How to Explore Chicago in 48 Hours or Less

Audrey Fairbrother
September 8, 2017
How to Explore Chicago in 48 Hours or Less

There’s never a dull moment in the Windy City. That’s why the Hotel Engine and Travelers Haven team is ecstatic to travel to Chicago for the Worldwide ERC’s Global Workforce Symposium from September 27-29. Each year, the Symposium brings the nation’s top mobility industry professionals together to discuss the dramatic shifts and trends influencing today’s global workforce. Through a series of educational sessions, industry panels, and an exhibitor hall, attendees will collaborate on how to best navigate the challenges and opportunities surrounding modern globalization.

In preparation for this exciting weekend in Illinois, Hotel Engine’s very own Rachel Meyer, Director of Talent Management and Chicago native, gives her recommendations on the top attractions and hotspots to see during a weekend visit.

What to Do

You can find something to do year-round, but early fall in Chicago boasts an especially fun variety of activities for people of all ages.

Check out a comedy show.

Chicago has one of the nation’s best comedy scenes. Check out The Second City, a famous comedy bar that helped launch the careers of top comedians, including Bill Murray, Steve Carell, Tina Fey, Joan Rivers, Stephen Colbert, and Amy Poehler (to name a few).

Learn about the city’s architecture on a river boat tour.

Some of the best, most scenic views of Chicago aren’t from rooftops but from the river! Boat tours run day and night, and they’re a great way to learn more about how Chicago has grown from a small settlement into one of the largest cities in the world.

Attend a baseball game.

Home to the most recent World Series Champions, the Chicago Cubs, a baseball game in Chicago is a must. Chicago White Sox games are fun, too, and tickets are typically cheaper than ones at Wrigley Field.

Where to Dine/Drink

Photo courtesy of Eric Chan.

With many of the world’s top-rated restaurants, Chicago is one of the best foodie destinations. No matter what cuisine you’re in the mood for, you’ll be sure to find it in Chicago.

Grab a slice of authentic Chicago deep-dish pizza.

You cannot miss out on Chicago’s favorite slice. Pequod’s, Giordano’s, Gino’s East, or Lou Malnati’s are top local favorites. The pizza is so good that many of these restaurants also ship their pizza across the country!

Relax at Cindy’s Rooftop.

Looking for one of the best views overlooking the lake, Millennium Park, and the Art Institute? Look no further than Cindy’s on the top of the Chicago Athletic Association Hotel. With an open-air terrace bar and local seasonal cuisine, Cindy’s is an exquisite choice.

Escape to the idyllic English gardens of Celeste.

With a sophisticated atmosphere, Celeste has one of the most extensive Champagne and cocktail lists in the city. Get away from River North’s crowds and relax at the rooftop bar before heading down to the second floor’s Deco Room for a refined meal.

See also: The Top 6 Hotels for Business in Chicago

Where to Shop

You can find a whole new wardrobe between Chicago’s high-end designer stores and smaller, vintage boutiques.

Stroll along the Magnificent Mile on Michigan Avenue.

The Magnificent Mile is a 13-block stretch of a shopper’s paradise. Not only are there hundreds of stores to peruse through, but there’s also a variety of restaurants, hotels, and entertainment options. You could probably spend a whole weekend in just this area!

Do some high-end shopping in Gold Coast.

The Gold Coast neighborhood is home to many high-end designer brands and luxury boutiques with price tags to match — tread carefully.

Shop nearby the Damen El stop on the Blue Line in Bucktown.

If small boutiques are more of your style, check out the shops in Bucktown. There’s a variety of vintage, hipster, and off-the-beaten-path boutiques to pique your interests.


From relaxed evenings enjoying live music to dancing at popular clubs, Chicago has something for everyone.

Bar hop some of the best sports bars.

North Side’s Wrigleyville centers around Clark and Addison streets, where the Cubs’ home turf has given rise to many bars, restaurants, and parties. Some of the city’s best music venues and dance clubs are within a short walk through this neighborhood.

Listen to live blues at Kingston Mines.

For something more laid-back, Kingston Mines is a fun blues club located in Lincoln Park. With two stages, live music is always playing and the drinks are always flowing.

Sing along to top hits at Howl at the Moon.

This lively piano bar encourages song requests to be performed live on the main piano. Visit for a night of dancing and your choice of novelty bucket drinks.

Ready to see the sights in Chicago? Book your hotel through Hotel Engine and save 26% off public rates!

Article written by
Audrey Fairbrother

Audrey Fairbrother is the Content and SEO Manager at Hotel Engine. She spends her days writing about all things business travel, researching topics that are important to Hotel Engine's audience and cultivating the company's brand voice.

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