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Chicago - Sightseeing Tours and Activities

You will never run out of top things to do in Chicago since there are always fun and exciting activities to try. The best thing about it is that it has sightseeing tours and activities for everyone, no matter what their interests are. Artists and architects will find themselves lost in a sea of galleries, public art displays, and architectural wonders. Music fans, on the other hand, can choose from around 200 festivals and other events that feature the latest and the greatest artists. Even foodies will find themselves spoiled for choice: the Windy City is home to traditional American fare and ethnic dishes, and there are many different ways to tickle your taste buds.

 

Chicago Segway Tour

Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very ...

Location: Chicago

Starting from 4960

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

Take a tour of Chicago and visit the 360 Chicago (John Hancock Observatory)! This comprehensive half...

Location: Chicago

Starting from 4373

Chicago Crime and Mob Tour

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Ch...

Location: Chicago

Starting from 2466

Private & Custom Tours See All

Private Chicago Highlights Driving Tour

See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt ar...

Location: Chicago

Starting from 6790

Private Sunset Sails

Sailing Chicago's beautiful lakefront offers an experience not to be missed and views of the skyline...

Location: Chicago

Starting from 26577

Private Fireworks Cruise

Sailing Chicago's beautiful lakefront offers an experience not to be missed and views of the skyline...

Location: Chicago

Starting from 26577

Chicago Airport Roundtrip Transfer

Travel in comfort from the airport to your downtown Chicago hotel and back again with a Chicago Airp...

Location: Chicago

Starting from 3494

Private Arrival Transfer: Chicago Airport to Downtown Chicago

Why stress about finding a taxi at Chicago's busy airports when you can book a private car in advanc...

Location: Chicago

Starting from 1143

Private Departure Transfer: Downtown Chicago to Chicago Airport

Why stress waiting for unreliable taxis or bus transfers to Chicago's busy airport? Ensure peace of ...

Location: Chicago

Starting from 1143

Chicago Prohibition Tour

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour ...

Location: Chicago

Starting from 2893

Chicago Crime and Mob Tour

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Ch...

Location: Chicago

Starting from 2466

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark b...

Location: Chicago

Starting from 1783

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark b...

Location: Chicago

Starting from 1783

Chicago Lakefront Neighborhoods Bicycle Tour

See Chicago off the tourist beat on this guided bicycle tour. Your expert local guide will lead you ...

Location: Chicago

Starting from 2976

Chicago Crime and Pizza Walk

Explore Chicago's crime and pizza history on this two-hour walking tour through the River North and ...

Location: Chicago

Starting from 3215

Skydeck Chicago Admission

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of W...

Location: Chicago

Starting from 1329

Chicago CityPASS

Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the ...

Location: Chicago

Starting from 6842

360 Chicago Observation Deck (formerly John Hancock Observatory) Admission

The best views of Chicago can be yours at 360 Chicago (John Hancock Observatory)! Perched 94 stories...

Location: Chicago

Starting from 1243

Air, Helicopter & Balloon Tours See All

Chicago City Sights Helicopter Tour

Experience all of Chicago’s best sights from the air on this exciting helicopter tour! Aboard a stat...

Location: Chicago

Starting from 10220

Chicago by Night Helicopter Tour

Watch the Chicago skyline sparkle from the air on this thrilling nighttime helicopter tour! Aboard a...

Location: Chicago

Starting from 10220

Chicago Helicopter Tour Nighttime Experience

Experience the big city lights of Chicago on a 20-minute helicopter ride over the Windy City. Depart...

Location: Chicago

Starting from 10288

LEGOLAND Discovery Center Chicago

LEGOLAND® Discovery Center, a giant indoor LEGO world designed for families with children aged 3 to ...

Location: Chicago

Starting from 972

Outdoor Activities See All

Chicago Tandem Skydive

With our brand new custom built 20,000sf facility, on-site Flight Deck Bar and Grill with beer garde...

Location: Chicago

Starting from 13116

Chicago Architecture River Cruise

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago Ri...

Location: Chicago

Starting from 2017

Chicago Architectural River Cruise

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city...

Location: Chicago

Starting from 3303

Chicago Odyssey Dinner Cruise

Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated,...

Location: Chicago

Starting from 5297

Chicago Architecture River Cruise

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago Ri...

Location: Chicago

Starting from 2017

Chicago CityPASS

Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the ...

Location: Chicago

Starting from 6842

Chicago Architectural River Cruise

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city...

Location: Chicago

Starting from 3303

Lake Michigan and Chicago River Architecture Cruise by Speedboat

Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it ...

Location: Chicago

Starting from 2573

Lake Michigan Speedboat Ride

Feel the need for speed? This exhilarating speedboat ride takes you out onto Lake Michigan for the r...

Location: Chicago

Starting from 1667

Chicago Prohibition Tour

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour ...

Location: Chicago

Starting from 2893

Chicago Style Food Tour

Confused on what to see and do while in Chicago? It goes without saying that the Windy City has it a...

Location: Chicago

Starting from 3639

Willis Tower Skydeck Dinner

Enjoy a VIP dinner at Chicago’s Skydeck where you get breathtaking views of the city. Located in the...

Location: Chicago

Starting from 8573

Tommy Gun's Garage Dinner and Show

Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and y...

Location: Chicago

Starting from 4630

Blue Man Group at the Briar Street Theater in Chicago

See the Blue Man Group, one of Chicago's longest running shows, at the Briar Street Theater in downt...

Location: Chicago

Starting from 4733

Tickets for Kiss Kiss Cabaret at Uptown Underground

Welcome to your night done right with Top Shelf Retrotainment from Chicago's Best in Burlesque and V...

Location: Chicago

Starting from 2058

Viator VIP & Exclusive Tours See All

Shopping & Fashion See All

Transfer to Chicago Premium Outlets

Chicago Premium Outlets is the premier shopping destination in the Chicago metro area. Home to over ...

Location: Chicago

Starting from 18518

Magnificent Mile Morning Walking Tour in Chicago

Discover the Magnificent Mile’s surprising story and learn about some of the city’s most iconic skys...

Location: Chicago

Starting from 4287

Mag Mile Walking Tour of Chicago

Chicago's Magnificent Mile represents the best of both shopping and sightseeing. During this tour, y...

Location: Chicago

Starting from 2058

Holiday & Seasonal Tours See All

Private Fireworks Cruise

Sailing Chicago's beautiful lakefront offers an experience not to be missed and views of the skyline...

Location: Chicago

Starting from 26577

Fright Hike: Halloween Edition Chicago Bike Tour

Join us we unleash our Halloween "Fright" Hike bike tour through the city of Chicago. Professional a...

Location: Chicago

Starting from 2625

Chicago Holiday Lights Tour by Segway

See Chicago all decked out in holiday lights on a Segway sightseeing tour of the Windy City’s ...

Location: Chicago

Starting from 4985

Chicago - Sightseeing Tours and Activities


The hub of the Midwest, Chicago, Illinois is the third-largest city in the US that is well known for jazz, blues, house music, comedy, dining, shopping, architecture and fine cultural attractions. It boasts of a picturesque skyline that calls across the waters of Lake Michigan and shows an impressive sight that reveals world-class museums, huge parks and miles of sandy beaches.

 

Sightseeing destinations in Chicago

The most visited part of the city is its large central area that covers neighborhoods, including the Downtown, Streeterville, River North, Old Town, Central Station, the Gold Coast, Printer's Row, the South Loop and Greek Town. Collectively, these areas contain many attractions, skyscrapers and highly ranked institutions. There are also many places of interest that you can find in its other districts—the North Side, South Side and the West Side. The neighborhoods here are strongly identified with their sense of culture and being homely.

 

Top tour activities in Chicago

Here are things to do during your trip to Chicago:  

  • Enjoy its beaches - With its five Great Lakes forming one of the largest masses of freshwater on the planet, you should enjoy Chicago’s beaches, especially Lake Michigan. You can swim there and enjoy the surroundings, with nearly the entire waterfront and its parkland open to the public.
  • Visit its parks - As mentioned above, the city’s beaches have waterfront parks, which are a hub for organized and impromptu volleyball, soccer, tennis, basketball and other activities, especially during the summer months. You can also find fantastic parks inland.
  • Go for a food trip - Chicago is one of the great restaurant towns in the US, which means that it is a terrific place to find a specific kind of cuisine. The Devon Ave Indian corridor, Greektown, Chatham and Chinatown are just some of the great places where you find satisfy your food cravings.

  

Top tour attractions in Chicago

To get the most out of your Chicago trip, make sure you include the following attractions in your itinerary:   

  • Art Institute of Chicago - This is a world-class museum that contains hundreds of thousands of artworks, including pieces dating back thousands of years such as paintings, prints, photographs, sculptures, textiles, decorative arts and architectural drawings. It is known for its collection of Impressionist and post-Impressionist paintings, including “A Sunday Afternoon on La Grand Jatte,” by Georges Seurat, “Acrobats at the Circque Fernando” by Renoir and numerous paintings by Claude Monet. 
  • Millennium Park - Located in downtown Chicago, this park features the Jay Pritzker Pavilion, the Crown Fountain, the Cloud Gate sculpture and the Lurie Garden.
  • Michigan Avenue and the Magnificent Mile - Michigan Avenue is regarded as one of the most attractive boulevards in the US, and here you will find the famous Magnificent Mile that covers numerous boutiques, galleries and luxury shops. Other attractions include the Wrigley Building, the John Hancock Center and the Tribune Tower.

  

Chicago sightseeing tours and activities

There are plenty more to see in this beautiful city, and to make sure you have the perfect itinerary for your trip here, check out all Chicago sightseeing tours and activities here at La Vacanza Travel.