Chicago

• Shedd Aquarium – a favorite of mine since I was a kid! See belugas, sea lions, otters, and so much more at this great aquarium on the shoreline.
• Art Institute of Chicago – if you have kids old enough to appreciate art, this is a great art museum to check out! Another of my personal favorites! See classics like American Gothic (Grant Wood), Nighthawks (Edward Hopper), A Sunday Afternoon on the Island of La Grande Jatte (George Seurat), The Old Guitarist (Pablo Picasso), plus more from great artists like Van Gogh, Renoir, Toulouse-Lautrec, Cezanne, Monet, Cassatt, Gauguin, O’Keeffe, and many more! There are also kids’ workshop areas where they can create their own art.
• Millennium Park – when our kids were toddlers – this was their favorite! Art, architecture, and nature combine at this park that includes the famous “bean” which is actually called Cloud Gate. There is a lovely garden area with flowers, an amphitheater with outdoor concerts, and the toddler favorite – shallow reflecting pools that kids can splash around in.
• Watch a game at Wrigley Field – a Chicago classic! If it’s not baseball season, you can also take a tour of Wrigley.
• Chicago Children’s Museum at Navy Pier – kids can climb, play, create, and explore at this fun interactive museum with fun exhibitions like Water City and Treehouse Trails.
• Field Museum – see dinosaur bones, a huge replica of an ancient Egyptian tomb, and more at this classic museum! You can also make things in the Family Lab or see a 3D movie. This museum is near Shedd Aquarium and can be visited on the same day.
• Take a boat ride – get out on Lake Michigan for great views of the skyline or go down the river to enjoy looking at Chicago architecture. The most affordable boat rides for family are the Shoreline Water Taxis. If you are really into architecture, then you may want to check out a First Lady Architecture River Cruise, but kids may not enjoy this one as much.
• Chicago Sports Museum – if you’re a fan of any of Chicago’s sports teams (or really just sports in general), you’ll enjoy this interactive museum. Kids (and adults) can try skill challenges, step into a broadcaster booth, solve sports mysteries, and more.
• Griffin Museum of Science and Industry – visit the largest science center in the Western hemisphere, located in Hyde Park. From exploring a huge submarine to marveling at a tiny castle, there are so many exhibits to enjoy!
• Alder Planetarium – watch a planetarium show and check out the fun and kid-friendly space exhibits at this planetarium near Shedd Aquarium and the Field Museum.
• Lincoln Park Zoo – see nearly 200 species at this great zoo in the heart of the city – and it’s free!
• Navy Pier – this long pier contains lots of shops, eateries, and entertainment. You can walk a lot of it inside on a rainy or cool day. Outside, you’ll find an area with a ferris wheel and a few other classic rides that kids will enjoy. There are also free fireworks shows at night during the summer.
• SkyDeck – go to the top of the Willis Tower for amazing views and go out on The Ledge – a glass-box where you can look straight down at the city below.
• Color Factory – explore the world of color as you walk through 14 interactive art installations that are all very picture-worthy. Kids will like the giant ball pit with slides and playing with confetti. You can bundle the Color Factory and SkyDeck together to save!
• Museum of Ice Cream – do you like ice cream and cool picture opportunities? Then you may enjoy this museum where you get to try 5 different unique ice creams and walk through art installation rooms that are colorful and picture-worthy. It’s small and won’t take a ton of time, is a unique experience if you haven’t visited one before (they have them in other major cities), and kids will like the pool filled with sprinkles, but I do think the price is a bit too high for what you get, especially when you’re going as a whole family. If choosing between Color Factory and this one (both are somewhat similar), go with Color Factory unless unique ice cream is a big draw for your family.

There are SO many options! We recommend looking for something that is close to many of the places you’ll be visiting and/or close to a subway stop. We also prefer looking for options that sleep our whole family comfortably, which means no rooms with 2 double beds or 1 king bed plus pull-out couch (both of which are pretty common in big cities). Here are a few good options to check out:

• Residence Inn Chicago Downtown/River North – they have 2-bedroom suites and the location is great – near a subway stop and within walking distance to Millennium Park.
• Hyatt Place Chicago Downtown/The Loop – they have rooms with 2 queen beds and a pull-out couch, it’s in a good walkable location, and there’s an indoor pool.
• Browse other options with 2 queen beds in good locations with good reviews (we’ve set the right filters for you!) >

• Many of the attractions listed in the tab above have fees so try to decide what your must-dos are and budget accordingly.
• Free activities include: Lincoln Park Zoo, Millennium Park, and any other park or outdoor area.
• Check out the Chicago CityPASS if you plan on doing multiple attractions. It could save you money if you were already planning on doing several of the attractions on the list.
• You can stay in fancy hotel and eat at fancy restaurants, or stay in a more affordable hotel and eat quick food – there are so many options in Chicago to fit a range of budgets.
• If flying to Chicago, you do not need to rent a car! Public transportation is easy and I have always felt safe using it when primarily going to/from the airport and to the touristy areas of downtown. There are also plenty of taxis/Ubers/Lyfts around if you feel more comfortable doing that.

• If you go to Navy Pier, your kids are going to see the ferris wheel and the rides and want to do them. Just know they are not cheap. Each ride is $6-9/person and the ferris wheel is $15-18/person. So be ready to spend some money or tell your kids in advance that that’s not what you are there to do.
• This is a toddler-friendly town! There are a lot of vacations we recommend for all ages EXCEPT toddlers, but Chicago works! You can easily use strollers, hop on subways to get around, let them splash around in the reflecting pools of Millennium Park, watch the belugas swim at Shedd Aquarium, explore and play at the Chicago Children’s Museum, play in the ball pit at the Color Factory, and more.
• Don’t be afraid of the subway, but do teach your kids some street smarts if they aren’t used to being in a big city. Remind them to stay close to you and be aware of their surroundings.