Chicago, the vibrant city on the shores of Lake Michigan, is a metropolis rich in history, culture, and entertainment. With its stunning architecture, world-class museums, delicious food scene, and bustling neighborhoods, Chicago has something for everyone. Spencer and I recently got to spend three days in Chicago, so naturally I figured out how to fit a lot in a short time frame – while leaving time for exploring and relaxation.
Whether you are a first-time visitor or a seasoned traveler, planning a 3-day itinerary for Chicago will ensure you make the most of your time in this diverse city.
Spencer and I got to spend a long weekend exploring – which naturally meant I had to plan as much as I could to see a lot of the city. We utilized the Chicago CityPass to save money on major attractions. You can check out my full review of the CityPass here to see everything that’s included.
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Where is Chicago located?
Chicago, also known as the “Windy City,” is located in the state of Illinois, along the southwestern shores of Lake Michigan. It is a bustling metropolis and a major transportation hub in the United States.
When is the best time to spend 3 days in Chicago?
Chicago experiences four distinct seasons, each offering its own unique charm. The best time to visit the city largely depends on your personal preferences and what you want to experience during your stay. We went in the spring because of the weather and the availability of flights.
- Spring (March to May): Springtime in Chicago is characterized by mild temperatures and blooming flowers. This is a great time to explore the city’s parks and gardens, such as Millennium Park and the Chicago Botanic Garden. It is also the season for various cultural events and festivals, including the Chicago Gospel Music Festival and the Chicago Beer Classic.
- Summer (June to August): Summer is peak tourist season in Chicago, thanks to its warm temperatures and abundance of outdoor activities. You can take a stroll along Navy Pier, catch a baseball game at Wrigley Field, or attend the Taste of Chicago, the city’s premier food festival. Just be prepared for larger crowds and higher hotel rates during this time.
- Fall (September to November): Fall in Chicago offers pleasant temperatures and beautiful autumn foliage. This is a great time to explore the city’s neighborhoods, such as Wicker Park and Lincoln Park, and enjoy outdoor activities like kayaking on the
- Winter (December to February): Be prepared for frigid temperatures and constant wind here (it’s called the Windy City for a reason). The city is very decorated for the holidays. You’ll find cheaper accommodations in January and February.

How to get to Chicago?
Getting to Chicago is relatively easy due to the city’s excellent transportation infrastructure. Here are some of the most convenient ways to reach the city:
- By Air: Chicago is served by two major airports – O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Both airports offer numerous domestic and international flights, making it convenient for travelers to reach the city. O’Hare International Airport is one of the busiest airports in the world and is located approximately 17 miles northwest of downtown Chicago, while Chicago Midway International Airport is located about 10 miles southwest of downtown.
- By Train: Amtrak, the national passenger railroad service, offers convenient train connections to Chicago from various cities in the United States. Union Station, located in downtown Chicago, serves as the city’s main railway hub. It is well-connected to cities like New York, Washington D.C., Los Angeles, and many others.
- By Car: If you prefer to drive, Chicago is easily accessible via several major highways such as Interstate 90 (also known as the Kennedy Expressway), Interstate 94 (also known as the Dan Ryan Expressway), and Interstate 290 (also known as the Eisenhower Expressway). However, be prepared for heavy traffic, especially during peak hours.
We flew from Philadelphia to Chicago Midway on Southwest Airlines during their spring sale. Our flights cost $37 each – talk about finding cheap flights!
How to get around during your 3 days in Chicago?
Getting around Chicago during your 3-day stay is just as convenient as getting to the city. Chicago has an extensive public transportation system that allows you to easily explore all the attractions and neighborhoods. Here are some of the best ways to get around during your visit:
- Public Transportation: The Chicago Transit Authority (CTA) operates an efficient network of buses and trains that cover the entire city. The “L” train system is particularly popular and convenient for getting around. You can purchase a Ventra card, which allows for unlimited rides on both buses, trains, and subways within a certain period of time. It’s a cost-effective and efficient way to navigate the city. We got the three-day card and used the app to find the best transportation.
- Biking: Chicago is a bike-friendly city with a network of bike lanes and trails. Divvy, the city’s bike-sharing program, offers bikes for rent at various stations throughout the city. You can easily rent a bike for a day or purchase a pass for unlimited rides during your stay. Biking is a great way to explore the lakeshore trails and visit attractions like Millennium Park and Navy Pier. Our hotel, Staypineapple, provided free bikes for guests which we utilized one day to explore the city.
- Walking: Many of Chicago’s top attractions are located in the downtown area, making it easy to explore on foot. The city’s grid-like street grid makes it simple to navigate, and you’ll have the opportunity to take in the city’s architecture and vibrant street life as you walk from place to place. Plus, many of the famous landmarks like the Magnificent Mile, Cloud Gate (commonly known as “The Bean”), and the Chicago Riverwalk are within walking distance of each other. Be sure to wear comfortable shoes, we walked over 20,000 steps every day even using public transportation and bikes!

Where to Stay for your 3 days in Chicago?
Since you’re in the city for a short time, location is important when choosing a hotel. You don’t want to spend a ton of time getting to and from the city. We stayed at Staypineapple Chicago, located right in The Loop (aka city center).
We were in a prime location for sightseeing, including biking distance to the Art Institute of Chicago. We also had a view of the Chicago Theatre from our room! We could see Millenium Park down the road from us as well.
We also had plenty of ease using public transportation. It’s located near a bus stop, subway stop, and an L stop – it was perfect. Check out my in-depth review of Staypineapple.
Utilizing the Chicago CityPass for 3 days
We utilized the Chicago CityPass during our visit. It was a great way for us to save money on attractions and see a lot. Check out my Chicago CityPass review to see if it’s right for you – but know that this itinerary goes off the assumption that you’re interested in using it. If you are using it, Skydeck and Shedd Aquarium are included, and the three activities we chose were the Art Institute, Museum of Science and Industry, and Shoreline Boat Architecture Tour.
3 Day Itinerary for Chicago
Day 1 in Chicago
Breakfast at Copperfox Gastropub
Breakfast at Copperfox Gastropub is the perfect way to start your first day in Chicago. Located in the heart of the city, this trendy gastropub offers a diverse menu with delicious options for everyone.
We recommend trying their signature dish, the Maple Bacon Brunch Burger. This mouthwatering burger features a juicy beef patty topped with cheddar cheese, crispy bacon, a fried egg, and a drizzle of maple syrup. Spencer decided on the eggs benedict (and I don’t eat bacon, but it did come recommended).
If you’re in the mood for something sweet, I had the decadent fresh berries french toast. It was the perfect breakfast to fill me up before our first walking tour!

Chicago off the Grid Walking Tour
I found this walking tour from Free Chicago Walking Tours. It’s about 1.7 miles of walking around River North & The Loop but goes beyond the big ticket items (that were already on our itinerary to begin with!). It starts at the ACME Hotel and ends at the Chicago Cultural Center.
We learned about Death Alley, the “Corn Cob” buildings on the river, Pizzeria Uno (the home of the deep dish pizza), and the artists’ homes from the past. We even got to browse at Posh – a store started by flight attendants who brought things from Paris to sell to Americans.
We also got to visit Harry Caray’s restaurant which pays homage to the Chicago Cubs announcer. The building was also a headquarters for the mob in the 1930s. Now there is a small museum beneath the restaurant and is free to visit.

Lunch at Kong Dogs
While this won’t make “best eats in Chicago” lists anytime soon, it was an experience that I don’t regret. This little restaurant is located across the street and a few storefronts down from the Art Institute. Spencer and I didn’t want a fancy lunch, but we did want to sit down, so due to location, our options were limited.
Kong dogs are gigantic Chicago-style hot dogs, with plenty of toppings. Spencer got the Chicago special and I got the works (ketchup, mustard, cheese, more cheese). We also got fries to split with hot Cheetos and a sweet sauce on them. It was too much food haha. I know Kong is in the name and I should have expected them to be quite large, but not that large!

Art Institute
The Art Institute of Chicago is a must-visit for any art lover. It is one of the oldest and largest art museums in the United States, housing a vast collection of artworks from around the world. The museum is home to iconic pieces such as Grant Wood’s “American Gothic”, Vincent van Gogh’s “The Bedroom”, and Georges Seurat’s “A Sunday on La Grande Jatte”.
Upon visiting the Art Institute, make sure to pick up a map and plan your route to see the highlights that interest you the most. (Trust me and learn from my mistake!) The Institute is huge and can be overwhelming. With limited time, focus on what you really want to see or the museum’s masterpieces and famous collections. The museum offers guided tours if you prefer a more structured experience, or you can explore at your own pace.
When hunger strikes, the museum offers several dining options, including a cafe and a fine dining restaurant overlooking Millennium Park. Take a break, enjoy a meal, and soak in the beautiful surroundings before continuing your exploration.

Dinner at Weber Grill
Yes, you read that right. Weber Grill has a restaurant, and it’s famous for (you guessed it) grilled food. Weber Grill is a unique dining experience that every meat lover should try when visiting Chicago. Located just a short walk from Millennium Park, this restaurant is known for its delicious grilled dishes and its iconic Weber grills.
As soon as you step inside Weber Grill, you’ll be greeted by the mouthwatering aroma of sizzling steaks, burgers, and ribs. The restaurant has a cozy and welcoming atmosphere, perfect for enjoying a hearty meal after a day of exploring the city.
One of the highlights of dining at Weber Grill is the opportunity to watch the chefs in action. The open kitchen allows you to see the skilled chefs grilling your meal to perfection. From the moment you see those flames dancing in the grill, you know you’re in for a treat.

Sunset Shoreline Sightseeing Architecture River Tour
We decided to do this river tour over sunset – in theory for a unique sun view on the buildings, but it was cloudy. Despite the cloudy weather, the Sunset Shoreline Sightseeing Architecture River Tour is still a fantastic experience. This 90-minute cruise takes you along the Chicago River, providing stunning views of the city’s iconic architecture. As you glide past towering skyscrapers, knowledgeable guides share fascinating stories and information about the history and significance of these architectural marvels.
Even though we didn’t get to witness a vibrant sunset, the twilight ambiance added a different charm to the tour. The city’s buildings lit up beautifully, casting a magical glow over the river. The tour also offers an opportunity to see famous landmarks such as the Willis Tower (formerly known as the Sears Tower), the Tribune Tower, and the Wrigley Building up close.
The knowledgeable guides on board provide interesting facts and anecdotes about each architectural masterpiece, giving you a deeper appreciation for Chicago’s rich architectural heritage. You’ll learn about the birth of the skyscraper and the contributions of renowned architects like Frank Lloyd Wright and Ludwig Mies van der Rohe to the city’s skyline.
As you sail along the river, make sure to have your camera ready to capture the breathtaking views. The unique perspectives from the water allow you to capture the grandeur of the buildings from angles you wouldn’t get on land.
It’s important to note that on a boat you are not protected from the wind by the buildings. Also, if you decide to do a sunset cruise, the temperature significantly drops when the sun goes down. Bring layers!

Day 2 in Chicago
Breakfast at Chicago Waffles
This is now my go-to recommendation for breakfast in Chicago. There are a few different locations, we went to the one in South Loop, on our way to Shedd Aquarium. We used the free bikes from StayPineapple Hotel to get there. The small restaurant packs a lot – friendly, down-to-earth staff, unique decor, and of course – waffles!
It wasn’t until I read the menu that I was truly in love. They had a waffle flight! That’s right – FOUR types of waffles on one plate. Red velvet, chocolate, liege & green tea, and hazelnut & banana! I was in heaven.
Honestly, if you can think of a way to have a waffle, they have it. Bacon & Chicken, Heart Healthy, Cheddar & Short Rib, and even Blueberry Lemon Cheesecake.
If you’re not a waffle lover (who hurt you?) don’t worry – they have omelettes and burgers too.

Shedd Aquarium
Shedd Aquarium is a must-visit attraction during your three days in Chicago. Located on the shores of Lake Michigan, this world-class aquarium is home to a diverse range of marine life, making it a perfect destination for nature enthusiasts and families alike.
As you explore the aquarium, you’ll have the opportunity to witness stunning exhibits like the Oceanarium, where you can watch dolphins and beluga whales in action, and the Wild Reef, which showcases the vibrant ecosystems of coral reefs. One of the highlights of our visit was the 4D movies. Tickets are included with CityPass and we got to see the shark and octopus movies.
To make the most of your time at Shedd Aquarium, it’s recommended to allocate at least half a day for your visit. The aquarium can get quite busy, especially on weekends and during peak tourist seasons, so it’s advisable to arrive early to beat the crowds.
When it comes to ethical animal tourism, I am always split on zoos and aquariums. While Shedd does hold the highest accolades for ethical treatment – they also have beluga whales perform in a small tank.
I believe for zoos and aquariums it’s a matter of do they do more good than harm. I was happy to hear that the research done at Shedd is used practically in Canada to help wild beluga whales (which in general are not well known). In short, though, I had mixed feelings about visiting and I probably wouldn’t have if it wasn’t included in CityPass.

Lunch at Pizano’s Pizza
Deep-dish pizza is a must in Chicago – at least once. While Pizza Uno and Lou Malnati’s are famous for deep dish, Pizano’s was recommended by a local on the side of the road. As someone who lives outside of Philly, I wouldn’t recommend Geno’s for cheesesteaks even though they’re one of the most famous. So we decided to take the random stranger’s suggestion and headed to Pizano’s to try out their deep dish. I grew up outside of NYC, so deep dish will never replace a New York Slice, but I can respect the art. It was delicious!
If you’re a fan of deep dish pizza, why not take this pizza walking tour of Chicago?!

Afternoon at Leisure
After indulging in a delicious deep-dish pizza at Pizano’s, it’s time to explore Chicago at your own pace during the afternoon. The city offers a plethora of activities and attractions that cater to every interest.
If you’re a history buff, consider visiting the Field Museum of Natural History. This renowned museum houses a vast collection of artifacts and exhibits that showcase the natural world, ancient civilizations, and even dinosaurs. You can spend hours wandering through the halls and learning fascinating facts about our planet’s past.
If you’re in the mood for some shopping, head over to the Magnificent Mile. This vibrant stretch of Michigan Avenue is lined with upscale department stores, luxury boutiques, and trendy shops. From popular brands to unique local shops, you’ll find everything you need for a shopping spree.
We took a few hours to relax at StayPineapple in the afternoon so we’d be prepared for our evening walking tour. We enjoyed Pineapple Hour and unwinding for a bit.

Dinner
For dinner on day 2 of your 3 days in Chicago, head to the West Loop. The West Loop in Chicago is a food lover’s paradise, with a plethora of delicious dining options to choose from. We decided to get some drinks and light fare from a few places instead of a sit-down dinner.
From trendy new restaurants to longstanding favorites, this up-and-coming neighborhood is a culinary hotspot with something for everyone. Randolph Street, known as the culinary center of the West Loop, is where you can find a variety of eateries offering diverse cuisines and unique atmospheres. Whether you’re in the mood for gourmet burgers, artisanal pizza, farm-to-table fare, or creative cocktails, the West Loop has it all.

Evening Gangsters and Ghosts Tour
It’s time to embark on an intriguing evening adventure – the Gangsters and Ghosts Tour. Chicago has a rich history of organized crime, and this tour allows you to delve into the city’s dark past. In my honest opinion, it’s one of the best walking tours in Chicago.
Our guide was Grant, and he was fantastic. The Gangsters and Ghosts Tour takes you through the infamous streets of Chicago, bringing to life stories of notorious gangsters like Al Capone and John Dillinger. You’ll visit the sites where these criminals operated, including former speakeasies and hidden alleyways.
But the tour doesn’t stop at gangsters – it also delves into the haunted side of Chicago. Get ready to hear chilling tales of spirits and supernatural occurrences as you visit haunted locations such as the Congress Plaza Hotel and the legendary Death Alley.
The Gangsters and Ghosts Tour is a fantastic way to explore the city’s history while getting a taste of its spooky side. It runs in the evening, adding an extra layer of mystery to the experience. Be sure to bring comfortable walking shoes and be prepared to be captivated by the stories that unfold along the way.
Day 3 in Chicago
Breakfast at Yolk
It was really difficult to find a breakfast in Chicago that wasn’t a very expensive one. Most of the “best breakfasts in Chicago” posts were actually for brunch, so much later than we’d want, or were pricey and needed reservations. Luckily we found Yolk, a homey diner right in the Loop.
The cinnamon roll pancakes were exactly what I was hoping for when I saw the menu online – cinnamon rolls, dipped in pancake batter. YES! Can you tell I love a good sweet breakfast?
Spencer got sausage gravy on biscuits and it was also delicious. As any good diner would have, there are plenty of options for everyone!
Museum of Science and Industry
Spencer really wanted to visit this museum so I made it one of the two we visited during our time. Afterward, I must admit that even I was impressed. A visit to the Museum of Science and Industry is a must during your three-day itinerary in Chicago. Huge is the least impressive adjective I could think of to describe it. Located in the historic Jackson Park, this museum offers a fascinating blend of interactive exhibits, educational displays, and hands-on activities.

One of the highlights of the museum is the U-505 Submarine exhibit. Step aboard this actual German U-boat captured during World War II and learn about its history and the brave men who served on it. We wish we could’ve seen this, but the Chicago CityPass does not include it and it was sold out for our visit. So plan ahead!
The museum also houses an impressive collection of aircraft, including the first plane to fly around the world, the Spirit of St. Louis. Aviation enthusiasts will appreciate the chance to get up close to these historic planes and learn about aviation milestones.
To make the most of your visit, consider purchasing tickets in advance to avoid long lines. If you have the CityPass like us, make your reservations ahead of time and be sure to get there at your time or they may not let you in.

Lunch at Eleven City Diner
After a morning exploring the Museum of Science and Industry, head over to Eleven City Diner for a delicious lunch. This iconic Chicago eatery is known for its classic American diner-style menu and nostalgic atmosphere.
Upon entering Eleven City Diner, you’ll be transported back in time with its retro decor and vintage memorabilia on display. The friendly staff and cozy booths add to the overall charm of the place. The menu offers a wide variety of options, from traditional deli sandwiches to hearty burgers and classic comfort food dishes.
One of the must-try items at Eleven City Diner is their famous Reuben sandwich. Made with tender corned beef, tangy sauerkraut, Swiss cheese, and Thousand Island dressing, it’s a flavor explosion that will satisfy your taste buds. Spencer enjoyed this while I chowed down on a burger.
If you’re in the mood for something lighter, they also offer delicious salads and wraps. Their menu caters to all dietary preferences, including vegetarian and gluten-free options, ensuring that everyone in your group will find something they love.

Afternoon at Leisure
After indulging in a hearty deep-dish pizza lunch, it’s time to spend the afternoon at leisure exploring some of Chicago’s other attractions. One option is to take a leisurely stroll along the famous Navy Pier, located on Lake Michigan. This iconic landmark offers breathtaking views of the city skyline and the lake, along with a variety of entertainment options.
You can take a ride on the Ferris wheel, which offers panoramic views of the city, or enjoy a leisurely boat cruise on the lake. The Navy Pier also boasts a wide range of shops, restaurants, and entertainment venues, making it the perfect place to spend a relaxing afternoon.
If you’re a history buff, you might want to visit the Chicago History Museum. This fascinating museum chronicles the city’s rich history through a variety of exhibits and interactive displays. Learn about the Great Chicago Fire, explore the city’s role in the Prohibition era, and discover the stories of influential figures who called Chicago home.
We had a late lunch since the Museum of Science and Industry took a long time to explore. We decided to relax for a bit at StayPineapple before heading to Skydeck. We did a late dinner after Skydeck, so depending on time frame, you may want to eat beforehand.
Sunset at Skydeck Chicago
It’s time to head towards one of the most popular attractions in Chicago – the Skydeck Chicago. Located on the 103rd floor of the iconic Willis Tower, this observation deck offers breathtaking views of the city and its surrounding areas.
As the afternoon turns into evening, make your way to the Skydeck and prepare to be amazed by the panoramic vistas that stretch for miles. On a clear day, you can see up to four states from the observation deck, including Illinois, Indiana, Wisconsin, and Michigan.
One of the highlights of the Skydeck Chicago is the Ledge. This unique glass balcony extends out from the building, giving you the sensation of walking on air. Step onto the Ledge and feel your heart race as you look down at the city below. It’s a thrilling experience that you won’t want to miss.
We chose sunset (again) because of a different view with the sun shining. Watch as the sky transforms into a canvas of vibrant colors, casting a golden glow over the buildings and the famous Chicago River. The view from the 103rd floor is simply breathtaking. Capture this stunning moment with your camera and make memories that will last a lifetime.
Photographers should note that the Ledge is on the west-facing side of Skydeck, so the sun was pretty prominent in most of our photos. Plan your visit accordingly!
Tickets for the Skydeck Chicago can be purchased in advance to skip the lines. We used our Chicago CityPass and made reservations.

Final Thoughts
Chicago is a city that offers a wide range of attractions and activities for visitors to enjoy. With a well-planned three-day itinerary, you can experience some of the best that the city has to offer.
Don’t forget to leave some time for leisure and unplanned exploration. Chicago is a city that rewards those who take the time to wander its vibrant neighborhoods, uncover hidden gems, and connect with the locals.
Lastly, make sure to bring comfortable shoes and dress in layers. The weather in Chicago can be unpredictable, so it’s always a good idea to be prepared for any changes in temperature.
Read More about Chicago
An in-depth review of Staypineapple Chicago
How to Use Public Transportation in Chicago
Chicago CityPass: An Honest Review
I had no idea Chicago Dogs were called Kong Dogs! haha! They look delicious!
You had me drooling at deep dish pizza!
OMG, that Kong Dog looks amazing… yummy!