City Travel USA

Chicago Itinerary: 2 Days in Chicago

Last updated on March 30th, 2022

Chicago, or the Windy City, is an international hub of culture, transportation, and finance located on the shores of Lake Michigan in Illinois. The 3rd most populated city in the United States, Chicago is known for attractions such as Navy Pier and Willis Tower. Home of the deep-dish pizza, Chicago style-hotdog, and the Chicago Cubs. You will find architecture, food, and many attractions in Chicago for everyone to enjoy. This 2-day Chicago itinerary will show you some of the best of Chicago. 


If you only have 2 days in Chicago, use this itinerary to see the highlights:


Day 1 – Willis Tower, Cloud Gate, Chicago River, and Navy Pier

Today will take you to the West Loop, Loop, and Streeterville neighbourhoods.


Willis Tower 

Willis Tower is a 108 storey Chicago skyscraper. Standing 442.1 m high, Willis Tower is the third tallest buildings in the entire Western Hemisphere. The observation deck of Willis Tower, known as the Skydeck, is located on the 103 rd floor and is the tallest observation deck in the United States. The Skydeck of Willis Tower is a popular tourist attraction providing scenic views of the Chicago skyline, including a glass floor to view the streets below. Formerly known as Sears Tower, the skyscraper was renamed in 2009 to Willis Tower, however, locals still often refer to the building by its original name. On a clear day from the Skydeck’s Ledge you can view up to 4 states away.


Willis Tower 

Hours of Operation: Daily, March-Sept 9 am – 10 pm, Oct-Feb 10 am – 8 pm

Cost: $35 for adults 12+

Note: Last entry is 30 minutes prior to tower closing

Tip: It is highly recommended to purchase tickets in advance. 


From Willis/Sears Tower, head to the Cloud Gate. 


cloudgate chicago the bean

Cloud Gate 

The Cloud Gate is a world-famous public sculpture and an iconic Chicago landmark. The Cloud Gate is nicknamed the Bean due to its bean-like curved shape. Located in Millennium Park since 2006, the Cloud Gate is a 66-foot long stainless steel sculpture designed by artist Anish Kapoor. The Bean takes inspiration from liquid mercury, and its reflective surface distorts the Chicago skyline, making it popular for photos. You can touch the Cloud Gate and walk underneath the 3.7 m tall sculpture during your visit.


the bean chicago cloudgate

Cloud Gate 

Hours of Operation: Daily 24 hours

Cost: FREE

Note: Depending on the time of year you visit, Millennium Park hosts festivals and other events.


Bonus Activities: While in Millennium Park, you can also check out Crown Fountain and Buckingham Fountain.


Once finished at Millennium Park, the next stop on this Chicago itinerary is the Chicago River.


chicago river downtown - chicago itinerary

Chicago River 

The Chicago River is a 251 km system of rivers and canals that run through Chicago. Chicago River flows from Lake Michigan and connects to the Mississippi River. The most notable point to view the Chicago River is downtown on the Dusable Bridge along Michigan Avenue. From the DuSable Bridge, you can view the Chicago River and Lake Michigan while right in the middle of busy downtown Chicago.


Each year, the downtown section of the Chicago River is dyed green the Saturday before the 17th, in honours of St.Patrick’s Day. There are boardwalks along the river to walk along on your visit or river cruises available to enjoy the river by boat.


Chicago River

Hours of Operation: Daily 24 hours

Cost: FREE


After spending time viewing the Chicago River, head to Navy Pier.


navy pier from willis tower chicago

Navy Pier 

One of Chicago’s most popular attractions, Navy Pier, is a 1010 m long pier along the edge of Lake Michigan. Spanning 50 acres, Navy Pier includes gardens, shops, parks, restaurants, attractions, a Ferris wheel, festivals, and a marina. The activities and experiences available at Navy Pier attract millions of visitors each year. Navy Pier hosts festivals, events such as outdoor movies and live music, and fireworks, year-round, you can check out via the Pier website which will occur on your visit dates. 


Fireworks during my visit to Navy Pier

Navy Pier

Hours of Operation: Sun – Thurs 11 am – 8 pm, Fri – Sat 11 am – 10 pm

Cost: FREE

Tip: While at Navy Pier, be sure to try Chicago-style popcorn (cheese and caramel) from Garrett’s Popcorn. The combination of cheese and caramel may sound strange, but it tastes delicious. 


Day 2 – Lincoln Park and Deep Dish Pizza

Today will take you to the Lincoln Park neighbourhood.


Lincoln Park

Lincoln Park is a neighbourhood and park on the north side of Chicago along Lake Michigan. Chicago’s largest park Lincoln Park consists of a zoo, conservatory, a lakefront trail, North Avenue Beach, and more. Highlighted below are Lincoln Park Zoo and the Lincoln Park Conservatory.


Lincoln Park Conservatory

The Lincoln Park Conservatory is a 19th-century Victorian glass building that houses a botanical garden with various exotic plants from around the globe. Built in the 1870s, Lincoln Park Conservatory is one of the oldest public gardens in the United States. The building also houses various sculptures alongside the garden. 


Lincoln Park Conservatory

Hours of Operation: Wed-Sun 10 am – 3 pm 

Cost: FREE


Next to Lincoln Park Conservatory, is Lincoln Park Zoo, the next stop for today.


Lincoln Park Zoo

Lincoln Park Zoo is a 35-acre zoo in Chicago, Illinois. The free admission Lincoln Park Zoo is the 4th oldest zoo in North America. Founded in 1868, the zoo began with two sets of swans gifted to Lincoln Park. Within Lincoln Park Zoo, you can find more than 1000 animals from 200 different species, including lions, monkeys, and polar bears. My favourite animal to see is turtles.


Lincoln Park Zoo

Hours of Operation: Mon-Fri 10 am – 5 pm, Sat & Sun open until 7 pm through summer
Cost: FREE


From Lincoln Park, head for deep dish pizza for lunch/dinner. 


Deep Dish Pizza

Deep dish pizza is a local Chicago staple that has spread across the United States and worldwide. Round pizza dough is baked in a deep pan with toppings on the bottom and sauce on top. Since the 1940s, both Pizzeria Uno and Lou Malnati’s Pizzeria have debated being the original deep dish pizza. Both Pizzeria Uno and Lou Malnati’s Pizzeria are well-known and loved, and so the choice of which one to eat at is up to you.


During my trip, I dined at Pizzeria Uno and took Lou Malnati’s Pizzeria home. My deep dish pizza preference was Pizzeria Uno. 


Once you have finished at this stop you have completed this 2-day Chicago itinerary.


Have more time or finished this itinerary early?  Try these activities:

  • Shedd Aquarium 
  • Field Museum
  • Adler Planetarium
  • Art Institute of Chicago


Spending the holidays in the windy city? Check out this guide on Christmas in Chicago


Is Chicago Safe?

Chicago has been voted one of the best large US cities to visit by Conde Nast Traveler, with nearly 50 million annual visitors. Although Chicago has a bad reputation for crime and gang activity, it is generally safe for tourists and travellers.


You will want to take normal travel precautions, including staying away from known gang or high crime neighbourhoods, not walking around alone after dark, and carrying around an anti-theft bag/backpack. 


During my multiple visits to Chicago, I have never felt unsafe. I keep mainly to tourist areas and always observe my surroundings, just like any other travel destination. If you feel unsure, make sure to check online which neighbourhoods of Chicago to avoid before your departure.


Chicago Transportation

A major transportation hub of the Midwest, Chicago has many transportation methods and contains two airports, ORD and MDW. You can commute around Chicago by bus, train, taxi, private ride shares such as Uber, bicycle or walking. 


The Chicago Transit Authority (CTA) is the second-largest public transportation system in the United States, next to New York City’s public transportation system. The CTA operates 24 hours and services millions of people daily with 8 Chicago L trains and 129 buses. 


During my trip, I used Uber and walking to commute around Chicago. 


Tip: Download the CTA map onto your phone before your trip or use wifi to be able to navigate offline 


How to Get Around Downtown Chicago

Downtown Chicago consists of a loop. The Brown, Green, Orange, Pink, and Purple CTA L-trains service the downtown loop. The CTA currently uses a flat rate fare system, so the cost does not depend on the distance of the trip. There are also buses that service the downtown, and you can find the schedules on the CTA website.


How To Get Downtown From Chicago Airport

The Blue line CTA L-train runs from Chicago O’Hare, ORD, into downtown Chicago. The Blue line runs 24 hours daily.


Hope this information helped you plan your 2-Day Chicago itinerary.

Happy travelling!


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