Chicago Travel Guide – Top 10 Vacation Highlights

Situated in the state of Illinois, Chicago is the third-largest city in the United States. An international business center and shopper’s paradise, Chicago is an ideal vacation spot. Whatever time of the year you visit, and whatever your interests may be, Chicago is full of activities to make for a special holiday.
Chicago Travel Guide
Table of Contents

Chicago’s museums offer diversity in cultural experiences to suit almost any interest. The Art Institute of Chicago features some of the most impressive collections of Impressionist and Post-Impressionist art in the United States. Visit here to get cultured during your stay. Even if you aren’t a fan of paintings the Institute also houses a famous collection of artifacts.

It’s worth taking a trip to the top of Willis Tower, even with the long lines waiting to travel up the 103 floors. The Willis Tower Skydeck is positioned on the 103rd floor at a height 1,353 feet, thereby offering breathtaking views of Lake Michigan, Chicago’s impressive skyline, along with the four states that are adjacent to Illinois.

The Field Museum of Natural History showcases a diversity of exhibits on natural history, including anthropology, archeology, zoology and geology. One of the highlights of their collection is Sue, the largest and best-preserved Tyrannosaurus Rex in the world.

Jutting out into Lake Michigan, Navy Pier offers opportunities for shopping, restaurants and music that make it a fun place for just about anyone. Navy Pier offers at least an entire day’s worth of Chicago activities – including Cirque du Soleil shows and the Ferris wheel. Don’t miss out on the Crystal Garden, a beautiful indoor botanical garden showcasing palm trees, fountains and other plants.

The Museum of Science & Industry is the largest science museum in the western hemisphere that is also worth a visit while in Chicago. The museum boasts an IMAX Theater and fun interactive science experiments that supplement its world-class exhibitions.

For an enjoyable excursion right in the city, look no further than Millennium Park. An outdoor artistic space, Millennium Park is one of those places you need to experience at least once. Go here to lounge in the scenic gardens or under the avant-garde Jay Pritzer Pavilion.

Also take a tour with the Chicago Architecture Foundation. Spend two hours or even half a day sightseeing around Chicago and learning about various architectural landmarks around the Windy City. While tours are available by walking or bus, the boat ride is the most popular option.

Chicago is home to some of the most iconic landmarks of the United States: from towering skyscrapers, to green open spaces and cultural activities. If you’re coming for a few days in Chicago, take some time and visit some of these must see attractions. You won’t be disappointed in what Chicago has to offer.

1. Field Museum of Natural History

With more than 20 million specimens, the Field Museum of Natural history boasts one of the finest and largest collections of biological, anthropological, natural and historic items in the world. The museum also hosts great touring temporary exhibits.

Situated on South Lake Shore Drive, the Field Museum had its first incarnation in 1893 as the Columbian Museum of Chicago. The main highlight of the Field Museum is arguably SUE – the largest, best preserved and most complete fossil of a Tyrannosaurus rex that was ever discovered. Sue is astonishingly huge and brings to life the glory of the Jurassic era.

Other highlights of the Field Museum include Evolving Planet, which spans 4 billion years of life on earth and contains displays, fossils, videos, sea and landscapes, as well as an expanded dinosaur hall.

The Field Museum also enables visitors to explore the culture of peoples from all over the world including Ancient Egypt, Africa, Tibet and the Arctic. Be sure to explore the Inside Ancient Egypt exhibit that features an extended display of Egyptian artifacts such as mummies, tombs and more.

2. Millennium Park

Chicago is home to many lovely parks, stretches of greenery that offer visitors some much needed peace and serenity. Situated on the east side of downtown Chicago, Millennium Park is a 24.5 acre work of art that combines culture, landscape and architecture.

Millennium Park was built with the aim of having it ready to celebrate the new millennium in the year 2000. However, due to delays and cost overruns, the park did not have its grand opening until the summer of 2004. However, the end result of the ambitious project is so spectacular that many have forgotten what it took to have it completed.

One of the main attractions at Millennium Park is the Jay Pritzker Pavilion an outdoor venue which hosts various concerts and performances on its stage. The Jay Pritzker Pavilion is made from brushed stainless steel. Rising 120 feet into the air, the Pavilion evokes ribbons flowing in the wind, which is no easy feat for a metal structure.

Criss-crossed pipes support the high-end sound system of the Pavilion which can seat 11,000 people. The multiple speakers distribute the sound evenly across all the seating areas, which work well at replicating the sound of an indoor concert hall.

Several free music events are held at the Jay Pritzker Pavilion from spring through fall, including the Grant Park Music Festival and the all popular Gospel Fest. In addition to music concerts, Millennium Park also hosts dance performances, theater and tours.

Lurie Garden is a surprisingly tranquil spot due to its high hedge that encloses it on both sides. The hedge was designed to protect the perennial garden from pedestrians, and symbolizes the description of Chicago as the “City of Big Shoulders”.

Along the eastern side is a hardwood footbridge that runs over shallow, running water. This is a very popular spot during the hot summer when people sit on the edge and dip in their toes.

The West Hedge is a topiary feature that is supposed to represent a classical Greek story. The Light Plate is an area of the garden that was designed to evoke a modern feel with a very bright and clean landscape. The Dark Plate pays homage to the garden’s landscaping history and features lush, dense vegetation.

The Boardwalk and Water Features are built from hardwood. The Boardwalk runs along the water feature that has a wide step on which visitors can sit. A lot of care went into the Lurie Garden landscape lighting, the highlight being the interior lights of the Shoulder Hedge which provide an interesting glow.

Referred to by locals as “The Bean”, Cloud Gate is a public sculpture that weighs more than 110 tons, measures 66 feet long and 33 feet high. A popular photo opportunity, Cloud Gate was designed using a large number of individual stainless steel plates, while its seamless surface was the result of thousands of hours of polishing.

The sculpture has the appearance of a giant drop of liquid mercury, while its mirrored surface offers amazing reflections of the city skyline, which is even more breathtaking on a clear, bright day. Visitors can walk beneath The Bean which is surprisingly concave.

The Crown Fountain is a very unique tribute to the people of Chicago that offers many hours of water-play and entertainment during the warmer months. The designer behind this landmark was inspired by historic fountains with gargoyles that have water spouting out of their open mouths.

Two fifty foot glass block towers display rotating video images of 1,000 residents. The giant faces smile for several minutes, then pucker their lips and a pipe embedded in the screen emits a large stream of water, which gives the illusion that water is spouting from their mouth. As a transition between the faces, the tower goes black and a cascading waterfall comes pouring down its sides.

Also cross the BP Bridge which connects Millennium Park to Daley Bicentennial Plaza and rises up high enough to offer some great views of the surroundings. After strolling around the Millennium Park all day, you will need refreshments. You may buy these at the Jay Pritzker Pavilion, or eat at the Park Grill, a charming restaurant situated on the park’s west side near the Ice Rink.

Whatever brings you to Millennium Park, you are certain to appreciate the huge green lawns that allow you to enjoy the great outdoors, all in the heart of downtown. During the winter months, you can experience the pleasure of ice-skating amid skyscrapers on the Ice Rink.

An island amidst the congestion of downtown Chicago, Millennium Park is truly worth the visit. While there, you will easily forget that you are still within city limits, if not for the skyscrapers looming in the background to remind you.

3. Willis Tower Skydeck

What better way to see Chicago than from above? Chicago is full of skyscrapers and the Willis Skydeck is a sure fire way to enjoy beautiful panoramic views, while getting a great educational experience. Visiting the Willis Tower Skydeck is also a great way to rise above the Windy City and get a good idea of how it is arranged.

If you’re looking for the quintessential Chicago experience, you will appreciate this offering from the Willis Tower Skydeck. Formerly known as Sears Tower, Willis Tower is the tallest building in North America. Built in 1973 as the Sears Tower, the building was renamed Willis Tower in 2009.

Located in The Loop, in central Chicago, Sears Tower held the title of the tallest building in the world for 25 years, but lost the designation in 1998. With its 108 floors, Sears/ Willis Tower is today the fifth tallest freestanding structure in the entire world.

Willis Tower sits on 2 city blocks and rises to a height of a quarter of a mile above ground. The building houses offices staffed by about 10,000 workers, in addition to a health club, retail shops, several restaurants and other services.

But more than its architectural stature, Willis Tower Skydeck offers the best and most amazing views of Chicago. On a clear day, visitors can peek into four states: Illinois, Michigan, Wisconsin and Indiana. The views are so breathtaking your mind will hardly be able to process the idea that you are that far up in the sky.

As if it wasn’t already a great attraction, the Willis Tower Skydeck went through a renovation that added various highlights. The Sky Ledge was added and features 4 glass boxes that enable you to take in the views straight down.

The Sky Ledge enables you to walk out onto a glass-floored section and look down 103 stories below your feet. The series of glass bays extend 4 feet out of the 103rd floor of Willis Tower to give you the sensation that you are floating in the air. There are also interactive Chicago history exhibits and high-powered telescopes available.

At Willis Tower, visitors can enjoy a sumptuous breakfast of the famous Chicago-style deep dish pizza on the 103rd floor, with a view of Chicago’s famed skyscrapers. The Willis Tower Skydeck and Giordano’s Pizza have teamed up for a casual dining experience at the highest level. Book your reservation at least 2 days in advance for breakfast or a deep-dish pizza dinner on the Sky Ledge.

If you’re truly seeking a bird’s eye view of Chicago – if birds even get that high up – then the Willis Tower Skydeck is your best bet. Do stay for the Sunset – it is recommended that you visit the Skydeck at 5pm or later to enjoy the breathtaking sunset views.

4. Chicago Cultural Center

Situated on East Washington Street, the Chicago Cultural Center lures visitors with its many free events including music, theater and dance performances, films, lectures and art exhibitions.

Built in 1897 as the first central public library of Chicago, the Cultural Center’s landmark building is also flocked by architecture buffs. The structure of the building comprises 3-foot thick walls that are faced with limestone and set 104 feet above a base of granite.

Its interior details are stunning due to the fact that the building was originally intended to be a showpiece building to boost Chicago’s reputation as a sophisticated city. The skilled craftsmanship is obvious from the use of rare imported marble, stained glass and glass mosaics, polished brass, and fine hardwoods, mother of pearl and colored stone.

The most notable features of the building are its spectacular stained-glass domes. The ultimate showstopper is the 38-foot in diameter Tiffany stained-glass dome that is located on the building’s southern side. Another larger dome features a Renaissance pattern made with more than 50,000 individual glass pieces.

The Cultural Center features some of the best art galleries, musical performances and more inside a Neo-Classical building. The Cultural Center also hosts some of Chicago’s best art exhibitions by international and local artists. Join other patrons who gather at Randolph Café to enjoy cappuccinos, juices, teas, pastries and scheduled performances of jazz, blues, folk, pop and cabaret.

5. Lincoln Park Conservatory

Situated on Stockton Drive in the northern side of Lincoln Park, the Lincoln Park Conservatory was built over 5 years from 1890 to 1895. It features 4 serene greenhouses: the Fernery, the Orchid House, the Palm House and the Show House, all of which display an amazing diversity of flora.

Each greenhouse boasts its own unique features. The Orchid House is home to more than 20,000 versions of the orchid species. The Fernery has ferns and other native plants that grow on forest floors. The Palm House is a tall domed structure with a 100-year old rubber tree standing at fifty feet tall. The Show House features a display that rotates constantly and hosts 4 flower shows throughout the year.

The Lincoln Park Conservatory also features a number of tropical halls that represent flowers and plants from around the world. Truly breathtaking, the Conservatory is packed to the brim with stunning exotic flowers and plants that enable you to enjoy a slice of tropical paradise right in the middle of Chicago. The Conservatory also has a serene koi pond.

During the summer months, venture outdoors to find a lush French garden full of a wide variety of flowers and plants, and a splendid fountain. Many residents of Chicago use this space to sit and read, or just toss around a football. The Conservatory is an ideal spot to take a break during your tour of Chicago, where you can relax and enjoy the beauty of nature.

6. Chicago Botanic Garden

Everything springs to life at the Chicago Botanic Garden amid a backdrop of pure serenity and beauty with plenty of interesting outdoor and indoor spaces available. A premier cultural destination, the Gardens are the perfect spot to take a break after a long engaging day of touring Chicago. There is something for every taste here, from the sublime to the simple.

Situated in Glencoe, the Chicago Botanic Garden is a beautiful place to visit. Opened in 1972, the garden has today evolved into one of the great living museums and conservation science centers in the world. There are 26 gardens and 4 natural areas of the Botanic Garden situated on 385 acres and around 9 islands. The Garden is also home to a renowned Bonsai collection.

The Garden is one of the treasures of Chicago, a living plant museum with event programs and activities throughout the year. A great photography destination, the Gardens are best visited during spring when tulips and other spring flowers are in full bloom. Visitors can admire blooms and interesting panoramas in every corner of the Garden. Go there and explore for yourself, and identify your favorite areas.

Crescent Garden is especially beautiful during the spring. This is when its 26,000 tulips have just opened and their numerous shades of cream and purple make them a wonderful spectacle, with the willow trees and lake in the background.

Stop by the Bulb Garden during spring when tulips of many varieties and colors blanket the beds at the garden entrance and along the pathway through the garden. At the Regenstein Center, you may see temporary photography exhibits that are quite interesting.

Another spring favorite is the Circle Garden which features a dancing fountain with 4 identical beds of spring tulips in yellow and pink, along with beautiful combinations of flowering trees, scrubs and annuals. Off to each side are two secret gardens as well that make for great landscape shots.

One of the best areas in the Botanic Garden to visit during spring is the Enabling Garden along with the upper walkway that features the Sensory Garden. The raised beds make it easy to get close to the plants and flowers by going near the bed ledges.

Both the gardens are a sheer delight to the senses, with stunning color combinations, textures and smells of the mix of annuals and perennials dazzling your senses. These gardens are also home to some of the most beautiful and unusual tulips in the world.

The Sensory Garden woodland is lined with white spire birch trees and numerous ferns and wildflowers. Visit in time to see the bleeding hearts as they just begin to bloom in the woods.

Other blooming treats are the redbud, crabapples and cherry trees which are found all over the Botanic Garden and along one of the most stunning paths along the lakeside between the English Oak Meadow and the Japanese Garden.

Crabapples form a canopy of flowers that is lovely and magical to photograph. You will also enjoy the Iceland poppies of the English Oak Meadow. Also spend some time exploring the blooms and lovely architecture in the English Walled Garden.

Finally, stop by the Heritage Garden, a circular garden that is divided into four quadrants. Seven of its beds display plants in accordance with their geographic origins, while 14 others display the major plant families grouped in accordance with their scientific classification. You will particularly like the Persian Buttercups.

7. Art Institute of Chicago

Chicago is home to a dynamic and stimulating art scene. The River North area of Chicago boasts a very high concentration of galleries with more than 100 calling the area home. With so many galleries, diversity in art is unavoidable.

While there are galleries that feature all sorts of art including the contemporary, European and American Impressionist, ethnic and international paintings, installations, furniture and sculpture, perhaps the city’s best known art collection is found at the Art Institute of Chicago, which hosts one of the largest artistic collections in the world.

The Institute holds a massive collection of art that spans 5,000 years and features works of American, African, Asian, European, Modern and Contemporary art. There are sections for Armor, Textiles, Photography and Architecture. The museum offers year-round exhibitions in addition to special temporary ones. An ongoing series of performances, workshops and lectures take place here every day.

One of the premier art museums in the world, the Art Institute of Chicago showcases its great art collection in several different mediums: paintings, sculptures, drawings, photographs, prints, architectural drawings, textiles and videos. The museum also plays host to several traveling exhibits including works by Van Gogh and Monet.

Every couple of months, the Art Institute of Chicago opens a new exhibition that covers a different artist and time period. These range from modern times to the antiquities.

A significant piece in the history of Chicago, the Art Institute’s gates are guarded by two famous big lion sculptures that welcome art patrons from the world over. While strolling through the Art Institute, you can admire a number of pieces ranging in all manners of style from post-modern to impressionist.

The Modern Wing of the Art Institute of Chicago is a striking building designed to offer a stark contrast from the classic Beaux-Arts style of the main part of the museum. This is fitting, seeing as the art inside the 2 structures is dramatically different as well.

The Institute has many contemporary art offerings, as opposed to the previous displays of more classic works. The Modern Wing holds many permanent collections and some important traveling exhibitions.

Situated in Grant Park, the Art Institute of Chicago features a diversity of wonderful exhibits. These include the African collection of African exhibits such as wood sculptures, furniture, ceramics, textiles, masks and bead work from Southern, Central and West Africa.

There is also the Amerindian collection of Meso-American and Andean textiles, ceramics, sculpture and metalwork, and the South American Indian figurative art and ceramics.

Also visit the Ernest R. Graham Study Center for Architectural Drawings, where you can view a distinguished collection of over 130,000 architectural drawings and sketches.

The European Painting collection offers a range of over 950 works from the Middle Ages to the 1900s. This department’s greatest strength lies in its collection of French paintings dating from the 19th century.

The European Decorative Arts collection features 25,000 objects including metalwork, furniture, ceramics, enamels, ivory and glass from the 1100s to the present day, as well as sculpture from the medieval ages to the 1900s.

At the Department of Textiles, you can admire over 13,000 textiles and 66,000 sample swatches that date from 300 BC to the present day. The collection represents Africa, Asia, Peru, Indonesia, Guatemala, Mexico, North America and Europe through selections of pre-Columbian textiles, printed fabrics, needlework, tapestries, European vestments, lace, woven silks and velvets.

Regarded as one of the finest and most comprehensive collections in the world, the Department of Modern and Contemporary Art features over 1,500 sculptures and paintings that represent every significant movement in America and Europe during the 20th century.

After a full day of wandering around fascinating exhibits, you will probably need a snack. Various on-site dining options are also offered at which you can choose to have a meal. Luckily, you can take a break from the feast of art by dining at the Court Café or the Garden Restaurant. You can also shop for souvenirs and gift items at the museum shop of the Art Institute.

8. Museum of Science and Industry

Chicago is a cultural city at which you can find museums dedicated to all passions and interests. Don’t miss out on the famous Museum of Science and Industry. Situated on 57th Street and Lake Shore Drive, the museum boasts a collection of more than 35,000 artifacts, and also hosts various excellent touring exhibits.

Housed in a building originally built to serve as the Palace of Fine Arts, the Museum of Science and Industry features special exhibits such as Leonardo Da Vinci, Body Worlds and CSI: The Experience which is in great demand, drawing both tourists and locals.

The Museum of Science and Industry was opened in 1933 and is touted as the largest science museum in the western hemisphere. Not only is this museum an excellent educational experience, it is also great fun for visitors to enjoy.

The first interactive museum in North America, the Museum of Science and Industry is fun for this very reason. It’s not just about gazing at boring displays, but you actually get a hands-on approach to learning. Whether it’s hearing a whisper travel across a long hall, or touring a genuine submarine, there are many sensory experiences to add the Museum of Science and Industry to your Chicago itinerary.

The Museum of Science and Industry has various highlights. The Coal Mine takes visitors fifty feet underground into a real mineshaft for a memorable experience.

The U-505 Submarine is a real German submarine, and the only one that was captured during the Second World War. It is quite a sight to view the giant U-boat up close, while touring its insides makes for a very unique experience.

Another attraction is the Omnimax Theater, a wrap around movie screen that rises five stories high, enveloping the viewer to provide a sense of “virtual reality”.

9. Navy Pier

Chicago’s Navy Pier offers visitors scores of dining and entertainment options, and boasts a rich history. Situated on East Grant Avenue, on Lake Michigan, the Navy Pier in Chicago has been a landmark in the city since it first opened in 1916.

Originally designed both as a shipping and recreational facility, the Pier also served as a site for military training during the two world wars, a venue for exhibitions and concerts, and a temporary home for a university campus. Today, Navy Pier is a showcase of a unique collection of shops and restaurants, in addition to unequaled exhibition and recreational facilities.

Navy Pier is a bustling 1.5 mile long boardwalk that is guaranteed to please the needs of any visitor. Navy Pier is lined with restaurants and studded with small shops that could keep you occupied for hours, although there are plenty of other activities to fill a day spent at Navy Pier.

One of the main highlights of Navy Pier is Cirque du Soleil. The largest theatrical producer in the world, Cirque de Soleil is not your typical circus. Captivating audiences from around the world, their performances feature gorgeous costumes, amazing acrobatic acts, unique music and many different shows to choose from.

Cirque du Soleil coordinates some of the best theater in Chicago. From the moment the curtain is drawn, you will embark on an experience of a lifetime. The world famous entertainment company offers an unbelievable evening of entertainment in Chicago, with breathtaking visuals and stunning acrobatics in the shows that will keep you glued to your seat.

Navy Pier Park is also popular spot during warmer months and hosts the famous 150-foot high Ferris wheel, a merry-go-round and a high-flying swing ride. If you enjoy the outdoors, you will enjoy spending some time on the Pier, riding the Ferris wheel. Also in Navy Pier Park is the Skyline Stage which features top music performances from May to September.

Gateway Park is a 19-acre park that enhances the lake front of the city. This is a particularly fun-filled entrance to the Pier, with a water fountain that has computerized jet streams. The Family Pavilion is one of the popular areas of Navy Pier, which is home to the IMAX Theater, the Crystal Gardens indoor botanical park, as well as many shops and restaurants. The IMAX Theater shows current movies on a massive screen.

South Arcade has more restaurants and shops, and also houses the Amazing Chicago’s Funhouse Maze, the Chicago Shakespeare Theater and the 3-D ride Transporter FX. The experience of watching one of the masterpieces by Shakespeare at the Pier’s theater stage is unlike any other.

Festival Hall is the section of Navy Pier dedicated to trade shows and exhibitions. Festival Hall comprises a large exhibition space, meeting rooms, high ceilings and a full range of electrical and telecommunication needs. Festival Hall is also home to the Smith Museum of Stained Glass Windows, which is a display of 150 historic and beautiful stained glass pieces.

Dock Street, which runs the length of the South Dock of Navy Pier, is reserved for pedestrians, joggers and cyclists. It therefore makes for a splendid place to walk and take in the atmosphere of Navy Pier. Four performance areas feature entertainment opportunities that range from mimes, jugglers and stilt walkers to singers, musicians and comedians.

On select summer evenings, you can also watch fireworks set up to entertain evening visitors to the Pier. For the best views of the spectacular Chicago skyline and lakefront, visit the East End of the Pier.

Navy Pier is the ideal spot in Chicago for enjoying some delicious lunch or even a sunset stroll. Due to its plethora of entertainment options, this legendary Chicago destination has something for everyone that can be enjoyed both night and day.

10. Chicago Architecture Foundation River Cruise

One of the best ways to experience Chicago is via a tour. This will give you a unique perspective of the city, often at the hands of an expert guide who tells you the history and story of every place you visit.

You can take a bike tour, a walking tour or a cable car tour. You may even tour Chicago via helicopter or on a horse and carriage. You may take a tour with a theme or go on those that take you through certain ethnic or historic neighborhoods such as Greektown or Old Town. Whichever tour you opt for, none comes close to a great way of seeing Chicago than by boat.

Seeing Chicago by river offers a view that is completely unique from that had from the sidewalks and roads of the city. Here, you can enjoy a meal on the boat and eat at your leisure as you contemplate the magnificent architecture of Windy City. You will find it dazzling to spend a day on the water while soaking up the sun and watching the waves ripple out from behind the boat.

The Chicago Architecture Foundation River Cruise provides a unique perspective to some of the architecturally significant sites in Chicago through its guided and narrated cruise tour which lasts approximately 90 minutes. The cruise goes past some of the major landmarks and buildings of Chicago. The dock is situated at the south eastern corner of Michigan Avenue and Wacker Drive.

This is a unique and great way to have a peek at over 50 architecturally significant sites while cruising along the Chicago River canyon that is created by the tall towers of the Windy City. Most of the buildings lining the river were designed with the river in mind and offer a different perspective than when viewed from the side street.

There are even interesting legends to some of the buildings. Take for instance, the chair of the Civic Opera House which is also known as “Insull’s Throne”. The story goes that this building was designed as a giant armchair with its back facing New York City because the daughter of financier Samuel Insull was rejected by the New York Metropolitan Opera, and so he had this built for her.

The only problem with this story is that Insull did not have a daughter; although this little detail has not prevented the story from becoming a well-accepted fact.