Things to Do in Chicago: Full Travel & Food Guide

Chicago is not just a city Frank Sinatra sang about; it is the kind of place that offers something for everyone with its stunning combination of tall skyscrapers, a lively town with Midwestern charm, and lots of green spaces. Chicago is the third-largest city in the US with a population of about 2.7 million.

Also known as the "Birthplace of modern skyscrapers," there are many famous places to visit in Chicago other than the beautiful skyline. It is considered a paradise for foodies, sports lovers, and curious souls — thanks to its professional baseball, football, and basketball teams, outstanding museums, and delicious food around every turn.

Here is a full travel guide to Chicago that helps you get the most out of your trip.

The ideal season for your Chicago trip is spring (April to May) and between September and October when the temperature is warm and pleasant, crowds are convenient, and there are lots of festivals. If you are visiting in the summer season, just keep in mind that this season is full of events and has warm weather, but it is also the busiest season of the year. If you do not mind the chill, then go in winter — that is the cheapest time to find hotels and flights.

Here’s what to expect throughout the year:

Chicago offers a great public transportation system that includes buses and trains. You can also go for Lyft, Uber, and cabs to explore the city.

Though the train system is faster, buses also take you almost anywhere in the city. For your convenience, bus stop signs have instructions for getting route info by text.

Chicago's most popular public transportation option is the train, known as the "L" (short for “elevated”). It is the easiest way to get from Midway Airport or O'Hare to downtown.

Another good option is Lyft and Uber. Between them, Uber is often more budget-friendly, but not always.

Slightly costlier than rideshares, but it is easy to find metered taxis all over downtown and the surrounding areas.

The Windy City has lots of options where you can stay in comfort. Some of the best hotels in Chicago are:

Opened in 1920, The Drake Hotel is a famous historic landmark located at the top of the Magnificent Mile. The plus point is that you can also enjoy Oak Street Beach, located just a block away from the hotel. Since its opening, it has also welcomed famous guests like Walt Disney, Prince Charles, Princess Diana, and many more.

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If you are visiting with family and want to stay in the same room, then The Peninsula Hotel is a great option for you, thanks to its large hotel rooms. It also has a Michelin-starred restaurant, so you can enjoy a satisfying meal after you are tired from swimming in its rooftop pool.

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The Palmer House Hilton is the second-largest hotel in Chicago with more than 1,600 rooms. The hotel also hosted former President Bill Clinton, Frank Sinatra, and many others. The main highlight was the formation of the "Big Ten Conference," which was the site of the meeting for guests.

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From iconic landmarks to hidden gems, there’s no shortage of exciting activities in the Windy City. Whether you love museums, lakefront walks, live music, or shopping, these top things to do in Chicago will help you experience the city’s best attractions.

Navy Pier is one of those locations in Chicago that offers something for every age group, like local food spots, indoor parks, free outdoor music, boat rides on the lake, and much more. Don't forget to visit the Centennial Wheel — this 200-foot Ferris wheel is the Pier's main attraction that offers amazing lake views and cozy temperature-controlled cabins. If you are there in summer, you will also enjoy fireworks that light up the sky every Wednesday and Saturday.

This picturesque place by Lake Michigan has three beautiful buildings — the Shedd Aquarium, the Field Museum, and the Adler Planetarium — all of which are surrounded by gardens and parks. There are many things to do here, like exploring history, stars, and ocean life, or enjoying a fun lake ride.

Who wouldn’t want a peaceful walk by the river, where you can stroll under sparkling lights, drink on a patio, or paddle through the skyscraper canyon in a kayak? The must-see attraction here is Art on theMART, which is the largest video-projected work in the world. You can also hop on a tiki party boat, enjoy bird watching or fishing, and explore a historic bridgehouse.

Chicago's theatre scene is just as exciting as the city itself. There is always something to watch with more than 200 theatres in the city. Just make sure to check Hot Tix for half-priced tickets and for discounts, visit during Chicago Theatre Week in February.

If you want full fun, head to Millennium Park Campus, which offers plenty of activities in every season. In winter, you can go ice skating on the plaza, and in summer, enjoy outdoor dining by the Cloud Gate. Enjoy summer festivals, free shows, splash in the Crown Fountain, and watch outdoor movies at the Jay Pritzker Pavilion. After that, take a stroll through Lurie Garden, where you can spot beautiful birds and colorful butterflies.

Chicago has two exciting observation decks in its tallest skyscrapers. At TILT in 360 CHICAGO, the platform slowly tilts you forward for unbelievable views of the city, The Magnificent Mile, and Lake Michigan from 1,000 feet up. At the Skydeck in Willis Tower, you can step onto The Ledge — a glass box that is over 1,300 feet above the ground and sticks out 4 feet from the building.

Chicago has 25 beaches and 26 miles of lakeshore, which makes it a beach city where you can relax by the skyscrapers. If you have to select one, go for North Avenue Beach, located just north of Downtown, where you can do yoga and play beach volleyball. Another great option is Oak Street Beach, which is the closest beach to Downtown. What makes Chicago's beaches special is their free admission and full security with lifeguards from 11 a.m. to 7 p.m. in summer.

In 1907, the Green Mill was opened as Pop Morse's Roadhouse. The place was frequently visited by famous gangster Al Capone, and his favorite booth is still there today. The Green Mill also appears in movies like Prelude to a Kiss, High Fidelity, and Soul Food. It is also believed that to escape from the police, Al Capone and his friends used hidden tunnels under the bar.

Located in Chicago's Gold Coast area, Oak Street is a perfect spot for you if you want to splurge. This is a small but luxurious shopping area that features designer stores like Tory Burch, Jimmy Choo, and Armani, along with Harry Winston and a Vera Wang Bridal salon.

Lincoln Park is a famous spot for boutique shopping that offers stores selling everything, such as gifts, clothes, furniture, and more. Don't forget to visit famous spots like Art Effect, Alice and Wonder, and Enzo Custom.

Chicago is a paradise for food lovers, offering everything from legendary deep-dish pizzas and classic steakhouses to creative fusion dining and global flavors. Whether you’re craving comfort food or looking for a Michelin-star experience, this list highlights some of the best places to eat in Chicago that will satisfy every appetite.

If you want a wide variety of cuisines, head to Au Cheval, one of the most famous eating spots in Chicago, popular for its roasted marrow bones and chicken liver. Don't forget to try their most loved cheeseburger, made with juicy beef patties, mouth-melting American cheese, Dijonnaise, and homemade pickle. For more taste, you can also add bacon, fried egg, or foie gras.

Address: 800 W Randolph St, Chicago, IL 60607, United States

Opened in 1921 by Italian immigrants, Gene & Georgetti's is one of the oldest dining spots in Chicago. The menu features chops, steaks, and authentic Italian dishes like Veal Scaloppine, Eggplant Parmesan, and Chicken Marsala, loved by famous guests like Keanu Reeves and Frank Sinatra.

Address: 500 N Franklin St, Chicago, IL 60654, United States

Noodle lover? Then Joy Yee's Noodle Shop is the spot for you with its huge noodle menu. You can find this spot in three locations in Chicago: Naperville, Chinatown, and Evanston. The spot is not only famous for its delicious noodles but also for being the first in the city to serve Taiwanese-style bubble tea.

Address: 2139 S China Pl, Chicago, IL 60616, United States

Go to Giordano's if you want true flavors of pizza, which is made from recipes that come from an Italian Easter Pie made in Mama Giordano's hometown. It has 65 locations worldwide.

Address: 815 W Van Buren St, Chicago, IL 60607, United States

Two taxi drivers and a friend started this restaurant in 1966, which slowly transformed into the most beloved dining spot with locations across Texas and Chicagoland. Their most famous dish is pizza that has a cornmeal-style crust, cheese on the bottom, toppings on the cheese, and sauce to finish.

Address: 162 E Superior St, Chicago, IL 60611, United States

Lou Malnati first worked at the very first restaurant in Chicago that made deep-dish pizza. Later in the suburbs, he opened his pizza restaurant. The pizzas here are made fresh from mozzarella cheese from Wisconsin dairy, ripe tomatoes from California, and tasty sausages made from a secret blend of spices.

Address: 805 S State St, Chicago, IL 60605, United States

Located in the Gold Coast, this French Mexican dining spot is managed by chef Carlos Gaytan, who went from a dishwasher to the first Mexican chef to earn a Michelin star. The menu features Barbacoa, spicy roasted octopus, and French onion soup with a touch of poblano pepper.

Address: 720 N State St, Chicago, IL 60654, United States

1. For Driving, use the ParkChicago app – Download the ParkChicago app when you bring a car to pay for street parking. Create an account with your credit card and license plate number. After parking, enter the zone number from the signs into the app to pay. Always check the signs before parking, as some streets are permit-only, and a few unmarked streets are free.
2. Get a CTA Pass – The CTA (trains and buses) is easy to use, so you don't need a car if you are staying in the city. Get a pass — $15 for 3 days of unlimited rides or $20 for 7 days. You can easily get passes from many places, like CTA station kiosks, pharmacies, supermarkets, and airports.
3. Learn the Grid System – Chicago streets are lined in a grid pattern. The center point is where Madison Street and State Street connect in the Loop. Street numbers get bigger the farther you go from this center in any direction. Some streets are uneven or diagonal, but one thing is the same: East is always toward Lake Michigan.

Wrapping up, from lively neighborhoods to the popular skyline along Lake Michigan, there are lots of Chicago tourist attractions suitable for every age group. Imagine soaking in beautiful views from famous landmarks, exploring interesting museums, and just walking peacefully along the lakefront. The city also doesn't disappoint foodies with its diverse food options that include everything from deep-dish pizza and the famous cheeseburger to French onion soup and spicy roasted octopus. The best part is that for any reason you visit, Chicago welcomes you with its warm Midwestern beauty.