How to Spend Three Days in Chicago: The Best Itinerary


As the third biggest city in the USA, it shouldn’t come as a surprise that Chicago is a city that’s always on the move. Chicago provides an excellent balance of local lifestyle and tourist attractions, creating a unique blend of locals and travelers wherever you go.

Especially in the warmer months, you will find endless outdoor spaces to explore. From the family-friendly Lincoln Zoo to the Riverwalk, that leads to a stunning stretch of beautiful lakeside parks. 

Beyond The Bean, Chicago is also famous for its hot dogs and deep-dish pizza. But you will also find a variety of international cuisine to complement your hearty American dishes. 

Throughout your three days in Chicago, you will discover more than just food and outdoor fun. This itinerary will take you to the best cultural attractions, museums, and arts so you can experience all that Chicago has to offer. Let’s get started!

Where to Stay

Chicago is a vast city that spreads for miles along Lake Michigan. With several great neighborhoods to choose from, it can be a challenge to decide where to base yourself. The fun activities and scrumptious restaurants listed in this 3 day Chicago itinerary cover most of the downtown area, riverside and along the lake.

To save yourself on time and to have many of the great local attractions within walking distance, we suggest basing yourself in The Loop. This will give you easy access to museums, restaurants and iconic attractions like The Bean. 

River North is another prominent example, although a slightly further trek to the lakeside attractions, you will be close to the Riverwalk, the Magnificent Mile and Navy Pier.

Chicago has an expansive public transport system, so it is easy to travel further on the train. You may find cheaper accommodation further out of the city towards Old Town and Wrigleyville, close to Wrigley Field, North Avenue Beach and the Lincoln Park Zoo. 

When to Go

The best time to make the most of your 3 days in Chicago would be in the summer. Chicago’s winters can be bitterly cold and incredibly windy, so walking around and enjoying the parks is that much harder. 

The summer presents the perfect opportunity to walk along Lake Michigan, explore the various parks and attractions along with catching a Cubs game. Music festivals come to town and the outdoor patios flood with patrons. After a long winter, the atmosphere peaks and it is overall an exciting time to be in the city.

Spring and fall bring milder temperatures, which are still great for being outdoors. You will also experience lower crowds at popular attractions but with a similar atmosphere found in the summer months. 

Day 1: Parks and Museums

Before getting into the long walks past classic architecture and shopping downtown, start your 3 days in Chicago with some fun and laughter. The Navy Pier is a must-see for anyone coming to Chicago for the first or fifteenth time. 

If the name didn’t already give it away, then the pier, which extends well out into Lake Michigan, was formerly used by the navy. But when you arrive, you will find it full of exciting attractions, from live entertainment and performances to fireworks held every two weeks through the summer. 

The major highlight of the pier is the views back towards downtown Chicago and the intimidating Lake Michigan. Although you can see it all from the pier, give yourself an even better view from the top of the Navy Pier’s Centennial Ferris Wheel. From the top you will be able to point out such important landmarks like the Hancock Center, and Willis Tower.

Once you are back on solid ground, walk back along the pier, stopping at one of the many inviting bars and restaurants along the way. If you’re feeling peckish, this would be the perfect spot to grab a bite to eat. Otherwise treat yourself to a pint at the Offshore Rooftop and Bar.

After a refreshing drink and some magnificent views, enjoy the waterfront stroll to Grant Park or jump in an Uber to save on some time. Grant Park is a gorgeous downtown park, spacious in one regard and crammed between the towering buildings and the monstrous lake in another. 

Grant Park is an outstanding example of Chicago’s balanced urban development. After arriving, take the time to explore the green spaces and soak in the bustle of the city with the iconic Buckingham Fountain splashing behind you. Walk the lakeside path, spotting monuments, statues and far off sailboats as you wander.

After exploring Grant Park, continue making your way south towards multiple fun and educational attractions. Soon you will have your pick of natural history museums, aquariums and America’s first planetarium. Depending on how quick you like to explore, you may not have time to hit up all three. Nevertheless, we will help you choose.

The Adler Planetarium was the first of its kind in America, allowing you the chance to see things that are literally beyond the scope. For budding astronomers, those fascinated with life beyond earth and secret Pluto fans, the Adler has it all.

Kids will love the Shedd Aquarium, one of the best in the country. Discover a world of life below the water featuring colorful schools of fish, dangerous sharks and the Giant Pacific Octopus!

Having said all that, the Field Museum (natural history) offers something for everyone. Exhibits are constantly changing, providing new and exciting experiences for those returning to Chicago. But one thing stays the same, the enormous T-Rex skeleton that greats you as you walk in. 

By purchasing the Chicago CityPass, you can access all three activities. You can save up to 50% on these attractions and also be able to visit the Art Institute, Observation Deck and the Museum of Science and History. Save money and time with the chance to skip the line.

Alternatively

Next to the Field Museum, you will notice a behemoth stadium staring right back at you. This is Soldier Field, the home of the Chicago Bears. If you are interested in local history, but of the sports kind, you can take a tour of the oldest stadium in the NFL. 

Beginning in the South Courtyard, your guide will take you through the historic South Concourse, which has images of leaves representing the lives of fallen soldiers. After seeing the famous Doughboy Statue, you will enter the stadium and explore field level views of the playing surface.

Afterwards, explore the visitors’ locker rooms, the Skyline Suite and the iconic Colonnades from 1924. Grab yourself a VIP Tour so you can walk out onto the field and live the sporting dream.

Where to Eat

I you decide not to dine on Navy Pier, make your way to Seoul Tacos for a delicious lunch that won’t break the bank. Combining mouthwatering Korean and Mexican Street food, the tacos here are some of the best and cheapest in Chicago. 

For your first dinner in Chicago, you won’t have to travel far from Grant Park thanks to the aptly named Grant Park Bistro. The trendy restaurant serves contemporary American fare. While its full bar serves up the best craft beers and creative cocktails. 

Day 2: The Bean and Baseball

After a big day of wandering museums, the walking doesn’t stop. Chicago is an immense city, with attractions spread all throughout. But one of the most popular activities is a simple stroll through all the hustle and bustle of downtown Chicago. 

Slicing through the Business District like a hot knife, the Chicago Riverwalk is a beautiful way to capture ‘everyday Chicago’ on your three-day getaway. Starting from Wolf Point, the Riverwalk extends for over a mile along the Chicago River. 

As you follow the trail, you will pass an envious variety of local cafes, the perfect spot for a morning coffee and a light snack. As the city residents rush by on their way to work, kick back and enjoy the scenes. The trail continues on until the river meets Lake Michigan. 

After completing the walk in the morning, the Riverwalk may compel you to return later in the day. As the sun goes down, what was once a casual dining area is turned into a happening part of the city. Come back for outdoor games, live music and happy hours!

Once you complete the Riverwalk, you will have been guided down to Millenium Park. Similar to the Navy Pier and Grant Park, you will have expansive views of the city skyline and plenty of space to enjoy a picnic if you wish. Millenium Park is also great for kids with an extensive playground and green space to run around on. 

When you are exploring the park, you will stumble upon the beautiful Crown Fountain, a reflecting pool. You may also come across live music in the amphitheater. Continue walking through the endless manicured gardens until you reach arguably Chicago’s most iconic attraction, The Bean.

Also known as Cloud Gate, The Bean would surely be the most photographed attraction in the city. At over 30ft tall (9.1m) tall and 60ft (18.2m) long, The Bean is much larger in person than you would expect. Created from polished chrome, the unique reflective piece is the perfect spot for a round of ‘selfies’. Get up close to The Bean and use the odd shape of the structure to warp your appearance.

Cloud Gate and Millenium Park, among other major attractions, are a part of Chicago’s Loop. You can walk this area alongside a knowledgeable guide for free (excluding tip!). With excellent narration and local insight, you can explore these destinations, Chicago’s interesting architecture and even the beginning of the historic Route 66. 

After lunch-we have a fantastic recommendation below-make your way towards Willis Tower. You would have seen the famous skyscraper from several locations around Chicago, but now it’s time to see all of Chicago from the top. 

Once you have appreciated the size of the tower from below (for 25 years it was the tallest building in the world) make your way to the Skydeck at the highest point in the building. You can even use your CityPass for entry! From the Skydeck you will see all of Chicago and as far as the eye can reach. 

If you love a slice of adrenalin, then trade the Skydeck for a glass bottom where beneath your feet is nothing but clear glass and the city 1000ft (305m) below. If that doesn’t get your heart racing, then nothing will. 

When the sun falls on Chicago between April and October, that can only mean one thing, it’s time for some baseball. Whether or not you are a fan of the sport, Wrigley Field is a beautiful place to be at dusk and a true Chicago experience. Not to mention the excellent people watching. 

The neighborhood of Wrigleyville, which hosts the Chicago Cubs, also enjoys a thriving hospitality scene. Before and after the game, the bars pack out with fans celebrating of commiserating, and is the perfect place for a bit of bar hopping to end day two in Chicago. 

Where to Eat

Begin your Chicago morning with a hit of euphoria. Brunch at The Dime will wake you up immediately thanks to bottomless mimosas and general revelry that will have you pumped for a day of adventure. 

For lunch, you simply have to try some of the best deep-dish pizza in town. Chicago’s specialty pizza is stuffed with mounds of cheese and is the perfect lunch to see you through the day. The two iconic restaurants are Giordano’s and Gino’s. Being so close to one another, pick from either as you can’t go wrong.

For a pre-game meal before heading to Wrigley Field, dine out at Smoke Daddy BBQ. Right across the road from the stadium, try some of the best brisket in town while enjoying the views from their outdoor patio. 

Day 3: Shop ‘til you Drop

After strolling the Riverwalk to begin day two, start your last day in Chicago by walking the Magnificent Mile. Chicago’s answer to New York’s Fifth Avenue is home to an abundance of flagship stores, gorgeous boutiques and several shopping malls. You could spend all morning, and frankly, all day hopping between each shop while admiring the old buildings that line the Mile. 

Also along this ‘magnificent’ stretch of road are cafes and restaurants and some of Chicago’s most well-known buildings. Here you will find the Chicago Water Tower, Wrigley Building and the home of the Tribune. 

Before Michigan Avenue reaches the Chicago River, you will walk by the City Gallery. For an interesting, and free activity, wander inside and explore a world of Chicago-focused photography and installations. 

Speaking of free art, after finishing the Magnificent Mile, explore the Theater District which has a high concentration of public art. Chicago has many Picasso sculptures randomly located throughout downtown. Examples include Picasso’s Untitled, the Flamingo and the Monument with Standing Beast. 

Once you have your fix of shopping and the arts, it’s time for some adventure. Finish your time in the city by kayaking along the Chicago River. With your guides from Urban Kayaks, you can experience incredible views of the city soaring up from all directions. 

Suiting all skill levels, the tours include introductory paddles through the city center, to history tours, a happy hour kayak to the Riverwalk’s Island Party Hut and a colorful sunset tour. Whichever you choose, it will be a memorable end to your 3 days in Chicago.

Where to Eat

Treat yourself to the best breakfast in Chicago by starting off day 3 at the Kanela Breakfast Club. With a selection of health acai bowls, to French toast and a jaw-dropping selection of bagels, enjoy a perfect breakfast. Whatever you order, wash it down with their specialty Sofiemosa, a Belgian ale mixed with fresh orange juice.

For lunch on your last day, visit the Chicago French Market. Rather than just a single restaurant, enjoy a French-inspired food hall. But don’t let that limit what you choose to eat, as you can sample cuisines from all over the world. Start off with Belgian fries before trying some taro bubble tea and finishing with some pho.

Final Thoughts

From day 1 to day 3, your adventures in Chicago will involve plenty of sightseeing and a ton of delicious food. Whether you get around on foot, on the train or in the back of an Uber, like the locals, you will always be on the move.

Being such a big city, we couldn’t fit everything in. Portillo’s says hello! Yet Chicago is the kind of city you could visit a dozen times and still find fresh things to do. 

But with an outstanding balance of local eats, iconic attractions and a splash of local culture, this 3 day Chicago itinerary is the perfect recipe for exploring the Windy City. 

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