3-Day Itinerary for Chicago: Weekend Trip Guide for Families

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My son and I went on a surprise mother-son trip to Chicago, Illinois and it was such a fun getaway It’s one of my favorite cities in the US, and I was so excited to finally share it with him. Chicago has some of the biggest and best museums, awesome parks and a skyline filled with amazing architecture. Whether you’re visiting Chicago with kids or without, this 3-Day Itinerary for Chicago is a great starting point to help you plan the best trip to the windy city. 

Updated 4/26/24

3 Day Itinerary for Chicago- Skyline

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3 Day Chicago Itinerary

Day 1

  • Fly to Chicago & Uber or take the L-Train downtown
  • Check into the Fairmont Chicago
  • Visit the Chicago Museum of Science & Industry
  • Dinner at Beatrix River North

Day 2

  • Breakfast at Wildberry Pancakes
  • Explore Millenium Park & take pictures at The Bean
  • Visit the Shedd Aquarium
  • Shopping on Miracle Mile
  • Dinner at The Sugar Factory

Day 3

  • Breakfast at Stan’s Donuts
  • Take pictures at the Michigan Avenue Bridge
  • Maggie Daley Playground
  • Check out of the hotel & fly home!

When to Visit Chicago

Chicago is such a fun city to experience all year-round, and after visiting during all four seasons in Chicago it’s hard to pick a favorite! Weather-wise, late spring to early fall in Chicago are ideal.  Late spring in Chicago typically has milder temperatures with beautiful weather throughout. Summer in Chicago means warm weather and taking advantage of the city’s beaches and awesome outdoor dining venues along the river. Fall in Chicago allows you to see the turning leaves in the parks, and even as it grows colder many Chicago eateries are equipped with heaters for outdoor dining. 

On this recent trip, we visited Chicago in late April.  The weekend before our trip, the weather was in the low 80s, but during our trip it was 50s and rainy. That said, the weather in Chicago in April can be all over the place, so be sure to keep an eye on it and be prepared with rain jackets. And fortunately, there’s no shortage of things to do in Chicago in the rain!

Fox at Millenium Park Chicago

Getting Around Chicago

With two major airports, Chicago is one of the easiest cities to get to. Coming from Pittsburgh, the flight is a little over an hour, making it one of our favorite weekend getaways from Pittsburgh. Chicago O’Hare is one of the largest international airports in the world, and it’s located northwest of downtown Chicago.  It offers tons of options to fly into Chicago nonstop, but it’s also one of the busiest airports in the world- so plan accordingly!  Midway International Airport is a smaller, more manageable airport that’s located southwest of the city. Southwest is one of the most popular airlines out of Midway. Both airports are about 30 minutes or less from the city, pending traffic. 

While you’re in Chicago, ride sharing like Uber and Lyft is very popular. There’s also a great train system in Chicago called the L Train that connects various neighborhoods, the airport and downtown Chicago. It’s super easy to use, and kids under 7 ride free on Chicago trains with a paying adult. 

Chicago in April Toddling Traveler

Things to do in Chicago for a Weekend

There are so many fun things to do in Chicago with kids or without. Chicago has some of the best and biggest museums in the world. It also boasts great shopping, beautiful buildings, rivers and more. Below are several things to do for a Chicago weekend trip. 

Museum of Science and Industry

MSI Chicago is the largest science center in the Western Hemisphere, and it’s at the top of our list of things to do with kids in Chicago. Aviation lovers can explore a real plane and flight simulator, as well as other modes of transportation like a submarine, trains and more. My toddler particularly loved the Farm exhibit where you can climb on real tractors and the awesome mirror maze. The hands-on Idea Factory at MSI, as well as the other interactive exhibits, makes it one of the best Chicago museums for kids. 

You can also find several rotating exhibits at Chicago’s science museum. When we were there, the Art of Brick was on display, with dozens of beautiful creations made out of Legos. There’s even a play area at the end of the exhibit where visitors can attempt different building challenges. It’s perfect if you’re looking for unique things in Chicago for kids- and kids at heart! 

Pro Tip: Be sure to purchase tickets in advance at the Chicago Museum of Science and Industry. They are still operating on a timed schedule. 

Chicago Museum of Science with kids

Shedd Aquarium 

The amazing Shedd Aquarium is one of the best Chicago attractions for families, and it’s jam packed with sea life throughout. The main floor of Shedd is split into different ecosystems, ranging from Amazon River the Great Lakes. There’s also a separate elevator that takes you to the coral reef section, which has several sharks in addition to coral reefs throughout. One of the highlights for visiting Shedd Aquarium with kids is the Polar Play Zone downstairs.

The Polar Play area at Shedd includes starfish touch tanks, a penguin play area and a submarine for kids to explore. (The play area alone makes the aquarium one of our favorite things to do in Chicago with toddlers!) Here you can also get up close with dolphins and the infamous Beluga Whales at the Shedd Aquarium. There’s also an awesome Pacific Northwest exhibit where you can catch a dolphin show as well. 

Pro Tips: Advanced tickets are highly recommended at Shedd Aquarium. We highly recommend getting there when the aquarium opens to avoid the long entry lines and take full advantage of everything Shedd has to offer.

Shedd Aquarium Chicago Toddling Traveler

Millennium Park

Whether you have 1 day or 3 days in Chicago, Millennium Park is another can’t miss Chicago attraction. (And it’s perfect if you’re looking for free things to do in Chicago!) The focal point of Millennium Park is The Bean. This bean shaped sculpture is one of the most popular places to take pictures in Chicago, with the reflective surface capturing both the city’s skyline and tourists at the same time. 

In addition to The Bean, the park is a popular concert venue. It also has a beautiful garden and walking paths throughout. Believe it or not, we even saw a fox in Millennium Park on our last visit there!

The Bean Chicago Millennium Park

Maggie Daley Park

While it’s technically part of Millenium Park, the Maggie Daley Park (aka the Millennium Park playground) is so amazing that it deserves its own section. The highlight of Maggie Daley Park is the amazing Play Garden, and it’s one of the absolute best things in Chicago for kids. It’s a huge playground with a variety of different climbing structures and slides for different ages. There are also several different swings, a fun boat play structure and even a splash pad for littles. (If you’re looking for free things to do in Chicago with toddlers, this is a can’t miss!) 

In addition to the Play Garden, the park includes mini golf, ice skating, a climbing wall and more. 

Best Things to do with kids in Chicago Maggie Daley Park

Wendella Boat Tour

Taking a Chicago architecture boat tour is a classic Chicago experience that you should do at least once. Wendella is one of the most popular boat tours in Chicago, and it departs from several locations including the Michigan Avenue Bridge. The tour guides are extremely knowledgeable, and it’s a great way to see the city while learning about the history of Chicago. (One of our favorite fun facts about Chicago is that the river actually flowers backwards!) There’s also a full bar on board that serves alcoholic and non-alcoholic drinks. 

Book your Chicago boat tour here.

Pro Tip: If you’re looking for a family-friendly Chicago boat tour, be sure to check out the 45 minute tour. We were booked on the 90 minute tour and it was definitely long for my little guy, who was just shy of 5 years old. 

Weekend in Chicago Boat Tour architecture

Shopping on the Magnificent Mile

Chicago has some of the best shopping with a variety of high end and every day brands. Magnificent Mile stores include everything from toy stores and gift shops to luxury apparel. If you need a caffeine fix, you can also stop to enjoy the Starbucks Reserve Roastery, the largest Starbucks in the world. 

If you’re going to Chicago with kids, the Lego and American Girl stores are usually a big hit! Fortunately for parents (or maybe unfortunately for their wallets) both stores are located in the same place at the Water Tower Place in Chicago. 

Lego Store Chicago

More fun things to do for a Chicago weekend getaway

  • Visit Navy Pier and ride the Centennial Wheel
  • Go to a Chicago White Sox game 
  • Head to Wrigleyville for live music (one of my favorites for a girls weekend in Chicago)
  • Visit a Ping Pong bar like AceBounce or Spin Chicago
  • Visit one of several Chicago breweries like Lagunitas Brewery

Kid-Friendly Places to Eat in Chicago

Chicago has a great mix of restaurants for foodies as well as fun and casual places to eat for families. Some of our favorite kid-friendly restaurants in Chicago for breakfast, lunch and dinner are listed below. 

  • Stan’s Donuts is the best place for donuts in Chicago, and it has a huge variety of donut flavors to choose from. The pink, diner style decor is super cute, and there’s seating inside if you want to eat your donuts there. 
  • Wildberry Pancakes and Cafe serves some of the best breakfast in downtown Chicago, and it’s in a great location right next to Millennium Park. The menu is huge, and it’s famous for the large list of pancake options.
  • Sugar Factory is great if you’re looking for fun things to do in Chicago for a birthday. The restaurant is known for its huge sundaes and fun drinks, all of which can be made with alcohol or without. Sugar Factory also has a great menu, including some creative options like rainbow sliders. 
  • Beatrix is a small chain of locally owned restaurants in Chicago. They serve breakfast, lunch and dinner with a constantly changing menu. It also has a great, upscale casual atmosphere that’s open and great for gathering all day long. We went to Beatrix River North and it has outdoor seating as well. 
  • Giordano’s is known for its infamous deep dish pizza. It’s pretty touristy, but it’s worth the stop if you want to try some of the best deep dish pizza in Chicago. Rosebuds or Eataly Chicago are two additional restaurant options for Italian food in Chicago. 
  • Portillo’s is home to another popular Chicago food, with a huge selection of hotdogs. It’s famous for the Chicago style hotdog with toppings like tomatoes and pickles on a poppy seed bun. 

Where to Stay in Chicago 

If you’re looking for one of the best Millennium Park Chicago hotels, the Fairmont Chicago at Millennium Park is a great option. You can’t beat the central location right next to Millennium Park, and it’s a block away from the Michigan Avenue Bridge that’s the start of Magnificent Mile. The rooms are spacious with a variety of rooms and suites available. There’s also a restaurant on site as well as a spa (a great option if you’re looking for a hotel spa in Chicago!)  

If you’re visiting Chicago in the summer or winter, they also have fun themed activities at the Fairmont Chicago. In the summer, they’re part of the “Fairmont Lake House,” and the winter hosts the Fairmont Lodge.

Book the Fairmont Chicago at Millennium Park here.

Looking for additional Chicago hotels that are great for families or kid-free getaways? We also recommend the following hotels:

Fairmont Chicago Millennium Park

What would you do with a long weekend in Chicago? I’d love to add to our list for next time!

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3 Day Itinerary Chicago Weekend Trip

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