How To Make The Most Of 48 Hours In Chicago


My name is Anna, I am 23 years old and I am currently working as a flight attendant in Dubai. I love traveling all around the world and enjoy sharing travel tips on my recently launched blog: annajustgofly Feel free to follow me on Social Media for frequent updates and exclusive travel tips if you like this post!

In today’s post, I would like to share top things to do in Chicago with you! I was there at the end of August this year, so please keep in mind that most of the activities
How To Make The Most Out Of 48 Hours In Chicago

Chicago – the city of smelly onions!
Wait? Smelly onions?
That is exactly what the word actually means!
Onions used to grow wild around the Chicago River, which made the city smell like the stinky vegetable. Luckily the perfume of the city has changed in the meantime!

What to do in Chicago in 2 days:
This guide was created to make it possible for you to enjoy 48 hours in Chicago to the maximum. The city offers a lot of great attractions and activities and reflects the real, authentic American lifestyle.

Day 1:

Millennium Park
Architecture River Boat Tour
Broadway Show

Day 2

Willis Tower
Neighbourhood Bike Tour
Deep Dish Pizza


Navy Pier
Museum of Science and Industry


Millennium Park

What makes the Millennium park so amazing are the numerous points of interest and pieces of art you will come across while enjoying a walk through the green lawns. The most iconic sight you will find is the famous cloud gate at AT&T plaza. You will also come across the Jay Pritzker Pavillion, which is hosting small events in the centre of the park. I really enjoyed strolling around the Crown Fountain and Wrigley Square. If you would like to rent a bike or inline skates you can rent them at McDonald’s Cycle Centre in the park!

River Boat Tour

Once you have explored Millennium Park it is time for you to walk up the famous Michigan Street (Attention! Danger! Shops all around you!) until you reach the Chicago River. There you have the chance to join a boat tour, which takes you up and down the river and along the shore of Lake Michigan. I decided to do the Chicago Architecture River Cruise which took about 1,5 hours and offered spectacular views on the cities’skyline. During the cruise, which costs around 40$, a guide will provide you with interesting information and historical facts. You can enjoy sparkling wine for 10$ each on board!

Broadway Show
No matter if you are travelling as a couple, by yourself or with your whole family – you will definitely enjoy a show in one of Chicago’s theatres! Since I found discounted tickets for Aladdin on I chose that show for the evening. The breath-taking spectacle took place in the beautiful Cadillac Palace Theatre in the heart of Chicago and was definitely a magical pick! Flying carpets and a good sense of humour included!


Willis Tower

Did you know that Willis Tower is the second tallest building in the US? From the Skydeck on the 103rd floor you can enjoy a spectacular 360 view on Chicago and Lake Michigan. Use this unique opportunity to take amazing pictures from The Lodge, which is a balcony built on a floor made of glass with a view 400m down straight! One thing that is really important to consider before visiting the tower is the weather. I would recommend you to go on a clear and sunny day, otherwise the ticket is not worth the 22$ entrance fee. Get there as early as possible to avoid touristic crowds during the day!

Chicago Neighbourhood Bike Tour

By now you have a good impression of what Chicago's’ city centre has to offer, so it’s time to dive a bit deeper to explore the cosy neighbourhoods of the city. The sunny weather allowed me to join a bike tour, which I booked directly in Bobby's Bike Hike shop. This Lakefront Neighbourhood Bike Tour departs twice a day (9am and 1pm) and takes 3 hours. You will be surprised how quiet and peaceful life for the locals can be when exploring the calm and historical neighbourhoods surrounding the city centre. You will come across the Zoo, the largest park in Chicago “Lincoln Park” and the water-front passing by the beaches as well. I paid around 50$ for the tour which is quite pricey, but if it doesn’t hurt your budget too much the tour is worth its’ price.

Deep Dish Pizza at Dino’s East

The pie-like deep-dish pizza is the number one thing you have to try when visiting Chicago. There are plenty of famous restaurants you can choose from, but after asking some locals while searching for the best option I came to the conclusion that Gino’s East is the citizens’ favourite. I ate in the branch in LaSalle Street (walking distance from

Bobby's Bike Hike) and enjoyed the atmosphere and service a lot. Since the portions are really filling a small pizza is enough for 2 people. The restaurant is also famous for its’ thin crust pizza, which is something I would like to try next! On Wednesdays and Fridays, you can enjoy stand-up comedy shows in the pub – the schedule changes weekly!


Navy Pier

If you still got time and energy to explore another sight, go and visit Navy Pier! It is one of Chicago’s most famous tourist attractions and hosts various events, restaurants, exhibitions and a huge shopping centre. You will actually surround the pier during your Architecture River Boat Tour and spot the huge mall and the Navy Pier Ferris Wheel. The Bike Tour ended at the beginning of peninsula as well and we enjoyed a fantastic view on the Skyline of Chicago from there.

Science and Industry Museum

The Science and History Museum is a place you will enjoy even if you are usually not the biggest fan of museums. You can literally spend a whole day there, exploring 3 floors of interactive exhibitions. It is the largest science museum in the Western Hemisphere and features a U-505 Submarine Tour, a fun mirror maze, live shows and so much more! Mind the opening hours: the museum usually opens at 9.30am and closes at 4pm already (find exceptions on the museum website).


Chicago has so much to offer that 2 days are definitely not enough to get to know the entire city, but following this guide will give you a good impression of what the city is like. You will receive a lot of useful information, burn calories on your bike tour and gain them again at Gino’s East. You will enjoy a classic Broadway show and cover the most iconic sights the city has to offer. You will be able to enjoy views on the cities skyline from above, from the lake and even the waterfront.

I really hope you enjoy your stay and feel free to share your own experiences in the comments below