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The Perfect 2 Days in Chicago Itinerary in 2024

By Alex Dormer, Posted on 25 Feb, 2024 at 02:31 pm

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2 Days in Chicago Itinerary

Thinking about how to make the most out of your 2 days in Chicago itinerary? How about trying out their best dishes? What are the best places to visit in Chicago? What fun activities to do in Chicago? How to explore various museums and historical sites? Well, a two-day trip may not be enough to visit Chicago as it has a lot more to offer but you can take a short tour as a trailer to get a hint of their cultural diversity, tastes, and an experience to carry along, Here's a two day suggested tour guide for you:


A Quick Tip:

You may not need to rent a car as the public transportation system in Chicago is very well managed and the network of buses and subway trains can take you wherever you want to visit Chicago. It is suggested to get a 3-day CTA pass to get unlimited rides as well and Uber can always be a great option to choose from.


Day 01 of Chicago Itinerary:

It is suggested to start your day with a good breakfast and rise early to enjoy your two-day trip while you visit Chicago attractions to the fullest!


9:00 AM- Visit the Art Institute of Chicago:

Begin your adventurous tour with a visit to one of the Chicago must see attractions. The top-class museum, Art Institute of Chicago which is situated in Downtown Chicago encapsulates beautiful art collections reflecting the diversity of cultures and historic times. Stroll through the hall bearing art pieces that are masterpieces on their own such as the famous Picasso, Van Gogh, and Monet. Take a look at those famous art pieces and admire the thought process behind their paintings.


10:30 AM- Stroll Through Millennium Park:

After having a mindful art survey, you better stroll around Millennium Park which has stunning sculptures on display, the famous "Cloud Gate" that is affectionately known as "The Bean".

A grand festival also takes place here every summer season known as Lollapalooza Music Festival, where you may enjoy dancing on the rhythms. This park also has some cool attractions to add colors to your memories such as their Crown Fountain which has this visual effect of spitting water through a video screen, which looks cool. Additionally, they have an ice rink that temporarily runs to allow you to go ice skating in winter.


12:00 PM- Take a Boat Tour in Chicago River:

After a good stroll, you better relax in and take an architecture boat tour of the serene Chicago River, which is one of the most fun things to do in Chicago for adults. Sit back and relax while taking a tour of vintage gems and admire the architectural wonders around you reflecting their historical treasures.

You may find a guide there, telling you about the past stories and scenarios, while you get lost in the beauty of Chicago.


1:30 PM- Lunch Munch the Deep Dish Pizza:

After a wholesome tour around the city, you just need to refuel yourself with one of their best deep-dish pizza. To savour, you must try either one from two of the best pizzerias in town that are; Lou Malnati's and Giordano's.

Trying out a wholesome Chicago-style pizza is one of the must do things in Chicago. Keep a waiting time of 45 minutes in mind, as cooking deep-dish pizza takes some time.


3:30 PM- Sight-seeing from Skyscrapers Viewing Decks:

Enjoy sightseeing from one of the tallest buildings until the 1990s, which gives off stunning views known as Willi's Tower, formerly Seara Tower. There is this beautiful glass balcony where you can take some cool pictures and enjoy the panoramic views of the city.


6:00 PM - Dinner Options:

After the sun settles down you must start looking for some good restaurants to decide on what to have for dinner. There are a few well-known restaurant suggestions that you may love to try on:

  • The Grill & the Goat:

It offers a variety of deliciousness, inspired by various cuisines and will leave you with a flavorful experience.

  • Portillo’s:

If you're looking for some budget-friendly dinner options, then this is the right place for you. Dig into their Italian cuisine and savour all kinds of famous Chicago delights and don't forget to order their famous Chocolate Cake Shake which is a hit.

  • Gibson's Bar & Steakhouse:

If you're a steak lover, you must order something from their extensive menu, offering flavorful delights with a laid-back vintage ambiance.


7:30 PM- Evening Chicago Activities:

After you're done with dinner, head over to experience some Chicago activities, look for some live music concerts happening in the area randomly dance at an Indie rock band performing at some local club, or look for some good movie screenings or shows as there are many options: Riviera Theater, Vic, Metro or the Chicago Theatre.

You can also participate in some sports activities such as Blackhawks or Bulls games, Chicago's nightlife will never disappoint!


10:00 PM - Hop through Bars:

There are plenty of bars options to choose from such as Alice Lounge, Wicker Park, or Wieners Circle, to dance at the musical night and try on some of their best-served cocktails and beers from their extensive menu.


Day 02 Chicago Itinerary:

After getting a good sleep, start your day 02 tour with positive energy, wake up early, and head to the Chicago tourist attractions.


9:00 AM - Visit Museums:

Immerse yourself in the rich Chicago culture as the well-known Chicago tourist spots may include a visit to the museums so that you can admire their cultural richness and artistic skills. There's an area to dive into the history of Chicago, a specified area for museums known as Museum Campus, either you want to delve into ancient artifacts at Field Museum or you're looking forward to observing marine life at Shedd Aquarium or you better take a space visit by exploring the universe at the Adler Planetarium.

It is suggested to plan your museum visit and choose from plenty of options so you're clear-headed about what to visit, as there's a very short time to explore all of them.


1:00 PM - Take a Lunch Break:

After soaking in all the cultural values and admiring the ancient art pieces, head over to a nearby restaurant to have a lunch break. Delight your mouth with some authentic Italian dishes, their famous beef sandwiches, or hot dogs (caution: adding ketchup might feel like committing a crime to your Italian mates).

Some good options may include the Jay Pritzker Pavilion and Chinatown Food.


2:00 PM - Explore Local Culture:

Take a look at the neighborhood and indulge in the cultural richness of lively neighborhoods like Wicker Park, Lakeview, or Pilsen.

Discover their local shops and ancient art galleries enriched with a Mexican heritage featuring a charming collection of arts reflecting their strong Swedish influence and stroll through parks and zoos such as Oz Park and Lincoln Park Zoo. Capture lots of pictures as a memory and collect souvenirs from plenty of shops and boutiques.


5:00 PM- Magnificent Mile Shopping and Dining:

Shopping is also one of the fun things to do in Chicago as the Magnificent Mile is known for its quality products, upgrading your shopping experience and offering plenty of shops, boutiques, and departmental stores to shop from.

You can shop for gifts from luxury brands and gift shops and get some souvenirs for your loved ones. Don't forget to stop by this stunning Tribune Tower that offers historical treasures, and has the Great Wall of China, Taj Mahal, and Berlin wall embedded in there.


8:00 PM- Catch an Interesting Show:

Chicago Improv Show is known for its great comedy, which happens to be at the Second City. It is a renowned club where many influential actors began their careers, actors such as Steve Carrel, Tina Fey, Stephen Colbert, and many more.

You can also opt for smaller clubs as they are lighter on the pocket and may offer you a good laugh with their comedy shows.

So, what's the wait for? Visit Chicago to enjoy vacations with your family, there’s a lot more to discover in this lively city.

About Author

Alex Dormer

Alex is a successful travel blogger; he gives great tips to travel enthusiasts regarding how they can save money on their vacations. He's been to 40 + countries, and he mainly focuses on how to cut down costs during travel. 

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