4 Day Chicago Itinerary

We had a great time visiting Chicago as a family.  At the time of the trip, our daughter Kairi had just turned ten months, so we rented a nice AirB&b apartment and stuck to family-friendly activities.  To our surprise, Chicago was a fantastic place to explore with a young child.  The city’s transportation system was more than adequate to get us around and other than a few high-end restaurants, we were able to bring Kairi everywhere. Chicago’s food was excellent, and the attractions exceeded all of our expectations.  Below I wrote a comprehensive breakdown of our 4 day Chicago itinerary. We’ve provided the YELP and TRIPADVISOR links to all the locations we visited as well. Hopefully, it will help you get all the information you need to start planning a trip of your own to this great city.

What we wanted to accomplish

Our primary goal of the trip was centered around the food. Chicago is well known for its food scene and a big reason to why we visited. Knowing that it would be impossible to walk into some of these places, Trang made sure to book reservations months leading up to our trip. Some of the places are very well reviewed and not necessarily good for casual eaters.

As for sightseeing, we were set on hitting all the major attractions. Although, how much we explored the city depended on how well Kairi would do. We would either add or drop things from the itinerary if necessary.

Where we stayed

Kairi was a significant factor to where we stayed. Knowing that we needed household amenities like a full sized fridge and washer & dryer, we decided on the Airbnb route. We left it up to our good friend Geoff to decide. After some unexpected hurdles, we settled into a nice apartment. It was a great location near the Clinton/Lake metro station that was right in the middle of all the places we needed to visit.


Since parking in Chicago was costly we planned our 4 Day Chicago Itinerary so we could use the city’s public transit exclusively. As a result, we opted for a three-day unlimited ride card for twenty dollars per person ($25/person total with the purchase of the card). The city offer’s Unlimited Ride Cards of various lengths.  The cards are good for both the metro and bus transportation systems. Our experience on both was positive. Employees were on hand to help us get the stroller around the turn stalls, and were genuinely friendly. The bus ran on time, and it helped us to get to distant destinations like the Lincoln Park Zoo and the Navy Pier.

If you aren’t familiar with public subways and how to buy tickets for them.  The Chicago Transit Authority has a guide explaining How-To Buy Fares/Tickets from their vending machines

4 Day Chicago Itinerary

Day 1 – Half day settling in

Magnificent Mile
Magnificent Mile

Places we ate:

The drive going up north from Springfield was surprisingly quiet.  We got to Chicago at around 4 pm and settled in.  Our apartment had a great view of the skyline and all the amenities needed for us take care of Kairi.  We got ready and headed out for the rest of the night.

The Purple Pig

Around 6 pm we went to the downtown area to eat dinner at The Purple Pig.  Since they don’t offer any reservations, we had to wait about 70 minutes to be seated. They took down our name and said they would text us once our table was ready. We would then have 10 minutes to return to the restaurant before our table would be given to the next guest. For this reason we were able to explore more of the Magnificent mile.

Although the wait for seats was long, their food was worth it.  Out of all the dishes, we enjoyed the gnocchi the most.  As soon as finished, we walked to the Navy Pier to watch the fireworks.

4th of July at the Navy Pier

Sadly, the Navy Pier was packed, and the police were forced to close it just before we got there. So we decided to head south of the shore, where we found an open area and settled in just before the 9:30 pm showtime. The fireworks were as good as we had heard and it ended with an explosive climax that looked expensive.

After the show, we headed back towards our hotel following the thousands of people walking down the middle of the streets. We made a stop at the famous Chicago sign and attempted to get a pizza from Lou Malnati but had forgotten that most places were closed early due to the holiday.

The excitement of night must have caught up with us because we had no idea we had walked 2 ½ miles back to the apartment. We got back to the hotel around 11 pm and ordered some deep dish pizza from Duos. Sad to say but we were not a fan of their pizza. Chicago style pizza is different. It had a dry biscuit like crust, and was covered in what appeared to be canned tomatoes. Duos wasn’t a highly recommended pizza place, so we decided to hold judgment until we tried Lou’s or Giordano’s pies. Not long after that, we crashed for the night.

Day 2 – Touristing it up

4 Day Chicago Itinerary
Chicago Riverwalk

Our second day in Chicago started early with a 9 am breakfast reservation. Wanting to use the metro, we decided to purchase a 3-day pass to get access to Chicago’s public transportation. It cost $20 for the CTA 3-day pass plus the additional $5 fee for the Ventra card. While our hotel and destinations were all relatively close together, the public metro saved our feet from a long day of exploring.

Little Goat Diner

Our day started at the Little Goat Diner. Little Goat Diner served us three outstanding breakfast dishes. A corned beef hash, sausage biscuit, and French toast. Each had a significant twist that made them unique to the diner and real standouts in our opinion. Furthermore, the spacious restaurant and kid friendly amenities make it easy for us to recommend it to fellow family travelers

Wendella’s River & Lake Tour

After breakfast, we made our way towards the bottom of the Magnificent Mile to catch Wendella’s 11 o’clock river and lake tour. The boat ride was a success in our eyes. We learned a lot, saw a lot, and got time to rest as the sites came to us for a change. Some of the stand out moments for us were the historical facts.  We learned that Chicago’s name is of native american descent and translates to smelly onions.  Another interesting fact we picked up was that Chicago’s waterways are 3 feet lower in elevation to Lake Michigan, and it requires a lock to allow boats to move between the two.  After the 90-minute tour had finished, it was time to see the famous Cloud Gate at Millennium Park.

Recommend to take the tour in the morning because of the water reflection in the evening.

4 Day Chicago Itinerary Cloud Gate

Cloud Gate

The Cloud Gate (also known as the Bean) was created by Anish Kapoor. The Cloud Gate was a lot more impressive than I had thought. I’ve seen hundreds of pictures of the Cloud Gate beforehand, so I wasn’t expecting much. As we strolled up to it, I was thoroughly impressed by the work.

At a distance, you could see this giant reflective blob. The distorted reflection felt like everything was being pulled towards it. The underside of the Cloud Gate was where I reversed my initial thoughts of the statue and was thoroughly impressed. It was like looking through a kaleidoscope of moving people but with a dirty layer of hand prints covering them.

4 Day Chicago Itinerary Maggie

Maggie Daley Park

Being in the Millennium Park area, we decided to check out Maggie Daley Park. The small park is a young child’s dream. The park is littered with smaller play areas specifically designed for a particular age group. They all funnel towards a giant castle drawbridge that all the children were running back and forth on. The park looked so fun that I was jealous I couldn’t partake.

4 Day Chicago Itinerary Taste of Chicago

Taste of Chicago

Our fourth of July visit also allowed us to participate in the Taste of Chicago located in Grant Park. We rolled up to the ticket counter and bought two sets of 14 ticket sheets for $10 each. Thinking 20 dollars worth would be more than enough to get a full lunch, but we were disheartened to see items ranging anywhere between 5-12 tickets. It was eight tickets for a 20 oz bottle of Pepsi! Five dollars for a Pepsi is all sorts of crazy.

Although the prices were high, we were still able to try Lou Malnati’s pizza. Lou’s brick and mortar locations all had long lines and the cook time on their pizzas were at least 40 minutes. So thankfully we got to try a slice at the Taste of Chicago. It’s was alright, it hammered home that Chicago style pizza wasn’t our thing.

Afterward, we were set to check out Willis Tower (also known as the Sears Tower). Arriving at 4:30 pm, we discovered the wait time to view the Skydeck was hovering around 60-90 minutes. That’s when a helpful employee saw our concerned look and suggested that we come back tomorrow at 9 am. Explaining that the wait would be less than 30 minutes if we came back in the morning. We took his advice and decided to fit another meal before our 7:30 pm dinner reservation.

Au Cheval

Au Cheval is home to what some call the best burgers in America. After a 45-minute wait to be seated and 20 minutes to get our food, we can say it’s a delicious burger. But saying it’s the best in America would be splitting hairs because we’ve eaten similar tasting burgers at countless places. We also tried Au Cheval’s root beer float, and it was terrific, because of the house root beer’s strong licorice flavor which made the float taste completely different to the ones we’ve had before. As soon as we finished the burgers, we prepped for a quick turnaround for dinner at Girl & the Goat.

Girl & the Goat

With the Girl & the Goat being right across the street from Au Cheval we hung around for our dinner reservation.  Once in, we sampled five high-quality dishes and probably the best dessert we’ve had at a restaurant.  The chocolatey chocolate cake was served with a scoop of shiitake gelato.  It was so good that we ordered a second.

After the long day, we were all tired. Especially Kairi, it took her awhile to get to bed. Which was understandable but once she was out, she slept through the night. And we were able to relax for a bit before passing out.

Day 3 – Food

4 Day Chicago Itinerary
Willis Tower

Our focus for day three was high-quality food. To accomplish this, Trang has been calling for weeks to secure reservations at three Michelin star restaurants. You can read all about it in detail on our 3 Chicago Michelin Star Restaurants In One Day post. So I’ll gloss over these Michelin restaurants.

Willis Tower

Our third day started with us heading up to the Skydeck in the Willis Tower. We arrived at 9:30 am, and we were at the top within 15 minutes. We’re thankful for the employee that suggested for us to return in the morning.

Everything about the Skydeck was fast until we got in line for the glass ledge. Due to the fact that nobody was limiting the visitor’s time on the ledge but once it was our turn, it was pretty entertaining. The real fun came from watching other guests nervously walk onto the glass. Trang was one of them, refusing ever to look down. We took a few minutes for pictures and were back down on street level shortly after we finished.

Michelin Lunches

From there we headed to Blackbird for lunch. After a great meal, we made a pit stop back at the apartment before heading back out to a 1:30 pm reservation at Roister. Again, so good.

Lincoln Park Zoo

Lincoln Park Zoo

After our second lunch, we headed north to visit the Lincoln Park Zoo. For a zoo that is free to the public, we were very impressed. Most of the zoos that we’ve paid admission for were not even close to the variety of wildlife they had at the Lincoln Park Zoo.

However, just being there to hear the lion roar made it completely worth it for me. Also, all the animals looked like there were well taken care of. Therefore, we recommend the Lincoln Park Zoo to any family visiting the city.

The zoo closed at 5:30, and it gave us plenty of time to get back and prepare for our dinner at Grace. Since Kairi was unable to go, Trang opted to be the one to stay back. So for her meal, I ran down to the French Market and ordered her a poke bowl from Aloha Poke Co. Thankfully, Trang enjoyed the bowl and said she would recommend it to anyone visiting the Market.



Grace was an amazing experience. Easily the most high end, formal eating experiences I’ve ever had in the states. Chef Curtis Duffy’s restaurant lived up to the expectations we had set for ourselves after watching his documentary on Netflix.

Afterward, we arrived back at the apartment and relayed our experience to Trang. For the rest of the night, we prepped Kairi’s meals and charged our cameras. Day 3 was a remarkable day of eating.

Day 4 – Filling In The Holes

The Art Institute of Chicago
The Art Institute of Chicago

We extended our time in Chicago to check out a few more places. Our day started around 9 am as we headed to the Art Institute of Chicago.

The Art Institute of Chicago

My excitement quickly vanished when I read their list of items that were not allowed in their galleries. Checking in our camera bag is a non-starter for me, and a big reason why we never go to museums. I understand the bag would be relatively safe if I checked it in, but too much of my hobby relays on my camera gear. If I lose it, I’m out of a hobby. Also, the stroller and backpack baby carrier had to be checked in. We didn’t want to hold Kairi around in our arms for the entire gallery, so we decided to head out to an early lunch.

MingHin Cuisine

Our last planned meal of the trip was at MingHin Cuisine. A well reviewed Chinese dim sum restaurant that was able to seat us quickly. Like all dim sum places the items come out fast, and all the food tasted excellent. The casual atmosphere and short wait time made MingHin a great place to eat for any family visiting the nearby parks.

Navy Pier

Navy Pier

After lunch, we made our way to our final stop to the Navy Pier. Even from a distance, you can tell it was a kid friendly place.  With plenty of rides for the kids on the upper level, the pier also has a variety of shops and restaurants to enjoy below. The Navy Pier was a nice way to end our time in Chicago.

Chicago Is Worth It

Our overall trip to Chicago was fantastic. We showed up not expecting much but left with full bellies and lasting memories.

Additionally, if you’re interested, check out our Chicago travel video we made from trip. We like how the video turned out. It was the first time using a drone on one of our trips, and we loved it.

See It For Yourself

Lately, we’ve seen plenty of great deals on flights to Chicago so now is a perfect time to visit. Stand out locations like the Cloud Gate and Lincoln Park Zoo are must see spots with more than enough to keep you busy for a long weekend, or even a week long stay.

Please share our 4 Day Chicago Itinerary if you found it useful and be sure to check out our Travel Page for additional travel resources. Our 8 Day Greece Itinerary is really popular as well if you’re considering a trip to the Mediterranean!

Subscribe to our Newsletter

Amy's Farm Pumpkin Patch

If you found our post helpful and want to hear more from us in the future, please consider signing up for our Monthly Newsletter.  We promise to send you the most basic, to the point text newsletter you’ve ever seen!  Thanks in advance for the support,  it’s much appreciated.

Related Posts


Nice trip you had here. I have been to Chicago before but I only spent a night. it was Valentine’s day I remember perfectly. But I loved the Italian dinner I had with my hubby then. I was expecting my first son then . It was awesome, though it was quite cold.

I love your itinerary. Many of the places you listed were really interesting. Would love to visit one day.

Thank you so much. We recommend it for sure. The Chicago has so much to offer, more than enough to keep you busy. Four days didn’t even seem like enough.

Looks like a really great trip. I think I would also look for places that had awesome food that I couldn’t get anywhere else.

Chicago’s on my bucket list! Seems like there’s so much to do as see!!

This all sounds like a lot of fun! I need to go back to Chicago now

Thank you for such a wonderful trip blog! I bookmarked many of your suggestions for my upcoming trip. I especially loved the goat-themed dining day!! Well done!

So happy you found it useful! It means a lot. The Girl and the Goat and its sister restaurant are very good. I’m excited for your taste buds. Let me know what you thought of the food once you get back 🙂

I really like the information here about Chicago and I’ve tried to figure out how I can print it. Is there a way to do that? It has a lot of good information.

Hi Cyndi, Yeah we can for sure. I’ll email you a version that will have everything you need. We’re away from the house at the moment but I can send that to you tonight.

Leave a reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.