Planning a Business Trip to Chicago - How to Make the Most of It?

Planning a Business Trip to Chicago - How to Make the Most of It

If you've been chosen to travel to Chicago for a business trip, congratulations! You have some important things to do, and you're probably looking forward to getting there as soon as possible. At the same time, you'll want to make sure that you maximize your time in this amazing city. Use these tips for planning your business trip and get the most out of your trip.

Stay Near O’Hare Airport

If you're flying in and out of O'Hare Airport, stay somewhere within a reasonable distance. Being near the airport will make it easier for you to get around town when you're not working and make it more convenient for those early morning flights out of town. Numerous Airport Car Services for Chicago O’hare are available that you can check out.

If you plan on spending most of your time traveling during the day and getting back to your hotel before dark, look into getting an extended stay option on some websites like Airbnb or VRBO. So you can save money by cooking your meals in apartment-like conditions.

You'll also be able to rest easy knowing there is no one knocking at your door asking if they can get any "extra" work done. The housekeeping just got off work at 11 pm after cleaning all night long.

Arrive a Day Before the Trip

  • Arrive a day before the trip: If you’re traveling to Chicago for business, arrive a day early. You will be able to get acclimated to the city and explore it on your own before arriving at work. You’ll also be able to get good sleep and start your trip well-rested.
  • Explore the city on foot: Chicago is a great walkable city with many interesting places to see. Walk around downtown, go up down Michigan Avenue (a shopping street), or explore one of its many neighborhoods like Lincoln Park or Oak Park. You can feel free to stop along the way for coffee or lunch!

Use Your Hotel Concierge Service

One of the best ways to get a feel for the local culture is to talk with the concierge at your hotel. This person can provide you with insider information on everything, from restaurant recommendations to local transportation options, entertainment options, attractions, and shopping spots.

They can also give you an idea of what events are going on in town that may be worth attending while you're there. Finally, they'll likely have some great recommendations for local history and culture as well.

Dress Well and Professionally

When you’re on business, it’s a good idea to dress well and professionally. That doesn’t mean you have to wear a suit every time, but if you have the opportunity, go for it! Don't wear too much makeup or try too hard, though. You can remember that this is serious business, and your appearance should reflect that.

When dressing for your trip, pay attention to the weather as well as the occasion. If there's going to be snow on the ground during your visit and temperatures are expected to dip below freezing at night (or vice versa), pack accordingly! You don't want anyone saying: "Wow! She must be from Florida because she didn't bring enough layers!"

Forget the Crowded Tourist Attractions

The best way to make the most of your trip is by getting off the beaten path. Chicago is one of America's most popular tourist destinations and has been for quite some time, so it can be hard to find places that aren't overrun with crowds. If you want to avoid the tourist traps, here are some ways you can do so:

  • Visit museums that have history and character, like The Art Institute of Chicago or the Field Museum of Natural History.
  • Go on a walking tour of neighborhoods like Pilsen or Hyde Park that locals frequent.
  • See what different activities there are in each area. There might be something unique about each neighborhood! For example, Chinatown offers night markets where food vendors serve delicious dishes from all over Asia.
  • Choose family-friendly attractions where kids won't get bored easily (like Navy Pier). This will help keep everyone entertained throughout the day!

Explore Chicago’s Food Scene

It's no surprise that Chicago is famous for its deep-dish pizza, but it's not the only place in town to try. If you're looking for a slice of authentic Chicago pizza, there are many places you can go to get your fix. For example:

  • Lou Malnati's (1030 N State St, Chicago) - The classic "Chicago hot dog" is an all-beef frankfurter on a poppy seed bun topped with mustard, relish and chopped onions, tomato slices, and pickle relish. Served steamed and topped with celery salt or dipped in barbecue sauce served on a white bun. This popular iconic food item is so beloved that even President Obama has said he misses them when he goes home!
  • Gino’s East (619 S Dearborn St., Chicago) - Gino's East offers up another version of this classic dish in which the beef sausage patty gets smothered by gooey cheese sauce and then pressed into a thick deep-dish crust before being baked until golden brown! It's impossible not to love these delicious combinations of sweet caramelized onions melted over juicy meats baked together under creamy layers that melt away into one mouthwatering bite after another.

Enjoy Some Weekend Time in Chicago

Try to take some time off during the weekend, even if it’s just a long lunch. You can explore the city on foot or by bike if you’re feeling adventurous. There are plenty of restaurants that serve authentic foods from all around the world; try them out!

If you want to experience the best of the Chicago food scene, head over to Chinatown or Greektown, where there is authentic Chinese and Greek cuisine respectively. Chinatown is popular among locals because it has been there since the late 1800s, and many people have recommended this place for its good food at affordable prices.

Be sure to visit museums as well; there are a lot of places in Chicago that offer free admission on weekends, so don't forget about them! The Art Institute is one such place that has amazing exhibitions year-round along with interactive exhibits like "The BEAUTY."

It allows visitors an opportunity to be surrounded by contemporary artworks. It highlights diversity through various mediums, including fashion design, photography, and visual arts from around the world.

Focus On Work, but Enjoy the City

It is important to balance your work with some play. While you may not have time to see everything, focus on the most important things for your trip. It might be worth it to stay an extra night or two so that you can go out and explore at least a couple of places in Chicago during daylight hours.

In addition, make sure that the things you do while there are memorable experiences. That may mean working a little harder or staying up later than usual, but if it means having a better time when traveling, then it is worth putting in the effort!


In the end, Chicago is a great place to visit whether you’re there for business or pleasure. The city has so much to offer, both professionally and personally, and there are lots of resources available for those who are considering relocating.

If you’ve never been before but have been thinking about taking a trip there, then we hope this article has given you some ideas on where to start your research. Have fun planning your next adventure!

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