What to do in Chicago in 48 hours


Getting to know a city like Chicago in just two days is no small feat. But with a little research and some advance planning, you should end up with a real insight into this beautiful place, which is full of fun activities for all.

Start by identifying accommodation which is strategically placed near to the destinations which you most want to visit.

Tourists looking to discover places that are popular among the locals could do worse than book a food tour. These tours allow participants to connect with local culture, and learn a little more about their daily routines and way of life.

So when you first arrive in town, your first question should be: “are there any food tours near me?” This is where your journey really begins.

Getting to know Chicago in 48 hours

Chicago has so much to offer that short-term visitors will have to pick and choose the places they are most excited to visit.

One thing most travelers agree is on is that, if you visit Chicago, you shouldn’t miss out on the skywalk in Willis Tower. 

The tallest building in the city affords visitors a panoramic view from a transparent platform. The observation deck of the Willis Tower, called the Skydeck, boasts a series of opaque balconies that reveal a stunning view from 412 meters above ground level.  Not for the faint of heart, or anyone suffering from vertigo!

Another bucket-list Chicago location is Millennium Park, which usually features in any food tour Chicago has to offer. 

This vast space filled with greenery is also home to unparalleled architectural feats, including works of art such as The Bean and The Crown Fountain.

If you want to linger a little further in Millennium Park over a good meal, most visitors recommend nearby restaurants like The Gate, Remington’s, and Acanto. Here you’ll find a wide range of dishes at affordable prices, and these establishments’ excellent customer service has not gone unnoticed by tourists either.

Another great place to visit while in town is Lake Shore Park. Ideal for walking and enjoying the outdoors, this park is also a great spot to enjoy a typical Chicago hot dog or sandwich. Another major perk is that it is surrounded by museums, so you can quickly pop into major Chicago institutions like the Museum of Contemporary Art.

After a short tour of the downtown area, why not take a bus to the exceptional Wicker Park neighborhood, with its many activities to enjoy either alone or with friends.

Wicker Park stands out for its excellent social life – in addition to a wide range of restaurants and cafes, visitors have access to all kinds of stores on North Damen Avenue, from specialty dining to boutique fashion – this place has it all!

North Milwaukee Avenue is home to plenty of bars and entertainment venues; according to travelers, the most popular of these are the Double Door, Subterranean, and Davenport’s. We recommend staying for at least a few drinks, since the nightlife in this neighborhood is said to be the stuff of legends.

If you are a baseball fan, you should definitely visit Chicago’s major league stadium, Wrigley Field.

The surrounding neighborhood has long been home to Chicago’s working class, and has gravitated around this iconic stadium. Visitors can also visit sports bars and themed stores selling highly original sports-related gifts. 

As you travel between Wicker Park and Wrigley Field, check out the Summer House Santa Monica restaurant, a beach-themed establishment where you can enjoy all kinds of typical Chicago dishes. The menu includes meat, pastas, pizzas, fast food, and tacos, among others. Customers typically recommend the ahi tuna chips, but be warned: they are extremely spicy!

By now you should have lots of ideas and tips that will allow you to go sightseeing in Chicago while enjoying the typical foods of the city. On your travels, you should be able to get a sense of the city’s architecture, and how its residents live day to day. We hope that you now have a good starting point for getting to know Chicago in just a couple of days.

Some extra recommendations

If your stay in the Windy City is a short one, we advise researching the means of transportation available to you before traveling. You can save a lot of time by knowing in advance which buses or other forms of transport you can take to get from A to B, or where to purchase the tickets required for travel around the city.

Another good habit to acquire before visiting a new place is to check the payment options in the stores that you are planning to visit. This is important because, in some areas, stores only accept payment by cash, which will cost you precious time if you typically only travel with a credit card.

The more you can sort out before you start your trip, the more time you will have to enjoy your stay once you arrive. Organize your activities in advance, and be prepared.

Now that you have everything you need for your trip to Chicago, it’s time to pack your suitcase and get out there!