Chicago may just be the most magical place in the Midwest. Growing up, I lived 4 hours from Chicago and my family often took weekend trips to the city as our family vacations.
Chicago is a great place to go with friends or with family but I highly recommend visiting during the summer. In the winter, the wind and ice can be pretty wicked and would ruin a lot of the activities I’m about to recommend. It can also be very cheap to get flights to Chicago since O’Hare is such a large airport hub.
Things to do
Shop Michigan Avenue
Michigan Avenue is the heart of downtown Chicago and is commonly called “The Magnificent Mile”. The shops, street performers, and attractions stretch for literally a mile so bring your walking shoes. While downtown you can go to the top of the Willis tower (or a cheaper option which is right on Michigan Avenue is the Hancock Building) and see great skyline views of the city. My greatest memory of Chicago as a child is getting to pick out one new outfit for my American Girl Doll at the Michigan Avenue store. Are American Girl Dolls still a thing? We also always loved popping into the Ghirardelli Chocolate store on Michigan Avenue because they hand out free samples to everyone at the door.
Go to a Sporting Event
Not to sound biased but you should go to a Cubs game. Cubs games are awesome and the atmosphere at Wrigley field is like nowhere else. The stadium is a quick train ride from downtown so do some reading on the public transportation lines the night before the game. It’s the best and easiest way to get to Wrigley if baseball isn’t your thing maybe you’ll enjoy the Bulls, Blackhawks, or Bears games.
Visit the Bean at Millennium Park
It sounds funny if you’ve never heard of it before but there is a giant famous bean in downtown Chicago at Millenium park and it’s the best spot for a tourist photo that screams “I went to Chicago”. Google “The Bean Chicago” and you will understand.
Check out the FREE Lincoln Park Zoo
My boyfriend and I were pretty broke when we took our first mini-vacation together to Chicago so we decided to check out the Lincoln Park free zoo. We were AMAZED. The zoo was perfect for us, it had lions and tigers and monkeys and you could feed some animals and you didn’t have to be there all day to feel like you got your money’s worth because you literally didn’t pay anything to be there. I highly recommend checking it out if you have a family.
Take a boat tour off of Navy Pier
Navy Pier is a great area to explore but i would certainly book some sort of boat tour if you’re headed this way. The architecture tour is actually very interesting and teaches you a lot about downtown Chicago. I have also done some of the thriller speed boat tours that are entertaining as well! There are not many dining options on Navy Pier so I suggest having eating before exploring this area. Navy Pier often has fireworks shows in the summer so you should look up if that is happening when you visit!
See a Live Show
Chicago’s theater scene is amazing! I’ve seen so many great plays and musicals in downtown Chicago. The most memorable being Peter Pan and a musical called Kinky Boots. There is no one particular theater that stands out to me as the place to go so I would just choose the theater with the best show, price and location during your trip. I also never ran into a theater that was overly formal but for the most part I was seeing funny or family-friendly shows.
Visit the Aquarium or a Museum
To be honest, the educational part of vacation or being quiet in art galleries was never my cup of tea but my sister loved the art museums and my brother loved Shedd aquarium with the live sea life shows. If museums are your thing, Chicago has PLENTY to choose from!
Have an adventure at Six Flags
Have you noticed how nothing on my list is particularly relaxing? Chicago is a bustling city and what better way to burn some energy than riding roller coasters at Six Flags?
What to Eat
Oh my gosh, where do I begin!? Oh wait, I begin with Pizza! In Chicago you have to try a deep-dish Chicago-style pizza! My favorite place is Lou Malnati’s on N State Street. Any location is good but the one on North State Street is in a high-end area and people often drive buy in Luxury cars which make it fun to watch when you’re waiting to be seated. A tip is to call ahead because you can put your name down and if you know what you want they can get your pizza’s started before you’re even seated. You can end your meal with a cupcake from the Sprinkles cupcake vending machine just a few blocks away.
Another great deep-dish pizza spot is Gino’s East. Any pizza place is going to have long waits at peak hours so be expecting this meal to be a full experience and come early if you want to avoid standing in long lines.
Another family favorite of ours is Jake Melnick’s on Superior Street. This restaurant has a sports bar feel with giant juicy chicken wings, BBQ Platters, Burgers, homemade mac ‘n cheese, and hand cut fries. Their menu has so much that we could always please everyone at this place. The environment is lively and the meals are well-priced for being in the heart of downtown. They also take reservations a day in advance through Google.
If you’re looking for a fast-casual place for a quick lunch try Portillo’s this is a Chicago classic. It is pretty hectic inside because you order different meals from different counters but it is a unique and local experience with a lot of cheap options. In this old-style eatery you order at the counter, seat yourself and listen for your number to be called in just a few short minutes.
Where to Stay?
I strongly recommend staying downtown as close to Michigan Avenue as possible. Getting into downtown and trying to navigate the incoming traffic each day is a nightmare that I do not recommend. Do it once to get to the Hotel and from there, walk, uber, or take the train everywhere you need to go and it’ll be much smoother.
I remember growing up in the summers we would stay at the DoubleTree by Hilton on Ohio Street. We loved it for it’s rooftop pool and it was only a short walk to Michigan Avenue, Navy Pier and the Giant Bean.
One trip when we were all adults we stayed at a nice Waldorf Astoria property on the north tip of the Magnificent Mile on Walton Street. Oh my gosh, it was a beautiful palace-like hotel that I will never forget. This location was walkable to Michigan Avenue and our favorite Lou Malnati’s Pizzeria.
If I were to pack together the best 3-Day experience in Chicago, this is what I would do. Please let me know if you try this itinerary how it works for you! I hope you have a great time!
In the morning, start on the North end of Michigan Avenue and walk South exploring shops like Ghiradhelli, the Apple Store, Nike Store, etc. Before you cross the bridge stop for a quick lunch at Billy Goat Tavern (a hidden, timeless burger joint that has been around since 1934). After lunch, cross the bridge and walk to the Giant Bean for some great photos. From here, I would order a quick uber to Navy Pier to give your feet a rest. Explore Navy Pier for the afternoon and spend an hour on the Architectural Boat Tour (be sure to book your tickets for the boat tours in advance because they can sell out fast in busy seasons). The tours depart from Navy Pier or Michigan Avenue. After the Pier, freshen up for a great Chicago-Style dinner at Lou Malnati’s on North State Street (I highly recommend calling ahead for seating). End your night with a cupcake from the SPRINKLES cupcake ATM just a few blocks from Lou Malnati’s.
Hit the Lincoln Park Zoo for the Morning. If the weather isn’t great, do the Shedd Aquarium instead, both are wonderful but I prefer the Lincoln Park Zoo because it is free. Eat a late lunch/early dinner at Jake Melnick’s. Head to the hotel to freshen up before catching an evening theater show in town. There are so many great theater productions in Chicago!
In the morning, visit the top of the Hancock Building or the Willis Tour for skyline city views. Grab a casual lunch at Portillo’s. In the afternoon, attend a baseball game at Wrigley Field. There are many other sporting events you can attend if the Cubs are not playing in town but Cubs games have such an amazing atmosphere!