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2 Days in Chicago: A Weekend in Chicago Itinerary

ByMelissa

Chicago, known as 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 features famous 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 to enjoy. This 2-day Chicago itinerary will show you some of the best things to do in Chicago. 

millennium park in chicago is a must on your chicago itinerary

Are 2 Days Enough for Chicago?

While 2 days in Chicago is not enough to fully explore the city, two days is a good amount of time for an introduction to the windy City and will allow you to see some of the highlights. If you have more time, I would recommend 3-4 days in Chicago to explore at a leisure pace. 

This itinerary is perfect for a weekend in Chicago or any other time you plan to spend two days in Chicago.

2-Day Chicago Itinerary

This 2-day Chicago itinerary features some of the best things to do in the city, especially for first-time visitors. 

Two Days in Chicago: 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 chicago provides a great view of the navy pier

Willis Tower

Willis Tower is a 108-storey Chicago skyscraper. Standing 442.1 m high, Willis Tower is the third tallest building in the Western Hemisphere. The observation deck, known as the Skydeck, is located on the 103rd floor and is the most elevated observation deck in the United States. The Skydeck 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 Willis Tower in 2009, but 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 four states away. 

the skydeck at willis tower tilts out to look over the city of Chicago

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 before tower closing 

Tip: Purchasing tickets in advance is recommended. 

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

the bean is also known as the cloudgate in chicago, and is a must do for your chicago itinerary

Cloud Gate

The Cloud Gate is a world-famous public sculpture and an iconic Chicago landmark, 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. Drawing inspiration from liquid mercury, the Bean’s reflective surface distorts the Chicago skyline, making it a popular photo spot. During your visit, you can touch the Cloud Gate and walk underneath the 3.7 m tall sculpture.

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 throughout the year. 

millennium park in chicago hosts festivals and events throughout the year

Bonus Activities: While visiting Millennium Park, you can also see the 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, flowing from Lake Michigan to the Mississippi River. The most notable point to view the Chicago River is downtown on the Dusable Bridge along Michigan Avenue. From DuSable Bridge, you can view the Chicago River and Lake Michigan while right in busy downtown. 

Each year, the downtown section of the Chicago River is dyed green the Saturday before March 17th, in honours of St.Patrick’s Day. Ways to experience the Chicago River include: walking the boardwalks along the river or taking a river cruise to enjoy the river by boat. 

a chicago river cruise is one of the best ways to experience the city

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 and events, such as outdoor movies, live music, and fireworks year-round. You can check out the Pier website to find which events may occur on your visit dates.

navy pier fireworks chicago
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, try Chicago-style popcorn (cheese and caramel) from Garrett’s Popcorn. The combination of cheese and caramel may sound strange, but it tastes delicious.

Two Days in Chicago: Day 2 – Lincoln Park and Deep Dish Pizza

Today is the last day of this 2-day Chicago itinerary. You will explore the Lincoln Park neighbourhood.

lincoln park in chicago is a beautiful park

Lincoln Park

Lincoln Park is a neighbourhood and park on the north side of Chicago. The city’s largest park Lincoln Park consists of a zoo, conservatory, a lakefront trail, North Avenue Beach, and more. Featured in this Chicago itinerary are the Lincoln Park Zoo and the Conservatory. 

add lincoln park conservatory to your chicago itinerary

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 the Lincoln Park Zoo, the next stop for today. 

lincoln park zoo in chicago is a free thing to do

Lincoln Park Zoo

Lincoln Park Zoo is a 35-acre zoo in Chicago, Illinois. This free admission 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 animals to see are turtles and flamingos. 

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 in chicago is a must eat

Deep Dish Pizza

Deep dish pizza is a local Chicago staple that grew across the United States and is now enjoyed 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, so the choice of which one to eat at is up to you. During my trip to Chicago, I dined at Pizzeria Uno and took Lou Malnati’s Pizzeria to-go. My deep dish pizza preference was Pizzeria Uno.

unos pizzeria in chicago is one of the best places for deep dish

Finished this 2-day Chicago itinerary early? Here are more ideas of things to do in Chicago:

More Things to Do in Chicago

Are you planning on spending the holidays in the windy city? Check out this guide on Christmas in Chicago.

Is Chicago Safe?

Chicago is voted as 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 standard travel precautions, including not visiting known gangs or high-crime neighbourhoods, not walking alone after dark, and carrying 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, like any other travel destination. If you feel unsure, check which neighbourhoods of Chicago to avoid before you go. 

Is Chicago Expensive? 

While Chicago can be considered expensive compared to other US cities, it does not mean you cannot visit Chicago on a budget. Chicago is comparable in pricing to other major US cities such as San Francisco, although cheaper than New York City or Miami. One thing Chicago has is many free attractions and festivals, as well as free museum days to help if cost is a concern. You can enjoy Chicago on a budget or travel through the windy city in luxury.

if you have time, add a chicago river cruise to your chicago itinerary

How to Get Around Chicago

You can commute around Chicago by bus, train, taxi, or private rideshares 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 walked to commute around Chicago. 

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

Getting 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 trip distance. Some buses service the downtown, and you can find the schedules on the CTA website.

getting around downtown chicago

How to Get to Chicago, Illinois

To get to Chicago, Illinois, ride on a plane, train, or bus. If coming from nearby in the USA or Canada, you have the option of a road trip and driving to Chicago. Flights arrive in Chicago daily from worldwide destinations. A direct flight to Chicago from Toronto takes about 2 hours, or from New York takes approximately 3 hours. During my two visits to Chicago, I went on road trips. Driving to Chicago from Toronto is about 8 hours, or from New York takes approximately 12 hours.

How To Get Downtown from the Chicago Airport

One of the largest transportation hubs of the Midwest, Chicago contains two airports, ORD and MDW. Most flights fly into Chicago O’Hare, ORD. 

To get downtown from Chicago O’Hare, you will want to take the Blue line CTA L-train. The Blue line runs 24 hours daily, takes approximately 1 hour and costs $5 per ride from the airport. You can buy a reusable Ventra card or buy pay-as-you-go single-ride tickets. Tickets are valid for up to 2 hours and can be used to transfer to reach your end destination.

chicago is the windy city

Helpful Tips for Visiting Chicago 

  • The best time of year to visit Chicago is April – October.
  • The currency in Chicago is US Dollars, as is the rest of the USA
  • 21 is the legal drinking age in Illinois and the USA.
  • Tap water is considered safe in Chicago but often has a higher lead content, so you may prefer to drink bottled water.

I hope this information helps you plan your 2-Day Chicago itinerary for a weekend getaway. Happy travelling!

Travelling to the USA? Read more:

Melissa is the founder of My Beautiful Passport. A Canadian who has explored 20+ countries on 4 continents, she enjoys combining soft adventure and affordable luxury. Through sharing her own experiences, travel tips, and destination itineraries, she helps others plan their unique adventures whether it be at the beach, in the city, or in the mountains.