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As with many cities in the northern United States, the best time of year to visit Chicago is May through October. The downtown area is divided into several neighborhoods consisting of "The Loop," South Loop, West Loop, River North and Old Town. Although walk-able in some respects, "The Loop" is about 1.5 square miles and that is just a small portion of the downtown area. If this is your first time visiting the "Windy City," we suggest purchasing tickets for a variety of Chicago tours that will help to navigate all the different neighborhoods and tourist attractions.


By far the most cost effective way to visit a variety of Chicago attractions is the CityPass. Many of the larger cities in the United States offer their unique version of a Go Card or CityPass, which often include discount admissions and FastPass entries. Chicago is no different. Visit some of the world's best museums and skyscrapers while saving time and money on your ticket purchases.

Recommended Chicago Tours

Land & River Tours

To experience the best of Chicago, it's essential to see the city from both perspectives. Boasting a half-day itinerary that covers all major points of interest in downtown Chicago, the land and river tour offers a comprehensive overview of the history, architecture and popular attractions that make the city a great vacation destination. While the land portion of the tour is informative and fun, most people like cruising the Chicago River and Lake Michigan even more. Make sure to get pictures during the river tour as you cruise by Trump Tower, The Civic Opera House and Wrigley Building. Take notice as you pass under several steel drawbridges, like the DuSable Bridge, which are so close you can almost touch them. All these impressively engineered structures make great backdrops for selfies and group photos.

Segway Tours

Chicago is home to several companies that operate all types of Segway tours that wind through Millennium Park, The Loop and Museum Campus. Although expensive for a large group or family compared to other options, Segway tours offer the speed of a bicycle without having to exercise! Chicago temperatures can climb into the 90s during the summer months, so if you're looking for a tour that will allow you to breeze through without a sweat, choose a Segway. Most itineraries last for about 90 minutes and offer insightful facts about the historic architecture and fun things to do while vacationing in the city.

Bike Tours

Chicago is one of the most bike-friendly cities in America. The most impressive attraction for cycle enthusiasts is the 22 mile Lake Shore Bike Trail. It spans from Edgewater Beach in the North to the Museum of Science and Industry on the Southside. Throughout the summer, thousands of people flock to the trail for exercise and tour opportunities. You can rent bicycles all over the city or catch up with an organized bike tour group.

Ghost Tours

One of the lesser-known tour opportunities in Chicago happens after nightfall. Some significant events in the history of Chicago have made it one of the most haunted places to visit in the Midwest. The Great Chicago Fire, The Eastland Disaster and The Iroquois Theatre fire have all contributed to making Chicago a hotbed for paranormal activity. There are several reputable ghost tour companies operating from downtown Chicago and many of them offer convenient pickup locations near popular hotels and intersections.

Top Rated Chicago Attractions


If you're afraid of heights, Chicago is probably not the best place to visit. The best Chicago attractions are located 1,000 feet above ground. The Hancock Building and Willis Tower both offer interactive experiences that will make you think twice about stepping close to the edge. Trump Tower offers a restaurant and bar on the 16th floor with great views of the Chicago River and Wrigley building. Looking to dine a little higher up? Check out the Signature Room on the 95th floor of the Hancock building. It boasts magnificent views of Lake Michigan and the city.


Second only to New York City, Chicago boasts some of the best museums in the United States. If you're an art lover, check out the Art Institute or Museum of Contemporary Art. The Art Institute is world-renowned for its incredible collections of classic masterpieces as well as unique artifacts. If it's natural history you crave, then a visit to the Field Museum is definitely in order. Several floors of ancient artifacts and collections center around a massive T-Rex named Sue. She�s an archeological masterpiece and a "must see" for any history buff.


When is the last time you visited a zoo for free? When you vacation in Chicago, check out the Lincoln Park Zoo. It's FREE! Supported by taxpayers and private donations, the Lincoln Park Zoo has hundreds of rare animals that rival some of the best collections in the world. Although many of the animals live inside during the winter, it's still open for Zoo Lights, a magnificent display of Christmas lights that twinkle in the night sky for several weeks in December. Looking for something even bigger? Check out Brookfield Zoo located about 45 minutes from downtown. It has everything you could ask for in a world-class zoo, including a Christmas light spectacle that is sure to get you in the holiday spirit. There is an admission fee, but it's well worth it.

ALL Tours, Sightseeing, Museums & Attractions

The Chicago Explorer Pass is the best choice for big savings and flexibility. Save up to 42% off retail prices on admission to 3 attractions. Select from over 25 attractions. Do more and spend less!
For One Low Price you can Make the Most of your Vacation. The Chicago Explorer Pass-5 Attractions is the best choice for big savings. Save up to 42% off retail prices on admissions to 5 attractions of your choice. Select from over 25 top attractions.
You'll see it all with the Big Bus Tours Chicago-Classic Package. The Big Loop takes you to Chicago's most fascinating areas, including: Grant Park and Millennium Park, the Museum Campus, Navy Pier, down the famous Magnificent Mile, and over the Michigan Avenue Bridge
Enjoy 2 days of Chicago's Top Attractions with Big Bus Tours. Live English commentary by tour guides. Hop on, Hop off at your own pace. Also enjoy the Panoramic Night Tour along with a Classic Lake Tour with Shoreline Sightseeing.
Historic Chicago Tour
From: $33.20
Discover the historic and beautiful Chicago South Shore. Here, you will find the Lake Point Towers, the Museum Campus, the Buckingham Fountain and Grant Park, the home of Soldier Field. These and many more top attractions await you on a Historic Chicago Tour.
Chicago Gray Line Land and River Tour is a marvelous way to enjoy the sights of Chicago, such as the Loop, Soldier Field and Grant Park. See these and many other iconic symbols of the city from land as well as aboard a streamliner yacht that cruises the shoreline.

Gray Line Panoramic & Scenic Chicago Tour is a wonderful way to see the Northside of Chicago and iconic attractions like the Loop, Wrigley Field, Lincoln Park and the John Hancock Center.
Best of Chicago-Grand Tour provides an exciting overview of Windy City attractions. This sweeping tour takes you through North and South Side residential and business districts.
During the Grand Tour of Chicago and 360 Chicago Combo Tour, you will experience Chicago's historic South and North Sides. This exciting tour includes State Street, the Loop, manicured parks and stunning views from the 360 Chicago 94th floor observatory.

A Medieval Times Dinner and Tournament in the Schaumburg Castle recreates a legendary golden era in an exhilarating atmosphere of festivities, intrigue and drama. Illinois matchless dinner attraction transports you back in time to the splendor of the 11th century.
For One Low Price you can Make the Most of your Vacation. The Go Chicago Pass gives you UNLIMITED general admission to over 30 of the best attractions and tours. A FREE full color Guidebook gives you exclusive savings of up to 20% on shopping, dining and services.
For One Low Price you can Make the Most of your Vacation! The Go Chicago Pass gives you UNLIMITED general admission to over 30 of the best attractions and tours. A FREE full color Guidebook gives you exclusive savings of up to 20% on shopping, dining and services.
For One Low Price you can Make the Most of your Vacation. The Go Chicago Pass gets you UNLIMITED general admission to over 30 top attractions at 55% savings PLUS! A free full color guidebook that gives you exclusive savings of up to 20% on shopping, dining and services.
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