Allgemein Short Trips Travel

48 Hours in Chicago – What To Do

Last weekend we traveled to Chicago for two days. Chicago has always been on my bucket list, and since Boston is just a short two-hour flight away from Chicago we finally decided to go visit the Windy City!

During our trip we stayed at the Kimpton Hotel Allegro which was conveniently located at the Loop and within walking distance to all major sightseeing spots. Since we only stayed in Chicago for 48 hours we had to focus on seeing the main tourist attractions around town.

DAY 1 – Imperial Lamian, Architectural Cruise, Portillo’s

On the arrival day, our flight reached Chicago O’Hare at around 10:30 am. We decided to take an Uber into town which took approximately 40 minutes. After checking in, we were craving some delicious food and decided to try out a popular dim sum place a few blocks away. Seriously, if you like dim sum you’ll love Imperial Lamian. Located on W Hubbard St, this chic and modern Chinese restaurant will blow your mind away. We tried their signature rainbow dumplings with different flavors, dim sum, fried rice with prawns and their egg buns. The service was truly amazing and the restaurant comes with a great ambiance. I highly recommend this place when traveling to Chicago.

After lunch, we headed to one of Chicago’s most famous tourist activities: the architectural boat tour. Due to high popularity we decided to purchase the tickets two days in advance online. The architectural cruise of Chicago Line Cruises featured a 90-minute guided tour on Chicago River with explanations about Chicago’s history and its beautiful architecture and buildings.


In the evening, we headed to one of Chicago’s iconic hot dog places: Portillo’s. Their famous Chicago-style hot dog comes in a poppy seed bun with onions, tomatoes, pickles and mustard. It is not only a cheap food option but also super delicious! Make sure to stop by Portillo’s for their famous fast food. And for all the mural lovers out there, check out the iconic flamingo wall next to The Flamingo Rum Club one block away on N Wells St.

DAY 2 – Willis Tower, Big Bus Tour, The Bean, Giordano’s

On our second day we visited the Sky Deck at the Willis Tower to get a 360 degrees view over the city of Chicago. One big advice is to buy tickets for the observation deck one or more days in advance as they tend to sell out quickly. Also, go there early in the morning right when they open to avoid long lines and have enough time to take pictures in their famous glass floor boxes. The view on top is just amazing! It gives you a great overview of the scale and beauty of the city.


After the Sky Deck, we bought tickets for the sightseeing hop on and hop off tour with Big Bus Tours. Although this is super touristic the audio guided bus route covers all major sightseeing attractions of Chicago and allows to see the most in a short period of time.

One bus stop was directly next to the Cloud Gate which is often referred to as “The Bean”. For me personally the bean has always been the most iconic sculpture that I associated with the city. Therefore, a visit was a must! The bean is a great photo spot located in the Millennium Park and very popular among tourists and locals.


Afterwards, we stopped at one of the many Giordano’s restaurant locations right next to the Millennium Park. Giordano’s is probably the most famous out of all Chicago deep-dish pizza restaurants and it is always crowded. Chicago is famous for its deep-dish pizza which is baked in a pan and comes with its typical high edge walls filled with lots of cheese and tomato sauce. Eating a deep-dish pizza is something that should be on every to-do list when visiting Chicago.

On our last evening, we went for a walk on the promenade at the Chicago Riverwalk and watched the beautiful sunset. If you are looking for great shopping areas in the city, make sure to check out N Michigan Ave in the River North district, or stroll along the Navy Pier to enjoy views on Lake Michigan.

Although our trip to Chicago was short we tried to see as much as possible and get a feeling of the city vibes. I personally really enjoyed traveling to Chicago because everything is reachable in walking distance and there are so many restaurants and shops to visit. What are your favorite places to visit when staying in Chicago? Let me know in the comments below.



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