Chicago, Illinois Hotels and City Guide

Chicago - Travel Tips

When to Go

One of the great things about Chicago that really shows that it is a world class city is that you can have a great time here any time during the year. Due to scheduling, summer is obviously the most popular time to visit, but the city fills up again during the holidays, and thanks to the strong Midwestern sensibility here, there may not be a better or friendlier spot on the map to celebrate Christmas, Hanukah or the Solstice. Many people don’t get to choose which time of year to visit The Windy City, mainly because they are here for a convention, but if you are choosing a family vacation, late spring and early summer before things get too hot and humid are probably the most popular times. There are many major events throughout the calendar year here, so even if you are coming during a “slow time” there will be plenty going on, even if it is aimed more at locals than tourists. Not only can your hotel give you an excellent heads up of what is going on in the city, the tourist bureau website often keeps track of all of the comings and goings here. If nothing else, there is always pro sports events year round here, even in the slower summer months thanks to both the White Sox and Cubs. You may also want to check the convention calendar at the McCormick Place website to see if your visit coincides with any major shows. You’ll notice that getting rooms on websites like Priceline and Hotwire will become much more difficult during those busy times.

When to Visit – Seasons

When most people consult the calendar, they only look at the drawbacks to each month, but the reality is, in a world class city like Chicago, there are more benefits than drawbacks for every season under the sun. Starting out in summertime, the city is often packed with tourists, kids and families looking for fun. The beaches on Lake Michigan will be busy and the temps can range from warm and comfortable to outright steamy during August and late July. However, summer is also the time when most festivals are in town and there are major things to do every weekend. Summer is also prime time for baseball, which is always a big draw in Chicago, both on the north side and south side of the city. Fall can be chilly in October and November but still hot in September. Watching the leaves turn here is a wonderful way to spend a vacation, and since school is in session, it is often much less busy in and around the usual tourist attractions. Be sure to bring a coat in addition to your short sleeve shirts. Sports in the fall are all about college football, with Northwestern University football taking the center stage. The winter is all about staying warm and enjoy the wonderful holiday season. Temps can be downright frigid if you aren’t used to the climate. Distractions include the many holiday festivals, as well as the beginning of both the NHL hockey season and the NBA basketball season. Finally, the spring is a wonderful time to be here. The city can become a little crowded during spring break time and again in mid to late May when some kids are already out of school. March can be a bit rainy but a sunny spring day in Chicago is one of the greatest things in the world. You can often find excellent hotel deals during this time of year, as well.

Local Holidays:

New Year's Day (January 1)
Martin Luther King's Birthday (third Monday in January)
Washington's Birthday (third Monday in February)
Memorial Day (last Monday in May)
Independence Day (July 4)
Labor Day (first Monday in September)
Discoverers' Day (second Monday in October)
Veterans' Day (November 11)
Thanksgiving (last Thursday in November)
Christmas (December 25)

Local Customs & Language

Customs

One of the more formal cities in the country in the business world, Chicago as a whole is a fairly casual place. While a fairly busy city, it’s not an unfriendly one, so you’ll find lots of attractions, hotels, and restaurants that are family and traveler friendly. You may even spot a few helpful individuals who can get you back on track.

Language

It is absolutely required that you speak at least passable English if you wish to visit Chicago. People here are kind and will be patient with you, but don’t expect the average person to be bilingual. While this is a fairly diverse city, it will be difficult to find others who speak your language. Moreover, all official signage and materials are often printed only in English.

Tipping Advice 

It is customary to tip here. The United States has laws on the books that allow employers to pay tipped position employees far below minimum wage, assuming that the person will more than make up that difference with tips. The problem is that most foreign tourists assume that the room cleaning staff and the waiter at the restaurant they ate at last night is paid a living wage. Chances are, they aren’t. This fact should never be used to pressure you into tipping those you don’t think deserved it, but if someone does do a good job, consider tipping around 20% at a restaurant, at least $1 per day for the maid service at your hotel, a few dollars if the concierge manages to help you out at your hotel (tipping isn’t expected for simply answering a question but if tickets to a sold out show or event are found for you, tipping is customary). If a bartender gets you a drink, a $1 per drink is customary, although you may want to tip every other drink if you order something as simple as a beer and finally, don’t forget your caddy, bellhop or anyone else that you feel went above and beyond the call of duty.  

Health and Security

In the city of Chicago, you can dial 311 from any phone for non-emergencies and 911 for immediate police, fire and ambulance services. Most foreign cell phones will call 911, even if you don’t have service in the United States or the greater Chicago area. There are hospitals and medical facilities located around the country to help with any health emergencies you experience while traveling.

If you are attending a sporting event or a concert at the United Center or if you are attending a Chicago White Sox baseball game, be careful leaving the area after dark, especially if you aren’t sure where you are going; it is recommended that you take a cab back to a more tourist friendly area or back to your hotel. Everything else that you need to know is common sense. Hang on to your purse when in downtown at night and stay away from poorly lit areas if at all possible.

Disabled Travelers

The Americans with Disabilities Act mandates that most hotels, restaurants, and businesses offer accommodations to those with disabilities. Simply ask an attendant or employee about the services you require.

Tax Refunds

The United States does not use a value added tax system like most of Europe does. You cannot write away and get tax refunded to you. Some states, such as Louisiana, do offer a refund to foreign visitors, but even with that system, you have to spend a certain amount to have it refunded to you. In Illinois, no such system exists. It is important to note that when you are out shopping, tax is seldom (if ever) included in the price of the things you buy. Local sales tax and federal tax are always added at the register. Some items, such as food, won’t have any tax at all, while other items, such as gas or items over a certain price, may have more tax than others. At eateries around the area, you can expect to pay a 10% tax on your meals. Most other items include a 10.75% tax. Hotel rooms are taxed at 15.39%. Groceries and medications include a 2% tax.

Hotels in Chicago, Illinois