The Ultimate 4-day Summertime Chicago Itinerary

Chicago

The home of the Chicago Dog, Deep Dish Pizza, and some of the most breathtaking rooftop views you can ever imagine! Planning a Chicago Trip can be exciting, but there is so much to do and see in Chicago.

My husband and I first went to Chicago in June for three days, but we loved it so much that we stayed an extra day. We spent so much time on Tiktok trying to create the best itinerary for our trip, but we switched our plans the minute we arrived. There were so many more exciting activities that we learned about that we had no choice but to add. I didn’t include a lot of restaurants in the itinerary because Chicago has soooo many different restaurants that call for another post in itself.

Day 1

Go on an Architecture Cruise

One of the MUST-DOs of Chicago is learning about the different architectural styles in Downtown Chicago. Whether you love history or not, you will thoroughly enjoy the quick history of Chicago. It usually lasts 45 to 90 minutes, depending on your cruise. It also has a bar on deck for a quick drink and bathrooms. Make sure you take lots of photos of the buildings!

Visit the Navy Pier

The Navy Pier isn’t what you think it is. It used to be a training site for the U.S. Navy, but now it is full of restaurants, amusement park rides, and a children’s museum. It also has different shops for souvenirs and clothing stores. I would highly recommend scheduling your Cruise from the Navy Pier so that you can explore the Pier after the cruise. We got on the Ferris wheel, and it gave us a beautiful view of Chicago and Lake Michigan. We also tried our first Chicago Dog here, which left a big impression on us.

If you are in Chicago on certain days, there is a fireworks show here! Last but not least, they have an attraction called “Fly Over Chicago.” It is similar to the Soarin ride at Epcot in Disney World Orlando. We didn’t get the chance to do it, but several people recommended it to us.

Check out the Medieval Torture Museum

Yes, you heard right! This interactive museum provides over 50 different torture techniques that were used in Medieval times. Some of the tortures are not for someone who has a weak stomach. We spent an hour and a half in here and learned ALOT. They also have a little game you can play with your group if you want.

If you are someone who isn’t into looking at different Torture museums, you can visit:

• Museum of Ice Cream
• Chicago Art Museum
• Chicago Science Museum
• Wndr Museum
• Color Factory

Get some Deep Dish Pizza

You aren’t doing Chicago right if you don’t get some Deep-Dish Pizza! We visited Lou Malnati’s Pizzeria twice, but there are many options. Each deep-dish pizza restaurant has its own unique taste and style. There are other options, such as

• Giordano’s
• PeQuod’s
• Gino’s
• Lou Malnati’s

Day 2

Grab Coffee at the World’s Largest Starbucks

The Starbucks Reserve is the Largest Starbucks in the World. It is four stories tall and has a rooftop terrace on the fifth floor.

Level 1- Merchandise and Standard Coffee

Level 2- Coffee and Pastries

Level 3-Experimental Bar

Level 4 – Espresso and Cocktail Bar

Level 5- Rooftop Terrance

The Reserve was breathtaking! Even if you aren’t a big coffee fan, there is still something for you to try that you can enjoy.

Go on a Food tour

One of the must-do activities to do in Chicago is a food tour. There are multiple kinds of food tours, such as:

• Chicago Food
• Pizza
• Chinatown

We ended up doing the Chicago Food tour, which included deep-dish pizza, the Chicago dog, an Italian beef sandwich, and the original brownie recipe. Along with the food tour, you learn about Chicago’s history and what inspired each meal.

Visit Millennium Park and Flick the Bean

Millennium Park is one of the big attractions that Chicago has to offer. It contains different sculptures, architecture, beautiful fountains, and the famous “Bean.” As of June 2024, it is under construction, so you can’t get close to it, but you can still flick it! Also, the famous waterfall with the celebrities’ faces is under construction. However, during our food tour, our tour guide informed us that it was super beautiful to experience.

During the Chicago food tour, you will visit Millennium Park. After the tour, you can walk back to Millennium Park since it isn’t far away from your last food stop.

Go to a Chicago Cubs Game

I am not a baseball fan, but going to a Cubs game made me want to go back to another game. Chicago has two baseball teams: the Cubs and the White Sox. You can visit a White Sox game, but the Chicago Cubs are at Wrigley Field. Wrigley Field is famous because it is the second oldest baseball stadium in the United States. Wrigley Field also has so much history that I would suggest doing a tour and learning more about it.

Also, the view of the Chicago skyline from Wrigley Stadium is phenomenal. We went on a Wednesday, and it was super packed! The energy from the fans was over the top, making the Cubs game experience so memorable. Make sure to keep your game ticket so you can place it in your travel journal!

Have drinks at one of their Rooftop Bar

Chicago is known for having some of the best Rooftop Bars in the country. There is a bar for whatever vibe you are looking for, whether sporty, playful, upscale or simply laid-back. The views of the beautiful Chicago River or just Downtown Chicago are incredible from the Rooftops. Once you find some bars that you would like to visit, check their website because they might have a fun event going on during your Chicago Trip.

Day 3

Visit the Skydeck and/or 360 Chicago

The Skydeck and 360 Chicago give you an overall view of Downtown Chicago. However, if you are afraid of heights, this might not be the best idea.

Skydeck Chicago is located in the Willis Tower (Chicago’s tallest building) and has a walk-through museum that explains Chicago’s history and significance and allows you to view Chicago from the very top. It is a fun museum where you can take photos with friends and family, and it keeps you entertained. Once you have made it through the museum, you are taken to the top of Willis Tower to see all of Chicago’s beauty. You are in a glass box in which you can take photos, but you are only there for 90 seconds. You can return in line to take more pictures, though.

360 Chicago is a totally different experience of its own. It is an observation deck located in the John Hancock Building. You will be taken to the 94th floor to get a breathtaking 360 view of Chicago. One of the popular things to do in the deck is to try “TILT.” You hold on to a bar, and the window will tilt forward, and you will get a more thrilling view of Chicago……and the street from 94 stories high.

Go to a show

Chicago offers multiple genres of shows that are pretty much suitable for anyone! From comedy shows at The Laugh Factory to Broadway-style shows, there is something worth watching. We went to two shows: Drunken Shakespeare and The Chicago Magic Show.

Drunken Shakespeare is a reenactment of one of Shakespeare’s plays with a comedic twist. One of the actors will keep taking shots of alcohol and hopefully will be able to perform their lines still. It is not suitable for children, but it makes for a fun date night idea.

The Chicago Magic Show features popular magicians who have been featured on television. They come and perform a magic skit. They also have magicians in training who come table to table to perform a quick magic show. They offer a drink and food menu so you can have a laid-back experience.

Eat at Aviary Restaurant

We saw this restaurant on TikTok, and knew we had to try it out. It has a cocktail presentation and a tasting menu that fits the drink. The server will bring out the first food to taste and give a unique presentation and history of the drink.

The Aviary has a low-light, romantic feel, creating a sense of intimacy, which is perfect for a date night. However, you can also go with a group of friends and still feel relaxed and comfortable. It can be a little pricey ($145-185 per person), but it is a nice experience to splurge on.

They also have a speakeasy called “The Office” which you can have access to after your cocktail presentation orrrrrr just in general.

The Aviary was one of our favorite places to visit in Chicago, and of course, when we visit again, we will be back here!

Day 4

Visit Chinatown

Chinatown is a pretty nice-sized neighborhood in Chicago. You can experience authentic Asian food, and there are several shops where you can shop. The area has different parts, so plan your day exploring as much as possible.

I will warn you: Some restaurants only accept cash. Luckily, those restaurants have ATMs, but to avoid the ATM charge, have cash on hand.

Visit Aire Ancient Baths

THIS WAS MY ABSOLUTE FAVORITE PART OF CHICAGO.

The Aire Ancient Baths is a spa with pools with unique features. They have a room-temperature pool, a salt pool, a waterfall, two Cold pools, two hot and very hot pools, and a large jacuzzi. In addition to the pools, they have two different saunas and more.

You can get a massage as well, but most people opt for the pools. Some of the pools have complementary water and tea, which is soothing after a cold or hot plunge. If you forget to bring a bathing suit, they will provide you with a brand new one, and you can keep it if you want.

You can’t take pictures or videos because others will be at the pool. The pools aren’t private, but they aren’t usually crowded either. They are perfect for an intimate date or a relaxing solo date.

Eat at the 2D Restaurant.

Have you ever wanted to be in a comic book?

Well, the 2D Restaurant gives you that experience!

The 2D Restaurant where everything is in 2D! Besides the food, the food is 3D because it’s real, but everything makes it seem like you are in a comic book. Once you visit there, you can take pictures at their 2D gallery outside and upstairs. The food is good for the most part, but I wasn’t a fan of the gelatin cat. However, it is a super cute edible cat that is Instagrammable.

Go on a Night Cruise

What better way to end your Chicago trip than to see the beautiful Chicago Skyline at night? You can book a cruise or a yacht, or whatever you would like. A night cruise is similar to the architecture cruise from earlier times, but they ensure you get a good view of the skyline and the sunset. If you would like a quick drink, there is a bar available.

We did not get the chance to do a night cruise, but we did get to walk on the bridge over the Chicago River at night. From the view of the bridge, I know the cruise would’ve made the nighttime experience so much better.

Honorable Mentions

Buckingham Fountain

Lincoln Park Convestoary

Explore the Chicago Riverwalk

Chicago Gangster Walking Tour

Visit Grant Park

Dinner Cruise At Night

Enjoy Your Chicago Trip!