2 Days in Chicago

20 Must-See sights
2 days
from $307


If giants ever lived on the planet, this would be their birthplace. With so many skyscrapers around you can’t help admiring the skyline and scenic views of Chicago.

Enjoy the 2 days of towers, bridges, parks and all kinds of art Chicago can offer. 


*The itinerary depends on how many stops you want to make during the tour, and may be revised.

*The tour can be modified to meet your preferences.


Day 1

1. Magnificent Mile

2. John Hancock Center

3. Historic Water Tower

4. Holy Name Cathedral

5. Wrigley Building

6. Tribune Tower

7. DuSable Bridge

8. Chicago Riverwalk

9. Lake Point Tower

10. Navy Pier


Day 2

11. Loop

12. Willis Tower

13. Monadnock Building

14. Flamingo Sculpture

15. Chagall’s mosaics

16. Picasso Statue

17. Grand Park

18. Millenium Park

19. Cloud Gate

20. Crown Fountain


  • 2-days Chicago city tour with your friendly local guide;
  • Exploring more than 20 main attractions in Chicago;
  • Get acquainted with public art in the streets of Chicago;
  • Relax at Chicago’s parks;
  • Walk along luxurious Magnificent Mile;
  • Admire the most remarkable skyscrapers;
  • Visit the main cathedral of the city;
  • Look at the reflection of Chicago in Cloud Gate;
  • See photos of Chicagoans streaming water from their mouths;
  • Feel the hustle and bustle of the Loop.

Tour Itinerary:

Day 1

Magnificent Mile

More than 460 shops, 275 restaurants, more than 50 hotels – the most luxurious and the most expensive. This is the Magnificent Mile – the most swanky and stylish neighborhood of Chicago. It also has the highest concentration of the tallest skyscrapers in the USA and has many awards as one of the most beautiful, the most expensive and the best street for shopping. All the best is here!

John Hancock Center

One of the highlights of the Magnificent Mile, 100-floor John Hancock Center is considered the 7th highest building in the USA. This elegant construction is an excellent example of 20th century architecture of skyscrapers. The most interesting places inside the Center are: observation deck with unforgettable view, the restaurant with panoramic windows, the highest swimming pool and ice-rink in the world.

Historic Water Tower

Built in 1869 in neo-gothic style, the Water Tower makes a bright contrast with contemporary buildings around and looks like a European medieval castle. The Tower is one of the most significant Chicago’s attractions due to its historical value and your private guide will tell you some interesting facts about this monument. Inside you can find exhibition of local photographers.

Holy Name Cathedral

Another historical monument of Chicago is the city’s main cathedral. The 46-m tall cathedral can accommodate more than 2000 visitors. All the most important religious events of Chicago take place here. The neo-gothic Cathedral impresses with its beauty both outside and inside, having a rich interior with bronze statues and colorful stained-glass windows.

Wrigley Building

Deservedly admitted one of the most beautiful buildings in Chicago, the Wrigley building will dazzle you with its whiteness and beauty. The building consists of two sections connected by passage. The higher section is 134-m tall and is decorated with sophisticated clock. Built in 1924, nowadays Wrigley building saves its historical value and combines it with high technologies which make the building comfortable for more than 3000 people working in offices here. 

Tribune Tower

Built in 1925, this skyscraper was meant to be a home for a headquarter of the Tribune Newspaper. Nowadays the newspaper still has an office here and the building delights tourists and Chicagoans with its original architecture. Due to gothic elements, the 141-m tall Tribune Tower seems to rise endlessly to the sky. Besides beautiful architecture here you can see unique collection of stones taken from the most world-famous monuments such as Taj-Mahal or the Great Wall of China.

DuSable Bridge

To get to another bank of Chicago River we will cross a very remarkable 122-m long DuSable (or North Michigan) Bridge. Built in 1920, it became the first duplex bridge in the world. This drawbridge is lifted in 8 min to let the high boats go by. The bridge is decorated by two towers with beautiful bas-reliefs. One of the towers houses a historical museum of Chicago River.

Chicago Riverwalk

Chicago is the city which can definitely be proud of its stunning embankment. The southern bank of Chicago River was made to be a large pedestrian area where people can walk and have a good time. The area is decorated with nice green plants and offers plenty of different entertainments. But, of course, the highlight here is a gorgeous view of Chicago River and magnificent skyscrapers rising above the city and reflecting in the water. Unforgettable scene!

Lake Point Tower

 197-m tall Lake Point Tower is quite distant from other Chicago’s skyscrapers and rises above the city and Lake Michigan. That’s why it will surely attract your attention. Housing numerous apartments, this building is considered to be a very prestigious place to live. Locals come here to take photos of this stylish construction loved by everybody who sees it.

Navy Pier

Being more than 1-km long, the Navy Pier is a place with high concentration of fun things to do and scenic views of Lake Michigan. It attracts millions of people every year coming here to experience this magic place: from visiting exhibitions or cultural events to flying a balloon and taking part in water race. The great time is guaranteed when you are at Navy Pier.

Take your time to explore the place. Take a photo with a statue of the Captain, visit Crystal Garden or Smith Museum with stunning collection of stained glass windows. Don’t miss a chance to ride a legendary 45-m high Ferris Wheel and see fantastic views of Chicago.

Day 2


Let’s start our day with immersing into bustling atmosphere of business Chicago. Loop district is the center of business, finance and commerce of the whole Illinois. Numerous offices of influential companies located in high skyscrapers create bustling and lively atmosphere of Chicago. But despite this energetic rhythm Loop is a great place to walk, explore Chicago and spend a nice time in some entertaining places.

Willis Tower

Completed in 1974, this strict and majestic skyscraper became the highest building in the world and was keeping this record for 25 years. Nowadays Willis Tower is in the list of Top-11 world’s highest buildings. It feels simply breathtaking to stand near this legend! Take memorable photos of the Tower and if you have more time in Chicago we advise to go up to observation deck which opens amazing views.

Monadnock Building

Although this 60-m high building is not so tall as many other Chicago constructions, it is definitely a must-see attraction.  When it was built in 1873, Monadnock became the largest office building in the world for that moment. Made of dark brown bricks, it attracts everyone was its simplicity and elegance and houses hundreds of offices of famous brands.

Flamingo Sculpture

It’s not a secret that Chicago has a status of the city of public art: wherever you go in Chicago, you will surely see plenty of interesting installations and sculptures in the streets. One of such original city’s jewels is a 16-m tall Sculpture of Flamingo located in Federal Plaza and created by famous sculptor Alexander Calder. Painted in bright red color, this abstract sculpture looks very remarkable and impressive making a contrast with dark skyscrapers around.

Chagall’s Mosaics

Another art treasure which can be seen in Chicago streets is famous mosaics of Mark Chagall. This masterpiece is called “Four seasons” and occupies the area of 280 sq.m. near the building of the First National Bank of Chicago. Thousands of pieces of colorful glass and stones create an extremely picturesque scene and add color and brightness to Chicago’s landscape.

Picasso Statue

As you have already understood, in Chicago you don’t necessarily need to visit museums in order to see famous pieces of art. One of the main proofs of it is untitled Picasso Statue which is installed in Daley Plaza. The cost of its creation is more than 350 000 $. Picasso didn’t take any money for his work and just wanted to make a gift to people of Chicago. The master has never told what his sculpture meant so you should use your own imagination.

Grand Park

The “Green heart” of Chicago, Grand Park occupies the area of 1,29 sq.km. The huge green area is located between Michigan Avenue and waterfront of Lake Michigan. This Park is loved by both locals and tourists and for a good reason: the beauty of nature, famous attractions such as magnificent Buckingham Fountain or a collection of sculptures called Agora, and plenty of fun things to do will make you want to stay in the park for whole day!

Millenium Park

Opened in 2004, Millenium Park immediately became one of the most-visited attractions in Chicago. It also has numerous awards for its unique design, beautiful landscape and accessibility for public. Millenium Park is a perfect place to relax, enjoy calm atmosphere in the center of busy Chicago and explore plenty of original attractions and open-air exhibitions.

Cloud Gate

Now prepare your cameras because we are going to see one of the most popular places for photoshooting in Chicago. The 10-m high sculpture called “Cloud Gate” is made of perfectly polished steel and plays a role of a huge mirror which reflects all the scene. It will fascinate you with its simplicity and originality at the same time!

Crown Fountain

During our Chicago tour we can’t skip one of the most unique fountains in the world. The Crown Fountain is the masterpiece of technologies and creativity. Two 15-m tall towers show photos of Chicago residents which stream water in large basin of black marble every 5 min. This scene looks very exciting!


  • * The itinerary is subject to change


Extra costs (per person):

Entrance fees


Activity Level: moderate
Maximum travelers: 5
Meet up & End location: lobby of your hotel
Start time: any time
Extra hours: If you are having a good time and want your Chicago 2-day tour last a little bit longer, you are welcome to do that. Please note: You will be charged 25 USD per an extra hour.
Tipping suggestions: If you feel like you had a good experience, your guide would appreciate a tip. It's not mandatory. It's your decision whether you want to give your guide a tip.

What you get:

  • + A friend in Chicago.
  • + Private & customized tour.
  • + An exciting pastime, not just boring history lessons.
  • + An authentic experience of local life.
  • + Flexibility during the tour: changes can be made at any time to suit individual preferences.
  • + Amazing deals for breakfast, lunch, and dinner in the very best cafes & restaurants. 
  • + A photo session amongst spectacular Chicago scenery that can be treasured for a lifetime.
  • + An expert advice on what to do, where to go, and how to make the most of your time.

*This two-day tour in Chicago can be modified to meet your preferences.