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The ultimate 3-day Chicago road trip itinerary in 2022

Finest View of Chicago from Intercontinental

Looking to spend 3 days in Chicago but don’t know where to start? Well, this guide is here to help you out!

Chicago is one of the most populated cities in the United States and sits on the shores of Lake Michigan. Known as ‘the Windy City’, Chicago attracts millions of visitors each year and it’s no surprise why.

With its iconic attractions, towering skyscrapers, and scenic views, this city has made it onto many people’s bucket lists.

But how should you spend your 3 days in Chicago? This guide will go through the must-visit sites, how to get around the city, and the best places to stay.

Without further ado, here is the ultimate 3-day Chicago road trip itinerary in 2022 !

Useful Info for Spending 3 Days in Chicago

How to get to Chicago

Chicago O’hare International Airport is the city’s primary airport and is located just 16 miles (26 km) from Downtown Chicago. However, you’ve also got Chicago Midway International airport too.

Flying is one of the most popular ways to reach Chicago as between them, both airports offer inbound and outbound flights to over 240 destinations across the world. You’ll also find plenty of great deals on domestic flights within the United States too.

If you’re wanting to save some money you can catch a bus or train to Chicago from other major cities in the U.S.

The most popular coach routes are from New York, Buffalo, Dallas, Minneapolis, and Detroit. However, Greyhound also runs 20 express routes to and from major cities and has five locations within the city.

Catching a train is another popular choice, and the best option is Amtrak. They offer routes to over 500 destinations within the United States and Canada, so you’ll easily be able to reach the city.

Many of the coach and bus trips to Chicago often run overnight if you’re traveling a long way, which will also help you save on accommodation costs.

Chicago Riverwalk

Best time to visit Chicago

Chicago’s high season runs from June to August, and temperatures range from 61°F (16°C) to 85°F (29°C) during this time.

You’ll also find plenty of festivals and sports games to attend in the summer months, but be prepared to pay top prices for accommodation.

If you’d prefer a quieter and cheaper experience, then visiting Chicago during the shoulder season is a great option.

The city’s shoulder season falls between April-May and September-October, and you’ll also find the tourist attractions to be much less crowded.

Between April and May, temperatures range from 39°F (4°C) to 71°F (22°C) while during September and October, the temperature fluctuates between 45°F (7°C) to 76°F (24°C).

Although the weather is cooler and you’re likely to see more rain, you can get great bargains on accommodation and transport.

The Educational Pavilion, otherwise known as the Honeycomb in Lincoln Park

How to get around in Chicago

Chicago is super easy to get around as public transport is efficient and runs regularly.

The best way to explore the city is by using the ‘L’ Train. There are 8 colored network lines that will take you to most of the areas and attractions in Chicago. Two of these run 24 hours a day, while the others typically operate between 4 am to 1 am.

You can purchase single standard passes, but it’s cheaper to purchase a one-day or three-day pass depending on your itinerary.

Buses are also a great way to get around as 129 routes run throughout the city. Some of these bus routes run on a 24-hour basis, while others operate until 11 pm or  2 am.

If you’re looking to head out into the suburbs then you can take the Metra Rail.

Taxis can also be found throughout the city but they aren’t cheap, although Uber and Lyft are available here.

However, one of the coolest ways to get around the city is by water taxi. They offer a fast and affordable way to travel along the Chicago River, Lake Michigan, and between tourist attractions.

They do only run between May and September/October though so you’ll need to keep this in mind.

Although you can hire a car and drive around the city center, I wouldn’t recommend it – especially if you only have 3 days in Chicago. The traffic is a nightmare and parking is extremely limited (and very pricy).

The Cloud Gate (aka The Bean) in Millennium Park

Where to stay in Chicago

There are endless neighborhoods within the city so deciding where to stay in Chicago isn’t an easy decision. So, here is a quick guide to the main areas of the city:

Downtown Chicago/The Loop  – perfect for first-time visitorsRiver North – the best place to stay for nightlifeWicker Park – one of the coolest areas in ChicagoThe Gold Coast – a beautiful area along Lake MichiganMagnificent Mile – known for luxury stays and shopping

There are plenty of great areas to stay within the city, but these are just a few of the most popular ones. If you’re interested in knowing more about each neighborhood, make sure to read my detailed guide about the best areas to stay in Chicago.

If you’re in a rush, here are my top recommendations for different budgets.

Viceroy ChicagoPhoto credit: Viceroy Chicago via Booking.com

LUXURY – Viceroy Chicago

Viceroy Chicago is situated in the scenic Gold Coast area and is just minutes away from the Magnificent Mile and Lake Michigan. This hotel has all the facilities you could need for a luxury stay including a rooftop bar and lounge, a fitness center, on-site dining, and a seasonal rooftop pool.

Hotel EMC2, Autograph CollectionPhoto credit: Hotel EMC2 via Booking.com

MID-RANGE – Hotel EMC2

Hotel EMC2 is located in Streeterville and is right by the Magnificent Mile and Downtown Chicago. Millennium Park and Navy Pier are also just 1 mile (1.6 km) away. Not only are the rooms beautiful and spacious, but this hotel also has on-site dining available, a fitness center, and a dry-cleaning service.

Central Loop HotelPhoto credit: Central Loop Hotel via Booking.com

BUDGET – Central Loop Hotel

All guest rooms at Central Loop Hotel have custom-designed furnishings and comfortable beds with down duvets and plush pillow-top mattresses. They also include work desks with ergonomic chairs. Complimentary exercise equipment and air purifiers are available for room delivery upon request.

Overview of the ultimate 3-day Chicago road trip itinerary in 2022

Breakdown of your 3 days in Chicago

Day 1: Breakfast at ​​Goddess and the Baker, Millennium Park (Cloud Gate, Crown Fountain, Lurie Garden), The Art Institute of Chicago, Navy Pier, Dinner at Giordano’s, Sunset at Milton Lee Olive ParkDay 2: Breakfast either at Beatrix or Wildberry Pancakes & Cafe, Starbucks Reserve Roastery, Magnificent Mile, Chicago Riverwalk, Chicago Theatre, Chicago River Architecture Cruise, Nature Boardwalk at Lincoln Park Zoo, Sunset at North Avenue Beach, Dinner at Portillo’s Hot DogsDay 3: SkyDeck Chicago, Breakfast at Mojo Coffee, Grant Park & Buckingham Fountain, Museum Campus (Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field), Dinner at Lou Malnati’s Pizzeria

Day 1

Breakfast at ​​Goddess and the Baker 

Grabbing a bite to eat at the Goddess and the Baker is the perfect way to fuel your day of exploring. It’s famous for its great food, amazing coffee, and fun treats!

They have a wide selection of breakfast options including yogurt parfait, omelets, bagels, and waffles so you won’t have a problem finding something to your taste here.

There are multiple locations of Goddess and the Baker, but this one is right across from Millenium Park (the next stop on your 3 day Chicago itinerary). You can either have breakfast first thing in the morning or after you’ve visited the park – it’s completely up to you!

Millennium Park and The Bean

After (or before) breakfast, make your way to Millennium Park which is one of the most famous landmarks in Chicago.

Spanning over 24.5 acres, this park is home to many popular attractions including the Cloud Gate (aka ‘The Bean’).

The Cloud Gate is a public sculpture that was designed by British artist Anish Kapoor. It’s made up of 168 stainless steel plates and weighs in at a whopping 110 tons!

You can walk around the sculpture, take photos, and even go underneath it. Thanks to its reflective surface, it has quickly become one of the most Instagrammable places in Chicago. So be prepared for the crowds as this is one of the most popular things to do in Chicago!

After you’ve had your fill of The Bean, continue exploring Millennium Park. There’s plenty to see and do here including visiting the Lurie Garden, which is a 2.5-acre public garden, or checking out the Crown Fountain which is a work of art in itself!

Cloud Gate, aka the Chicago Bean in Downtown ChicagoCloud Gate, aka The BeanThe Crown Fountain (first photo) and Lurie Garden (second photo)

The Art Institute of Chicago

The Art Institute of Chicago is another popular attraction as it’s one of the world’s largest (and oldest) art museums.

Aside from its ever-changing exhibitions, the museum has a permanent collection of around 300,000 art pieces which is pretty impressive.

These ongoing exhibitions include the ‘Of Gods and Glamor’ exhibit, ‘a New View of African Art’, and the ‘Landscape in Light’ exhibit.

The museum attracts around 1.5 million people annually and is a must-visit on your 3 day trip to Chicago.

It’s important to note that the Art Institute of Chicago is closed on Tuesdays and Wednesdays, so you’ll have to time your visit right if you want to visit this spot.

Otherwise, it’s open between 11 am – 5 pm from Thursday to Monday and general admission costs $25 per person.

TOP TIP: In case you want to visit multiple attractions, take a look at the Chicago CityPASS which can help you save 48% or more on the top attractions. It includes access to The Art Institute of Chicago, Shedd Aquarium and SkyDeck Chicago among many other popular sites.

Navy Pier

Next up on your 3 days in Chicago itinerary is a visit to Navy Pier, a 3,300-foot-long pier that sits on the shores of Lake Michigan.

It’s one of the most popular tourist destinations in the city and it’s easy to see why with its many attractions, shops, and restaurants.

You’ll find plenty to do here including fairground rides, live music performances, theater productions, and special events. Not to mention the incredible views to be had from the pier itself!

One of the unmissable things to do in Navy Pier is going on a ride on the Centennial Wheel, which is a 200-foot tall Ferris wheel. From the top, you’ll be able to see amazing views of the cityscape and beyond! Since it’s a fairly popular attraction, it’s best to purchase your tickets in advance.

If you’re looking to do some shopping, Navy Pier is also home to a variety of stores selling everything from souvenirs to clothing.

Dinner at Giordano’s 

And when you’re ready to refuel, there are plenty of restaurants and cafes in Navy Pier to choose from including the food court which has options to suit all tastes.

My personal recommendation for today’s dinner is Giordano’s. They have multiple locations throughout the city but this one is actually at Navy Pier so you won’t have to wander far.

Giordano’s is home to the best deep dish pizzas in all of Chicago, and you’ll find plenty of tasty topping options here.

Some of the most popular choices include ‘meat and more meat’, the ‘Chicago classic’, and the ‘super veggie’. You can even make your own if you fancy!

In case you’re not in the mood for pizza, they also have a delicious range of pasta dishes and sandwiches. If you’re looking to see (and taste) the best of Chicago in 3 days, this is the restaurant you need to visit!

Sunset at Milton Lee Olive Park

Watching the sunset at Milton Lee Olive Park is the perfect way to end the first day of your 3 days in Chicago.

The park is named after Milton Lee Olive who was given a medal of honor for his actions in the Vietnam War.

It’s located on a man-made peninsula that juts out onto Lake Michigan, so naturally, it boasts spectacular views – especially at sunset. You’ll also find plenty of walks here that offer superb views of the Chicago skyline.

However, the highlight of Milton Lee Olive Park has to be the fountains! There are five circular fountains in total and each one is connected by walking trails.

Day 2

Breakfast either at Beatrix or Wildberry Pancakes & Cafe 

Breakfast is the most important meal of the day, and these two places are incredible!

Both Beatrix and the Wildberry Pancakes & Cafe have multiple locations throughout the city and you’ll find one relatively close to the Magnificent Mile (the next attraction on your 3 day Chicago itinerary).

Wildberry Pancakes & Cafe is one of the best choices when it comes to breakfast places in Chicago. As the name suggests, pancakes are their specialty and you’ll be spoiled for choice with all of the different flavors on offer.

There are also plenty of other breakfast options available including eggs, bacon, sausage, bagels, and more. Their French toasts are also incredible!

Breakfast at Wildberry Pancakes & Cafe

If pancakes aren’t your thing, another great option for breakfast is Beatrix. This restaurant has a focus on healthy and flavorful food with plenty of vegan and vegetarian options available.

You’ll find everything from avocado toast to quinoa bowls on the menu, as well as a selection of fresh juices and smoothies.

Breakfast at Beatrix

Starbucks Reserve Roastery

After breakfast, make your way to the Starbucks Reserve Roastery. This is a must-visit for any coffee lover!

Starbucks Reserve Roastery is home to a selection of the rarest and most extraordinary coffees on earth. Not only that, but it’s the largest Starbucks in the world with five floors covering over 35,000 sq ft.

Usually, you’d head to a Starbucks for a quick coffee but not here! The Starbucks Reserve Roastery offers interactive tours, a rooftop deck to admire the city views, and delicious pastries.

Trust me, if you’re into coffee then you don’t want to miss out on this place during your 3 day trip to Chicago.

Magnificent Mile

The Magnificent Mile is without a doubt one of the most popular places to visit in Chicago. It’s one of the most famous shopping destinations in the world and is home to huge shopping centers, boutique stores, and plenty of designer shops.

However, there is so much more to do here than just shop! Some of the most popular attractions include the John Hancock Center, the Wrigley Building, and the Tribune Tower. You can also head to the free gallery within the Water Tower.

If you’re looking to do some shopping, you’ll find everything from high-end stores to budget-friendly options. And when you need a break from shopping, there are plenty of restaurants and cafes to choose from.

Chicago Riverwalk

After exploring the Magnificent Mile, make your way to the Chicago Riverwalk. This is a great spot to relax and take in the views of the city.

The Chicago Riverwalk is a 1.25 mile (2 km) path that is made up of four districts; the Arcade, the Civic, the Confluence, and the Esplanade.

The path starts from Lake Street and runs along the Chicago River until it reaches Lake Michigan.

Along the way, you’ll get to see a variety of public art including banners, murals, and sculptures so make sure you take your time walking this path.

However, the highlights of the Chicago Riverwalk have to be the iconic Wrigley Building and the DuSable Bridge. With so much to offer, this riverwalk needs to be on your 3 days in Chicago itinerary!

River North Chicago

Chicago Theatre

The Chicago Theatre was constructed in 1921 and designed by Cornelius Ward Rapp and George L. Rapp. It was the first lavish movie palace in the United States and was incredibly successful.

This led to the owners (Balaban & Watz) constructing other theaters of its design throughout America.

The whole design of the theater is based on luxury, which is clear just by taking a look at the grand lobby inside.

During your stay in the city, I’d recommend catching a show here to fully experience this incredible building. You can take your pick from comedy shows, live music performances, and theater productions.

However, if you don’t have time then simply head inside and go on a tour – trust me you won’t regret it!

Chicago River Architecture Cruise 

If you’ve only got 3 days in Chicago, then going on a river cruise has to be at the top of your list. Chicago River architecture cruises usually last around 1.5 hours and typically start at DuSable Bridge.

One of the best choices is this river cruise that will take you down the Chicago River and past some of the city’s most iconic buildings.

You’ll also learn all about the history and architecture of each building from your knowledgeable tour guide. Best of all, it allows you to skip the ticket office and board straight away!

Alternatively, this 1.5-hour river cruise is a great option as well.

If you’re a bit short on time or want to keep the children entertained, then this family-friendly river cruise is a great choice. It’s only 45 minutes long but will still show you the city’s most breathtaking landmarks.

Boat on a river in Chicago

Nature Boardwalk at Lincoln Park Zoo 

After your architecture cruise, make your way to the Nature Boardwalk at Lincoln Park Zoo. This is a great spot to unwind and take a break from all the hustle and bustle of the city.

The Nature Boardwalk is an oasis within the city with plenty of trees, flowers, and greenery. There’s also a pond where you can spot turtles, ducks, and other wildlife.

One of the unmissable sights within the Nature Boardwalk is the Educational Pavilion which is one of the most unique things you’ll see during this 3 day Chicago itinerary.

The honeycombed shaped pavilion is constructed of prefabricated wood elements and the arched structure forms a place to shelter during your exploration of the park.

If you have some extra time on your hands, I also recommend checking out the Lincoln Park Zoo. It’s one of the oldest zoos in the country and it’s completely free to visit!

Sunset at North Avenue Beach

There’s no better way to appreciate a new city than by admiring an epic sunset. Chicago has plenty of incredible opportunities for this but watching the sunset at North Avenue Beach just hits differently!

It’s one of the city’s most popular beaches and is located within Lincoln Park so you won’t have to walk far after visiting the Zoo or the Nature Boardwalk.

Not only is North Avenue Beach beautiful, but you’ll also find an awesome beach house here too. The building is inspired by an ocean liner and offers a top deck where you’ll get spectacular views – especially at sunset.

Make sure to stay a bit longer after the sunset to see the city all lit up. It’s truly an incredible experience!

Dinner at Portillo’s Hot Dogs

Chicago has endless options for dining, but you definitely need to try Portillo’s Hot Dogs during your 3 days in Chicago.

This Chicago born-chain is famous for its juicy hot dogs, tasty burgers, and delicious chocolate cake. Their Italian beef sandwiches are also a big hit. They even have vegan hot dogs so they cater to every dietary requirement.

After a long day of exploring, eating at Portillo’s Hot Dogs is the best (and tastiest) way to refuel.

Day 3

Skydeck Chicago

To truly make the most out of your 3 days in Chicago, you’ll want to head up to Skydeck Chicago during your visit. Located on the 103rd floor in the Willis Tower, Skydeck Chicago offers breathtaking views of the city.

If you head up there on a clear day you’re really in for a treat, as you’ll be able to see up to 50 miles (80 km) away including four American states!

Are you feeling daring? If so, you should head out onto the ledge. The ledge is made up of four glass view boxes, and you’ll get a completely unobstructed view of Chicago. However, this probably isn’t suitable for people with a fear of heights, as it’s pretty daunting!

Since it’s one of the most popular attractions in Chicago, I recommend heading there first thing in the morning right when it opens (usually around 8.30 am – 9 am). It’s also advisable to book your tickets in advance so you don’t lose any time waiting in the line.

Chicago skyline view from Skydeck Chicago

Breakfast at Mojo Coffee

Mojo Coffee is a great place to fuel yourself for the last day of this 3 day Chicago itinerary.

You’ll find plenty of locations throughout the city but I’d recommend heading to this one as it’s located right next to the Willis Tower. Plus, it’s the very first cafe they’ve opened in Chicago after their success in New Zealand!

Mojo Cafe offers plenty of tasty food options, including waffles, shakshuka, salads, poached eggs, and avocado on toast for starters.

They also have a delicious range of smoothies including ‘cold brew & chocolate’ and ‘pear, pineapple & spirulina’.

Also, if you’re a coffee lover, grabbing a cup here is mandatory – and you can also take some freshly roasted coffee beans home with you.

Grant Park & Buckingham Fountain

After you’ve had your fill of the views from Skydeck Chicago and you’re stomach is full, make your way to Grant Park. This is one of the most popular spots in the city and it’s easy to see why.

The park is huge (319 acres to be exact!) and there’s so much to see and do here. From gardens and sculptures to museums and fountains, there’s something for everyone in Grant Park.

One of the most popular attractions in the park is Buckingham Fountain. This iconic fountain is one of the largest in the world and uses around 15,000 gallons of water per minute.

The fountain also performs a water show hourly so make sure you time your visit right to witness it. You can also decide to come back after nightfall when you can enjoy a light and music display with the water show.

Museum Campus 

After you’ve explored Grant Park, make your way to Museum Campus. This 57-acre park is home to some of the best museums in the city including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

If you’re visiting with kids, they’ll definitely want to check out the Field Museum. This world-renowned museum is home to Sue, the largest and most complete Tyrannosaurus Rex fossil ever found.

Adults will appreciate the Shedd Aquarium which is one of the largest indoor aquariums in the world. And if you’re interested in space, the Adler Planetarium is a must-visit.

Visiting all 3 museums is pretty time consuming so I would recommend choosing one or two that take your fancy, so you can take your time and not rush around. No matter which museum you choose to visit, you’re sure to have a great time at Museum Campus!

TOP TIP: To make the most out of your visit and to save some cash, I’d recommend getting the Chicago CityPASS. It allows you to visit five of the city’s top attractions (including all 3 museums in Museum Campus) and you can save up to 48% off the normal ticket prices.

Chicago Skyline View from Museum CampusView of the Chicago skyline from Museum Campus

Dinner at Lou Malnati’s Pizzeria 

After a day of exploring, you’re going to want a delicious dinner. And there’s no better place for that than Lou Malnati’s Pizzeria.

This iconic pizzeria has been serving up delicious deep dish pies since 1971 and is hands-down the best place to get pizza in the city. They use an exclusive sausage blend, vine-ripened plum tomatoes, and Wisconsin cheese to make the most delicious toppings.

You can either create your own pizza here, or you can try one of their many tasty options including the ‘Malnati Chicago Classic’, ‘The Lou’, and the iconic pepperoni.

Lou Malnati’s Pizzeria also has a wide variety of pasta dishes, salads, sandwiches, and desserts.

They have multiple locations throughout the city, this one is the closest to Millenium Park. There is no better way to end your 3 days in Chicago, than by dining here!

There are so many awesome sites to see within the city, but luckily spending 3 days in Chicago is plenty of time to see the top attractions.

Whether you’re looking to relax on the shores of Lake Michigan, explore some of the city’s many museums, or go shopping along the Magnificent Mile – there is something for everyone.

If you have any further questions about your 3 day trip to Chicago then don’t hesitate to get in touch with me. You can contact me via email, social media platforms, or by leaving a comment below.

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2 comments

graliontorile August 17, 2022 at 8:01 am

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