Welcome to downtown Chicago, where business prowess meets cultural vibrancy. Explore iconic architecture, world-class dining, shopping, and cultural treasures. Whether you’re visiting for business or leisure, or a bit of both, this guide has everything you need to know to navigate the Windy City’s core.

Downtown Chicago, known as “The Loop,” stretches from Lake Street on the north end to Van Buren Street on the south, Wabash Ave on the east and Wells Street on the west. The Loop, also known as Chicago’s central business district, is home to countless corporate offices, financial institutions, and college universities.

Business travelers visiting the hub of America’s third largest city are in for a treat as Chicago’s downtown is steeped in rich culture, worldly architecture and unrivaled cuisine.

City Metrics

High Walkability/Public Transportation Options

Median Age is 34

Cityscape: Skyscrapers/Theatres/Fine Dining

Chicago’s weather

Chicago experiences all four seasons — some to the extreme. The winters are very cold with snow and the summers are hot and humid. Most visitors say the best time to visit Chicago is in the spring (April to June) and autumn (September to November). The weather is fickle in a city like Chicago. Be sure to stay up to date with your phone’s weather app and hourly features.

City Customs & Business Culture

Generally speaking, Chicago is a casual city, full of hard workers, sports fans, big eaters, and good tippers. On the business front, Chicagoans are known for their professionalism and punctuality. Business attire is typically formal, especially in the financial and legal sectors. Punctuality is highly regarded in business meetings, so arrive on time or a few minutes early.

Currency/Average Cost of Goods:

USD is the currency in Chicago. Most locations accept all forms of payment (cash, debit, credit cards), although contactless payment is preferred.

Average food costs include (as of 2022):

  • Inexpensive meal $20
  • Mid-range, three-course
  • meal for 2ppl $82
  • Domestic beer $7
  • Cappuccino $5.23
  • Soda $2.63
  • Water $2.24

Chicago Social Etiquette & Manners

Chicago, like any major city, has its own set of social and cultural etiquette rules. Here are some general etiquette standards to keep in mind when traveling to Chicago.

  • Politeness and Respect — Chicagoans are generally friendly and polite, so a simple “please,” “thank you” and a “respectful attitude” will go a long way.

  • Tipping — Tipping is customary in Chicago, so tip servers in restaurants, bartenders, taxi drivers, and other service providers. The standard tip for restaurant service is around 15-20% of the bill.

  • Public Transportation — When using public transportation, especially during rush hours, yield your seat to the elderly, pregnant women, or individuals with disabilities. And, always let passengers off the train or bus first before boarding.

  • Sidewalk Etiquette — On a busy sidewalk, try to maintain a quick pace, don’t stand shoulder to shoulder in groups, and stay to the right to allow others to pass.

  • Personal Space — Chicagoans appreciate personal space, so maintain a comfortable distance when interacting with others, especially in crowded areas like public transportation.

  • Smoking Rules — Smoking is prohibited in many public places, including restaurants and bars. Pay attention to no-smoking signs and designated smoking areas.


While Downtown Chicago is safe, crime can occur anywhere. It’s essential to take precautions to minimize your risk. Just like any major city, there are neighborhoods with higher crime rates, so it’s advisable to research specific areas you plan to visit and take appropriate safety measures.

Areas like the Loop, River North, and the Magnificent Mile are generally safe for pedestrians.

Chicago Traveler Safety Tips

  • Always take precautions and stay in well-lit and populated areas
  • Use reputable, licensed transportation
  • Avoid displaying cash and valuables
  • Travel in groups
  • Avoid public intoxication
  • Trust your instincts
  • Use your phones SOS feature if someone threatens you
  • Dial 911 for emergencies


Chicago is served by two major airports, O’Hare International Airport (ORD) and Midway International Airport (MDW). The choice of airport often depends on your travel plans, destination, and proximity to your desired areas in Chicago or the suburbs.

O’Hare International Airport (ORD)

Located in the northwestern part of Chicago, approximately 17 miles (27 kilometers) from downtown Chicago.

  • O’Hare primarily serves the northern, northwestern, and western areas of Chicago, as well as the surrounding suburbs.
  • International Flights: O’Hare is one of the busiest international airports in the United States and offers numerous international flights to destinations around the world.
  • Transportation: O’Hare is well-connected to downtown Chicago and the suburbs via the ‘L’ train system (the Blue Line), taxis, shuttles, and rideshare services like Uber and Lyft.

Midway International Airport (MDW)

Midway International Airport is situated on the southwest side of Chicago, approximately 10 miles (16 kilometers) from downtown Chicago. While it does offer some international flights, Midway is known for its domestic routes within the U.S.

  • Midway primarily serves the southern and southwestern areas of Chicago, as well as nearby neighborhoods and suburbs.
  • Transportation: Midway is accessible from downtown Chicago and surrounding areas via the ‘L’ train system (the Orange Line), taxis, shuttles, and rideshare services.

Traveling to Downtown Chicago from O’Hare

  • An Uber ride from O’Hare Airport to downtown Chicago can range from $35 – $50 for a standard UberX ride. Fees will be higher during peak hours or busy times.
  • Taxis in Chicago typically charge a flat rate for rides between O’Hare Airport and downtown. The flat-rate fare was around $40 to $50, excluding tolls and gratuity.Make sure to check with your taxi driver for the most up-to-date rates before hiring the car.

Getting Around

To efficiently use public transit in Downtown Chicago and its surrounding areas, start by obtaining a Ventra Card, a reusable contactless fare card, which can be used on buses and trains. Using the Ventra app or website, business travelers can access schedules, maps, and real-time updates for a seamless and cost-effective way to explore downtown and its neighborhoods, including both O’Hare and Midway airports.

The ‘L’ train system (including the Red, Blue, Green, Orange, Pink, Brown, and Purple Lines) is the backbone of public transportation within the city. Additionally, the CTA (Chicago Transit Authority) buses complement the ‘L’ system, covering various routes.

Business Services

Downtown Chicago offers business travelers access to a plethora of business support services such as conference centers, language, printing, copying, and shipping services, coworking spaces, networking organizations, and general business support services such as legal, accounting, and consulting.

Home’s Essentials

Downtown Chicago offers various options for pharmacies, supermarkets, and stores where you can purchase hygiene products.


  • Walgreens & CVS Pharmacy:
    Downtown Chicago has numerous Walgreens and CVS Pharmacies, some open 24/7. Both stores offer prescription services, over-the-counter medications, personal care, and health and beauty products.

Supermarkets/Grocery Stores:

  • Jewel-Osco:
    Located in various parts of downtown Chicago, Jewel-Osco is a popular supermarket chain offering a wide selection of groceries, fresh produce, and household items.
  • Mariano’s: Mariano’s has a few locations in the downtown area and provides organic and gourmet products.

  • Whole Foods Market: Whole Foods Market has a downtown location offering organic and natural foods, fresh produce, and a variety of health-conscious options.

Hygiene and Personal Care Products:

  • Target — The Target store in downtown Chicago carries an extensive selection of personal care and hygiene items, as well as household products.

  • Walmart Express — The Walmart Express stores provide a variety of everyday essentials, including hygiene and personal care products.

  • Dollar Stores — You can find Dollar General and Family Dollar stores in some downtown areas, offering affordable options for hygiene products.

Business Attire Shopping

Downtown Chicago offers a variety of excellent shopping options for business attire, from upscale department stores to specialty boutiques, all conveniently located in the North Michigan Avenue shopping district.

    1. Nordstrom (Nordstrom Michigan Avenue) — Nordstrom is known for its high-quality business attire, including suits, dress shirts, dresses, and professional accessories.
    2. Neiman Marcus — Neiman Marcus offers a wide selection of designer business clothing, including suits, dresses, shoes, and accessories.
    3. Bloomingdale’s — This upscale department store offers a range of business attire for men and women, from formal suits to professional separates.
    4. Brooks Brothers — Brooks Brothers, known for its classic business attire, offers suits, dress shirts, ties, and other professional clothing for men and women.
    5. Ann Taylor — Ann Taylor offers a range of women’s business clothing, including suits, blouses, and dresses, known for their professional yet stylish designs.


Chicago is a food lover’s paradise that offers a wide variety of unique culinary experiences. Below are a few “musts” for anyone traveling to the Windy City.

Chicago’s Iconic Pizza

  • Chicago is famous for its deep-dish pizza, and you can’t visit without trying it. Lou Malnati’s, Giordano’s, and Gino’s East are popular spots for this indulgent pizza style.
  • For a quicker pizza fix, try a slice of Chicago-style thin-crust pizza at Art of Pizza or My Pi Pizza.

Chicago-Style Hot Dogs

  • A true Chicago experience involves tasting a Chicago-style hot dog. Portillo’s, Superdawg, and The Wiener’s Circle are known for their classic Chicago hot dogs topped with mustard, onions, relish, sport peppers, celery salt, and a pickle spear.


  • Chicago is renowned for its steakhouses. Head to Gibson’s Bar & Steakhouse, RPM Steak, or Joe’s Seafood, Prime Steak & Stone Crab for a top-notch steak dinner. Don’t forget to try the creamed spinach and the loaded baked potato.

Fine Dining with a View

  • Enjoy fine dining with breathtaking views of the city at places like The Signature Room at the 95th in the John Hancock Center or Cindy’s Rooftop in the Chicago Athletic Association Hotel. These restaurants offer a combination of gourmet cuisine and stunning panoramas.

Chicago’s Diverse Food Scene

  • Chicago’s downtown area is home to a wide array of international cuisine. Explore Randolph Street’s “Restaurant Row,” where you’ll find everything from upscale Mexican (Rick Bayless’ Frontera Grill) to contemporary American (Blackbird) and Japanese (Momotaro). Alternatively, head to Eataly for a taste of Italy right in the city.

Local Attractions

Downtown Chicago offers a blend of art, culture, architecture, and entertainment. Whether you’re interested in art, history, or simply taking in the city’s breathtaking skyline, the following iconic destinations are a can’t miss for anyone visiting Chicago — business or leisure.

Millennium Park

  • Millennium Park is a modern urban oasis known for its iconic “Cloud Gate” sculpture, often referred to as “The Bean.” The park also features stunning gardens, and interactive art installations, and hosts outdoor concerts and events in the Jay Pritzker Pavilion. It’s a hub of cultural activity and a great place to relax.

The Art Institute of Chicago

  • One of the oldest and largest art museums in the United States, the Art Institute of Chicago boasts an extensive collection of art spanning centuries and continents. Don’t miss famous works like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jette.”

Navy Pier

  • Navy Pier is a bustling entertainment destination along Lake Michigan. It offers a wide range of attractions, including restaurants, shops, the Chicago Children’s Museum, and the iconic Navy Pier Ferris Wheel. It’s also a popular spot for fireworks displays during the summer.

Chicago Riverwalk

  • The Chicago Riverwalk is a scenic promenade along the Chicago River. Stroll along this picturesque pathway to enjoy beautiful views of the city’s architecture, dine at waterfront restaurants, or take an architectural boat tour to learn about the city’s history and iconic buildings.

Willis Tower Skydeck

  • Formerly known as the Sears Tower, the Willis Tower features the Skydeck, offering breathtaking panoramic views of Chicago and the surrounding area. The glass-bottomed “Ledge” extends from the building’s side, providing an exhilarating perspective from the 103rd floor.

Tips from Suite Home staff

[Craig to support?]

Interesting City Fact

The Chicago River flows backward! Quite the engineering feat, in the early 20th century the Chicago Sanitary and Ship Canal was constructed to prevent pollution and sanitation issues in Lake Michigan. This massive engineering project reversed the flow of the river, diverting it away from Lake Michigan and towards the Mississippi River system. Today, you can see the Chicago River flowing backward, away from the lake. And! The city dyes the river green every year for the St. Patrick’s Day celebration.


“I spend a lot of my life—maybe even most of my life these days—in hotels. And it can be a grim and dispiriting feeling, waking up, at first unsure of where you are, and what language they’re speaking outside. The room looks much the same as other rooms. TV. Coffee maker on the desk. Complimentary fruit basket rotting on the table. The familiar suitcase.

All too often, particularly in America, I’ll walk to the window and draw back the curtains, looking to remind myself where I might be, and it doesn’t help at all. The featureless, anonymous skyline that greets me is much the same as it was in the previous city—and the city before that.

This is not a problem in Chicago.

You wake up in Chicago, pull back the curtain, and you KNOW where you are. You are in a big, brash, muscular, broad-shouldered motherf***in’ city. A metropolis, completely non-neurotic, ever-moving. A big-hearted but cold-blooded machine with millions of moving parts. A beast that will, if disrespected or not taken seriously, roll over you without remorse.

It is also one of America’s last great NO BULLSHIT zones. Pomposity, pretentiousness, putting on airs of any kind, douchery, and lack of a sense of humor will not get you far in Chicago.”

-Anthony Bourdain