City break (noun): a short holiday spent in a city, such as when on business travel.

Before there was bleisure travel, there was the city break—the short space of leisure time that grants you access to the cultural and culinary amenities that big cities offer. In this series from TripIt, we explore some of the world’s best cities for planning a quick getaway or extending a work trip.

Here are our tips for making the most of your city break in Chicago.

Where to fly in

Chicago metro area is served by two major airports: Chicago O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). 

ORD is located 17 miles northwest of downtown Chicago, bordered by the neighborhoods of Rosemont to the north and Schiller Park to the south. From the airport, you can take the Chicago Transit Authority (CTA) Blue Line rapid transit train service—affectionately known as the “L”—to the city. The average ride between the two takes 40-45 minutes. 

MDW—located southwest of the city—is several miles closer to downtown Chicago, and just about 20 minutes away via the Orange Line. Cabs and ride shares are available upon arrival at both airports, but they cost the most of the ground transportation options.

Where to stay during your city break

city break chicago

If you have a flair for the trendy over the traditional, you’ve arrived in the right city. In recent years, hotels have cropped up across many neighborhoods outside of The Loop (i.e., Chicago’s downtown). The Ace Hotel Chicago in the West Loop, for instance, is just a few minutes’ walk from the neighborhood’s bustling restaurant scene. The hotel also features on-site dining, a rooftop lounge and garden, and spacious guest rooms with free Wi-Fi. 

Traveling solo? The Freehand Chicago in the River North neighborhood offers a variety of accommodations—from shared quad rooms to penthouse digs. The ‘hostel-hotel’ features the Broken Shaker—located just past the ground floor lobby—serving food and drinks in the lounge space by night. By day, you can grab a coffee at on-site Café Integral and return to the lounge to access free Wi-Fi and catch up on emails. 

In the Windy City on business? Here are our picks for where to stay:

  • If you’re attending an event at McCormick Place—the largest convention center in North America—you can’t beat the convenience of the Hyatt Regency McCormick Place. Ask for a north-facing room for panoramic views of the city skyline and Lake Michigan.
  • If a hotel in a prime downtown Chicago location is what you’re after, look no further than the W Chicago – City Center. Conveniently located in The Loop, the W Chicago is easy walking distance from Union Station, Willis Tower, and Millennium Park. After work, you’re just a few blocks from the designer stores on Michigan Avenue. 
  • Stay just steps away from the Chicago Riverwalk at Virgin Hotels Chicago. This chic hotel features complimentary Wi-Fi access throughout, four on-site restaurants, 24-hour business and fitness centers, plus communal spaces where guests can work, eat, socialize or relax.

How to get around

city break chicago

While Chicago’s public transportation system isn’t as extensive as, say, New York City’s, the L is still your most affordable mode of transport—and often your fastest, too. Eight color-themed lines traverse the city, accessible with a Ventra Card, disposable Single-Ride or 1-Day Ventra ticket. Cards and tickets are available for purchase at Ventra Vending Machines, located at every L station. You can also ride CTA buses with your Ventra Card (or cash).

Alternatively, Lyft and Uber are available in Chicago and are likely your best option for getting around the city if you’re staying in an area far from an L station. 

Pro tip: Use TripIt’s Navigator feature to search transportation options available to you. It will show you the estimated costs and travel times for each option, so you can decide which works best. You can find Navigator within your flight, hotel and rental car details screens. Plus, if you add a restaurant reservation to your itinerary (more on where to eat below), Navigator also helps you find the best transportation options for getting to your table.

Where to eat

city break chicago

Chicago cuisine is at once steeped in tradition, yet masterfully inventive. Curating a list with a few of my favorite restaurants was no easy task. That said, all roads lead to the two-mile stretch of Randolph Street in the West Loop. Your first stop should be Top Chef Stephanie Izard’s Girl & the Goat. Think shareable plates showcasing global flavors, a well-traveled wine list to match, a rotating beer selection with a focus on Chicago breweries—all within a vibrant, yet welcoming atmosphere. Girl & the Goat accepts reservations—and we’d encourage you to make them as soon as possible—but allows for walk-ins, too. Or, you could try Izard’s Little Goat Diner, located across the street from Girl & the Goat, for more casual digs and eats. 

A few blocks away from Randolph Street you’ll find Fulton Market District, the meatpacking district of Chicago. Here, you can choose from delicious spots like The Publican and Publican Quality Meats for dishes true to the district, or go the less traditional route and venture to Momotaro for modern Japanese cuisine.

In pursuit of wine and cheese? Head to Michigan Avenue to The Purple Pig—where the flavors of the Mediterranean meet the energy of the Windy City. Michelin recognized for eight years running, The Purple Pig should be your go-to spot for lunch with colleagues, dinner with friends, or a glass of wine anytime.

Came all this way for deep-dish pizza? Been there! Choose from iconic pizza shops like Lou Malnati’s, Giordano’s, Pequod’s, Pizano’s, and so many more—this is Chicago, after all. 

Looking for more trip inspo? Check out Summer in the Cities: Chicago in the New York Times. 

What to do on your city break

city break chicago

Looking to get some sightseeing in while you’re in town? Whether you’re a history buff or an architecture aficionado, you’ll love taking a boat tour on the Chicago River. Not only will you experience some of the best views of the city’s skyline, you’ll also gain a wealth of knowledge about the buildings and their storied history. Chicago Architecture Foundation River Cruise, Shoreline Sightseeing Architecture River Tour, and Seadog River and Lake Architecture Tour all offer this unique sightseeing experience. 

If you’re visiting Chicago during baseball season, be sure to catch a Chicago White Sox game at Guaranteed Rate Field or a Chicago Cubs game at Wrigley Field—depending on your allegiance! Now, to decide between a slice of deep dish pizza or a Chicago Dog…

If your family tagged along on your city break, there are plenty of kid-friendly things to do, too. Start your day at the Lincoln Park Zoo. Then, head to the Family Pavilion at Navy Pier—home to the Chicago Children’s Museum, indoor botanical gardens, restaurants, shops, and much more.

Adults only? By day, visit the The Art Institute of Chicago. By night, head to the Theatre District and catch a show at iconic venues like the Chicago Theatre, Goodman Theatre, or 200+ other theatres located across the city. Hint: Check Hot Tix—a program of the non-profit League of Chicago Theatres—to see if there are discounted tickets available for the show you want to attend. 

Looking for an after-hours activity? Head to one of the city’s many speakeasies, like The Office (located just below an equally-interesting The Aviary) or Three Dots and a Dash, to time travel back to the grittier days of Chicago’s Prohibition era—without the worry of breaking the law, of course.

About the Author

Amanda Wowk is a freelance writer, founder of Amanda Wowk Creative — a content writing services company — and avid traveler. Her experience spans the travel industry, supporting clientele in travel tech, luxury travel, and consumer brands. When she’s not helping clients tell their stories, Amanda writes about her own experiences to inspire others to travel as far, wide and frequently as possible.

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