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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.

 

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Chicago Architecture River Cruise

Chicago Architecture River Cruise

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branc

Location : Chicago

Starting from2014

EMI starts at 179.88 per month

Chicago Prohibition Tour

Chicago Prohibition Tour

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the sale of alcohol was banned for more than

Location : Chicago

Starting from2889

EMI starts at 258.04 per month

Chicago Segway Tour

Chicago Segway Tour

Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham Fountain, Navy Pier, Lake Michigan and

Location : Chicago

Starting from4953

EMI starts at 442.39 per month

Skydeck Chicago Admission

Skydeck Chicago Admission

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers s

Location : Chicago

Starting from1327

EMI starts at 118.52 per month

Chicago Crime and Mob Tour

Chicago Crime and Mob Tour

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s criminal underworld as you investigate sto

Location : Chicago

Starting from2437

EMI starts at 217.67 per month

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

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-day tour is the perfect introduction to the Windy City. Visit the highlights of the North Side and

Location : Chicago

Starting from4452

EMI starts at 397.64 per month

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

Admire all of Chicago's fabulous lakefront sights and attractions on this 40-minute Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from

Location : Chicago

Starting from1006

EMI starts at 89.85 per month

Tommy Gun

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 you'll be transported back to the roaring twenties. You'll be entertained by gangsters and flapper

Location : Chicago

Starting from4623

EMI starts at 412.91 per month

Chicago Style Food Tour

Chicago Style Food Tour

Confused on what to see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond. Combine them all by tantalizing all of you

Location : Chicago

Starting from3634

EMI starts at 324.58 per month

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

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 buildings in the design-rich city. Appreciate the interiors of the Marshall Fields Building, Chase To

Location : Chicago

Starting from1781

EMI starts at 159.07 per month

Chicago Grand Half-Day Tour

Chicago Grand Half-Day Tour

This comprehensive half-day tour of Chicago is the perfect introduction to the Windy City! Discover the highlights of Chicago’s North Side and South Side and enjoy a scenic drive along the Outer

Location : Chicago

Starting from3168

EMI starts at 282.96 per month

Chicago Architectural River Cruise

Chicago Architectural River Cruise

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.

Location : Chicago

Starting from3298

EMI starts at 294.57 per month

Chicago City Sights Helicopter Tour

Chicago City Sights Helicopter Tour

Experience all of Chicago’s best sights from the air on this exciting helicopter tour! Aboard a state-of-the-art helicopter, you'll enjoy a magnificent view of Lake Michigan and fly past several top C

Location : Chicago

Starting from10205

EMI starts at 911.48 per month

Willis Tower Skydeck Dinner

Willis Tower Skydeck Dinner

Enjoy a VIP dinner at Chicago’s Skydeck where you get breathtaking views of the city. Located in the Willis Tower, the Skydeck perches 1,353 feet (412 meters). Your evening includes your choice of a c

Location : Chicago

Starting from8561

EMI starts at 764.64 per month

Blue Man Group at the Briar Street Theater in Chicago

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 downtown Chicago. The phenomenon that has visited cities around the globe is integrating new technology i

Location : Chicago

Starting from5021

EMI starts at 448.46 per month

Chicago by Night Helicopter Tour

Chicago by Night Helicopter Tour

Watch the Chicago skyline sparkle from the air on this thrilling nighttime helicopter tour! Aboard a heated, state-of-the-art helicopter, soak in amazing views of Lake Michigan and fly past several Ch

Location : Chicago

Starting from10205

EMI starts at 911.48 per month

360 Chicago Observation Deck (formerly John Hancock Observatory) Admission

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 above the Windy City, the 360 Chicago provides commanding views of Lake Michigan and Chicago’s towe

Location : Chicago

Starting from1241

EMI starts at 110.84 per month

Chicago Lakefront Neighborhoods Bicycle Tour

Chicago Lakefront Neighborhoods Bicycle Tour

See Chicago off the tourist beat on this guided bicycle tour. Your expert local guide will lead you to Chicago’s best quiet neighborhood streets, city parks and scenic beaches on the North Side of

Location : Chicago

Starting from2972

EMI starts at 265.45 per month

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful political history. Explore the Windy City at your own pace during a hop-on hop-off bus tour

Location : Chicago

Starting from1452

EMI starts at 129.69 per month

Chicago Explorer Pass

Chicago Explorer Pass

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 42% on ticket prices. This multi-attraction pass, valid for 30 days after your first use, provides admission to your

Location : Chicago

Starting from4861

EMI starts at 434.17 per month

Famous Tastes of Chicago Food Tour

Famous Tastes of Chicago Food Tour

What should a visitor see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond that it can often be hard to decide where

Location : Chicago

Starting from3634

EMI starts at 324.58 per month

Lake Michigan and Chicago River Architecture Cruise by Speedboat

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 is on a cruise on the Chicago River! You'll learn all about Chicago's history and landmarks befor

Location : Chicago

Starting from2569

EMI starts at 229.46 per month

Chicago Urban Adventure Cruise

Chicago Urban Adventure Cruise

This popular 1.5-hour daytime river and lake tour, the Urban Adventure Cruise, delights families of all ages with incredible views of Chicago's world-renowned architecture and stunning skyline. Lively

Location : Chicago

Starting from2397

EMI starts at 214.09 per month

Art Institute of Chicago Fast Pass Admission

Art Institute of Chicago Fast Pass Admission

Art lover or not, the Art Institute of Chicago – the second-largest art museum in America – is not to be missed. Located in Chicago’s Grant Park, this amazing museum features an extraordinary collecti

Location : Chicago

Starting from2248

EMI starts at 200.78 per month

Chicago Odyssey Dinner Cruise

Chicago Odyssey Dinner Cruise

Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior.

Location : Chicago

Starting from5290

EMI starts at 472.49 per month

Chicago Crime and Pizza Walk

Chicago Crime and Pizza Walk

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

Location : Chicago

Starting from3050

EMI starts at 272.42 per month

Chicago Pizza and Beer Tour

Chicago Pizza and Beer Tour

On this Chicago pizza-tasting tour with a friendly guide, visit four local pizzerias to try Chicago’s famous pizza and relax over cold beer or fine wine. Travel by comfortable mini-coach through city

Location : Chicago

Starting from5137

EMI starts at 458.82 per month

Spirit of Chicago Sunset Dinner Cruise with Buffet

Spirit of Chicago Sunset Dinner Cruise with Buffet

Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Field and more while y

Location : Chicago

Starting from6512

EMI starts at 581.63 per month

Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs

Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs

Experience Chicago on a walking and food tour of the central business district. Visits to legendary sites such as Palmer House Hotel, Marshall Field’s Building, and Millennium Park are punctuated by s

Location : Chicago

Starting from3409

EMI starts at 304.48 per month

Chicago City Tour with Optional River Cruise

Chicago City Tour with Optional River Cruise

Don’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at

Location : Chicago

Starting from2248

EMI starts at 200.78 per month


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.