Chicago – the third biggest city of United States of America (USA) is one of the world’s great cities to visit with so many wonderful attractions. The splendid skyline situated on freshwater Lake Michigan will enchant you with its vibrant & lively city life, cultural happenings, architectural wonders, charming neighborhoods, delicious food, and some interesting history. This city is perfect for all ages and interests as it has many and varied things to do. This city is often named as “The Windy City” and is famous for many festivals like Music and Taste of Chicago food festival. So let’s take a virtual tour of best things to do in Chicago city tour – Chicago Travel Guide.
Note: I was hosted by ChooseChicago(official destination marketing organization) and its co-partners – CityPass Chicago, Big Bus Chicago, Chicago Architecture Foundation Center, Chicago Food Planet and Shakespeare Theater to feel Chicago, but views and opinions are my own, not influenced by anyone.
Chicago Attractions | Best Things to do in Chicago City Tour – Chicago Travel Guide
A 110 story skyscraper which was the tallest building once upon a time and holds its title for about 25 years. At present this is the 2nd tallest tower in USA and 16th tallest in the world. Designed by famous architect Adrian Smith who is known for designing famous tallest buildings like Burj Khalifa(Dubai) too.
Step onto its 103rd floor which is an Observatory Deck also known as The SkyDeck Chicago for the splendid views of the city. There are special 4ft extended transparent glass balconies on this floor where you can feel hanging in the air above the ground from 103rd floor and could observe the city under your feet.
Opens 365 days a year
A public park located within the Loop area is the most famous among Chicagoans. As this park is located within the heart of downtown is always hosting many events, farmer markets on special days, greenery, art / sculptural displays, it is like the town square of Chicago. This spectacular gathering point is surrounded by beautiful skyline and is like an oasis within the concrete cityscape. In winters during snowy times, this park converts into a beautiful ice rink for skating around.
TICKETS – Free to Enter
A wonderful mirror-finished steel sculpture which looks like a drop of mercury is located in Millennium Park and officially known as “The Cloud Gate”. Designed by Indian born British artist Mr. Anish Kapoor this steel sculpture with special mirror polish reflects the city skyline in various manners. You can see many distorted and various versions of the city skyline on this sculpture due to its curvatures and fine polish. This sculpture was the result of one of the design competition and now is the most photogenic location or the symbol of this city. Adults and children especially enjoy this place to see their distorted faces and also the city skylines which is same as mirror house effects.
Two huge 50-foot glass towers facing each other with an excellent display of art, video sculpture combination of residents of Chicago. With the display of faces of residents, also the water fountains gushing out from the lips at regular intervals of time this fountain is favorite among kids and even adults too in the summertime or hot afternoons. A large amount of water is thrown from the lips of the all multimedia display from both the sides and it looks like a person is throwing water from their mouth.
JOHN HANCOCK CENTER (360 CHICAGO)
From the 1000 foot above the ground, on the 94th floor, enjoy the splendid views of Lake Michigan and stunning city views with adorable skyline from the top. At present this is the 4th tallest building in Chicago and 9th tallest in the USA. This residential building houses many hotels & offices too and it is the 3rd highest residential tower in the world.
Step on to its Observatory deck – 360 Chicago for having 360 ° views of the whole city with a clear view of distance to 80 miles on a clear day.
Opens 365 days a year.
Here you can also feel the most unique and thrilling experience of the world by feeling like falling down from the 94th floor. Tilt is the transparent whole façade windows where you have to hold the railings and stand to look down and within few seconds this façade is tilted down to certain angle and left in that position for few minutes. During this tilt on the edge of the floor and leaning against the window, you will feel like falling down from the top floor. This kind of experience cannot be found anywhere on the tallest building anywhere in the world.
For TILT experience you have to purchase separate tickets for 8 USD. Chicago Citypass holders get some discount for Tilt tickets.
Admire the magnificent and world-famous Chicago skyline which is also one of the world’s tallest skyline. This city skyline boasts of having four of America’s tallest buildings.
Where to get the best view of Chicago’s Skyline?
- Solidarity Drive – Stretching from Grant Park to Adler Planetarium. This stretch has a lovely waterfront with small grass stretch and benches.
- From the grounds of Adler Planetarium
- Near the North End of Navy Pier
- At the top of observatory deck of John Hancock Center.
- From the Grant Park
ARCHITECTURE RIVER CRUISE
A 75 minutes boat cruise to see the famous architectures across the Chicago River. With the live commentary about these buildings, architects you will sail across 40 iconic buildings and would get the opportunity to learn about Chicago history, how this city is built and rebuild after Great Fire and also upcoming architectural growth in this city. You must be amazed to know world-famous architects of many famous tallest buildings of the world and belong to Chicago. This cruise sails across all three branches – Old Post Office Building, Willis Tower & East Bank Club.
Located on Lake Michigan, this aquarium houses many exotic species of marine creatures including sea horses, stingray fish, dolphins, whales, etc. from local Lake Michigan, world-famous Amazon rainforest, wide oceans, and Caribbean Reefs. It has approximately 32,000 aquatic creatures.
Activities at Shedd Aquarium –
- Touch the textured sea creatures in Polar Play Zone
- Grab a 4D show featuring many interesting sensational marine life short movies
- Enjoy the Dolphin show.
Outside the Shedd Aquarium, there is café / Restaurant for eating out with wonderful Chicago skyline views.
FIELD MUSEUM OF NATIONAL HISTORY
The Field Museum which is a natural history museum is one of the largest natural history museums in the world. It has been opened from 1893 and has approximately 24 million exhibits from all over the world. It showcases rich cultural and historic exhibits from ancient civilizations like Egypt, Asia, Africa, and the ancient Americas. The main atrium of Stanley Field Hall welcomes you with 37m Titanosaur which is the key feature of this museum. From last year 125 year, this museum adds precious exhibits every year. You can also grab 3D show to feel how the exhibits are excavated or story behind the exhibits.
This was the first planetarium of the USA which includes an actual observatory. Located in Museum Campus, Grant Park, beside Lake Shore you get chance to experience Solar System, history of telescopy, landing on the moon and many varieties of shows.
Located on the south of Magnificent Mile at Michigan Avenue which is a white-colored iconic building of this city. It is one of the famous building in Chicago. This clock tower is designed as per Gothic style and with intricate details on limestone façade which is a perfect classy example of architecture.
Your visit to Chicago is incomplete without visiting Navy Pier. Located on the shoreline of Lake Michigan, it is spread across 50 acres with many parks, waterfront restaurants, amusement rides, drama theaters, IMAX movie theater, event areas, and is one of the top family attractions in the Mid-West of USA.
It is also famous for its 65 meter Centennial Wheel and other amusement rides. In summers, you can also experience fireworks over the city skyline which occurs twice a week. There are many cruises options from here like dinner cruises.
An antique style of the trolley which is a free shuttle from State street and few stops in between takes you to Navy Pier.
CHICAGO SHAKESPEARE THEATER
Located on Navy Pier this non-profit theater broadcast Shakespearean productions. This award-winning theater is the city’s most versatile performing Arts Center of the city.
CHICAGO CHILDREN’S MUSEUM
Located at Navy Pier, this museum is famous among young children (ages 10 and under). This 3 story museum has a big splash and many DIY theme-based activities.
HISTORIC WATER TOWER
This Gothic styled tower which was built in 1869 is very iconic as it is one in a couple of buildings which survived Great Chicago Fire on October 8 – 10, 1871. This 3 days fire burnt the whole city but as this tower is made up of limestone unlike other nearby wooden buildings, it survived till now. It looks like a small castle which was the second oldest water tower and is located on wonderful Magnificent Mile.
This iconic historic area in Chicago which consists of world-class architectural buildings, parks, theaters, restaurants and vibrant shopping street forms the true downtown of Chicago. At the south end of Loop is the museum area.
MUST DO ACTIVITIES IN CHICAGO | Best Things to do in Chicago City Tour – Chicago Travel Guide
- Stroll across the Magnificent Mile to feel the vibrant and eclectic vibes of this fascinating city. Magnificent Mile is also known as Le Boul Mich and it starts from Oak Street to the riverfront at Michigan Avenue. This upscale stretch is famous for high-end shopping and will amaze you with many choices. It houses largest Ralph Lauren store in the world and also many fine dining avenues. Hancock Tower and other famous sky scrappers are also located across this stretch.
- Take an Architecture Tour depending on your choice of transportation. Architecture tours are given by walking tours, river tours, L(public transportation) tours to admire the history of Chicago’s architecture.
- Chicago is foodies heaven and there are many authentic Chicago style signature dishes which you must try on when visiting this place. Pamper your taste buds by authentic Chicago style deep dish pizzas, signature styled hot dogs and gourmet popcorn. These signature dishes cannot be found anywhere in the world. Go for Chicago Food Tour.
- Ride the L which is an elevated railway track passing through the busy streets of Chicago. These tracks are surrounded by skyline and it is one of the best ways to feel the city vibes. This L runs throughout the city and comes under the public transportation system.
- Grab a seat at Chicago Shakespeare Theatre or at Chicago Teater Chase. I was invited for the wonderful Wizard of Oz show by Chicago Shakespeare Theater and it was really wonderful.
- Admire the murals or street art on Magnificent Mile or State street.
- Walk along the river or cross the bridges with beautiful views of the river.
How To Reach Chicago? | Best Things to do in Chicago City Tour – Chicago Travel Guide
By Air – Chicago’s International airport – O’Hare is one of the busiest airports in the world. All major national & international airlines connect Chicago.
By Rail – Amtrak train network connects this city with around 50 trains arriving and departing daily.
By Car – This city is connected through wide Interstates & highways like I-90, I-94, I-55, I-210, and I-294.
By Bus – You can also reach here by buses from Greybound lines, Peoria Charter from nearby counties and Mega bus lines.
How To Commute In Chicago? | Best Things to do in Chicago City Tour – Chicago Travel Guide
By foot, Taxis / Uber, Public transportation from CTA/ RTA. The public transport comprises of 8 rail lines across the city which are L, 200 buses and 11 Metra lines from suburbs.
You can also purchase 1 day, 3 Day or 7 Day CTA pass for unlimited bus and L rides. Many people hire bikes to move around the city. Click here to check your routes and pass details on CTA’s official website.
You can also take Hop On Hop Off Big Bus tours which showcase all best attractions in their whole day trip. Also they organize night tours too. Big Bus tours are very convenient and I found it very interesting as they have live commentary by friendly guides who use to tell some interesting facts and history of the city.
Avoid self-drive as parking can be a hassle. If you are bringing your car, then find the nearby affordable parking slots through Spot On App.
What To Eat & Drink In Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide
- Deep Dish Chicago styled Pizza especially at Lou Malnati’s and Giordano’s Pizza. Your visit to this city is incomplete if you don’t taste these special deep crust or stuffed crust pizzas from Lou Malnati’s or Giordano’s.
- Gourmet flavored Popcorn.
- This city is also famous for craft breweries and so lot many options to have craft beer.
- Tap water is safe for drinking.
- As this city is foodie heaven you will find cuisines from all over the world. There are more than 7300 restaurants and in which 22 of them are Michellein Starred ones.
Where To Stay in Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide
I stayed at 2 locations to feel the different feel of the city. My choices are
EMBASSY SUITES BY HILTON DOWNTOWN – Click here to book your stay at Embassy Suites.
Positives of Embassy Suites
- Lavish Breakfast Buffet
- Lavish complimentary evening Happy Hours spread
- Big room size
- Close proximity to many restaurants as it is located on the famous restaurant street of Chicago
WYNDHAM GRAND CHICAGO RIVERFRONT – Click here to book your stay at Wyndham Grand.
Positives of Wyndham Grand Chicago Riverfront
- View of the river from the room
- Located in a prime location with many famous attractions at a walkable distance
When is the best time to visit Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide
- The best time to visit Chicago is from late Springs (late April) through Fall (mid-October).
- May, June and July are peak seasons with many tourists and outdoor events. Summer is the peak season
- In April, August, September, and October the crowd is manageable and you will find hotels in good rates too.
- Afterward, the weather is extreme cold by falling down to -6 degrees Celsius. This extreme cold slowly starts from November and then gear up from December to March-end. If you love snow, festive markets of Christmas then December is the ideal month to visit. You will find many Germany styled festive Christmas markets and can go for ice skating too.
Where To Shop in Chicago? Best Things to do in Chicago City Tour – Chicago Travel Guide
- Take a look at shopping street of Magnificent Mile, Macy’s at State Street, Burlington’s at downtown, Bloomingdale’s.
- Daily and essential needs can be bought from Walgreens and 7-Eleven grocery stores.
- If you are driving or renting a car then go for the premium factory outlet malls for high-end brand shops at affordable range. For this you have to drive to the suburb of Aurora which houses Chicago Premium Outlet Mall and you will find all big brands here like Coach, Michael Kors, Tommy Hilfiger, Calvin Klein, Nautica, Timberland, Columbia, Nike, Adidas, Crocs and many more.
TIPS FOR FIRST TIMERS IN CHICAGO | PLAN YOUR CHICAGO TRIP
- If you are visiting both the Observatory decks, museums, aquarium, and planetarium then purchase CityPass as it costs 108USD for Adults and 89USD for Children. Then this pass will be a money savior option with time-saving too at many places due to skipping of queues.
- Book your stay near the Downtown, Magnificent Mile or State Street.
- This is a windy city, so be prepared for it by carrying a light jacket with you.
- As many places can be done by walking tours, and the gardens are also widespread, you have to walk a lot and therefore wear comfortable footwear.
- Chicago is safe with normal precautions to take. Their touristy locations are very safe but some suburbs of south Chicago which are residential are not safe.
- People of this city are welcoming and soft-spoken. Families traveling with children will find this city very enjoyable.
- Try the famous local food.
- Take a river or lake cruise.
- If you are renting a car then select pickup of a rented car from Airport as it is a very cost-effective option.
- Chicago Tourism is classified or categorized into
- Architectures tours,
- Museum Tours,
- Nature – Parks / Gardens tours,
- Lake / River Tours, Food & Culture Tours, and
- Sports / Dance Music Festival tours.
You can select as per your choice and as per my recommendation do at least one activity from each category.
NIGHTCLUBS OF CHICAGO – BEST THINGS ABOUT CHICAGO
- Chi Bar
- Redhead Piano Bar
- House of Blues
- Kingston Mines
- Bub City
- The Bassment
FAMOUS FESTIVALS OF CHICAGO – BEST THINGS ABOUT CHICAGO
Chicago is an event and festival city. And so you can find many events or festivals all year round. Check more events and shows on by clicking here.
- World-famous Taste of Chicago
- Chicago Blues Festival
- Chicago Jazz Festival
- Wells Street Art Festival
- Glencoe Festival of Art
- Chicago International Film Festival
- Chicago Gourmet
FACTS ABOUT CHICAGO – Best of Chicago
- This city consists of 77 neighborhoods.
- What do you mean by Chicago? – Pottawatawine Native Americans used to live here before any explorers came to this part. They used to call this land as “Shikaakwa” which means a smelly onion. They named it on smelly onion as this land was a big swamp before and was very smelly. After the arrival of French explorers, traders & missionaries in the late 17th century this land further developed into a city but was named after “Shikaakwa” to “Chicago”.
- This city has the only unique river which flows backward in the world. Chicago River is flown backward by the reversal technique to divert the sewage away.
- First Blood Bank of the USA was founded here and also the first open-heart surgery of the world took place here.
- The Great Chicago Fire of 1871 which ran across 3 days whose initial spark is still unknown devasted the whole city as the buildings were made up of wood. But after 19th century this city rebuilt with new building materials and techniques which can survive such disasters too. And withing 20 years this city created a beautiful skyline which matches the world-class standards.
- It is the home to world-famous architects who have designed many of the world’s tallest buildings.
- Many Hollywood films have been shot here. Also a Bollywood film – Dhoom 3 starring Aamir Khan and Abhishek Bachchan have been shot here.
My Chicago City Tour Itinerary
DAY 1 – Late evening arrival – Took a stroll across the restaurant street and due to some jetlag gone for sleep early.
DAY 2 – Started Chicago city tour by Chicago Big Bus tours (started early)
Willis Tower Observatory Deck
Late Afternoon till Evening took River Architecture Cruise
DAY 3 – Early morning start – Headed to 360 Chicago Observatory Deck
Then proceeded to Shedd Aquarium
After having lunch at Shedd Aquarium with a view, returned back to Chicago Architecture Center for Exhibits tour displaying models of many famous buildings of the world and Chicago city designs.
DAY 4 – Riverwalk in the morning
Strolling across Magnificent Mile
As I was invited by Chicago Food Planet for taking a food tour, so done a 3 hours food tour with them.
Evening at Downtown, Loop and again shopping at Magnificent Mile. All done by walking tours.
DAY 5 – Morning at Navy Pier.
Lunch at Navy Pier
Attended Play – “The Wizard of Oz” at Chicago Shakespeare Theater
Shopping at Downtown
Dinner at famous Giordano’s Pizzeria (At Giordano’s there is always a waiting of 30 to 40 minutes and always it is full of people). There are many Giordano’s Pizza outlets in the city.
DAY 6 – Early morning headed to car renting outlet at International Airport and then proceeded to Aurora for Chicago Premium Outlet Mall and then proceed to explore Illinois state and its counties like Urbana, Champaign, Peoria, and capital city – Springfield.
Now it is very long and so after this virtual tour do let me know about how this city excites you? I would love to know your candid views in the comments below. Also use hashtag #ChicagoHome with your lovely photos in this beautiful city on your social media network.
Are you in Illinois, then visit beautiful county Champaign which is 130 to 140 miles away from Chicago.
If you are on USA trip then read these guides for
- East Coast Road Trip.
- Visit Niagara Falls.
- New York City Tour.
- Washington City Tour.
- Visit Philly (Philadelphia).
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