3 Days in Chicago: Discovering the Best of the Windy City

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Chicago is such an amazing bustling city! Just having 3 days in Chicago can feel overwhelming because there is so much to do and see. But let me assure you, you can accomplish quite a bit in 3 days.

Our Chicago trip took an unexpected turn due to various factors. From the haze caused by Canada’s wildfires to unexpected rain showers, and to top it off, a bustling holiday weekend coupled with a NASCAR event in town, which led to street closures and limited access to popular spots like The Bean.

Luckily growing up in the midwest I have already visited Chicago several times (plus I plan to return!), so I still feel confident I can help you create an epic 3 day Chicago itinerary!

View of Chicago city skyline at night from Lake Michigan

When is the best time to visit Chicago?

Chicago is a city that truly comes alive during the summer months from June to August. It’s a bustling time filled with festivals, outdoor concerts, and lively events that showcase the city’s vibrant energy. However, with the increased activity comes larger crowds, so be prepared for some busy streets and longer lines at popular attractions.

For a more relaxed visit, consider spring (April to May) and fall (September to October) as ideal times to explore Chicago. These seasons offer milder weather, fewer tourists, and beautiful natural scenery. Spring blooms and fall foliage add a touch of charm to the city, making it perfect for outdoor activities and sightseeing without the summer hustle.

Winter in Chicago, while cold, can be a magical experience with festive decorations, ice skating rinks, and holiday markets. The city transforms into a winter wonderland, offering unique opportunities to explore its architecture against a snowy backdrop. Plus, you can find great deals on accommodations during the off-peak season. Consider your preferences and priorities to choose the best time to visit Chicago.

Looking out at Chicago on the Shoreline Sightseeing Architecture River Tour

Chicago CityPASS

If you only have 3 days in Chicago and want to see some of the city’s top attractions, check out the Chicago CityPASS. It includes admission to some of the most popular Chicago activities at a discounted price, saving up to 48% off regular admission fees. We used this for our trip, and it was perfect!

The CityPASS includes admission to the Shedd Aquarium and Skydeck Chicago, plus three of the following attractions:

  • Field Museum
  • Art Institute of Chicago
  • Shoreline Sightseeing Architecture River Tour
  • Museum of Science and Industry
  • Adler Planetarium
  • 360 CHICAGO Observation Deck

Best things to do if you have 3 days in Chicago

Chicago Architecture River Cruise

The Chicago Architecture River Tour comes highly recommended by both locals and visitors, and for good reason! It’s a must-do experience that showcases the city’s stunning architecture and captivating skyline from a unique perspective.

Sit back and relax on a leisurely cruise as knowledgeable guides share fascinating historical and architectural insights about the iconic buildings that line the Chicago River.


Stroll along the scenic Riverwalk and immerse yourself in the vibrant atmosphere of Chicago. This 1.25-mile-long pedestrian-friendly pathway offers breathtaking views of the city skyline, charming cafes, restaurants, and plenty of outdoor seating areas where you can enjoy a meal or simply relax and take in the beauty of the surroundings!

View of the Chicago Riverwalk from boat tour

The Bean

This one is a must for your 3 days in Chicago, especially if it’s your first time! Located in Millennium Park, the Cloud Gate sculpture, affectionately known as “The Bean,” is a beloved Chicago landmark.

Reflecting the city’s skyline in its polished, mirrored surface, this unique art installation offers a playful and interactive experience.

The Bean in Chicago

360 Chicago

Get ready for breathtaking panoramic views of the city skyline from the observation deck of 360 Chicago. Located in the iconic John Hancock Building, this attraction offers a unique perspective of Chicago from 1,000 feet above ground.

Shedd Aquarium

The Shedd Aquarium is an aquatic wonderland! Dive into the fascinating world of marine life and explore a variety of mesmerizing exhibits.

Get up close and personal with graceful dolphins, playful otters, and majestic beluga whales. This educational and entertaining experience will leave you with a greater appreciation for the wonders of the ocean. It’s the perfect family-friendly Chicago activity!

Dine at some of the best restaurants in the country

Chicago is internationally renowned for its culinary scene, with SO MANY amazing dining options. From trendy gastropubs to fine dining establishments, the city offers a gastronomic adventure for every palate.

One of the stand-out restaurants from our trip was Sunda New Asian. From tempting sushi rolls to flavorful noodle dishes and innovative fusion creations, Sunda delivered consistently good dish after dish.

From the moment we took our first bite at Sunda New Asian’s Chicago location, it captured our hearts, so we were thrilled to find out they were opening a location in Midtown Tampa!

Grant Park

Nestled in the heart of downtown Chicago, Grant Park is an urban oasis. Known as “Chicago’s Front Yard,” this iconic park is home to numerous landmarks and attractions.

You’ll especially want to admire the Buckingham Fountain, a breathtaking architectural masterpiece. Inspired by the Latona Fountain at the Palace of Versailles, this iconic landmark is one of the largest fountains in the world!

If you love big cities, check out my NYC guide, 3-day LA itinerary, and fun Miami restaurants guide!

While in operation, the Fountain produces a major water display for 20 minutes every hour starting at 9 AM. Beginning at dusk, a special light and music display accompanies the major display, with the final major display beginning at 10:35 PM.

Buckingham Fountain at Grant Park

Skydeck Chicago

As you can see, between the gloomy weather and smog from the wildfires in Canada our views were a little dampened, but still impressive!

For Skydeck Chicago, you will ascend to the 103rd floor of the Willis Tower and experience the awe-inspiring views from the glass viewing platform known as “The Ledge.” Take in the sweeping views and test your courage on the thrilling Tilt experience (this is an additional $10 if you choose to experience it).

Walk and shop the Magnificent Mile

Chicago’s Magnificent Mile is a shopper’s paradise! It offers a mix of luxury boutiques, flagship stores, and renowned department stores.

Make sure you take a break from shopping to admire the stunning architecture of the Magnificent Mile, with its towering skyscrapers and historic landmarks! This bustling avenue truly lives up to its name, providing an unparalleled retail experience.

Magnificent Mile in Chicago Illinois

Adler Planetarium

Take yourself on a celestial journey at the Adler Planetarium, a hub of astronomical exploration and education. Engage in interactive exhibits that unravel the mysteries of the universe, from the history of space exploration to the captivating phenomena of black holes. Expand your knowledge of the cosmos and awaken your sense of wonder!

The Adler Planetarium in Chicago

Field Museum

The Field Museum is a renowned institution that houses an extensive collection of artifacts and specimens that tell the captivating stories of Earth’s past.

From the awe-inspiring Egyptian mummies to the fascinating Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered, the Field Museum offers a journey through time and an opportunity to deepen your understanding of the world around us!

Blue Man Group

See one of Chicago’s longest-running shows, The Blue Man Group! It combines comedy, music, and multimedia theatrics into a mind-blowing performance that will leave you in awe. Watch as the energetic blue-faced performers captivate with their rhythmic drumming, enthralling visuals, and interactive antics.

This one-of-a-kind theatrical experience is a testament to the group’s innovative creativity and has made them a beloved staple of Chicago’s entertainment scene!

Check out a speakeasy

Chicago is certainly not short on speakeasies! With only 3 days in Chicago, we didn’t get to hit nearly as many as I would’ve liked, but what we lacked in quantity we made up for in quality.

Three Dots and a Dash was such a fun and tropical vibe! The drinks were fire, the vibes were immaculate, and it was within walking distance of our beloved Sunda New Asian! Making this the perfect pre or post-game spot for your dinner reservation.

Have a Chicago-style hot dog

No visit to Chicago is complete without indulging in a classic Chicago-style hot dog. This iconic culinary creation features a poppy seed bun loaded with an all-beef hot dog, topped with mustard, onions, sweet pickle relish, tomatoes, pickles, sport peppers, and a sprinkle of celery salt.

We grabbed ours from a stand right outside of The Field Museum, and we loved it!

Chicago style hot dog in Chicago

Visit the largest Starbucks in the world

If you’re a fellow coffee lover, you simply can’t miss out on the grandeur of visiting the world’s largest Starbucks—Chicago’s Starbucks Reserve Roastery. This elevated Starbucks concept takes coffee appreciation to new heights, offering a curated selection of rare and small-batch coffees from around the globe as well as menu items you probably won’t recognize from your average Starbucks.

This coffee haven is spread across five floors, and each offers its own menu!

Boat day

Especially if you’re visiting Chicago in the summer, a boat day is a must! It’s the epitome of Chicago summers. Whether you do a Lake Michigan sunset cruise or a private boat rental, nothing beats a day out on the water!

Navy Pier

The Navy Pier offers plenty of attractions and activities for of all ages. From thrilling rides to the mesmerizing views of Lake Michigan and the city skyline, there’s never a dull moment here.

Make sure to catch the fireworks display that lights up the sky every Wednesday and Saturday night during the summer season, creating a magical ambiance that’s perfect for a romantic evening or a fun night out with friends and family.

Don’t forget to explore the various shops, restaurants, and entertainment options that make Navy Pier a must-visit destination in Chicago!

Fireworks at The Navy Pier in Chicago

Bonus things to do if you have time to spare during your 3 days in Chicago

  • Lincoln Park Conservatory A stunning botanical haven that showcases a variety of plant species, from towering palms to rare orchids. It’s a great free thing to do in Chicago!
  • Jackson Park— An expansive park with lush greenery, scenic trails, and picturesque lagoons. Check out The Garden of the Phoenix, an exquisite Japanese garden within the park.
  • WNDR Museum A fun museum full of multi-sensory, contemporary art installations.
  • Ice Cream Museum Another fun museum! It’s immersive, interactive, and full of fun photo ops!
  • Lincoln Park Zoo— This free-admission zoo is the perfect family fun activity if you still have time to spare during your 3 days in Chicago.
  • Bike along the Lakefront trail— This scenic 18-mile trail offers stunning views of the lake and city skyline! Get a bike rental here.

Where to stay in Chicago

Chicago is a city brimming with diverse neighborhoods and a multitude of accommodation options. As you plan your Chicago itinerary, keep in mind the proximity of your chosen hotel to your planned activities and attractions. Here are some top picks for where to stay in Chicago, all located in the bustling Loop area where the main action happens:

  • The Blackstone Autograph Collection The Blackstone offers a blend of historic charm and modern luxury. With stunning views of Lake Michigan and proximity to iconic landmarks like Millennium Park and Grant Park, this hotel is the perfect base for exploring the city.
  • Sentral Michigan Avenue Situated along the vibrant Magnificent Mile, Sentral Michigan Avenue provides easy access to world-class shopping, dining, and entertainment. The hotel’s contemporary design, upscale amenities, and central location make it a popular choice for both leisure and business travelers.
  • Bluegreen Vacations Hotel Blake, Ascend Resort Collection Experience boutique elegance at Hotel Blake. The hotel’s stylish rooms, personalized service, and convenient location make it a standout option if you’re seeking a memorable stay in Chicago.

For availability and rates for your specific dates check out available accommodation options here.

Are you ready for an epic 3 days in Chicago?!

I hope you’ve enjoyed this whirlwind tour of the city for your 3 days in Chicago! From exploring iconic landmarks to savoring delicious cuisine and soaking in the vibrant atmosphere, Chicago has so much to offer in a short time.

Whether you’re a first-time visitor or a returning traveler, there’s always something new to discover in this dynamic city. Here’s to more amazing travels and unforgettable experiences!

Before you go, be sure to follow me on Insta @guidedbydestiny and check out some of my other Midwest blog posts:

Fun things to do in the Twin Cities

Weekend in St. Louis

Perfect weekend in Chattanooga

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