We took a road trip from Ohio to Wisconsin and wanted to break up our drive. I’ve never been to Chicago so it seemed like a good stopping point. Although my husband isn’t a fan of big cities, he agreed to a one-night stay.
No matter what city you visit, just be prepared for traffic jams as well as higher hotel costs and parking fees. However, we have a few tips to help you make the most of a short trip!
It’s true—the closer you are to the city, the more you’ll spend on hotels and parking. However, if you’re planning to sleep in the city, I highly suggest spending the extra money and staying in a hotel that is close to the action.
Figure out what activities you want to do while you’re there and book a hotel that is centrally located. If your activities are within walking distance, then you help offset the higher cost of the hotel with no parking or Uber/Lyft fees.
We decided to stay at the Embassy Suites Downtown River North because it was within walking distance to everything I wanted to see. We arrived in Chicago around 10am and planned to leave early the next morning. Since we didn’t have a ton of time, I wanted to see as much as we could in that short time. Not only were we able to walk everywhere we needed, but the hotel offered some added benefits too!
We are huge fans of the Hilton hotels so we use the brand anytime we can. Embassy Suites, specifically, is such a great option too. For us, we love the fact that they have suites with two beds plus a pull-out sofa. This size room is perfect for a family of five or six. The suite also has a refrigerator, small sink and microwave. In addition, they offer a free cooked-to-order breakfast as well as an evening reception with free snacks and drinks (including alcohol).
I already mentioned that parking fees can add up, but you’ll also want to check the cost of your hotel’s overnight parking. In many cases, the only option available is valet, which can come at a steep price. Overnight parking at this Embassy is $79. Yikes! That combined with the higher hotel costs may scare you away from city hotels, but know that other options are available.
Often times, alternate parking is available right around the corner! We use the Spot Hero app to find parking options that are nearby. We’ve done this in several cities and it has saved us a ton of cash! In Chicago, we found parking for $24 at a garage right next to our hotel!
Just be sure to check if in and out privileges are included if you plan to leave at any point. For our reservations, the cheaper rate was only available if we parked our car and left it. Since we were only in the city for 24 hours, that deal worked for us.
And don’t forget that even if your parking garage is a little farther from your hotel, you can still use the short-term parking at the hotel entrance to drop off/pick up your luggage. No need to lug your suitcases to your hotel and back!
There are a variety of activities that are free or inexpensive, but others can cost you a pretty penny. Be sure to research the cost of your activities so you have an idea of how much you’ll spend. And with only having about 12 active hours in Chicago, it’s especially important to plan so you can make the most of your trip!
If you search for activities to do in Chicago, more than likely the 360 Observation Deck or Skydeck will be mentioned. It seems like either would be a cool activity, but I couldn’t justify the cost. We needed to purchase 6 tickets–three adults and three kids. The cost of general admission tickets to the 360 Observation deck was $174—and if we added the tilt and view option, that’d be an EXTRA $60. And Skydeck was $189! Ehh…we’ll pass on those!
I like to get a big bang for my buck. Not only were those activities pricey, they also weren’t near the hotel or other activities we planned. That means adding those to our itinerary would have added even more to our cost since we’d need an Uber/Lyft.
If you are looking to do several activities in a big city, check out CityPass or GoCity. Although we’ve never actually used these, they offer a variety of options to visit different attractions for one price. Some passes have unlimited activities for a certain number of days, while others allow a certain number of attractions over a period of time.
We knew our stop in Chicago would be short so we planned activities that were do-able in that timeframe. As you can imagine, big cities have tons to do, but you only have time for so much. So be realistic when you’re creating your itinerary! You can take a look at our itinerary and walking path below.
We got to Chicago around 10am and stopped at our hotel before parking our car. Most hotels offer luggage hold so we were able to drop off our luggage and then park our car before we headed out to explore the city.
The first stop on the list was Millennium Park. It was also nearing lunch time so we stopped by Wildberry Café on the way for a quick bite. They had a pretty long wait so we ordered a few sandwiches to go and ate them in the park.
We took a quick peek at the Millennium Monument on our way to Cloud Gate (also known as the iconic mirrored bean). After snapping some pics, we headed over to Crown Fountain. This 50-foot glass block tower projects the faces of Chicago citizens on LED screens. The fountain looks as if the faces are spewing water from their mouths. In the summer, kids can cool off by splashing around in the reflecting pool.
Right near the Crown Fountain is the Boeing Gallery South. This open-air gallery is home to modern and contemporary art installations that rotate throughout the year. The exhibit that was there when we visited had a variety of rock sculptures that the kids were able to climb. It was a beautiful area with these pretty glass gems hanging from the trees. The area is shaded so it’s a perfect spot to take a break.
We chose the order of our activities to follow one big loop back to our hotel. The next stop on our list was the Play Garden at Maggie Daley Park. This playground is beautiful and the kids had a blast playing in all of the different areas. There was also a nature event going on the weekend we were there so the kids were able to participate in their free activities. This was a great place to let the kids burn off some steam!
Next, we headed over to the Buckingham Fountain for a quick photo opp. We grabbed some drinks from a small shop and sat on the patio for a bit to rest before we started our trek back to our hotel.
We continued our walk stopping at the Riverwalk. This 1.25 mile long path is home to shops, restaurants and other businesses. We didn’t walk the entire Riverwalk, but did get to experience a good piece of it. If we had more time, I would definitely like to come back and explore more of the restaurants and bars! I think one of the architectural boat tours would also be fun.
Since we had our lunch and did a lot of walking and playing, ice cream sounded like a good way to finish up our afternoon! Lucky for us, Ghiradelli was right on the way back to our hotel! The kids loved the surprise stop as well as some time to rest.
After we left Ghiradelli, we headed back to our hotel. We grabbed our bags from the luggage hold and checked in. We relaxed for a bit before heading to the hotel’s evening reception. During the reception, guests can enjoy complimentary snacks and beverages. There are a variety of drink options available, including beer, wine and spirits. The reception usually lasts around 1.5-2 hours. Once we grabbed some drinks and snacks, the kids were ready for some pool time!
We were getting hungry so we headed to the Navy Pier for the evening. We walked around outside and then grabbed some quick service meals at the many options inside. All of the kids were happy to skip a sit-down restaurant and just pick something they liked from the food court.
Afterwards, the kids were all excited to try dragon’s breath, which is a frozen desert made from cereal dipped in liquid nitrogen. When you put it in your mouth, it makes it look like you’re breathing fire (smoke) like a dragon. Our son, Cohen, has wanted to try this forever so when he saw it, he was super excited! All the kids got a kick out of it.
Side note: from what I’ve read, it sounds like the FDA warns that ingesting this snack could actually be harmful—especially for kids with asthma. So although it looks cool, it may not be the safest—even though it’s still being sold.
By the time we were done at the Navy Pier, we were exhausted. We walked back to our hotel and called it a night! In the morning, we enjoyed our complimentary cooked to order breakfast. I love a good omelet and the kids prefer buffets–Embassy gives you the best of both worlds. Many of the Hilton hotels offer free breakfast, but Embassy Suites is our favorite!
Once we finished up with breakfast, we grabbed our car and continued on our road trip to Wisconsin. Although less than 24 hours in the city doesn’t offer time to see everything, you can still see a lot. Plus, all of our activities were free—with the exception of things we ate.
There are so many kid-friendly activities that look like they’d be a lot of fun. We are huge fans of science centers, museums, zoos, botanical gardens and aquariums—and Chicago has several options! If you’re a member of any of these places at home, check to see if you have a reciprocal membership. Often times, you can get free or reduced admission to others around the U.S. This is a great benefit that can save you money!
What are your favorite places to take your kids in Chicago? Any tips you have for navigating the city? We’d love to hear them!
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