Best Chicago Itinerary 4 days – Things To Do This Weekend

Read about Chicago Itinerary 4 days with the best things to do in Chicago city tour.

Chicago – the third biggest city in the United States of America (USA), is one of the world’s great cities to visit, with so many beautiful attractions. The splendid skyline on freshwater Lake Michigan will enchant you with its vibrant & lively city life, cultural happenings, architectural wonders, charming neighborhoods, delicious food, and fascinating history.

This city is perfect for all ages and interests as it has many 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. Due to its historic location on Big Route 66 of US, Chicago is also the famous historic city that is worth visiting too. So let’s take a virtual tour of the 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 Itinerary 4 Days – Best Things to do in Chicago City Tour 

WILLIS TOWER

A 110-story skyscraper was the tallest building once upon a time and has held its title for about 25 years.  Currently, this is the 2^nd tallest tower in the USA and the 16^th tallest in the world. Designed by famous architect Adrian Smith who is known for designing the famous tallest buildings like Burj Khalifa(Dubai) too. 

Step onto its 103^rd floor, an Observatory Deck, also known as The SkyDeck Chicago, for the splendid views of the city. There are unique 4ft extended transparent glass balconies on this floor where you can feel hanging in the air above the ground from the 103^rd floor and observe the city under your feet.

Opens 365 days a year

MILLENNIUM PARK

A public park within the Loop area is the most famous among Chicagoans. This park is situated in the heart of downtown and always hosts many events, farmer markets on special days, greenery, and art / sculptural displays; it is like the town square of Chicago. This spectacular gathering point is surrounded by a beautiful skyline, like an oasis within the concrete cityscape. In winter, during snowy times, this park converts into a beautiful ice rink for skating around.

Visit Millennium Park is highly recommended in your Chicago itinerary 4 days tour.

TICKETS – Free to Enter

THE BEAN

A wonderful mirror-finished steel sculpture that looks like a drop of mercury is located in Millennium Park and is 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. Due to its curvature and fine polish, you can see many distorted and multiple versions of the city skyline in this sculpture.

This sculpture was the result of one of the design competitions 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 the same as mirror house effects.

CROWN FOUNTAIN

Two massive 50-foot glass towers face 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 a 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 multimedia display from both sides, and it looks like a person is throwing water from their mouth.

JOHN HANCOCK CENTER (360 CHICAGO)

From 1000 feet above the ground, on the 94^th floor, enjoy the splendid views of Lake Michigan and stunning city views with an adorable skyline from the top. At present this is the 4^th tallest building in Chicago and 9^th tallest in the USA. This residential building houses many hotels & offices too, and it is the 3^rd 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 picture of the distance to 80 miles on a clear day.

It is open 365 days a year.

TILT EXPERIENCE

Here you can also feel the most unique and thrilling experience of the world by feeling like you are falling down from the 94^th floor.  Tilt is the transparent whole façade windows where you have to hold the railings and stand to look down, and within a few seconds, this façade is tilted down to a certain angle and left in that position for a 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 in the tallest building in the world.

For the TILT experience, you must purchase separate tickets for 8 USD. Chicago Citypass holders get some discount for Tilt tickets.

CHICAGO SKYLINE

Admire the magnificent and world-famous Chicago skyline, which is also one of the world’s tallest skylines. This city skyline boasts of having four of America’s tallest buildings.

Where to get the best view of Chicago’s Skyline? – Chicago Itinerary 4 Days

• Solidarity Drive – Stretching from Grant Park to Adler Planetarium. This stretch has a lovely waterfront with small grass stretches 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 architecture across the Chicago River. With live commentary about these buildings and architects, you will sail across 40 iconic buildings and will get the opportunity to learn about Chicago’s history, how this city is built and rebuilt after the Great Fire, and also upcoming architectural growth in this city. 

You must be amazed to know the world-famous architects of many famous tallest buildings and who belong to Chicago. This cruise covers all three branches – Old Post Office Building, Willis Tower & East Bank Club. 

SHEDD AQUARIUM

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, the 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 a café / Restaurant for eating out with fantastic 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 in 1893 and has approximately 24 million exhibits from all over the world. It showcases rich cultural and historical exhibits from ancient civilizations like Egypt, Asia, Africa, and the ancient Americas. 

The central atrium of Stanley Field Hall welcomes you with a 37m Titanosaur, which is the key feature of this museum. For the last year 125 years, this museum has added precious exhibits every year. You can also grab a 3D show to feel how the displays are excavated or the story behind the exhibits.

ADLER PLANETARIUM

This was the first planetarium in the USA, which included an actual observatory. Located in Museum Campus, Grant Park, beside Lake Shore you get a chance to experience the Solar System, the history of telescopy, landing on the moon, and many varieties of shows.

WRIGLEY BUILDING

Located on the south of Magnificent Mile at Michigan Avenue, a white-colored iconic building of this city. It is one of the most famous buildings in Chicago. This clock tower is designed in per Gothic style and with intricate details on the limestone façade, which is a perfect classy example of architecture.

NAVY PIER

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, and event areas, and is one of the top family attractions in the Mid-West of the USA. 

It is also famous for its 65-meter Centennial Wheel and other amusement rides. In summer, you can also experience fireworks over the city skyline, which occurs twice a week. There are many cruise 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 that survived the Great Chicago Fire on October 8 – 10, 1871. These 3 days of fire burnt the whole city, but as this tower is made up of limestone, unlike other nearby wooden buildings, it has survived. It looks like a small castle, the second oldest water tower on the great Magnificent Mile.

CHICAGO LOOP

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.

Check Air Tickets to Chicago (Book your flight to 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

Where to stay in Chicago is a very important thing as this city has many beautiful locations with many hotel choices. During my Chicago city tour, 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 – Chicago City Tour

Chicago is an event and festival city. And so you can find many events or festivals all year round. Check out 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
• Lollapalooza
• 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 “Shikaakwa,” which means a smelly onion. They named it 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 17^th century, this land further developed into a city named after “Shikaakwa” to “Chicago.”
• This city has the only unique river which flows backward in the world. Chicago River is flown back by the reversal technique to divert the sewage away.
• The First Blood Bank of the USA was founded here, and the first open-heart surgery in the world took place here.
• The Great Chicago Fire of 1871, which ran across 3 days and whose initial spark is still unknown, devastated the whole city as the buildings were made of wood. But after the 19^th century, this city was rebuilt with new building materials and techniques, which can also survive such disasters. And within 20 years, this city created a beautiful skyline that matches 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, has been shot here.

Chicago Itinerary 4 Days

• DAY 1 – Late evening arrival – Took a stroll across the restaurant street and, due to some jetlag, went to sleep early.
• DAY 2 – Started Chicago city tour by Chicago Big Bus tours (started early)
• Lunch stop
• Willis Tower Observatory Deck
• Millennium Park
• From late Afternoon till Evening, I took River Architecture Cruise
• Had Dinner
• DAY 3 – Early morning start – Headed to 360 Chicago Observatory Deck
• Then proceeded to Shedd Aquarium
• Field Museum
• Alder Planetarium
• After having lunch at Shedd Aquarium with a view, I 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
• Take a Chicago food tour, a 3 hours food tour with the history of Chicago.
• 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 the famous Giordano’s Pizzeria (At Giordano’s there is always a waiting of 30 to 40 minutes and it is always 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 to explore Illinois state and its counties like Urbana, Champaign, Peoria, and the capital city – Springfield.

Now you how perfect a Chicago itinerary 4 days and do let me know 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. 

WATCH SOME INTERESTING FACTS ABOUT CHICAGO IN HINDI 

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

• Where to stay in Milwaukee.
• East Coast Road Trip.
• Visit Niagara Falls.
• New York City Tour.
• Washington City Tour.
• Visit Philly (Philadelphia).

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