A Business Traveler’s Guide To Chicago


Why is Chicago called the Windy City? There’s no definitive origin for the moniker. Sure, the winds off Lake Michigan have something to do with it. So does the previously held belief that early Chicagoans, especially politicians, tended to be full of themselves. 

That’s good information to know when you head to Chicago on a business trip in case you need an ice-breaker. Here’s more.


  • Incorporated in 1837
  • Third-largest U.S. city, with just over 2.7 million people
  • World’s first skyscraper, Home Insurance Building, completed here in 1885
  • Hosted the 1893 World’s Fair, which helped put Chicago on the international stage

Chicago O’Hare International Airport (ORD)

Where to Go:

One of the busiest airports in the world, O’Hare is infamous for a mix of high traffic and winter weather. Delays are common. In that case, there’ll be time to explore all the airport has to offer. And if you’re coming into Chicago on time, count your blessings. 

  • Get a workout in at the O’Hare Hilton. You’ll have to move outside of security for this, but if you get to the airport early, or find that your flight is delayed significantly, you can purchase access to the fitness center, pool, sauna, and whirlpool for $20.
  • For its size, O’Hare was always thought to lack quality food options. That’s no longer the case. Tortas Frontera by Rick Bayless, for example, offers delicious Mexican plates with margaritas aplenty. 
  • De-stress before or after your flight by hitting the Yoga Room in Terminal 3.
How to Get to Downtown Chicago

CTA Blue Line
Cost: $5
Time: 40-45 minutes

Cost: $30-$40
Time: 40+ minutes

Cost: $24 per person
Time: 40+ minutes

Chicago Midway International Airport (MDW)

Where to Go:

Unless you’re flying a smaller airline, you’ll most likely be heading to O’Hare. That can be unfortunate: Midway is less busy and closer to downtown Chicago, although travel advice site The Points Guy ranked it as the worst airport in America. It’s not that bad if you find these spots: 

  • Eat at Arami. One of the most popular sushi places in Chicago has set up shop at the airport. Find it in Concourse A. 
  • The Billy Goat Tavern shows up often on “must-visit” lists for its tasty burgers and Cubs mythology. If you can’t get to the original location during your business trip, head to Concourse A.
  • Learn about the Battle of Midway. The airport gets its name from the decisive World War II naval battle, and there’s a display honoring the Allies’ victory in Concourse A.
How to Get to Downtown Chicago

CTA Orange Line
Cost: $2.50
Time: 20-25 minutes

Cost: $35-$40
Time: 25+ minutes

Cost: $18 per person
Time: 25+ minutes

Chicago Dos & Don’ts

Chicago Dos & Don’ts

You’ve likely heard of Midwestern charm. Chicagoans certainly have it. Still, there are some things to keep in mind so you don’t stick out for the wrong reasons.


  • Eat loaded hot dogs and deep-dish pizza. Chicago is known for both. Just maybe mix in a salad or a workout. 
  • Explore Chicago beyond the Loop. Like any big city, Chicago’s culture can only be experienced by venturing outside the main tourist spots. 
  • Pack for all weather, especially if you’re traveling to Chicago in the fall, winter, or spring. Lake effect is a very real thing, and temperatures can nosedive in a matter of hours. 



  • Just eat loaded hot dogs and deep-dish pizza. Chicago is a diverse, multicultural city with cuisine to match. 
  • Call it Chi-Town. The locals don’t really use the term, so you’ll be spotted as a visitor right away. 
  • Rely on cars. Public transportation in Chicago is very good. Traffic in Chicago is not. If you turn to Uber or Lyft, expect to pay high rates. 
Your Chicago Playlist

Your Chicago Playlist

The eponymous “Chicago” delivered softrock favorites, although that’s just one genre Chicago-based or raised musicians helped define.

Getting Around: 4 Tips To Master Chicago Transportation

Getting Around: 4 Tips To Master Chicago Transportation

The Chicago Transit Authority covers much of the city, making it a standout in the Midwest in terms of its public transportation. Here’s some helpful advice on how to best get around town:

1. Avoid ride-sharing or driving.

Getting an Uber has become almost second nature for many business travelers, but it’s not ideal in Chicago. The combination of bad traffic and comprehensive public transportation makes ride-sharing a less cost-effective option. Ditto for driving, especially with parking scarce downtown.


2. Download the Ventra app. (iOS | Android)

Although it’s far from perfect, the Ventra app is still a useful companion for business travelers. It features guides, maps, real train times, and enables you to purchase fares on your phone.


3. Familiarize yourself with the train map.

Eight color-coded lines make up the “L” system of trains in Chicago. Get to know what colors go where with this handy train-tracker map on the Chicago Transit Authority website.


4. Consider walking.

WalkScore.com ranks Chicago as the sixth-most walkable city in the United States and easily the most walkable one in the Midwest. In other words, bring your walking shoes. You’ll save money and get some exercise to boot.

Where To Host A Business Meeting In Chicago

Where To Host A Business Meeting In Chicago

In need of an office space to meet with clients? Want to add some flair to your meeting or a change of scenery to keep things fun? Here’s where to look:

Lockdown a spot with Peerspace.

Peerspace rents office spaces for as low as $20 an hour. You can choose based on location, look, or amenities—and in a city that boasts the architecture and views of Chicago, there are plenty of options that will wow your clients and colleagues. 


Chicago Sports Museum

As one of the most passionate sports cities in the United States, it’s no surprise that Chicago  dedicated a comprehensive museum to local athletics. The Chicago Sports Museum features interactive exhibits and unique displays that will impress even non-sports fans. For business travelers’ purposes, you can book space at the museum for large or small gatherings with catering options. 


Office Evolution O’Hare Chicago

Proximity to Chicago O’Hare International Airport makes Office Evolution a perfect venue for business travelers on a tight timeline. Book a conference room for as little as $20 an hour, which includes complimentary coffee and tea. Office Evolution also includes a fitness center, so you can get a workout in before or after your big meeting. 


Offsite Chicago

Located on the West Loop in the heart of the city, Offsite Chicago is an all-inclusive event space geared for technically savvy businessmen and businesswomen. Rent space for as few as 10 and as many as 100 guests. New to shared offices? Don’t worry—the friendly Offsite staff is there to guide you through your whole experience. 


Guaranteed Rate Field

Will you allow one baseball pun? Here goes: Hit your meeting out of the park by hosting it at the ballpark, specifically the home of the Chicago White Sox. Guaranteed Rate Field offers year-round service for corporate events, with fully-catered menus by award-winning chefs.

6 Only-In-Chicago Places To Set Up Your Personal Office

6 Only-In-Chicago Places To Set Up Your Personal Office

Sometimes you need to escape your hotel room or the convention center to really get to work. Chicago has plenty of unique settings for your on-the-go office.

ACME Hotel Company

The old-school name belies the modernity of this establishment. Tech-friendly with loads of amenities, the ACME Hotel Company welcomes visitors and businessmen alike to its downtown Chicago location. The creative space, open to the public, is appropriately called “Between,” and features free coffee, Wi-Fi, and a do-it-yourself snack bar. But get here early—it fills up quick


Bourgeois Pig Cafe

Go back in time at this Lincoln Park cafe. The old row home space opens to wooden floors, bookshelves, and newspapers with a congregation of students and young professionals with laptops covering the tables. The food and coffee are worth sampling, and the patio, although it gets crowded, makes for a nice outdoor setting. 


Harold Washington Library

The main branch of the Chicago Public Library system, the Harold Washington Library celebrates the city’s architecture with a stunning copper-green roof, large windows, and a red-brick exterior. The library opened in 1991 and serves as an intellectual oasis downtown. It’s also open until 9 p.m., so you can slide over for some solitude to complete your day’s work. 


Millennium Park 

Why not knock off a tourist stop while catching up on emails? Like any city park, Millenium Park (pictured above) offers visitors Instagram-ready sites with plenty of green space. Carve out your own area, set up for prime people-watching, and be productive while you’re at it. 


The Newberry Library

The Newberry Library is a worthy stop for any business traveler to Chicago. While there are reading rooms (open Tuesday to Saturday), the library’s real treasure is its rare book collection and exhibits. Work and learn in an internationally-renowned institution that dates back to 1887.


Sleeping Village Coffee Shop

Is it a bar? A cafe? A music venue? Yes. Although it’s outside of the downtown area, which makes travel a bit of a burden for visitors, the Sleeping Village Coffee Shop is a popular destination among young professionals. The cafe effuses energy from the late morning to the early morning. Check the event calendar while you’re there, as the venue hosts acts almost every night. You just may find a new favorite musician. 

Where To Stuff Your Face In Chicago

Where To Stuff Your Face In Chicago

Travel to Chicago hungry. Also, maybe allow yourself two or three cheat days so you can gorge at these eateries with a clear conscience.

Chicago Diner

Think of Chicago food—what comes to mind? Pizza? Hot dogs? Sausage? How about vegan food? That’s the promise of the somewhat ironically named Chicago Diner, proudly “Meat free since ‘83.” But don’t think this is all veggies per se: Try poutine (gravy, vegan cheese, and green onions over fries), jalapeño poppers stuffed with vegan cheese, or the wonderfully Chicago pierogi quesadilla. 



Entente is something of a paradox. It’s a high-end modern American restaurant, and yet it’s reasonably priced. It’s a swanky setting but features an eclectic soundtrack that includes 21st-century favorites. That alone makes it stand out in a crowded field of quality Chicago food establishments. 


Fat Johnnie’s Famous Red Hots

Fat Johnnie’s Famous Red Hots looks the part more than anything. It’s a simple hot dog shack on Chicago’s West Side that delivers the goods at a reasonable price. While there are quality dogs everywhere in Chicago, the journey and dive appearance of the joint lends an authenticity that more modern locales can’t match. 


Gibsons Bar & Steakhouse

In need of a good, old-fashioned steak? Gibsons is your place. The restaurant promises high-end dining with a welcoming atmosphere that includes just about everybody, from locals celebrating birthdays to business travelers taking advantage of one of Chicago’s prime eateries. 


Jim’s Original

Hard to hear “Polish sausage” and “Chicago” without thinking of comedian Chris Farley’s performance with the Superfans on SNL. We hope you enjoy this Chicago food staple at Jim’s Original while avoiding the heart attacks that plagued Farley as he cheered on da Bears.


The Original Brownie

Did you know that the original brownie was introduced at the Chicago World’s Fair in 1893? That legacy continues at the Palmer House Hilton (the brownie was created in the Palmer House Kitchen), the Lockwood Restaurant, and Potter’s Chicago Burger Bar, all of which serve the original chocolatey goodness.  


Pequod’s Pizza

Any deep-dish pizza place that’s famous for caramelized crust seems like it should be on any visitor’s to-try list. Similarly to Fat Johnnie’s, authenticity reigns supreme here. A lot of chains have popped up boasting Chicago originals. Pequod’s, on the other hand, is a Chicago original.

Where To Sneak A Workout In Chicago

Where To Sneak A Workout In Chicago

Club Pilates 

Although all forms of yoga and other alternative workouts have boomed in popularity, pilates remain a favorite among health-conscious travelers. Gain a physical and mental boost by visiting one of the three Club Pilates locations, all of which offer an introduction class for free


Northerly Island Outdoor Space

Like most everywhere else mentioned in this article, the Northerly Island Outdoor Space tells a unique Chicago story: Architect Daniel H. Burman of World’s Fair fame imagined a series of manmade islands on Lake Michigan that would connect Grant and Jackson Parks. Northerly is the northernmost point of that island chain and features running/biking paths and spectacular views of Lake Michigan and the Chicago skyline.  


The 606

In need of green space for the ever-growing Logan Square neighborhood, Chicago got creative. Thus, the 606 was born out of an old train line. Now, you can run, walk, or jog the trail through several neighborhoods while taking in the usual sites of the city. 


Run the Chicago Lakefront Trail

The name is self-explanatory: This 18.5-mile trail hugs the shoreline of Lake Michigan on the East Side of Chicago. Runners and bikers are welcome, especially those new to exercising along the Great Lakes. Cooler by the lake is a very real thing, and the effect can make for ideal conditions—albeit a bit breezy—during the summer months. 


Title Boxing Club

Well, this may not be “sneaking” a workout in, considering how rigorous boxing training can be, but it is an option for adventurous business travelers and those just looking for a physical challenge. Sign up ahead of time at one of Title Boxing Club’s three locations for a free session.

Best Bars In Chicago To Unwind From Work

Best Bars In Chicago To Unwind From Work

Once synonymous with the Prohibition era (for better or worse), Chicago remains a great city to wet your whistle, especially on a business trip. Here’s a list of spots that run the gamut from low key to top of the world:

The Signature Lounge at the 96thJohn Hancock Center 

A view from the Willis Tower (formerly known as the Sears Tower) will put you back $24, so why not get a similar vantage point and some quality cocktails with it? Head to the Signature Lounge at the 96th in the John Hancock Center to take in (seemingly) all of Chicago while sipping an Old Fashioned.  


Cindy’s Rooftop Bar

Cindy’s Rooftop Bar crowns the Chicago Athletic Association Hotel with an inviting, stunning lounge and restaurant. Head to the open-air terrace to drink in—figuratively speaking—panoramic views of Millennium Park, the Art Institute of Chicago, and Lake Michigan. 



This is a no-nonsense bar in Andersonville. You won’t find the bells and whistles of modern establishments. There’s no promise of great views. There aren’t even TVs. No, the Hopleaf is about quality beer in copious amounts and tasty bites. 


Kingston Mines 

Few late-night spots can match Kingston Mines for atmosphere, food, and entertainment. With a menu heavy on barbeque, and live music on two stages, the Lincoln Park establishment provides a welcome sensory overload. 



You know it’s a true dive bar because it’s cash-only. You’ll be thankful for that ATM stop, though, when you walk in to find delicious pub food, live music, and a photo booth to fit the retro decor. 


VU Rooftop Bar

Venture to Chicago’s South Loop for this rooftop bar 22 stories up. With two patios, three bars, and views aplenty, the VU is a perfect getaway for business travelers finishing up their meetings for the day. 


The Whistler

What is the Whistler? “A [self-described] bar, (art) gallery, record label, and (music) venue.” In other words, it’s a place where business travelers can support Chicago’s independent art and music scene while enjoying cocktails from a menu that’s always changing.

What To Do On Your Chicago Bleisure Day

What To Do On Your Chicago Bleisure Day

Chicago airports are infamous for their delays, so why not plan ahead and give yourself an extra day to get home? Or, you know, explore Chicago? Here’s what your itinerary could look like if you take a bleisure day:

Breakfast at the French Market

Transport to Paris for breakfast. Well, not really, but this market is modeled off those found in Europe, and it features some of the best baked goods and coffee Chicago has to offer. 


Visit Museums 

With stunning architecture and a variety of exhibits, Chicago museums deserve your attention. 

American Gothic – Grant Wood, image courtesy of Wikimedia CommonsHere are three to check out: 

  • Art Institute of Chicago: Located in Grant Park, the world-famous Art Institute of Chicago houses more than 300,000 works. 
  • Museum of Science and Industry: Travel back to the 1893 World’s Fair by entering the former “Palace of Fine Arts,” now home to hands-on exhibits meant to spark minds young and old. 
  • Chicago History Museum: Emerging in the mid-19th century, Chicago grew quickly, earned the world’s attention, and continues to thrivehow did it get here? 


Jackson Park 

In many ways (if this article is any indication), modern Chicago grew out of the 1893 World’s Fair. Jackson Park was the main site of the event, although now it’s filled with green spaces and gardens that make it perfect for a lazy afternoon. 



Make no mistake. Chicago is a sports town, maybe the best one in the country. After all, the city has franchises in the four major sports leagues (including two in Major League Baseball), Major League Soccer, the National Women’s Soccer League, and the Women’s National Basketball Association. So even if the preferred Wrigleyville-Chicago Cubs game double isn’t in the cards, there’s a good chance someone will be playing, no matter the time of year. 

MLB: Chicago Cubs/Chicago White Sox MLB: Chicago Cubs/Chicago White Sox NHL: Chicago Blackhawks NHL: Chicago Blackhawks
MLS: Chicago Fire MLS: Chicago Fire NWSL: Chicago Red Stars NWSL: Chicago Red Stars
NBA: Chicago Bulls NBA: Chicago Bulls WNBA: Chicago Sky WNBA: Chicago Sky


Second City Comedy

The comedy venue famous for improv has launched the careers of some of the best-known comedians of all-time: Dan Akroyd, Bill Murray, Jim and John Belushi, Chris Farley, Jane Lynch, Rachel Dratch, among many others have come through its doors. You can find showtimes and tickets here.

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