I guess it's safe to say that when traveling to Chicago you should always carry some loose dollar bills because you'll never know when you'll need them. Let's talk tipping because every city has its own rules and Chicago is no different, from the moment you arrive at the airport to when you check out of the hotel. The number one inquiry: How much do you tip cab or ride share drivers?
Occasionally, the rules will differ for business travelers, according to Kiplingers.com Washington, D.C. editor Stacy Rapacon, who advises that "service providers at more high-end hotels or resorts may be accustomed to receiving more generous tips that are in the upper range of what is considered standard."
Airport/Hotel Baggage Handlers
If you're lugging around more than two pieces of luggage, let a baggage handler help you out. Depending on the sizes of the suitcases, tip $1 to $3 per bag.
A number of hotels offer free shuttle service to and from Midway and O'Hare airports. You're saving a ton of money, so why not be generous with the driver who has to deal with that monotonous job all day long? Shell out anywhere from $5 to $8. Same goes if you're traveling in one of the paid shuttles; it is considered courteous when you tip at least $5.
The concierge's job is to be on the pulse of what's hot in town. The job also requires him or her to fulfill special requests, including reserving dinner reservations, theater tickets, and spa appointments. Now, if you happen to go over to the concierge desk and inquire about the best sushi restaurants in town, they're good about ticking a few off from the top of their heads. Tip a few bucks. If you have the person look up directions or make a few phone calls, tip no less than $5. If you have an elaborate plan to secure hard-to-get dinner reservations at one of the top restaurants in Chicago or theater and sporting tickets (e.g. Bulls or Broadway on Chicago), then the concierge is expecting a minimum of $20.
Gourmet Tea and Coffee Shops
You'll find that more of the upscale and "hipster" shops, like Cafe Integral at Freehand Chicago, have tip jars next to the cash register. Here's when you tip: If you place a complicated coffee order, tip the barista $1. Those ordering a simple cup of joe or tea should not feel obligated to tip.
Cash is always king, but hotel bartenders (and restaurant servers) are the most understandable when you tip them by credit card (or room charge). Beer and wine drinkers should tip $1 for each glass, while cocktail enthusiasts should pony up a bit more for the extra effort. That's anywhere from $2 to $3 per drink.
Hotel Doormen/Bell Staff
Should you tip them for opening the door? Our official hotel tipping guide says no. A smile and "thank you" are good enough, however, if you require them to hail a cab, then shell out at least $1. Several hotel properties offer specialized services for pets, and common sense should prevail when it comes to gratuity.
Here's a great guide to tipping housekeeping.
If you plan on clubbing while visiting Chicago remember one thing: Chicago is not Las Vegas. The average doorman is supposedly not allowed to accept tips—he risks losing his job if he accepts cash for allowing patrons to skip the line, etc. If you want good service at a busy bar, tip at least $1 every time you order. Those ordering bottle service should tip as though they're being served at a restaurant: a minimum of 18 percent gratuity. And if there is a bathroom attendant, there's no need to tip unless you use the amenities (hairspray, lotion, grooming supplies, mints).
If you do, tip at least $1.
Is this a business trip? Always remember that tipping is not optional, it is mandatory. For casual gatherings, at least 18 percent is expected. In Chicago restaurants, if you have a party of six or more, the gratuity is usually included in the bill.
Hotel Room Service
If you get delivery at your hotel, it's pretty much the same. Tip at least $2 to $3.
Tips are pretty much the same across the board. Hairstylists, manicurists, and massage therapists get at least 15 percent of the total bill.
Taxi Cabs, Lyft, Uber
Cab drivers in Chicago can be a point of contention, especially with visitors to the city. Always remember that you can charge your entire ride to a credit card. You can also tip on the card (some drivers will try to hustle you and say no), but if you have a few spare dollars, tip with cash. Thinking of taking Lyft or Uber instead? Any gratuity is considered in the cost of the ride that you pay with your credit card; it's up to your discretion to tip extra if the driver helps you with luggage.
A $1 tip is sufficient.