Chicago Guide: Planning Your Trip

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Chicago is a pulsating and diverse city full of art, culture, top-rated restaurants, and outdoor fun along the lakefront and Chicago River. Known for its architecture, travelers can get an up-close look at notorious buildings, like 875 North Michigan (previously known as the John Hancock Center) or the Willis Tower, through guided cruises along the river or via narrated walking tours. Professional sports, deep dish pizza, Navy Pier, and Chicago-style hot dogs are also big magnets for visitors.

Planning Your Trip

Best Time to Visit: The best time to visit Chicago is in the spring or fall when temperatures are the most pleasant and when crowd sizes are smaller. These seasons often offer the best deals at hotels and area attractions.

Language: While English is widely spoken, over 19% of the population in Chicago speaks another language , including Spanish, Polish, Chinese, and German.

Currency: The Standard US dollar is widely used as well as all major credit cards.

Getting Around:  The "L" train (short for “elevated train”) is the quickest, cheapest, and easiest way to get around the city. The Chicago Transit Authority (CTA) also operates the bus system. The Metra Rail regional train system makes stops around the city as well as to neighboring suburbs and cities.

Travel Tip: Most of Chicago’s museums have a "free day", which is worth looking into, especially if you have multiple people in tow and are looking for extra savings. Visit museums early, or just before closing, to avoid crowds.

Things to Do

The top things to do in Chicago include visits to Millennium Park and the Cloud Gate sculpture, Willis Tower, Navy Pier, Chicago Riverwalk, The Art Institute of Chicago and museum campus, and beaches along the lake front. Be sure to try a slice of deep dish pizza and order a Chicago-style hot dog from a food cart. Take a cruise with the Chicago Architecture Foundation on the Chicago River to learn about famous buildings. Festivals and events like Lollapalooza in Grant Park and Taste of Chicago are also popular.

·     Navy Pier is one of the most-visited sites in Chicago as it offers plenty of shopping and dining options as well as events and attractions. Ride Centennial Wheel, visit the Chicago Children’s Museum, see a show at Chicago Shakespeare Theatre, and enjoy a classic river cruise. Don’t miss the Crystal Gardens, located in a six-story glass atrium, a unique-to-Chicago experience.

·     Reaching 110-stories, Willis Tower is one of the most recognizable buildings in the city. Step outside the building into a glass box for an experience on the Skydeck’s Ledge.

·     Museum Campus is home to three of the city’s most popular museums: Adler Planetarium, Field Museum, and Shedd Aquarium.

Explore more attractions with our full-length articles on Chicago’s Most Impressive Architecture, The Nine Best Chicago Tours of 2020, and The Top 20 Things to Do in Chicago.

What to Eat and Drink

From Michelin-rated restaurants like Alinea in Lincoln Park, Acadia in the South Loop, and BOKA in Lincoln Park to hot dog stands serving up Chicago-style dogs (steamed poppyseed bun, relish, celery salt, chopped onions, large slices of tomatoes, sport peppers, pickle and mustard) to Italian beef sandwiches to deep dish pizza from Lou Malnati’s, Chicago has it all. Latinos and Latinas make up the second largest ethnic population in Chicago and Mexican food is widely popular. You can try the Michelin-starred Topolobampo or explore Pilsen, Little Village, Humboldt Park, and the Lower West Side neighborhoods for fantastic food options. With more than 7,300 restaurants to choose from, you won’t go hungry in this city.

Chicago has a bustling night life, full of bars and restaurants perfect for sipping a cocktail, beer, or wine. If you want to try a Chicago-specific drink, order The Chicago Fizz, made with rum, port wine, lemon juice, and an egg or try The Chicago Cocktail, made with brandy and champagne. Beer is also a staple in Chicago. Goose Island, Revolution Brewing, Lagunitas Brewing Company, Half Acre, and Dovetail Brewery are all celebrated breweries and they all offer tours.

Explore our articles on Nightlife in Chicago: Best Bars, Clubs, & MoreThe Best Brunch Spots in Chicago; and The 6 Best Chicago Brewery and Beer Tours of 2020.

Where to Stay

Staying downtown, close to city attractions, restaurants, and nightlife, is a good bet, especially if you’re new to the city and want to visit the top tourist sites. You may want to consider, however, staying in one of Chicago’s trendy neighborhoods, close to the “L” for public transportation, to have a more authentic "local" experience. Logan Square, West Loop, Pilsen, Bucktown and Wicker Park, and Andersonville are all fun neighborhoods with loads of restaurants, shopping, and streets perfect for wandering. You’ll find that there’s a variety of hotels, no matter where you stay in the city, with available nights at diverse price points.

 “Explore different neighborhoods with our articles on Visit These Top Chicago Neighborhoods on Your Next Visit, The 9 Best Chicago Budget Hotels of 2020, and The 9 Best Chicago Hotels with a View.

Getting There

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

 Chicago O’Hare International Airport and Chicago Midway International Airport both have nonstop flights from many U.S. cities and a few international destinations. You can rent a car, take public transportation, or book a cab or rideshare to get anywhere in the city. The Blue Line “L” train will take you from O’Hare International Airport to downtown. 

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.

·      Chicago Midway International Airport is situated on Chicago’s south side, eight miles from downtown. You may want to fly into this airport if you’re on Southwest Airlines for decent domestic flight deals. Fewer flight routes are offered at this airport compared to Chicago O’Hare.

·      Chicago O’Hare International Airport (ORD), located in northwest Chicago, is the largest airport in the Midwest, providing connections to more cities more often than any other airport in the world. ORD is a hub for United and American. Give yourself plenty of time to navigate this airport as it’s large, often crowded, and there’s usually traffic coming in and out of the airport.

Money Saving Tips

·      Explore many architectural sites and buildings, as well as outdoor landscapes like parks and beaches, for free. Marvel at Buckingham Fountain, the Chicago Cultural Center, Millennium Park, the South Shore Cultural Center, and more.

·      The Chicago Architecture Center offers discounts at restaurants and hotels around the city. You can also use their maps and take yourself on a walking tour to see some of the most prominent buildings and sites.

·      Venture through the Lincoln Park Zoo, free of charge, all year long. Don't miss the zoo's animal farm.

·      Most museums in the city have a “free day”: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Field Museum, Shedd Aquarium, Chicago History Museum, Chicago Children’s Museum at Navy Pier, Museum of Contemporary Art, Peggy Notebaert Nature Museum, DuSable Museum of African American History, and many more. Special exhibits are excluded.

·      Visit the National Museum of Mexican Art, which is always free, and see 10,000 works of art.

·      Bike or run on the Lakefront Trail or the Northerly Island Trail to enjoy lake views, beaches, and the Chicago skyline.

·      Visit Chinatown and see the Chinatown Gate, Nine Dragon Wall, and Ping Tom Memorial Park—all free. If you time it just right, you can see a Dragon Boat race.

·      Be sure to check potential savings that are being offered at your hotel. Many packages include discounts or free tickets at area attractions as well as at restaurants and bars that are located in the same building.

·      One of the best ways to save money in Chicago is to walk, bike, or take public transportation to get where you’re going. The “L” is cheap, fast, and easy to use. Rent a Divvy bike and explore the city on two wheels with their app full of maps and resources—a day pass is $15 per day.

·      Airbnb and hostels offer affordable and unique accommodations in the city.

·      The Chicago Riverwalk is fun to stroll, and you can often take part in free events and listen to live music while enjoying the views on the Chicago River. The City Winery is a popular spot for live entertainment, enjoyed with a glass of wine and a cheese board.

·      Street markets, food trucks, and hotel and bar happy hours are a great way to experience the city at a discount.

·      Chicago has multiple free seasonal trolleys. Take the free trolley from the Art Institute of Chicago to Navy Pier, with many stops along the way. The Randolph Street Market also offers a free trolley.

Learn more about the cheapest ways to have fun by exploring the Top Free Things to Do in Chicago and Great Things to Do in Chicago for Under $10.

Article Sources
TripSavvy uses only high-quality, trusted sources, including peer-reviewed studies, to support the facts within our articles. Read our editorial policy to learn more about how we keep our content accurate, reliable and trustworthy.
  1. City—Data.com. "Illinois Languages." 2020

  2. Enjoy Illinois. "Chicago's Latino Neighborhoods." April 4, 2020.

  3. City of Chicago. "Facts and Statistics." 2020

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