From Deep-Dish to Skyline Views: Your Chicago Travel Guide for an Amazing Journey

Chicago | Introduction

Chicago, the largest city in the state of Illinois, stands as the United States' third-largest metropolis, following only New York and Los Angeles. Nestled east of the mighty Mississippi River, it holds a pivotal role as a major crossroads in the heart of the Midwest. Its history dates back to the 19th century when it flourished as an essential hub for transportation and industry. Despite the cataclysmic Great Chicago Fire of 1871, which nearly razed the city to the ground, Chicago displayed remarkable resilience in its reconstruction. Throughout the 20th century, the city transformed into an epicenter of culture and the arts, and post-World War II, it solidified its stature as a vital commercial and financial stronghold.

A visit to Chicago is akin to embarking on an immersive cultural odyssey. The itinerary revolves around marveling at its iconic architecture, savoring the delights of its diverse culinary landscape, and immersing oneself in its rich tapestry of arts and cultural events.

Chicago | Transportation

Airport transportation

Chicago has two airports, the main airport, O'Hare Airport (ORD), is located about 16 miles north of downtown, and the other major airport, Midway Airport, is located about 10 miles south of downtown. Most travelers enter Chicago from ORD. ORD has the option of taking the subway, an Uber/taxi, or a shuttle bus into the city. The Uber/taxi ride is usually about 30-45 minutes and costs $40-50, while the subway can be taken on the Blue Line or Red Line, which takes 45-60 minutes and costs $5. If you don't have a lot of baggage, it's actually quite convenient to take the subway, but we were stuck in traffic at lunchtime in our Uber ride, which lasted about an hour.

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Transportation within the city

Chicago is well served by public transportation, making it easy to get to and from downtown attractions by subway or bus. There are six subway lines: Blue, Red, Green, Orange, Brown and Pink. Fares are $2.5 one way and you can choose from options like single-ride tickets, one-day passes, or multi-day passes.

The transportation tickets in Chicago are part of a unified system called the Ventra card. With the Ventra app downloaded, you can purchase tickets directly from your phone, making it even more seamless to navigate the city's public transportation system. The app also supports convenient payment methods like Apple Pay and Google Pay, allowing you to easily manage your fares without the need for physical tickets. We actually pre-purchasd a seven-day pass and storing it on your smartphone, you were well-prepared to explore various attractions.

Chicago | Accommodation

Among the recommended areas to stay, Millennium Park vicinity stands out as an excellent choice. Its strategic location provides proximity to major attractions. Additionally, you'll find a variety of dining establishments nearby, adding to the convenience of your stay.

If you're looking for alternative options, slightly westward locations along the subway line can also offer great choices. These areas benefit from the city's efficient public transportation system, ensuring that you can easily reach attractions and explore various neighborhoods without hassle. Ultimately, selecting accommodation close to Millennium Park or within convenient reach of public transportation allows you to maximize your time in Chicago, making the most of your visit to the city's vibrant and diverse attractions.

Looking for a hotel in Chicago?

We stayed at two hotels, Hyatt Centric The Loop Chicago and Fairmont Chicago Millennium Park, both of which were very nice hotels.

Recommended Hotel | Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago is located a little bit away from Millennium Park, but not too far, at the Monroe subway station. The area is quite busy with restaurants and stores. The rooms are clean and spacious. The Aire Rooftop Bar on the upper floor of the hotel has a good night view.

Hyatt Centric The Loop Chicago

Recommended Hotel | Fairmont Chicago Millenium Park

The Fairmont is a relatively high class hotel, very close to Millennium Park, and the rooms and facilities are nothing to fault. We were upgraded to a high floor suite with a living room, dining room, and a separate room, with a great view of the city.

Fairmont Chicago Millenium Park

  • Expedia
  • Agoda
  • Chicago | Attractions

    Chicago has many famous attractions. When you look at the map, you'll notice that most of these attractions are conveniently located within the city, not far from the shores of Lake Michigan. You can use Grant Park to the south and Lincoln Park to the north as central points for planning your activities. This way, you can efficiently explore the city's attractions while enjoying the scenic beauty of Lake Michigan.

    Chicago has many museums, art galleries, observation decks, etc. If you are interested in going to more than two museums and observation decks, consider purchasing a CityPASS or Explorer Pass.

    The Chicago CityPASS includes tickets for the Shedd Aquarium and Skydeck Chicago, plus the option to choose three more from a list of six attractions, including the Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, and Shoreline Sightseeing Architecture River Tour.

    On the other hand, the Explorer Pass offers a list of attractions, allowing you to choose from two to seven tickets based on the attractions you wish to visit. Travelers can refer to the ticket descriptions and decide on the best options for their interests and itinerary. These passes can help you save money and streamline your visits to Chicago's top attractions.

    Chicago CityPASS

    Chicago Explorer Pass

    Attractions | Grant Park

    Grant Park is a 319 acre urban oasis right in the heart of downtown Chicago along the picturesque shores of Lake Michigan. Within its borders, you'll discover a wealth of celebrated attractions, including The Art Institute of Chicago, Millennium Park, the iconic Buckingham Fountain, and the renowned Museum Campus, which houses several captivating museums. A leisurely walk along the scenic Lakefront Trail allows you to seamlessly explore these iconic landmarks while savoring the captivating vistas of the lake and Chicago's breathtaking skyline. Given the trail's considerable length and the time needed to fully appreciate the museums and other points of interest, it's highly recommended to plan for a well-paced two to three-day itinerary to make the most of your visit to Grant Park and its captivating surroundings.

    Attractions | Art Institute of Chicago

    Chicago Art Museum, located in the center of Chicago, is one of the three major art museums in the United States and one of the oldest in the world, built in 1891. The museum has an extremely rich collection of works, especially known for its large number of masterpieces by Impressionist artists, including Monet, Van Gogh, and Renoir. The collection is mainly Western, but also includes artworks from other countries around the world that span thousands of years.

    Art Museum of Chicago Tickets

    Upon entering the museum, visitors can obtain a map and guide. Given the immense size of the collection, the museum provides a thoughtful one-hour route marked on the guide, highlighting the most significant artworks. However, even following this one-hour path, you'll find yourself navigating through almost the entire museum. During our visit, there was also a special exhibition featuring Cézanne, which we were eager to explore. We spent the entire afternoon wandering the museum, leaving only when it closed for the day.

    The Chicago Art Museum is also one of the attractions on Historic Route 66, which starts right across the street from the Chicago Art Museum. Route 66 is the legendary highway in the United States during the Great Depression, connecting Chicago to Santa Monica in Southern California's Los Angeles, and is important to the history of western migration during the Great Depression and World War II.

    Attractions | Millenium Park

    Millennium Park is a 24.5-acre park in the heart of Chicago. With artwork, fountains, and an open-air concert hall, the park is Chicago's center of public art. The huge silver art installation in the center of the park is one of Chicago's landmarks, designed by British artist Anish Kapoor and made of 168 stainless steel panels. Because of its shape, people usually call it "The Bean", though its official name is "Cloud Gate".

    The fountain in Millennium Park is a very special one, called "Crown Fountain". Designed by artist Jaume Plensa, the fountain is flanked by two 14-meter-high glass tile towers displaying the faces of Chicagoans. The design symbolizes the diversity and cultural background of Chicagoans, and is especially beautiful at night. In addition to the beautiful water features, it is also a great place for many visitors to enjoy the water in the summer.

    The must-do in Millennium Park during the summer months is the open-air concerts. During the summer months, there are usually free concerts every day, and often more than one on the weekends. More information can be found on their the official website

    The Chicago Symphony Orchestra also performs here. The open-air music venue, known as the Jay Pritzker Pavilion, was designed by Frank Gehry and boasts a unique appearance with its speaker-like structures and distinctive canopy.

    During our visit, we had the pleasure of attending two weekend performances of Rachmaninoff, followed by a rap concert on a weekday evening. Many people enjoy picnicking on the lawn during the evening performances. On weekends, we even witnessed some individuals who went all out with tables, chairs, and candlelit dinners. I also bought a deep-dish pizza and savored it while enjoying the show. It was a fantastic experience.

    Attractions | Buckingham Fountain

    Located in the heart of Grant Park, the Buckingham Fountain, designed by Edward H. Bennett, is huge and spectacular. Inspired by the Latona Fountain at the Palace of Versailles, the fountain is in use from April through October and features a nightly light show.

    Museum Campus

    The southernmost part of Grant Park is the Museum District, home to the Field Museum, the Shedd Aquarium, and the Adler Planetarium.

    Museums | Field Museum Natural History Museum

    Field Museum is a natural history museum with a large collection of exhibits. If you use a City Pass, you can visit all the special exhibitions, including a 3D movie of your choice. Although it is a natural history museum, there are also exhibitions of other artifacts, such as the Egyptian Exhibition and the Forest Ecology Exhibition.

    Field museum tickets

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    The jewel of the exhibit is Sue the T-Rex, the world's most complete Tyrannosaurus Rex fossil, measuring 12 meters long. Also on display is Maximo, the fossil of Titanosour, a new dinosaur species discovered in 2010 and the largest known dinosaur, larger than brontosaurus.

    Museums | Chicago Aquarium Shedd Aquarium

    The Chicago Aquarium features marine life from around the world, including sharks, dolphins, sea lions and sea turtles. The aquarium's Marine Theater hosts a different show every day, featuring a cute little white whale.

    Attractions | Navy Pier

    Navy Pier boasts an eye-catching Ferris wheel, standing tall at 50 meters. You can spot it from the lakeside of Grant Park, and it becomes even more enchanting when it lights up at night. To reach Navy Pier, I highly recommend taking the Water Taxi from the Museum Campus. This scenic route allows you to enjoy the beautiful views of Lake Michigan and is an excellent way to take in the Chicago skyline.

    Tickets for Ferris Wheel at Navy Pier

    Navy Pier offers a wide range of entertainment facilities, restaurants, and shops. It even has a pier theater, a mini-golf course, and more, making it a perfect destination for families to enjoy together.

    Attractions | Oak St Beach

    Nestled amidst the towering skyscrapers of the northeastern part of downtown, Oak Street Beach is a small but stunning stretch of sand, measuring just about 200 meters in length. Here, you can get up close to the crystal-clear waters of Lake Michigan while simultaneously enjoying the captivating blend of the beach and Chicago's urban architectural scenery. Despite its relatively short length, when you see people playing volleyball on the sand, lounging in beach chairs, and sheltered under umbrellas, you might just feel like you're at a seaside resort.

    Attractions | Lincoln Park

    Lincoln Park is a large park on Chicago's northern lakefront, covering approximately 1,208 acres. The park has a zoo, greenhouse, nature museum and several beaches. We spent one afternoon walking through it. The Nature board walk here is very suitable for walking, and there is a small farm in the park, which gives the city kids a chance to get close to the farm animals in the neighborhood.

    The Lincoln Park Zoo, located within the park, is a free-to-enter zoo that boasts a relatively diverse range of animal species compared to other urban zoos. In fact, it's one of the oldest zoos in the United States, with roots dating back to 1868.

    Attractions | Old town Chicago

    The Old Town neighborhood of Chicago is located just across from Lincoln Park, and it's not far to walk between the two. Alternatively, you can take the Brown Line to the Sedgwick station. There are plenty of charming shops near the station, creating a lively atmosphere. Old Town features a diverse range of architectural styles, including Victorian-era buildings, Italian influences, and modern designs. As we strolled through the area, we reached the landmark of St. Michael Catholic Church.

    Attractions | Magnificent Mile

    The Magnificent Mile is a 1-mile-long shopping street in downtown Chicago and one of the city's most popular attractions. It earned its name because this street is lined with high-end boutiques, luxury hotels, and renowned restaurants. However, the real magnificence of the Magnificent Mile lies in its architecture and urban scenery. You'll find many iconic skyscrapers here, such as the John Hancock Center and the Wrigley Building, creating a truly spectacular cityscape.

    If you are looking for a cup of coffee, stop by Starbucks Reserve on the Magnificent Mile. This is the largest Starbucks in the U.S. There is a dining area on the top floor where you can sit and watch the crowds on the Magnificent Mile while sipping your coffee.

    Attractions | Chicago Riverwalk

    The Chicago Riverwalk is a scenic waterfront promenade that stretches along the south bank of the Chicago River for approximately 2 kilometers. Along this riverfront pathway, you'll find numerous restaurants and shops to explore. It offers a beautiful perspective of Chicago's architecture from the riverside.

    Despite the surrounding skyscrapers and bustling activity, the Chicago Riverwalk offers a relaxed and leisurely atmosphere. With canoeing and sightseeing boats passing by, and the presence of bridges and canals, it can feel like you're strolling along a modern architectural version of the canals in Venice.

    Join the River Cruise if you are interested in learning more about the history of the buildings around you. Sail slowly on the Chicago River and listen to your guide explain the history of Chicago and its famous buildings such as the Willis Tower, the John Hancock Center and the Wentworth Building.

    Chicago Boat Tours

    Observation Deck | Skydeck Chicago

    The Skydeck Chicago, located at the top of the Willis Tower, provides an excellent vantage point for admiring the Chicago cityscape. Tickets are included in the Chicago CityPass, making it a popular attraction. What sets the Skydeck apart is its specially designed glass observation deck, known as the Ledge, which hangs from the 103rd floor of the Willis Tower, soaring to a height of 1,353 feet (412 meters). Stepping onto this observation deck, with unobstructed views all around, feels like floating in the air at the 103rd-floor level, offering a thrilling experience. We arrived just before sunset, allowing us to witness the transition from day to night, which was truly spectacular.

    Skydeck Observation Deck Tickets

    Observation Deck | 360 Chicago

    360 Chicago is another renowned high-rise observation deck in Chicago, located on the 94th floor of the John Hancock Center in downtown Chicago. Unlike the Skydeck, this vantage point offers clearer views of the lakeshore scenery. The panoramic viewing room, Tilt, extends outward from the 94th floor of the John Hancock Center, reaching a height of 1,000 feet (305 meters).

    360 Chicago Tickets

    Attractions | MCA Chicago

    The Museum of Contemporary Art Chicago is a dedicated institution for showcasing modern art. Its exhibitions feature a rich and diverse array of artistic forms, including paintings, sculptures, photography, video, and new media works.

    MCA Chicago Tickets

    Attractions | Chicago French Market

    The Chicago French Market is an indoor market located near the Ogilvie Transportation Center and the Randolph/Washington CTA station in downtown Chicago. It features numerous stalls and shops where you can purchase gourmet food, crafts, and other goods. One of its main attractions is the variety of food stalls, including Parisian-style restaurants, delicatessens, bakeries, dessert shops, and cafes. The food offerings here are diverse, ranging from French and Italian cuisine to Southeast Asian and Middle Eastern dishes, among others.

    Attractions | Wrigley Field

    Wrigley Field is the home stadium of the Chicago Cubs and was constructed in 1914, making it one of the oldest baseball stadiums in the United States. If you have the time, attending a Chicago Cubs game can be a fantastic experience. The stadium's architecture is distinctive, featuring elements of both romanticism and neoclassicism, and it stands as a landmark in the heart of Chicago.

    Chicago | Food

    Chicago is also a foodie city with many famous restaurants. The city is also known for its affordable food such as Chicago-style hot dogs and Chicago Pizza. Check out more on this post.

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