Chicago Travel Tips for Business Travelers
Chicago, the third-largest city in the United States, is a bustling hub for commerce, finance, and innovation. With major industries like tech, manufacturing, healthcare, and logistics, the Windy City is a regular destination for business travelers from around the world. Whether you're visiting for a conference, meeting a client, or attending a networking event, traveling efficiently in Chicago requires planning and awareness.
To help make your business trip smooth and productive, here are essential Chicago travel tips designed specifically for business travelers.
1. Getting to and from the Airport
Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW).
O’Hare Airport:
Located about 17 miles northwest of downtown.
Offers more international flights and is one of the busiest airports in the world.
You can get to downtown via the Blue Line “L” train, taxis, ride shares, or airport shuttles.
Travel time: 40–60 minutes depending on traffic.
Midway Airport:
Located about 10 miles southwest of downtown.
Smaller but more convenient for domestic flights.
Connected to downtown via the Orange Line “L” train.
Travel time: 25–45 minutes.
Pro Tip:
Use a ride-share service (Uber or Lyft) for convenience, especially during late arrivals or early departures. However, during rush hour (7–9 a.m. and 4–6 p.m.), the CTA trains might be faster and more predictable.
2. Choose Business-Friendly Accommodations
Business travelers need more than just a place to sleep. Many Chicago hotels cater specifically to corporate guests by offering fast Wi-Fi, 24-hour business centers, and easy access to public transportation.
Top Business Hotels:
The Palmer House Hilton: Centrally located with conference facilities and historical charm.
Hyatt Regency Chicago: Close to the Loop and the Magnificent Mile.
Kimpton Gray Hotel: A stylish option with business perks and tech-friendly rooms.
Loews Chicago Hotel: Near Navy Pier with excellent meeting spaces and amenities.
Pro Tip:
Stay in The Loop, River North, or Streeterville if you want to be close to offices, conference centers, and major attractions.
3. Getting Around the City
Chicago's grid layout and public transit system make it fairly easy to get around, even during a tight business schedule.
Public Transit:
The Chicago Transit Authority (CTA) operates buses and trains.
“L” trains (short for "elevated") cover most of the city. The Blue and Red Lines run 24/7.
Fares are affordable and Ventra cards can be used for both trains and buses.
Ride Shares and Taxis:
Uber and Lyft are readily available.
Traditional taxis are also easy to find, especially in the downtown area.
Walking:
Many downtown destinations are within walking distance.
Make sure to pack comfortable shoes if your meetings are close by.
Pro Tip:
Download the Ventra app for mobile fare payments and real-time train/bus updates. Also consider using Google Maps or Citymapper for route planning.
4. Make Use of Co-Working Spaces
If you're in Chicago for multiple days and need a professional environment to work outside your hotel, consider using a co-working space.
Top Co-Working Spaces:
WeWork (multiple locations): Offers day passes and business amenities.
Industrious (River North and Fulton Market): Known for its high-end, quiet workspaces.
1871 (Merchandise Mart): Ideal for tech professionals and networking.
Pro Tip:
Some co-working spaces offer free trial days or discounted visitor passes. It’s worth checking their websites or calling ahead.
5. Where to Eat for Business Meetings
Chicago is known for its food, but when it comes to business lunches or dinners, you’ll want to choose places that balance atmosphere, noise level, and convenience.
Great Business Dining Spots:
The Gage (Millennium Park area): Upscale pub fare with a professional vibe.
RPM Italian (River North): Chic and ideal for client dinners.
Wildberry Pancakes & Café: Excellent for early morning breakfast meetings.
Beatrix (Streeterville): Great for casual lunches and quick bites.
Pro Tip:
Make reservations in advance, especially during lunch hours (12–1:30 p.m.) and after work (5–7 p.m.). Many Chicago restaurants fill up fast.
6. Prepare for the Weather
Chicago’s weather can be unpredictable. Winters are cold and windy, while summers are hot and humid. Spring and fall can vary widely.
Seasonal Tips:
Winter (Dec–Feb): Bring a heavy coat, gloves, and layers.
Spring (Mar–May): Dress in layers and carry an umbrella.
Summer (Jun–Aug): Stay hydrated and dress lightly.
Fall (Sep–Nov): Cool and crisp—perfect for walking, but bring a jacket.
Pro Tip:
Always check the forecast the day before your meetings, especially if you’ll be walking or using public transit.
7. Combine Business with Pleasure
If you have some downtime, take advantage of what Chicago has to offer. It’s easy to squeeze in a little sightseeing even with a tight schedule.
Quick Attractions Near Downtown:
Millennium Park: Take a selfie with “The Bean.”
Art Institute of Chicago: World-class museum just steps from many offices.
Chicago Riverwalk: Great for a post-meeting stroll.
Navy Pier: Enjoy views of Lake Michigan and quick bites.
Pro Tip:
Many museums and attractions open early or close late—check schedules to find quick windows to explore between meetings.
8. Stay Connected
Chicago is generally well-connected with cellular networks, and most public places offer Wi-Fi.
Connectivity Tips:
Most hotels and cafés provide free or paid Wi-Fi.
Co-working spaces and airport lounges are good spots for secure internet.
Mobile hotspots can be a good backup if you’re on the go.
9. Safety and Business Etiquette
Chicago is safe for business travelers, especially in downtown areas. Like any major city, it's important to stay aware of your surroundings.
Tips:
Avoid walking alone late at night in unfamiliar areas.
Use well-lit streets and busy transit stations.
Keep your laptop and valuables secure.
Business Etiquette:
Be punctual. Chicago professionals value time.
Dress smart—business casual is the norm unless otherwise specified.
Handshakes are still common but check if your contact prefers alternatives.
Final Thoughts
Chicago is a dynamic city with a strong business culture, excellent amenities, and a convenient layout for travelers. Whether it’s your first visit or your fifth, planning ahead will help you stay efficient and enjoy the city.
From airport transfers to dining and workspace options, being prepared means you can focus on what really matters—building relationships and getting business done. Need reliable executive transportation for your Chicago business trip? Visit www.eliterideschicago.com to book your service today.
