Quick Chicago Itinerary for 1 to 3 Days

If you’re heading to Chicago for the first time, it can be a little confusing to figure out how to fit all the things you must see or do into just a few days. 

To help you out, I wrote this complete itinerary which can be used to plan a visit for 1-3 days. But don’t worry if you’re visiting for a little longer, I also added some extra activities for those of you who have more time. 

Chicago is also a great city for kids as it has plenty of hands-on opportunities for play which I have listed in its own special section below to save my fellow parents a little time when planning a trip.  

How Many Days in Chicago is Enough?

3 days is a good amount of time to explore all of Chicago’s best attractions without feeling too rushed during your visit. 

That being said, if you’re limited on time you can easily squeeze a quick visit into just 1 day if you’re happy to skip a couple of activities or expand your itinerary to include many more off-the-beaten-path things to do if you have more time.

Buy a City Pass if you are visiting lots of attractions: If you plan on visiting many of Chicago’s most famous tourist attractions, it may be worth buying a Chicago City Pass that gives you access to several iconic things to do for one single price. If you visit enough places, the pass can save you quite a lot of money! 

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Getting to Chicago from O’Hare Airport

Getting downtown from Chicago O’Hare Airport is super easy since there is a direct train. You can buy tickets at the machine as it’s easy and clear. However, that’s where the easy part ends.

As soon as I got to downtown Chicago I quickly learned that the last person to ask for directions is the local police. 

To my surprise, the first policeman sent me in the wrong direction as I was told by some nice people who were willing to help me. The second policeman had no idea which way was North or South in Chicago. I just had to gamble and walk in the direction I thought was correct and in less than 20 minutes I somehow got to my hotel.

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How to Get Around Chicago

Getting around Chicago is pretty simple as there are plenty of options including public transport and taxis, but the best options for tourists are either walking or getting a ticket for a hop-on hop-off sightseeing bus.

Hop on Hop off Bus

If you’re looking for the easiest way to see all the sights in Chicago, get a ticket for the Sightseeing bus. 

This bus runs all day and stops right at all the major tourist attractions in the city and with your ticket you can get on and off as many times as you like, making it the most convenient option if it’s your first visit to Chicago. 

Exploring Chicago on Foot

While some people prefer to use a tour bus to get around a new city, I would say that you can surely walk around downtown Chicago. There’s nothing wrong with the sightseeing bus, but I didn’t have any issues walking around.

Chicago’s architecture definitely impressed me with its nicely decorated skyscrapers. I ended up spending the evening at the Sweetwater Tavern and Grill with some friends. Afterward, I walked to my hotel feeling perfectly safe.

Talking about Chicago’s skyline, I have to say that it was definitely more impressive than that of New York. It didn’t have much flora, but neither did any American big city.

Chicago Public Transport

The public transport network in Chicago is called the CTA and offers 8 “L” train lines and countless bus routes covering the entire city and two of the trains (the Blue and Red lines) even run 24/7. 
Tickets are quite affordable and available for purchase at any train station.

You can pay in cash for a single ride on buses or get a reloadable Ventra Transit Card from a machine at any train station. If you download the app you can also reload your card from your phone.

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Where to Stay in Chicago

Chicago is a relatively condensed city with the majority of tourist attractions located within walking distance of each other in the downtown area. 

That means staying in the Loop district or on the Magnificent Mile is the best location giving you easy access to the city’s best attractions, restaurants, shopping, and nightlife. 

I stayed in a hostel to save some money in Chicago and the place was nice and clean, as most of the hostels are in the US are, but way too big for socializing and meeting people. A funny detail about this hostel was that it dealt with Latin American guests by putting a sign instructing people to place used toilet paper in the toilet bowl instead of the bin.

Here are a few great hotels I recommend booking for your stay in Chicago:

• The Langham Chicago – An incredible 5-star hotel with unbeatable city views from all rooms. The luxurious bathrooms might make you never want to leave the room but their award-winning wellness retreat is a must.  
• Pendry Chicago – This beautiful 4-star hotel is nothing short of luxury with its endless list of facilities and regal rooms featuring marble decor and breathtaking views. 
• Godfrey Hotel Chicago – If you’re looking for an incredible mid-range hotel, this beautiful boutique option boasts a modern design and an amazing rooftop bar and lounge open all year round. 
• HI Chicago Hostel – Offering both private and shared dorm rooms, this budget hostel provides a vibrant atmosphere and affordable prices in a great location. 

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Things to Do in Chicago in 1 – 3 Days

1. Get High at the Skydeck in Willis Tower

Start any day by visiting the tallest building in Chicago, the Willis Tower, formerly known as the Sears Tower. 

I was told this place was incredibly crowded and I wouldn’t get to take any photos while standing on the glass floor. But I played it smart and got there at 8 AM with the ticket I purchased online which meant I didn’t have to stand in line and became the first visitor of the day. 

It was super weird to be there by myself for the first 10 minutes, but definitely worth it!

If you’re looking for another unique viewing deck to see the city, an alternative to the Willis Tower is 360 Chicago where you can lie against a slanted glass window on the 94th floor. 

Recommended Tours:
Willis Tower Skydeck and The Ledge Ticket
Small Group Walking Tour with Skydeck and Boat

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2. Take Pictures with The Bean at Cloud Gate

The second attraction of the day was the famous “Bean”, officially known as the Cloud Gate. 

This big sculpture in the Millennium Park attracts tons of tourists every year, for a good reason. It’s a fun place to see your reflections, take a few photos, and enjoy the rest of the park afterward. 

Millennium Park is not only known for the bean, but it’s also home to some awesome fountains, museums, and impressive sculptures.

Recommended Tours:
​​Millennium Park Self-Guided Walking Tour
Ultimate City Attractions Bike Tour

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3. Experience the Riverwalk

This 1.25-mile-long walking path follows the Chicago River from Lake Street all the way to Lake Michigan west with four different areas including the Esplanade, The Civic, The Arcade, and the Confluence.

A vibrant hub of art and culture, the riverwalk banks are often buzzing with street performers, public art installations, and busy riverfront bars and restaurants with plenty of people enjoying what the city has to offer. 

Whether you visit during the day or night for a romantic stroll, the Riverwalk is an absolute must on any Chicago itinerary. 

Recommended Tours:
Riverwalk Self-Guided Walking Tour
Must-See Chicago 90-Minute Walking Tour

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4. Visit the Art Institute of Chicago

I think this is perhaps the best museum in all of Chicago and what’s even better is that it’s great for kids too. 

The Art Institute of Chicago is one of the oldest art museums in the world being founded in 1879 and today holds the second biggest collection of impressionist art (only beaten by the Louvre in Paris). 

With such a diverse portfolio of works, the Art Institute has plenty to impress visitors of all different tastes, plus the institute is home to the Ryan Learning Center which not only boasts a fun multisensory gallery but also provides the opportunity for families to do experiments and create art of their own for the ultimate hands-on experience. 

Recommended Tours:
Art Institute of Chicago Skip-the-Line Ticket
Art Institute of Chicago Guided Tour

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5. Stroll the Magnificent Mile

If you’re looking for another great walk that will allow you to experience the buzzing commercial district of Chicago, the Magnificent Mile should be your next stop!

Dotted with luxury shops, beautiful architecture, deluxe hotels, and upscale restaurants, this area runs along North Michigan Avenue from Oak Street down to the river and is the best place to lap up Chicago’s great atmosphere on an evening walk.

Recommended Tours:
Magnificent Mile Walking Tour

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6. See the Chicago Architecture Centre

In a city of beautiful skyscrapers, it’s no surprise that one of the best places to learn about Chicago’s foundations is the Chicago Architecture Centre. 

Originally formed as a foundation to save the historic Glessner House, the Architecture Centre has evolved to become a place where you can learn about the importance of design as well as hear stories about the city’s history. 

The center offers tours and exhibitions as well as hosting events throughout the year so check the website before your visit to see what’s on. 

Recommended Tours:
Architecture Center Exhibit Admission
Elevated Architecture Walking Tour

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If You Have More Time, Add These Activities

7. Explore Some More Museums

As with most US cities, Chicago is home to several incredible museums with lots to learn. 

I’ve covered the most famous ones already but since everyone has different tastes, I decided to list a few more great choices below that should absolutely be added to your itinerary if you have more time!  

• Chicago Cultural Center
• The Field Museum 
• Museum of Science and Industry
• American Writers Museum
• Chicago History Museum
• Chicago Sports Museum
• DuSable Black History Museum

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8. Catch a Game at Wrigley Field

What’s more quintessentially Chicagoan than eating a Chicago Dog at a Baseball game? 

Wrigley Field is the oldest baseball park in the National League and a great place to enjoy some sun while catching a game of this iconic American sport. You can check the game schedule here to see what’s on during your vacation but make sure to grab a ticket in advance.  

9. Visit Garfield Park Conservatory

This beautiful botanical conservatory is one of the biggest in the country with 8 different greenhouses to explore whether it be for 1 hour or 5!  

The glasshouses at the Garfield Park Conservatory are open year-round and in summer you have an additional 10 acres of outdoor gardens with ponds, and nature play spaces to enjoy for the whole family.  

10. Enjoy Navy Pier

You don’t have to go far to find a seaside-like carnival in Chicago. 

Located in the middle of the Chicago River, Navy Pier is a huge 3,300 ft pier home to the famous Centennial Wheel alongside many other classic amusement park rides and carnival games. 

There is no admission fee for the pier so you will only need to pay for the rides you choose, plus there is always something going on here so check the website if you are looking for cool, free events. 

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Things to Do in Chicago with Kids

Learn at the Chicago Children’s Museum

Located on Navy Pier, the Chicago Children’s Museum tops the list of things to do in Chicago with kids. 

This interactive play space provides an incredible place for kids to learn, play, create, and imagine through hands-on exhibitions and innovative playgrounds. 

The museum has plenty of different areas to suit kids of all ages with rooms for babies and toddlers, spaces for kids 4-8, and plenty more advanced exhibitions for 9+ year-olds. 

Take a River Cruise

The Chicago River is constantly dotted with boats, kayaks and more floating up and down this vibrant area of the city, so it’s no surprise that jumping on board a river cruise can be a great activity for the whole family to enjoy. 

With countless different themes to choose from, you can easily find something to pique your interest while keeping the kids entertained as you float by some of the city’s biggest attractions. 

Recommended Tours:
45-Minute Family-Friendly Architecture River Cruise
Chicago Lakefront: Seadog Speedboat Ride

Taste New Flavors on a Food Tour

Pizza, hot dogs, popcorn, and rainbow ice cream, doesn’t that sound like every child’s dream? 

Chicago is known to have some of the best (mostly unhealthy) foods in the country so taking a food tour with your family is sure to be a hit with the whole team. 

But don’t worry, these tours aren’t all fatty foods, Chicago also boasts a wide range of delicious fusion cuisines brought over by immigrants from all around the world. Make sure to try the Jibarito Sandwich and Polish Sausage! 

Recommended Tours:
Favorite Foods Guided Walking Tour
Downtown Pizza Guided Walking Tour with Tastings

Experience Shedd Aquarium

No family visit to Chicago is complete without a stop at the huge Shedd Aquarium. 

This iconic place is home to aquatic animals from all around the world including sharks, penguins, octopuses’ and even belugas whales!

In addition to the endless tanks that let you get up close and personal with the animals, the aquarium also offers the chance to touch or feed strays and starfish plus 4-D and virtual reality experiences to learn more about the creatures.  

Relax at North Avenue Beach

To take a break from the hustle and bustle, head straight to North Avenue Beach where you can spend time swimming or simply relaxing on the sandy shores. 

But what makes this beach really stand out is the “Beach House” which is a cool building in the shape of an ocean liner-inspired. It even has portholes that you can look out of for a great view. 

Surrounding the beach you will find plenty of eateries, sports facilities, and rental shops if you want to try some watersports. 

Visit the Museum of Icecream

Probably the most colorful museum in Chicago, the Museum of Icecream is any child’s dream day out! 

With unlimited samples, it may take you all day to pry your kids away from this place but don’t worry, there’s lots of fun to be had by the whole family. 

Not only will you learn about the complete history of ice cream with multisensory displays, but you can also play desert putt-putt and dive into an actual sprinkle pool. 

See the Animals at Lincoln Park Zoo

For those of you looking for some more free things to do with kids in Chicago, you can’t go past the Lincoln Park Zoo. 

This huge zoo covers 35 acres and is home to countless animals from all over the world including lions, kangaroos, sloths, and more. 

Note that while the entrance is free, the parking here can get pretty pricy so it may be best to arrive by other means if you wish to save a little money. 

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What to Eat in Chicago?

Chicago pizza! I couldn’t leave Chicago without having a taste of some of its famous deep-dish pizza. Luckily for me, I happened to be there during the Taste of Chicago festival where some of the best restaurants in the city set up stalls and sell samples of their food.

It was an incredibly hot day so walking around in the sun wasn’t easy, but worth it. I got to try some awesome Chicago-style pizza that I fell in love with – sorry New York City!

But Pizza isn’t the only thing Chicago has to offer! if you’re looking for a quick bite you can’t miss the Chicago Dog or Chicago Popcorn, and for dessert, fudge is the answer!  The city also boasts an incredible range of innovative cuisines that blend international flavors to explore. 

You’ll find a lot of the best food in Chicago in the West Loop Area, but make sure to hunt out some of the city’s most famous restaurants such as Au Cheval and Lem’s Bar-B-Q.