As part of our effort to make sure your stay in Chicago proves as joyous as you expect it to be, we thought of writing down some quick tips on the matter. Having interviewed locals and, most of all, our experienced guides, who know more about the city than scholars, we came with a brief guide on how to ensure a truly amazing stay in Chicago!

  1. Make a List of the Places You Simply MUST Visit

We begin with this simple yet necessary advice, for Chicago, with its wealth of sights, monuments and attractions can easily seduce you to the extent that, the last day of your stay in the city, you find out that you have not visited some of its most famed and astonishing spots.

So, first things first. Draft a list of the “must-see” places, and make sure you schedule to visit them during the first couple of days in the city. Such a list must include:

  • The Millennium Park


This fantastic place, teaming with sublime artistic creations, amazing fountains and gardens and relaxing spots, is almost every day of the year the venue of live concerts, open to the public. So, grab a glass of local beer and spend some hours to this lore of beauty.

  • The Loop

The beating heart of Chicago’s business district, comes alive every morning, flooded with crowds of people striving to make the most of life. Thus, if you want to sense the city’s vibe, this is the place to be.

The place is also home for some of Chicago’s greatest architectural marvels, such as the Willis (Sears) Tower, the Cultural Center, the Jeweler’s Building, the Thompson Center, and the Board of Trade and more.

Should you wish to feast your eyes on this area from another perspective, join a boat tour on the Chicago River.

  • The Magnificent Mile (Michigan Avenue) 

Chicago’s famed and ever buzzing shopping street.

  1. Spend Time at the City’s Lakefront

Chicago’s vast lakefront seems more like a coast leading to the ocean! When the weather is warm, crowds of locals and visitors enjoy there their favourite outdoor kicks, including sunbathing, cycling, rollerblading, boating, or romantic rambling along the gentle waves of the lake.

One of the best ways to roam around the area is a Segway ride. Start from the celebrated Navy Pier, see up close the Oak Street Beach, and have a rest for a couple of minutes at the North Avenue Beach – or for a short meal with its famous beer and burgers.

  1. Don’t Let the Monuments Overshadow Chicago’s Neighborhoods

While Chicago boasts museums, monuments, parks and attractions, it is and always be a city of neighbourhoods. Only there will you be able to get a glimpse of what living in Chicago really means, so please – do not let its terrific monuments overshadow Chicago’s daily face.

The Lincoln Square, Andersonville, and the Wrigleyville with its second oldest baseball field in the country, the array of bars and restaurants and music venues – yes, there lies the soul of Chicago. Devote at least a day in just roaming its streets and walkways.

  1. Eat – Eat as much as You Can 

It may sound strange, but it is true: despite its history and incredible monuments, in spite of its stunning lake and fascinating museums, most Chicago visitors return home saying their best experience was by far related with local foo!

With hundreds of restaurants and bars, reflecting the city’s diverse and multiethnic origins, Chicago offers them a journey of taste within a passage through cultures.