your night with a walk through Time Out Market Chicago, a food hall featuring a selection of the city’s top chefs and eateries all under one roof. Grab a small bite (or several) and sip a drink while exploring the space. Then head to Emporium Arcade Bar, a funky, retro hangout packed with classic arcade games, pinball machines, and a great beer selection. Good luck trying to beat my Pac-Man score!
If you like the idea of sunset cocktails, make your way to Aba, a rooftop spot known for its Mediterranean vibes, killer cocktails, and skyline views. When you’re ready for dinner, stop by Au Cheval, a diner-style restaurant that’s become legendary for its burgers—arguably some of the best in the city. It’s the perfect way to end an incredible trip and your last night in the Windy City!
Related Read: Find yourself with some extra time? Check out our 10 best things to do in Chicago guide for more must-see sights and activities!
Where to Stay in Chicago
Chicago is the third-largest city in the United States, so deciding where to stay can be tricky! Our advice would be to stay in the Loop. It’s a fun downtown area that encompasses many of the city’s top attractions, and lots of the activities we’ve mentioned in this blog start and end here.
We’ve made it easy for you by choosing three of our favorite hotels in the Loop. If these hotels still have availability, they will be your best bet!
Luxury – $$$
The Langham Chicago is a luxurious 5-star hotel just two blocks from the Magnificent Mile, so you really couldn’t choose a better location. The rooms ooze elegance, and the bathrooms are the stuff that dreams are made of, with marble surfaces and deep soaking tubs. You can also enjoy state-of-the-art fitness center, a refined afternoon tea experience, and one of Chicago’s top-rated restaurants
Prices at the Langham start at $550 USD per night. Check out all of the options and book this luxurious stay on Booking.com now!
Mid-range – $$
Located in the heart of downtown Chicago, Club Quarters Hotel Central Loop offers a comfortable and convenient stay just a short walk from the Willis Tower Skydeck and Quincy/Wells Subway Station. The modern rooms offer everything you need, including free WiFi, a flat-screen TV, and a coffee machine with complimentary bottled water. But perhaps the main reason that we love this place is because of its in-house English-style pub, which offers over 100 varieties of beer and scotch whiskey.
Prices here range between $180 USD and $400 USD per night. Check availability for your travel dates and reserve your stay on Booking.com!
Budget – $
Budget stays in Chicago don’t get much better than the HI Chicago Hostel. This is a clean and modern spot that’s located in the vibrant South Loop, so it’s perfect for exploring the city’s buzzing nightlife, top museums, and world-class dining. There are 4- to 10-bed dorms available as well as private rooms, and breakfast is included! With a welcoming atmosphere, shared spaces to meet fellow travelers, and an unbeatable location, this hostel is the ideal base for soaking up Chicago’s energy without breaking the bank.
Dorm beds here typically start at about $35 USD and private rooms at about $110 USD per night, with private options starting at $115 USD. Check out all of the options and book your stay over at Booking.com!
For more options, see all of Chicago’s listed hotels here!
Renting a Car in the USA
The United States is a vast country with diverse landscapes, from bustling cities to scenic national parks. While public transportation exists in major cities, renting a car is often the best way to explore the country’s wide-open spaces and hidden gems.
We always book with Discover Cars and can’t recommend them enough. It’s super easy to compare prices, check company ratings, find the right vehicle for your needs, and add affordable full coverage insurance. If you want a full breakdown, check out our Discover Cars review here.
Tips for Renting a Car in the USA
- Drive on the right: In the U.S., vehicles drive on the right-hand side of the road, and the driver’s seat is on the left. If this is different than your home country, take some time to adjust before hitting busy streets!
- Know the local rules: Speed limits, road signs, and driving laws can differ between states. For example, turning right on red is generally allowed after a complete stop, unless a sign indicates otherwise. Always check the specific rules for the states you’ll be driving in.
- Add full insurance: We always recommend full coverage rental insurance, especially in the U.S., where long distances, varying road conditions, and unpredictable weather can lead to unexpected situations. Discover Cars makes it easy (and affordable!) to add this peace of mind when you book.
- Choose the right car: Consider the nature of your trip. For city driving, a compact car is convenient, while for road trips or national park visits, an SUV might be more comfortable. With Discover Cars, it’s easy to filter by vehicle type, transmission, fuel efficiency, and more to find the perfect fit.
What You Need to Rent a Car in the USA
- A valid driver’s license from your home country.
- An International Driving Permit (IDP) is recommended if your license is not in English or uses a non-Roman alphabet. Some rental companies may require it, so it’s best to check in advance.
- A credit card in the driver’s name is typically required for the security deposit.
- Most rental companies require drivers to be at least 21 years old, with a young driver surcharge applicable for those under 25. Some companies may have higher age requirements, so make sure you double-check.
Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring the USA on your own terms!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
Thanks for reading!
As one of the most famous cities in the U.S., Chicago was high on our list of “must-visits”. Luckily, it exceeded our expectations, from famous art museums, skyline views from Lake Michigan, and more hot dogs than I’ve ever consumed in one weekend. If you follow this itinerary, I know you’ll love Chicago just as much as we did!
Before you go, check out our other USA blogs! We have more city itineraries, guides on where to stay, and top things to do no matter where your travels take you. Here are a few related blogs to inspire your next trip – cheers!
How to Spend THREE DAYS in Nashville, Tennessee: 3-Day Itinerary
5 Best Things to do in Minneapolis, Minnesota
How to Spend THREE DAYS in Denver, Colorado: 3-Day Itinerary