Your Trip to Chicago: The Complete Guide


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No matter your reason for traveling to Chicago, it definitely is a fun city to visit. Family vacations, weekend getaways, honeymoons, and business travel, there's something to keep everyone busy.

Chicago is easy to get around and it offers great places to stay. It also has an ever-growing collection of impressive restaurants, fantastic cultural opportunities, and many fun activities for the family. Let's explore Chicago and give you plenty of ideas to make the most of your visit. Be sure to review our ultimate guide to Chicago.

Getting to Chicago 

Chicago, the hub and heart of the Midwest, provides several options for getting here whether it be by plane, train or automobile. No matter which mode of transportation you take, it's relatively easy to get into the city.

Chicago has two airports with O'Hare International Airport being the busiest. It's a popular stop for catching connecting flights to elsewhere, so it often sees more passengers than others. The other airport is Midway International Airport. It is considerably smaller and can be easier to get in and out of.

No matter which direction you're coming from, driving into Chicago is relatively simple. It's a major hub for the Midwest, so all the major interstates in the area run through it. Rush hour is very congested. If you can, try to plan around the morning and evening commutes.

Another option is to take the train into Chicago. Amtrak uses the city as a main hub for the area and their trains go directly to Union Station in downtown. If you're coming from a Chicago suburb, the Metra commuter train is an affordable and speedy option. 

You might also consider parking in one of the suburbs and catch the Chicago Transit Authority's (CTA) trains into the heart of the city. You'll find hotel deals in the suburbs and train and bus fares are reasonable, so this is a great way to save money on your stay.

Where to Stay in Chicago

Attracting visitors from across the United States and around the world, there are numerous Chicago hotels and places to stay. You can be certain to find accommodations catering to any budget and taste, from cheap hotels and hostels to premium luxury hotels, and everywhere in between.

If you want to immerse yourself in the full Chicago experience, for instance, consider staying at a hotel with the best views of the city. Coming into town with the family? Quite a few hotels are very family-friendly. Can't stand to leave your furry friend at home? You'll also find a number of pet-friendly hotels.

Should a romantic getaway be on your radar, we can recommend places like the Waldorf Astoria and the Peninsula Hotel among the best romantic stays. For something a little more intimate and cozy, a bed & breakfast is a great idea.

There are also great hotels near O'Hare and you can always check out what hotel packages are available to get a deal on something special.

What to Do in Chicago

There is always something to do in Chicago. You will surely want to hit some of the top attractions the city has to offer, like the Hancock Observatory (with the famous tilting 360 Chicago Observation Deck) and Shedd Aquarium. Toss in a few free destinations such as Millennium Park and Lincoln Park Conservatory and Zoo and you'll stay busy for days.

Chicago has a great lineup of museums as well. A number of them offer free days throughout the year. Thursday evenings are the best time to get into many museums without paying admission. You'll also find some great theater in the city and there is a way to score tickets at half the normal price.

No matter what time of year you travel to Chicago, there's always an event going on. In the winter, for example, you can go ice skating in Millennium Park or hit Chicago Theater Week or the Chicago Auto Show. If you're in town for St. Patrick's Day, you won't be able to miss the tradition of dying the Chicago River green

Food tours are a hit in May, and as summer rolls around things really get going. Arts and music festivals pop up all over the city beginning in June. Grant Park is home to the weekly Chicago SummerDance and Millennium Park hosts a summer film series every Tuesday.

Of course, you can always hit a Chicago Cubs or Chicago White Sox game and join some of the most dedicated baseball fans in America. Football fans will want to catch the Chicago Bears at Soldier Field and hockey fans can watch the Chicago Blackhawks at the United Center.

Where to Eat in Chicago

Chicago is known as one of the top dining destinations in the country and you can grab diverse bites anywhere in the city. There's fine dining downtown, a variety of international cuisines in many neighborhoods, and even the airports have great restaurants. It's a city where you certainly won't go hungry—or thirsty.

On your gastronomic tour of the Windy City, there are three staples you can't miss: Chicago hot dogs, Chicago-style pizza, and a steakhouse. The Chicago hot dogs are no average franks, they're plump and topped with an amazing array of toppings. Don't be caught putting ketchup on your dog, though, as it goes against strict Chicago traditions—yellow mustard only. 

As much as many people adore the city's signature deep-dish pizza, we also understand it's not for everyone. However, there are ​other fantastic pizzas being dished up in the city and you can't leave without a taste of at least one.

When it comes to steakhouses, few places in America rival what Chicago has to offer. Some of Chicago's steakhouses thrive on tradition and others add modern culinary twists to the old-fashioned ways. There's a little bit for every taste and budget.

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