Layover Tour in Chicago

Fast-paced tour
5 hours
from $187


We are not exactly sure how Chicago can combine the most beautiful places in the world and the most dreadful horror stories and legends.

If you have little time in the city, this tour will give you all you need – a bit of fun, a bit of culture and architecture and the most fascinating facts from the history of Chicago. 


1. North Michigan Avenue & Magnificent Mile

2. Holy Name Cathedral

3. Tribune Tower

4. Chicago Riverwalk

5. Chicago Theatre

6. Loop

7. Willis Tower

8. Millenium Park

9. Cloud Gate

10. Crown Fountain 


*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.


  • Private 5-hour Chicago tour with your friendly local guide;
  • Explore main Chicago’s attractions and things to do;
  • Admire the majesty of one of the highest buildings in the world;
  • Enjoy stunning urban scene while strolling along Chicago Riverwalk;
  • Feel the city vibe in Loop district;
  • Walk along one of the most expensive shopping streets;
  • See the legendary Chicago theatre;
  • Relax and discover original attractions at Millenium Park;
  • Take photos of the unique Cloud Gate.

Tour Itinerary:

North Michigan Avenue & Magnificent Mile

One of the best places to start our exploration of Chicago and to immerse in the atmosphere of this city is undoubtedly the Northern part of Michigan Avenue – the main artery of Chicago. The area around the Avenue is called the Magnificent Mile. And when you see this place you will understand why: this is the most luxurious and the most elegant part of the city. The area of 290000 sq.m is full of high-class boutiques, restaurants and hotels. By the way, 5 of the 85 highest buildings in the world are located here, in the Magnificent Mile, which is also considered one of the world’s 10 best shopping streets.

Holy Name Cathedral

Now let’s make sure that Chicago is the city not only of skyscrapers but also of historical monuments with old architecture and rich history. Just near the Magnificent Mile you will find Holy Name Cathedral which is the most significant religious monument of Chicago and home to the one of the largest Catholic dioceses in the USA. This Cathedral was built after destructive Great Chicago Fire of 1871. The Cathedral is built in Gothic Revival style and has extremely beautiful interior. Massive bronze doors, red-black altar, monumental bishop’s throne and two sophisticated organs create a very sacramental atmosphere.

Tribune Tower

Just at the end of North Michigan Avenue you will notice one eye-catching building called Tribune Tower. This famous skyscraper was built in 1925 in Neo-Gothic style and has an interesting combination of contemporary architecture and gothic bas-reliefs and spires. Tribune Tower has a height of 141 meters and is home to influential “Chicago Tribune” newspaper. If you come closer to the base of skyscraper you will have a unique chance to see the collection of stones taken from the most famous world’s monuments such as Parthenon, Coliseum and the Pyramids. See the pieces of architectural legends all in one place!

Chicago Riverwalk

How pleasant it is – to have a promenade along picturesque embankment of Chicago river and enjoy a wonderful scenery of the city. Majestic skyscrapers, beautiful riverside, bridges, boats going along the river… All of it creates the unique image of Chicago which makes people fall in love with the city. Chicago Riverwalk is a perfect place to stroll, please your eye with beautiful landscape, just relax and observe local life. And of course prepare your cameras because the views you will see are gorgeous!

Chicago Theatre

Built in 1921, Chicago Theatre immediately became the center of Chicago’s cultural life. It’s a place for glorious theatre performances, shows, comedies and concerts. The theatre can accommodate more than 3000 spectators and is highly popular among both demanding judges of art and curious visitors. The rich interior, neo-baroque architecture and bright facade with sparkling signboard will make you feel like you are in America of 1920s.


And now we are going to explore the heart of Chicago – Loop district. It is a business, financial and political center not only of Chicago but also of the whole Illinois state. Loop provides almost 50% of the city’s office space. Magnificent skyscrapers, bustling streets, business and endless energy – this is the image of Loop. But you will find out that Loop is also a great place for shopping, eating and having a drink. Moreover, housing numerous museums, galleries, theatres, it is also perfect for exploring Chicago’s cultural life. The variety of things to do in Loop is infinite because this district has everything you want!

Willis Tower

#1 among the highest buildings in Chicago, #2 among the highest buildings in the USA, #11 among the highest buildings in the world. Do you want to see it? We guarantee that you will get impressed with the majesty of this 443-m tall skyscraper. If you have more free time in Chicago, it’s a must-do thing for you to visit the observation deck on 103rd floor which opens fantastic views of the city. 

Millenium Park

And though Chicago is an urbanistic megapolis, it has plenty of green zones. One of the most popular is Millenium Park which is a most-visited tourist attraction in Chicago. The area of 99000 sq.m. provides anything you want for having a nice time: beautiful green plants, cafes and restaurants and lots of unusual contemporary constructions such as Cloud Gate and Pedestrian Bridge. Millenium Park will surely give you unforgettable emotions.

Cloud Gate

One of the highlights of Millenium Park is a very unusual sculpture which became one of the world's most popular tourist attractions. The Cloud Gate (it is also called “The Bean” due to its shape) is made of 168 sheets of steel polished to perfection. That’s why the 10-tones sculpture reflects all the area around including Millenium Park and Chicago’s skyscrapers. The Cloud Gate is considered to be the most photographed Chicago’s attraction and one of the city symbols.

Crown Fountain

If you associate fountains only with water stream, this fountain will change your impression of fountain conceptions and will surprise you by its originality. Due to high technologies this interactive fountain shows faces of Chicagoans whose mouths stream water. Crown fountain is surely must-see attraction in Chicago because there is no analogue of it anywhere else. It’s a favourite place for tourists wanting to take pictures of it and a popular meeting point for locals. By the way, the creation and design of this fountain cost 17 million dollars. Well… come and see if it was worth it!


Don’t hurry to leave Millenium Park after the end of our tour. Take your time and explore this wonderful area which has many interesting things to show you. Check out Chicago Cultural Center, Field Museum, Art Institute and famous Chicago’s Aquarium and Planetarium. 


  • * 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 private Chicago 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 layover tour of Chicago can be modified to meet your preferences.