Buckingham Fountain at night

Can ChatGPT Create a Perfect Chicago Weekend?

Published on May 18, 2023

One of the biggest media stories of 2023 has been the emergence of artificial intelligence platforms. With professionals of all stripes seeing if ChatGPT can create content as well as humans, we thought we’d see how good a tour guide it could be. We asked it to create a “perfect Chicago weekend,” one for two days and another for three.

By Dave Lifton (@daveeatschicago)

The bot responded with detailed itineraries, with two activities suggested for the morning, afternoon, and evening of each day, with a sentence or two about why it was essential. We’ve broken down the recommendations into three categories—Attractions, Food and Drink, and Entertainment—and offered our thoughts along with how eATLAS’ many Chicago-based adventures could enhance the experiences. Even though we didn’t specify, it’s clearly geared towards people visiting Chicago for the first time, so we’re taking that aspect into account.

Attractions: Here’s where ChatGPT was most successful. For those making a first-ever trip to Chicago, trips to Millennium Park, the Art Institute, Museum of Science and Industry, Lincoln Park, and the Magnificent Mile are undoubtedly essential for understanding why Chicago is a world-class tourist destination. It also recommended Skydeck at the Willis Tower, Field Museum, Navy Pier, and the Chicago Cultural Center.

The Navy Pier

That last group are all worthy options, but their descriptions all turned up issues. ChatGPT omitted that Navy Pier is geared towards families and its charms can often be lost on those traveling without children. The bot could have easily noted that the Field Museum is part of the Museum Campus, along with the Shedd Aquarium and Adler Planetarium, both of which are excellent. The Chicago Cultural Center was described as having “free art exhibitions, concerts, and events” but overlooked the beautiful G.A.R. Rotunda and Hall and Preston Bradley Hall. As for the Willis Tower, the platform called it the tallest building in the Western Hemisphere, which it hasn’t been since 2013.

For those spending most of their time downtown, check out our tours of the Loop, Navy Pier, Millennium Park, and the Magnificent Mile; sculptures by famous artists and neon signs in the Loop; and scavenger hunts in the Museum Campus, Lincoln Park and its zoo, and Navy Pier.

Food and Drink: For lunch, it naturally suggested getting deep-dish pizza (Lou Malnati’s, Giordano’s) and a Chicago-style hot dog or Italian beef sandwich (Al’s or Portillo’s). It’s practically sacrilegious to not sample at least one of those iconic dishes on a first trip here. And you couldn’t go wrong with its cocktail recommendations at either a speakeasy (Violet Hour, The Drifter) or rooftop bars (Cindy’s, Signature Room, or J. Parker’s), although calling the Signature Room, located 1,000 feet above Chicago in the John Hancock Center, a “rooftop bar” is an understatement.


On the other hand, the dinner recommendations were surprising, singling out Quartino and Spiaggia and heading to “trendy neighborhoods, like Wicker Park or Logan Square.” Those are all good ideas (although Spiaggia closed in 2021) but it gives short shrift to the rest of Chicago’s culinary scene. There’s no mention of how the West Loop/Fulton Market has become the epicenter of food culture in the city, nor does it mention neighborhoods like Chinatown, Pilsen (Mexican), Argyle St. (Vietnamese), Humboldt Park (Puerto Rican), or Devon Ave. (South Asian), all of which are beloved for their .

We truly believe that venturing from downtown is key to understanding Chicago. We have tours that explore the history, culture and architecture of such neighborhoods as Wicker Park, Pullman, Pilsen, Hyde Park, Uptown, Bronzeville, Old Town, Prairie Avenue, Northalsted (formerly Boystown), Fulton Market, and Printers Row.

Entertainment: The suggestions consisted of a Cubs game at Wrigley Field, show at the Chicago Theatre, river cruise, jazz at the Green Mill, and a performance at the Lyric Opera of Chicago. Here’s where the limitations of ChatGPT fully revealed themselves. Of those, only the Green Mill, one of several stops on eATLAS’ tour of neon signs in Uptown, is open daily (river cruises don’t operate in the winter). Sports and live performances—from ballet to theater to punk rock—are integral to Chicago’s cultural landscape, so the answer should have been as broad as possible to accommodate a broad swath of tastes. And to ignore Second City, the epicenter of American comedy and has numerous shows daily, is mind-boggling.

Conclusions: It was a mixed bag. The ideas offered by ChatGPT rank among Chicago’s most well-known tourist attractions. And for the most part, the bot seemed to have a sense of the city’s geography by grouping them by location. For example, it didn’t suggest following up a trip to the Museum of Science & Industry with a stroll through Lincoln Park. But it also suffered from incomplete or outdated information in spots and a lack of imagination, particularly in the dining and entertainment categories. You would still have a great time in Chicago if you followed these instructions to the letter, but you also wouldn’t have a sense of what the city is about.  

Leave a Reply

Your email address will not be published. Required fields are marked *

The Adventure starts when you say it does.

All eATLAS Adventures are designed and built by experienced eATLAS Whoa!Guides. They're always on. Always entertaining. And always ready to go.

Check out our Adventures!