Chicago is pure MAGIC! I love this city! I grew up in nearby Iowa but have only begun to frequent The Windy City in the past few years with my family. All of us have the best time seeing new things every time we go!
We have been to Chicago FOUR times just in the last year and a half! I have family in the Chicago suburb, Batavia (also the home of the U.S. ALDI headquarters, but more about that love story later!), so we always have a place to stay. Having a huge family sprawled across the U.S.A. is such a blessing – we are motivated to make trips to places that we may not otherwise, and they never seem to mind if we bunk with them, keeping our low-budget travels possible!
Getting There:
Flights into Chicago seem to be rather reasonable but we almost always drive.
Why?
Driving is still less expensive, even from Alabama.
We get to see FOUR beautiful cities on the drive up: Nashville, Louisville, Indianapolis and of course, the gorgeous Chicago skyline!
Having 2 kids still in carseats/boosters, it’s so much easier to have our own vehicle.
However, if you do choose to fly, Midway Airport seems to be a wise choice over O’hare. Midway is smaller, simpler to navigate and easier to get to and from.
Where to Stay:
If you don’t have family nearby like we do, I think a hotel near the Magnificent Mile would be perfect! Walking distance to so many attractions will keep you from having figure out transportation several times each day. I’ve seen some pretty great package deals on Tripadvisor and I LOVE that they give you tons of “Things to do” that you can save in a trip file! You can even buy tickets for attractions and tours along with your package. It’s a vacation planner’s dream!
Getting Around:
Even if you do have your own vehicle, you won’t want to be moving and parking your car several times in one day. This will cost you BIG time $! We’ve paid up to $32 to park in Chicago!
Make sure to pick a central spot and group your plans for the day at nearby, walkable locations.
Download and use the FREE ParkWhiz app before you get to the parking location. It will tell you where spots are available. You can choose a time slot (always allow for more time than you think). The app will give you a price for parking for that time and it’s usually close to HALF of what the same parking garage would charge if you waited and paid without the app.
Although there are several transportation options within the city, the L-train, busses etc., the easiest ones to grab and go like Uber and Lyft, aren’t always easy options for those with kids requiring car seats or boosters like ours.
Be prepared to WALK quite a bit. Even the distance from parking areas to museums and shops can be several blocks. But it’s worth it and also one reason I prefer to go to Chicago during the warmer months!
What to do (The best part!):
This city offers more to do than we could do in 100 trips to Chicago! You can FEEL the history there – it seems it’s an important part of everything you do while you’re there, like a common thread throughout the city. The people really value the city’s past and it shows.
The architecture is the heart of the city. Unique and unbelievable building designs catch your eye at every city block.
That being said, my recommendation is to take a:
Riverboat Architectural Tour:
I say do this FIRST thing! I’m so glad we did on our first trip. It familiarizes you with the city from the inside, away from the crowds. A guide tells you all about the history of the area from famous skyscrapers to quirky cylinder-shaped apartment buildings. It gave us our directional bearings as we walked and drove through the city later in our trip, and we recognized many buildings that we would have otherwise known nothing about.
*Budget tip: Purchase a CityPass or another kind of “choose your adventure” pass to bundle like a Chicago GoCard and save on these kind of attractions! This site compares and explains these bundles.
Willis Tower:
Formally known as Sears Tower, Willis Tower’s Skydeck is also an attraction “Option” on most bundle-type passes.
My kids think Willis Tower is the cherry-on-top of Chicago, like – there’s nothing better, and it is 103 floors up! They beg us to go every time we visit the city, but we try to keep most of our trips extremely budget-friendly and only opt for one or two “touristy” attractions because they are usually upward of $25 or more per person!
(Sidenote: Everything else we get to do is thanks to our ASTC Science Center Passport Membership!)
Although my legs totally turn into wet noodles when I walk onto the glass floor , I have to say it makes the BEST photos!
Our middle guy took all the time they would give us to do the craziest jumping, skydiving poses he could and I get queasy just thinking about it!
Navy Pier:
An entire day of fun all by itself! Home of the famous Navy Pier Ferris Wheel (also an attraction bundle option!), the pier has so many options for food and fun!
The Chicago Children’s Museum is inside, over two dozen restaurant options including the famous Harry Caray’s Tavern, not to mention, the gorgeous views of Lake Michigan, with waves bigger than I’ve seen at our Gulf Coast Beaches!
If you visit during the warmer months, take a towel and swimsuit (or a change of clothes) for the kids!
Just in front of the pier, is the Polk Bros. Park Fountain. It may not compare to the gigantic Buckingham Fountain just down the road, but you can PLAY in it!
I like this visual fountain comparison from the Chicago Tribune . The fountain is more of a giant splash pad and my kids had a blast cooling off on a hot day after a lot of walking!
“Must-do’s” on the WESTside:
Stop by the Cloud Gate sculpture, better known as “The Bean”, for some great photos on the way to the Chicago Art Institute where you can find collections of art from college Art History days that you’d never even dream of seeing in real life! It’s a very surreal experience!
Eat at the nearby Chicago Athletic Association at the Game Room. The atmosphere will take you back in time! Among other ridiculously-delicious appetizers, make sure to get the fried dill pickle spears!
All of this is walking distance to the beautiful Maggie Daley Park that features an “ice skating ribbon”, rather than a rink, in the winter!
And a little walk south from here will take you to Buckingham Fountain that I mentioned above!
The Magnificent Mile:
Do you hear Oprah’s voice EVERY time you say it? Just me?
Also known as Michigan Avenue, the shopping and eating options here are endless! I don’t have a shopping budget – I’m a bargain basement traveler! But, if your kids are into American Girl and the Lego Store like mine, they are in the same building and just 3 blocks from Dylan’s Candy Bar, Nike, Garret’s popcorn and the most gigantic Starbucks we’ve ever seen!
**Budget tip: we remind our kids to save money for trips like these if they want souvenirs or gift shop toys! There’s no way we can budget travel and purchase the things they “must have” at every shop we pass!
I LOVE that our oldest has a phenomenal travel spoon collection – but, sadly it’s getting harder and harder to add to!
**Make sure to see this post for information on how to visit most of the attractions listed below and 100’s of others around the U.S. for FREE!!**
The Field Museum:
A Natural History Museum with over 40 MILLION artifacts and the most iconic displays! It would take DAYS to see everything here! I give it 5 stars as a field trip location for homeschoolers!
Adler Planetarium:
Beyond anything I imagined a planetarium could be! We had to go twice to see it all! There are 3 floors filled from floor to ceiling with amazing things to see and experience here including some hands-on activities and the biggest telescopes we had ever seen!
Also a 5-star field trip day!
*Tip – Parking for Adler and Field at Soldier Field can be expensive but you can oftentimes find street parking if you drive to the front of the planetarium. Also, if you’re using your pass and going to neighboring museums like Adler and Field on the same day – you’ll just have to pay for parking once and walk to each museum!
Museum of Science and Industry:
Our favorite museum in the WORLD (so far!) and incredibly fun for the kids!
I am not exaggerating when I say this place is a MUST-DO with your kids! From weather, transportation (actual airplanes, trains and a u-boat!), bodies, technology, a mine cart experience and more, this place completely surpasses what I ever though a museum could be!
If I could give it ten stars, I would! I just did!
Shedd Aquarium:
What’s not to love about the beautiful water-living creatures you find at the aquarium! Located right next to the Field Museum and Adler Planetarium, the Shedd is a fun stop and makes for some gorgeous photos!
*Photo tip: Just outside Shedd Aquarium, are some of the best views of Lake Michigan and the Chicago Skyline!
Some of the “adventure passes” I mentioned above include the Shedd Aquarium as an option! Shedd is a bit pricey and is not included in our ASTC Passport Membership, so it would make a good choice from the bundle options.
What to Eat:
You MUST try a Chicago Dog with everything on it (even the spicy little peppers!). There are stands all over the place and even a few conveniently located between the Field, Adler and Shedd. It’s a great way to get a bite between museum stops!
My kids LOVE to grab a dog here especially because the menu says they have to “dance for the ketchup”!
Giordano’s or Lou Malnati’s? Don’t mistake one for the other, you have to TRY BOTH for yourself! However, I do love that Giordano’s will dish out every piece so you can get a photo of you and the 3 feet of cheese dangling from each slice!
Note: If you are driving around the outskirts of Chicago or heading out to the Suburbs bring LOTS of quarters! There will be TOLLS!
If I haven’t shown how much we LOVE Chicago yet, I’m telling you now! Go visit this beautiful, history-filled city!
If you have been there, let me know what you love to do, see, & EAT when you’re there!
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