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Look no further for the ultimate Chicago family vacation itinerary perfect for spending 3 days in Chicago with kids!

The magnificent city of Chicago receives recognition as being the ‘Best Big City in the U.S.’, as well as being the ‘#1 World’s Best City for Having it All’.

In this post, you’ll learn about what to see and do, how to get around, and how to plan a 3 day Chicago itinerary when visiting Chicago with kids.

In addition, our Chicago family vacation itinerary will guide you to the most popular things to do in Chicago while helping you plan the best visit ever!

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Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan.  Start planning your Chicago family trip now!
3 days in Chicago; Michigan Avenue Bridge

Chicago Family Vacation

If you’re wondering, “Is Chicago a good family vacation spot?”, I would overwhelmingly say, “Yes!”.

In fact, if you’re familiar with popular urban vacation destinations, it’s more than likely that Chicago is on your US bucket list!

Located on the shore of Lake Michigan in Midwest USA, Chicago, Illinois is a glorious city with a population of 3 million people.

Chicago is a tourist’s dream as it has a magnificent, walkable downtown area filled with gorgeous parks and sculptures, impressive museums, several famous Chicago foods, and beautiful lakeside views.

Perfectly blending the hustle and bustle of city life with a degree of friendliness that you’d expect from a small town, this diverse area is a must-visit metropolitan wonder.

Whether you’ve dreamed of walking through Millennium Park and photographing “The Bean” or you want to enlighten your kids by checking out the ever-popular Adler Planetarium, there are so many family-friendly Chicago attractions!

Oh, and psst…we LOVE Chicago so much, that we’ve written several other guides to help you plan your trip!

Best Time to Plan A Chicago Vacation

The best time for a Chicago family vacation is during the months of May, June, September, and October.

In other words, plan a family trip to Chicago when the weather is mild during the late spring, early summer, and early fall.

In addition, be sure to consider what to wear in Chicago depending on when you visit, as the weather varies drastically.

Though Chicago in summer can be hot and humid, many are drawn to the area during this time in order to take advantage of its lake activities and outdoor events.

Keep in mind, however, that Chicago gets very busy with tourists over the weekends and holidays.

We just so happened to visit Chicago in September over Labor Day weekend.

Though the sidewalks throughout the city were very crowded, the holiday weekend special events still made this a great time to visit.

Additional planning tip: If you’re not afraid to get bundled up and brave the cold, we’ve found that visiting Chicago in winter can be just as fun!

Read here to learn about our winter getaway in Chicago which includes the best things to do in Chicago in winter.

Chicago Family Vacation Itinerary: Day 1

The following breakdown of several family activities in Chicago can be applied to a two-day itinerary for Chicago, or extended to a 4-day Chicago itinerary.

Either way, here are our favorite Chicago vacation ideas that we’ve done time and time again.

  • Arrive in Chicago and admire the beautiful Chicago skyline
  • Check-in to your hotel
  • Have dinner at the iconic Portillo’s Hot Dogs

Arrive In Chicago

Day 1 of our 3-day Chicago family itinerary involved a 6-hour drive from our hometown (We love road trips!)

We found travel down Interstate 90 and into the heart of downtown Chicago to be an absolute breeze, with the exception of heavy traffic at times.

Considering driving to the Windy City too?

We have compiled essential tips on how to master a family road trip, and how to create “Are We There Yet” goodie bags to help make it the best road trip ever!

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Chicago Best Western rooftop deck
Best Western River North – Rooftop deck

Check-In To Your Hotel

For this Chicago family vacation, we stayed at the Best Western River North.

Best Western River North is centrally located to several downtown Chicago points of interest.

It is also really close to some great places to eat with kids, such as the SafeHouse, Portillo’s, McDonald’s, and Hard Rock Cafe.

Also adjacent to Best Western River North is a BP gas station and Walgreen’s pharmacy and convenience store.

Check-in was quick and efficient and the front desk staff was very friendly.

They even offer free ice cream sandwiches and sherbet push-ups around the clock!

Like most hotels downtown, there is a daily fee to park on-site. The lot is staffed by a parking attendant and is safe and secure.

Our room was comfortable and stylish; just large enough for 2 double beds and an additional cot. The hotel itself has a heated indoor swimming pool on the top floor.

Next to the pool is an outdoor rooftop deck with comfortable lounging chairs and amazing views of the city.

We loved taking a glass of wine up to the deck each night to relax while the kids swam. The presence of the rooftop deck was definitely the best selling point for us.

Breakfast is not included at Best Western River North, but for a small cost, you can visit the onsite restaurant for made-to-order breakfast items.


No family trip to Chicago is complete without experiencing the 5 famous Chicago foods that are the cornerstone to every visit.

Being right across the street from our hotel, Portillo’s was an easy choice to start off our epic Chicago food experience.

What started as a hot dog cart, Portillo’s restaurant serves up Chicago-style hot dogs, Italian beef sandwiches, burgers, salads, and other sides.

Their casual atmosphere, amazing food, and welcoming ambiance make this one of our most recommended kid-friendly restaurants in downtown Chicago.

Additional planning tip: If you’re looking for a complete foodie experience, schedule a Chicago Food Planet walking food tour that covers the Chicago hot spots.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Portillo's restaurant
Make sure a Chicago hot dog from Portillo’s is part of your Chicago itinerary!

Chicago Family Vacation Itinerary: Day 2

  • Walk and shop on Magnificent Mile
  • Take an Architectural River Cruise
  • Have lunch at Wildberry Pancakes and Cafe
  • Tour and take photos in Millennium Park
  • Spend time enjoying Navy Pier

Magnificent Mile

Start off your Chicago family trip by grabbing a cup of coffee and taking a leisurely walk along Chicago’s Magnificent Mile.

Magnificent Mile is the nickname of the long stretch of upscale shops and restaurants located along Michigan Avenue.

It is also home to the world-famous John Hancock building (home to 360 Chicago and TILT) and the historic water tower and pumping station that were two of the only structures to survive the Chicago Fire of 1871.

Walking along the bustling sidewalks of the Magnificent Mile is not to be missed in your Chicago 3 day itinerary.

Kid-friendly stops include the Disney Store, American Girl Place, Chicago-famous Garrett Popcorn, and Dylan’s Candy Bar.

Chicago 3 day itinerary planning tips: Depart your hotel at 9:30 AM on foot.

Plan to spend 20 minutes walking the entire Magnificent Mile from north to south, with additional time allotted for your choice of shopping and stops.

Architectural River Cruise

If you’re looking to plan a family vacation in Chicago, IL, our top recommendation is to get tickets to go on a Chicago architecture river cruise (if the weather and season permit).

After walking down Magnificent Mile to the south, you will come across the Michigan Avenue Bridge and Chicago’s Riverwalk.

Here is where you access the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady.

For GPS directions, use 112 E. Wacker Drive and look for their blue awning marking the stairway down the river walk dock.

Though there are a few other river cruise options, we absolutely loved our experience on the CAFC River Cruise and highly recommend it.

The boat was family-friendly, fun, and nostalgic, and the commentating was highly informative.

There is a full bar aboard that includes snacks, drinks, and cocktails.

Imagine a glorious float down the Chicago River learning about the towering skyscrapers – while sipping a Mimosa with Tony Bennett music playing in the background.

Chicago family vacation planning tips: Secure 10:30 AM CAFC River Cruise reservations.

Pick up your tickets at 10:00 AM and get in line no later than 10:15 AM to be the first to board the First Lady.

Seats are not pre-assigned and are first-come-first-serve.

Choose seats on the upper deck along the sides for the best-unobstructed photo ops.

The entire river cruise lasts 90 minutes.

Millennium Park

No vacation in Chicago would be complete without visiting Millennium Park! In addition, if you’re planning a family trip to Chicago on a budget, it’s nice to know that all of the attractions in Millennium Park are free!

After stopping for lunch at Wildberry Pancakes and Cafe, spend plenty of time visiting Chicago’s iconic Millennium Park.

Here is where you will find the most talked-about (free) attractions that people typically refer to when visiting Chicago.

Each of these attractions should be part of any Chicago trip with the family!

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of The Bean
Chicago Cloud Gate: “The Bean”

Cloud Gate

The most popular attraction in Millennium Park is the Cloud Gate sculpture.

Commonly referred to as ‘The Bean’, Cloud Gate is an art piece that is a great place to take Instagram photos and selfies, especially off of its reflective surface.

You can see the reflection of the Chicago skyline, walk under The Bean, and take photos from all sides.

Despite the crowds, the space is large enough to accommodate large amounts of visitors.

(It is highly unlikely to get a photo without other tourists in it, however.)

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Crown Fountain
Chicago Crown Fountain

Crown Fountain

Another highlight of Millennium Park is Crown Fountain.

Here, two huge 50ft LED screens light up while displaying the faces of average Chicago residents.

Every 5 minutes, the mouths of the faces spill water onto the ground creating a shallow reflective pool.

The fountains make a great place for kids to cool off in the hot summer months.

BP Pedestrian Bridge

The gigantic stainless steel BP Bridge connects Millennium Park to Maggie Daley Park.

Though there are other outlying sidewalks to get to Maggie Daley Park, make it a point to walk across this unique pedestrian bridge.

Its shiny silver surface, snake-like curvature, and prize-winning architecture make it an experience to remember.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Maggie Daley Park
Chicago’s Maggie Daley Park

Maggie Daley Park

As one of the most kid-friendly Chicago activities, be sure to visit Maggie Daley Park!

After crossing BP Pedestrian Bridge you will enter Maggie Daley Park.

Here you will find mini-golf, a climbing wall, and 5 playgrounds themed for different ages and abilities.

Large tube slides for older kids, innovative swings, and a splash fountain for younger ones are a few other highlights.

The rolling hills and valleys of rubber turf, as well as perfectly incorporated green space, make this a dynamic area that will keep kids entertained for hours.

For those families with small children or kids of all ages for that matter, Maggie Daley Park is a must-do during your Chicago itinerary.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Chicago lakewalk
Chicago’s Lakefront Trail

Lakefront Trail

Upon exiting Maggie Daley Park and heading towards the water you will come across an entrance onto Chicago’s Lakefront Trail.

Chicago’s scenic Lakefront Trail is an 18-mile paved trail that follows along the shoreline of Lake Michigan.

With separate lanes for walking, running, and biking, head north on this trail from the Millennium Park area to get to Chicago’s Navy Pier.

The 15-minute walk along Lakefront Trail will allow you to admire Lake Michigan and watch the on-water boats, kayaks, and wildlife.

Chicago family vacation planning tip: Plan to spend 1-2 hours visiting Millennium and Maggie Daley Park.

You may need more time if you have smaller children who want to spend more time at the park.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Chicago Navy Pier
Chicago Navy Pier: Photo courtesy of Choose Chicago

When considering what to do in Chicago in 3 days, no family itinerary is complete without a visit to the historic Navy Pier.

Over the past few years, Navy Pier has become one of the most popular things to do in Chicago as well as is one of the best Illinois attractions for families.

Likewise, there are literally so many things to do at Navy Pier Chicago with kids!

Ride the 200ft tall iconic Centennial (Ferris) Wheel and other outdoor amusement rides, or dine at one of its many restaurants.

Other activities at Navy Pier include the Amazing Chicago Funhouse Maze, Virtual Rush: Chicago virtual reality experience, and Lake Michigan sightseeing cruises.

Additional planning tip: If you’re looking for things to do in Chicago at night, save riding the Centennial Wheel for when the sun goes down!

Riding the Centennial Wheel at night is super fun and provides amazing views of Chicago’s lit-up skyscrapers!

*Click here for our exclusive FREE Family Vacation Packing List that is both customizable and printable!

Family Packing Checklist

Chicago Family Vacation Itinerary: Day 3

  • Visit 360 Chicago and ride TILT
  • Take a Chicago Big Bus tour
  • Have lunch at Giordano’s Pizza
  • Tour the Art Institute of Chicago
  • Attend a Blue Man Group Chicago show
  • Have dinner at SafeHouse Chicago
Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of 360 Chicago
View from 360 Chicago

360 Chicago Observation Deck + TILT

Start off this morning of your Chicago 3 day itinerary by walking through the north end of Magnificent Mile via Michigan Avenue (to Water Tower Place).

Here you find the (former) John Hancock building, which is home to the 360 Chicago Observation Deck and TILT.

Located on the 94th floor, the 360 Chicago Observation Deck provides unparalleled views of Lake Michigan and the Chicago skyline.

[Included in the Chicago CityPass]

It also offers interactive learning opportunities, a gift shop, and a modern bar and cafe.

For an additional cost, visitors of the Observation Deck can ride TILT.

TILT involves stepping onto a moving platform that slowly tilts you – in a standing position – outside the side of the building.

As you hold onto metal bars, the platform moves outward in 3 increments until you are angled in suspension over Michigan Avenue and the buildings below.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of TILT
360 Chicago TILT

Chicago itinerary planning tip: We had 9:00 AM reservations for 360 Chicago. This is a very popular Chicago attraction so I recommend visiting in the morning as such when crowds are fewer.

Plan to spend 45 minutes to 1 hour here.

Chicago Big Bus Tour

If you’re planning a trip to Chicago, we highly recommend doing a hop-on-hop-off Big Bus Chicago tour as a way to learn and see more of the city.

Tickets for Big Bus Chicago can be purchased online or at any of the advertised Big Bus stops.

There are 2 Big Bus Chicago stops on the same block as the John Hancock Building, so this is where we boarded and began our hop-on hop-off experience.

Chicago itinerary planning tip: It is important to refer to the Big Bus Chicago route map to plan the places and timing of your stops.

The lower half of the bus provides covered seating, while the top half of the bus is open air.

Rain ponchos are provided free of charge in the case of rain.

Giordano’s Pizza

Giordano’s Pizza

After boarding Big Bus Chicago at Stop #12, we rode continuously to Stop #4 at Millennium Park.

Here, we got off and headed for lunch at Giordano’s Pizza (130 E Randolph St, Chicago).

After having a slice of their famous deep-dish pizza while on the Navy Pier, we fell in love.

We couldn’t end our Chicago vacation without another round of this authentic Chicago-style pizza.

Additional planning tip: Plan to spend 1.5 hours at Giordano’s as the pizza alone take 45 minutes to bake.

Art Institute of Chicago

After lunch, we passed through Millennium Park to the adjacent Art Institute of Chicago.

One of the world’s greatest art museums, the Art Institute of Chicago goes out of its way to cater to families (+Kids under the age of 14 are free).

Our favorite family-friendly aspect was the Family Room.

Here, we got to create a customized family museum tour using the interactive Journey Maker.

Chicago itinerary planning tip: The Art Institute of Chicago is massive so plan to spend 60-90 minutes there, depending on the attention span of your kids.

Don’t forget to see Picasso’s, The Old Guitarist, and Grant Wood’s, American Gothic.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of  Blue Man Group
Photo courtesy of Blue Man Group Chicago

Blue Man Group Chicago

After finishing our tour of the Art Institute, we grabbed an Uber and headed to the Briar Street Theater.

Briar Street Theater is home to Blue Man Group Chicago, and is stop #5 of our Chicago 3-day itinerary!

Having heard so much about Blue Man Group, we were so excited about this unique experience.

In fact, as soon as we stepped into the bustling dark theater adorned with blue spotlights, we knew we were in for a treat.

A performance filled with music, art, obscurities, and crowd interaction, the Blue Man characters wow the crowd without ever speaking a word.

Never knowing what is going to happen next, the performance is highly engaging and keeps you at the edge of your seat.

This unforgettable experience is a must-see upon your next family trip to Chicago!

Chicago itinerary planning tip: We had 2:00 PM reservations for Blue Man Group Chicago.

The performance lasts 90 minutes with no intermission.

Uber drivers were readily available to take us back to the downtown Chicago area once the show was over.

Additional planning tip: If you’re looking for another Chicago activity that teens will love, check out Escape Game Chicago! Though we have not personally done one, the downtown Chicago location offers 5 different 60-minute escape rooms!

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of  SafeHouse
The secret entrance into SafeHouse

SafeHouse Chicago

(This location is temporarily closed due to the effects of the pandemic; check their website before visiting.)

After heading to the hotel to rest and get changed for dinner, we walked 5 minutes to our much-anticipated dining experience at SafeHouse Chicago!

Once arriving at the secret entrance, couples, families, and groups are welcomed in one-by-one and must give a password in order to be granted access to the restaurant.

If you do not know the password, silly actions must be performed in order to be let in while the rest of the visitors in the restaurant watch on.

Once inside, the dark, spy-themed decor and lighting are uniquely inviting.

Upon being seated, you are immediately given a name tag to identify your ‘agent name’. This is the name that the servers will refer to you as during your dining experience.

After ordering off the menu, children may participate in an interactive scavenger hunt or visit the in-house magician while waiting for their food.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Safehouse bar lights
SafeHouse Chicago

Chicago itinerary planning tip: Due to its popularity and that it is one of the best Chicago restaurants with kids, reservations are highly recommended at SafeHouse Chicago.

Also, you should know that the fun doesn’t end once your meal is complete. (There is a mysterious twist in getting out of the actual restaurant.)

Chicago CityPASS

There are literally so many things to do in Chicago that many people wonder about Chicago family vacation packages.

One of our best travel tips is that if you’re trying to see the best of Chicago in 3 days, the most affordable way to see the city is with the Chicago CityPASS.

In fact, you can save 50% on visiting Chicago’s top 5 attractions with this one purchase alone.

Grab your CityPASS here – you will not regret bundling your activities into this Chicago family vacation package.

Additional planning tip: Most of the museums have a separate entry and line for CityPASS holders which will also save you a great deal of time.

Chicago Family Vacation: Getting There

If you’re heading to Chicago with family, visitors typically travel there via plane, train, bus, or personal vehicle.

Chicago’s central location and the fact that it is accessible by many major interstates and highways make it easy to get there by car.

Be aware that there are several Illinois tollways as you drive into the city, so be sure to have spare dollar bills on hand.

If traveling from a farther distance, however, search for flights into either O’Hare International Airport or Chicago Midway International Airport.

How to Get Around Chicago

Chicago is a walkable city meaning that when staying downtown, the majority of the popular restaurants, sites, and attractions are all within walking distance to one another.

If staying downtown you simply do not need a car to get around once there.

For longer stretches, Uber vehicles are highly prevalent and can typically be found within 2 – 3 minutes of any given address.

In addition, Chicago is well-known for its convenient street system and its fantastic public transit system.

Where to Stay in Chicago

If you’re planning a vacation in Chicago, IL, there are several options on where to stay in Chicago.

Regardless, be sure to stay downtown so that you can do as little driving around as possible.

Choices downtown include staying within the Magnificent Mile, The Loop, or River North neighborhoods.

The Magnificent Mile is close to the John Hancock Building, Navy Pier, and upscale shopping.

The Loop is close to the Willis Tower and Millennium Park.

On the other hand, River North hotels are still within walking distance to major attractions but provide more budget-friendly options that often include pools and free breakfast.

Here are some of our favorite Chicago resorts for families:

Chicago Family Vacation: If You Have More Time

If you’re fortunate to be planning a Chicago 4-day itinerary, you’ll have time to do a few extra things.

The one area of downtown that we did not get to experience was the extremely popular Museum Campus which is home to several world-famous Chicago museums.

Places such as the Shedd Aquarium, the Field Museum of Natural History, and Alder Planetarium, are places that we will definitely visit during our next family vacation to Chicago.

The Museum of Science and Industry is another Chicago family favorite and should be considered if you like science and technology.

An important note is that both the Museum of Science and Industry and The Field Museum are both sensory-friendly Chicago activities for visitors with autism or sensory processing disorders.

[All Included in the Chicago CityPass]

Thank you to Choose Chicago, Best Western River North, Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, Chicago Food Planet’s Signature Food Tour at Navy Pier, 360 Chicago and TILT, Art Institute of Chicago, Blue Man Group Chicago, and SafeHouse Chicago for hosting our family’s visits. I was not compensated for this Chicago 3 Day itinerary article. All opinions are my own.


*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*

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Top U.S. family travel blog Travel With A Plan uncovers exactly what to do during 3 days in Chicago!  This perfect Chicago 3 day itinerary includes all of Chicago's most popular sights and attractions! #Chicago3dayitinerary #3daychicagoitinerary #chicagoin3days #3daysinchicago #chicagoitinerary #bestthingstodoinChicagowithkids #bestthingstodoinchicago #whattodoinchicago #thingstoseeinchicago #chicagovacationideas #chicagomustdo #chicagotravels #chicagotripideas #chicagothingstodo #chicagointhesummer #thingstodochicago
Top U.S. family travel blog Travel With A Plan uncovers exactly what to do during 3 days in Chicago!  This perfect Chicago 3 day itinerary includes all of Chicago's most popular sights and attractions! #Chicago3dayitinerary #3daychicagoitinerary #chicagoin3days #3daysinchicago #chicagoitinerary #bestthingstodoinChicagowithkids #bestthingstodoinchicago #whattodoinchicago #thingstoseeinchicago #chicagovacationideas #chicagomustdo #chicagotravels #chicagotripideas #chicagothingstodo #chicagointhesummer #thingstodochicago
Click here for our detailed 3-day Chicago itinerary that is perfect for families!  We walk you through where to stay, where to eat, a what to do during your 3 days in Chicago!  #Chicagowithkids #3daysinChicago #3dayChicagoitinerary #Chicagofamilyvacation #3daysinChicagowithkids #whatodoinChicagowithkids

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  1. What a fun trip to Chicago! I’ve had quite a few dog-friendly Chicago trips and we always have a great time. The Architectural River Cruise is a must! It’s such a wonderful way to view the amazing buildings.

  2. As a (former) Chicago resident, I can honestly say this is a great itinerary! Portillo’s Chopped Salad is my favorite and I grab one anytime I’m passing through Phoenix as they actually have a couple of Portillo’s locations.

  3. I would love the opportunity to do more of Chicago. Navy Pier was a big highlight but i’d love to do some of this other stuff!