Chicago Itinerary 2 Days

This is a glimpse of what to see in 2 days in Chicago from Chicago itinerary 2 days created by our travel experts. These are the attractions one must visit while planning a 2 days trip to Chicago.

2 Days in Chicago - Perfect Weekend Guide

One of the largest cities in USA, the vibrant city of Chicago in Illinois is located on Lake Michigan and boasts of a beautiful skyline. This lakeside city has the fourth strongest economy in the world. Chicago is a diverse and cosmopolitan city that hasn’t lost any of its genuine mid-western hospitality and friendliness.The city is known for its rich musical cultural heritage and is also a historic hub for transportation. More importantly, the city is famous for its sports! This Chicago Itinerary 2 days will help you explore Chicago fully:

What to pack for 2 days in Chicago vacation?

As you are going on a 2 days Chicago vacation, compact luggage is ideal. Carry a backpack that can fit in your belongings or choose a compact trolley bag. You only need one pair of shoes that you're wearing, make sure you pick sturdy ones for all the walking and sightseeing. Check the live weather of Chicago and pack just what's needed! Do not forget to bring extra batteries for your camera, you won't have time to move back-n-forth to your room to charge them. Pro Tips: Carry your Passport and photo identification proof with you at all times. Carry a Chicago local map, a hard copy or in your phone.

Are 2 days enough to explore Chicago?

It is slightly difficult to explore the entire city in 48 hours time, but you can easily visit the hand-picked 8-10 points of interest in Chicago on your trip. You will have to travel a bit if you want to cover all the popular places in Chicago within 2 days. So, if you have any particular place in mind, then plan your Chicago visit accordingly. If it is a weekend trip, check for special events happening and plan accordingly.

Trip Budget for a weekend trip to Chicago?

Chicago weekend itinerary budget would vary from is USD 508 to USD 434 as per your choices. There are enough free places in Chicago to ensure that unless there’s an exhibition or event you really want to see, paying is unnecessary.

How to spend 2 days in Chicago?

Day 1


Start your morning with the stunning view of the Willis towers in Chicago. Popularly known as the Sears towers, this tower was the tallest building in United States until the inauguration of The world trade centre.


Head to the Michigan Avenue in the afternoon and get a glimpse of the Michigan Lake as well. Enjoy Shopping at the Magnificent Mile and then head to the Millenium park, a public area at the loop and experience a lively and spectacular atmosphere.


Experience the feels of being in China by heading to the Chinatown. It is an ethnic Chinese neighbourhood in Chicago and has major of it’s population from the Southeast Asia. Dine at the authentic Chinese Restaurants there and shop for local artifacts.

Day 2


Start your last morning of your 2 days in Chicago by visiting the Lincoln Park Zoo, one of the oldest zoos in North America and a free admission zoo as well.


Spend your afternoon at the quiet Shedd Aquarium established in 1930. The Chicago Cultural Center should be a must visit. A reception venue, this place has many art exhibits as well as plays a host to many major events in the city.


Spend the last moments of your 48 hours stay in Chicago by visiting the Buckingham Fountain, one of the largest fountains in the world which is a replica of the Michigan Lake.

This Chicago Itinerary 2 days will surely help you plan a memorable trip.

Money saving tips for Chicago weekend itinerary:

  • Skip the restaurants and cafes for street vendors and supermarkets
  • Get 2 Day Chicago transport Pass if possible which offers free public transport, free entrance to the recommended attractions
  • Couchsurfing is a great way to save loads on accommodation expenses
  • Spend More Time In Fewer Places of Chicago

Where to eat in Chicago if you've 48 hours?

48 hours to enjoy the culinary delights of Chicago and the best you can do is opt for a buffet that offers local variety at a reasonable rate.

Where to stay in Chicago for a weekend?

You can book a hotel or apartment close to millennium park and this would save you lot of time for 2 days trip. You can also opt homestays to stay in Chicago. Prices for the same may be slightly steep, but it is the convenience that matters!

Recent Itineraries for Chicago in 2 Days

Spending 2 days in Chicago, Illinois? Refer these recently created 2 days 1 night Chicago travel itineraries.

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