Home to many iconic landmarks and a unique culture all its own, Chicago is one of the most special and significant cities in all of America. Situated on the banks of Lake Michigan, it's the third largest city in the country and has become known all around the world for its stunning skyline, rich history, industrial influence, and thriving nightlife scene with lots of live entertainment. CDC information for travelers. Hours/availability may have changed.


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Chicago is home to around 2.7 million people, with 10 million living in the surrounding metropolitan area, often known as 'Chicagoland', but the city attracts millions more each and every year, drawing in tourists from far and wide, all eager to see the sights and sounds of this famous place and experience the unique magic that only Chicago can provide.

If you're planning a trip to Chicago and would like to enjoy a fun, special way to enjoy this amazing city, why not take a trolley tour? Chicago Trolley & Double Decker Co. runs trolley tours of Chicago each and every day, taking countless passengers on the ride of their lives around the city, stopping off at a long list of landmarks and attractions along the way.

Chicago Trolley & Double Decker Co. got its start way back in 1994. At that time, it only had eight trolleys, but has grown and evolved over time to now feature a whopping tally of 39 trolleys, with 26 double-decker buses also forming the fleet. This company is the biggest tour operator in all of Chicago and the number one name to choose if you're looking for Chicago trolley tours.

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- Chicago Trolley Tours with Chicago Trolley & Double Decker Co.

Riding the trolleys around Chicago with Chicago Trolley & Double Decker Co. couldn't be easier. This tour operator runs a variety of trolley routes and tours around the city, with its primary route featuring a classic 'hop on and hop off' system that lets you get on and off at the various stops as you please, all with the same ticket.

Tickets can be purchased ahead of time online for discounted rates, and it's possible to buy multi-day passes too. If you happen to be visiting Chicago for a few days or weeks, the multi-day trolley tour passes are a good option, letting you ride the trolleys around Chicago as much as you like without needing to pay extra and replace your ticket each day.

Chicago Trolley & Double Decker Co. also runs speciality trolley tours around Chicago on select schedules at certain times of the year, and tickets for these trolley tours can also feature multi-day passes and additional options like discounted rates for kids. Read on to learn about the different options you can choose from when finding your next trolley tour of Chicago.

- Hop On Hop Off Tours

The classic Hop On Hop Off Tours from Chicago Trolley & Double Decker Co. start at 9 am and run through to the early evening, with the last tour leaving at 4 pm. These affordable, exciting trolley tours of America's third largest city offer something for everyone, and the route actually differs depending on the time of year. The summer months feature a Wrigleyville - Lincoln Park Zoo Route, while fall and winter offer a classic Downtown Tour.

All of these tours offer hop on and off service, letting you descend at any of the many stops along the way and get back on later without needing to pay for another ticket. These trolley tours pass by many of Chicago's landmark locations and along the city's most famous streets, offering some super views and easy access to the most popular bars, restaurants, live entertainment venues, shopping areas, museums, and much more along the way. Be sure to bring a camera along to preserve some of the magical memories you're guaranteed to enjoy on this awesome Chicago trolley tour.

- Chicago Land, Lake, and River Tour

The Chicago Land, Lake, and River Tour, as its name suggests, allows riders of Chicago trolley tours to enjoy an excursion on the city's waterways as well. Chicago is situated right on the banks of Lake Michigan and is also home to the famous Chicago River, so many visitors to the city want to experience the wonders of these waters for themselves. The Chicago Land, Lake, and River Tour lets you do just that, including a ride on the hop on/off trolleys around Chicago while also including a ride on either the Urban Adventure Cruise or Chicago by Night Cruise from Mercury.

- Holiday Lights Tour

The Holiday Lights Tour is a trolley tour that runs through the holiday season in Chicago from the end of November through to the Christmas period. This tour takes you on a magical trip through the city's winter wonderland spaces, allowing passengers to admire the many lights and holiday decorations of Chicago. If you're lucky, you might even get to take the tour in the snow and really feel the spirit of Christmas down every street and around every corner. This tour even includes a toasty bag of Hot Cocoa Garrett Popcorn to keep you warm along the journey, as well as a pair of ZooLights 3D glasses to appreciate some of the displays put on by Lincoln Park Zoo.

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Chicago Trolley Tips for Travelers

  • Overview, Photo: soupstock/stock.adobe.com
  • Tours, Photo: pigprox/stock.adobe.com
  • Cover Photo: littleny/stock.adobe.com

Attraction Spotlight: Skydeck Chicago

Located in Downtown Chicago, Illinois, the Skydeck of the Willis Tower is an iconic landmark for anyone who visits the famous windy city. Visitors who dare to walk out on to the clear glass box, known as “The Ledge”, will be able to see the entire city of Chicago at their feet from one of the tallest buildings in the world. It is truly a once-in-a-lifetime experience that is not to be missed!


Construction began on the Willis Tower, previously known as the Sears Tower, in 1970 when Sears needed more office space for their growing company. They decided to go one step further and build one of the tallest office buildings in the world!

The Skydeck was built by the architecture firm of Skidmore, Ownings, and Merrill, who ultimately designed The Ledge expansions as well.

Sears remained in the building until 1988 but the name of the building remained the same until 2009. Currently, the 110-story building attracts millions of visitors a year and is named after the global insurance company based out of London – The Willis Group.

The Ledge was opened in 1974 and provides visitors with a truly breathtaking way to view the city of Chicago. Ironically, the inspiration to build the Ledge came from the thousands of forehead prints left behind from visitors trying to see the city below. The movie, Ferris Bueller’s Day Off was also a huge influence on the decision to build Ledge – since in the movie, the main characters press their foreheads against the glass themselves.

The engineers designed the Ledge boxes to have almost no visible support system, making the experience equally beautiful and exhilarating. Now, thanks to the brilliant minds who got tired of seeing forehead prints on their beloved building, visitors have a pure and unobstructed view of the city below.

The Experience:

As visitors enter the Willis Tower, a large variety of museum-quality exhibitions greet and captivate them with stories about the infamous tower. Learn how it was built, how long it took, who has come and gone, and how it compares to other buildings around the world. There are high-quality video screens, an educational theater presentation, and even a large variety of hands-on and interactive exhibits for guests of all ages to enjoy as they wait their turn to ride the elevators to the top of the Skydeck!

Once visitors complete their short ride in the multi-media elevators, they will arrive at floor 103 – The Skydeck. This is where they can walk in a circle around the building and explore the city of Chicago like they never have before. Visitors can even see more than 50 miles in all directions on a clear day and if they are feeling brave enough, walk out onto the Ledge.

The Ledge is housed in the eighth-tallest building in the entire world and lets visitors step out into a clear glass box suspended at 1,353 feet (442 meters) over the city. The view is equally breathtaking and terrifying, but visitors should not worry, the glass boxes are made of 1,500-pound individual sheets of glass that are tempered for extreme durability.

There is so much to take in from the city at this height, Wrigley Field and the downtown area lit up at nighttime are two of the most enjoyable. Visitors will feel as if they are looking down into a dollhouse replica of Chicago – all the people, buildings, cars, and bridges down below will look like miniatures of the real thing.

Although the Willis Tower is one of the most popular tourist attractions in the city of Chicago, it is not to be missed. Visitors can even make a whole afternoon out of it – be sure to visit the world-class gift shop and café on the way out!

Additional Information:

The Skydeck Chicago, 233 S Wacker Dr, Chicago, IL 60606, Phone: 312-875-0066

More Things to do in Chicago

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Hotel Spotlight: The Palmer House Hilton

A Chicago landmark for over 125 years, the Palmer House Hilton is the longest continuously operating hotel in North America. The highlight of the property is its turn of the century ceiling which contains 21 large paintings and murals, recently restored by Lido Lippi. The lobby level features classic fixtures reminiscent of France's Fontainebleau, Versailles and Compiegne. The property is located on State Street near Chicago tourist attractions such as the Shubert Theatre, Ford Center for the Performing Arts, Adler Planetarium, and the Museum of Natural History.

There is an indoor pool and a fitness club. Business travelers can take advantage of modern amenities and privacy offered on the Executive Level. The Lower Arcade houses the Hair Salon which offers a barber, hair styling, manicure, and shoe shining. The 25-story property has 1,641 guest room and 88 suites.

The lobby level features the Windsor's Lobby Bar and Cafe for cocktails. The third and fourth floors are home to remodeled meeting, exhibition and ballroom facilities. The Crystal Room, with mirror walls and opulent chandeliers, can be hired for special occasions, such as weddings. The Grand Ballroom can accommodate more than 870 guests at a sit-down banquet.


Guests can dine at three different restaurants. Trader Vic's serves South Pacific Fare and exotic drinks. French Quarter is an American-style cafe with a lavish buffet and New Orleans-inspired cuisine. The 1940s-style Big Downtown offers new world cuisine: steaks, chops, burgers, pizza, pasta dishes, soups, salads, and desserts.


The hotel has been a favorite spot for wedding n Chicago since it first opened. In fact, the property itself was a wedding gift from Potter Palmer to his bride, Bertha Honoré. Choose from seven elegant ballrooms which can accommodate from 80 to over 1,000 guests for a wedding, reception, rehersal dinner, brunch and other events. You will be assigned a wedding coordinator who will help you with all the details.

Ask about the wedding package which includes a 4-hour bar, champagne, dinner and a wedding cake. Accommodate your guests in stylish rooms, suites, executive level rooms and accessible accommodations.

Next read: Best Time to Visit Chicago, Illinois & Other Travel Tips

Rooms & Suites

  • Guest Rooms: Guest rooms feature a plush bed, desk, internet, 37-inch flat screen tv and luxurious bath amenities.
  • Suites: The suites offer more living space and additional amenities. Each suite has separate bedroom with king bed.
  • Executive Level Rooms: These rooms were recently renovated and offer guests amazing amenities as well as key-only access. Access your room via a private elevator, skip past the line by using the private check-in, consult the private concierge to get the best theater tickets and enjoy complimentary breakfast.
  • Accessible Rooms: The hotel offers fully-accessible rooms, many of which include wheelchair accessible showers.

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Hotel Spotlight: The Peninsula Chicago

Located in the heart of Chicago, The Peninsula Chicago prides itself on offering spacious overnight accommodations, multiple upscale dining options, and a full-service menu of health and wellness amenities for all guests.

Rooms and Suites

Guests can choose from a few different varieties of rooms and suites for their overnight stay at The Peninsula. Each accommodation has its own unique atmosphere.

There are 5 different room choices - The Superior, Deluxe, Grand Deluxe, Grand Premier King,

and Grand Premier Double.

The Superior Room is the most spacious of the guest rooms at The Peninsula. They are over 500 square feet and feature a king size bed. Deluxe Room and Grand Deluxe Rooms feature either a king-size or double size bed. They are also both over 500 square feet in size and have views facing either Rush Street, Superior Street, or Michigan Avenue. Finally, the Grand Premier King and Grand Premier Double guest rooms have views of Michigan Avenue and over 500 square feet of guest space.

There are also 8 different suite choices at The Peninsula - The Executive, Junior, Deluxe, Premier Deluxe, Grand Deluxe, Lake, Water Tower, and The Peninsula Suite. Each of these options provides for an enhanced overnight experience. The Lake, Water Tower, and Peninsula Suites are all over 1000 feet in size, and all suites have at least one king size bed.


Accessible rooms allow for roll-in wheelchair access, communication kits (come with a door knocker, lights, and vibration alarm), TTY kits, doorbells, raised toilet seats, and roll-in showers. Also available on request are shower seats. Guests should reserve an accessible room specifically.


Most of the guest rooms and suites have similar amenities. They have bedside electronically controlled multi-function panels that allow guests to control the thermostat, lights, and television. Also, bedside is charging stations for both Android and iPhone cell phones. Rooms and suites also have a dressing table/vanity with a 14 inch, illuminated mirror, dressing closet, luggage area/luggage bench, a nutrition center with Nespresso machines, a minibar (fully stocked), in-room safe, and a work desk.

Televisions in each room are at least 55 inches in size and have a soundbar and cable access.

Bathrooms in each accommodation are made out of marble and have inset 19-inch televisions, bathrobes, slippers, and a hairdryer, and fully stocked bathroom toiletries and towels.

Other complimentary amenities include daily newspaper, access to thousands of publications with the PressReader, and a shoe shining service.


There are five different dining options available at The Peninsula.

Z Bar is a rooftop bar and lounge on the top of The Peninsula. The bar features unique, handcrafted cocktails and a menu full of globally inspired dishes. Guests can listen to live music and view art with the background of the city of Chicago. The dress code is casual chic and does not require any advance reservation. It is open seven days a week.

Shanghai Terrace offers guests a menu of Shanghainese and Cantonese that has been voted the top Chinese restaurant in the city. With unique, supper club decor and a smart casual dress code, lunch, dinner, and cocktails and bites (dim sum) are served Monday through Sunday.

Another option at The Peninsula is the Pierrot Gourmet. This European wine bar and cafe is open all day long, seven days a week, and serves coffee, pastry, flatbreads, and wine by the glass at street level. It has a casual dress code, and no reservations are required.

The other in-house restaurant at The Peninsula is The Lobby. The Lobby features a Contemporary American menu and serves food all day long - breakfast, brunch, lunch, afternoon tea service, dinner, and chocolate at “The Pen.” Reservations are strongly recommended, and children’s menus are available.

In-room dining is also available for guests. The nearly endless, international menu can be enjoyed 24 hours a day by calling room service.

Health and Wellness

One of the health and wellness options available at The Peninsula is The Peninsula Spa. The spa sits on both the 19th and the 20th floors of the hotel and takes appointments seven days a week. It has an extensive menu of both traditional and more contemporary spa options, like hot stone massage, aromatherapy, and Ayurvedic options. Appointments are required.

The hotel also has its own fitness center. Located on the 20th floor, the fitness center has a wide selection of both cardiovascular and strength equipment as well as more than 30 fitness classes offered complimentary to overnight guests. The fitness center also has a half-sized Olympic lap pool.

There is also an indoor hotel pool for guests to enjoy. The pool is heated to around 80 degrees all year round and also features poolside dining options. It is also located on the 19th floor of the hotel.

108 East Superior Street, Chicago IL, 60611, Phone: 312-573-6611

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