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Things To Do In Chicago At Night

There's a fabulous choice of things to do in Chicago at night. A bustling, busy and dazzling metropolis, Chicago doesn't sleep! Offering one of the most stunning cityscapes of night lights on the planet, you need to venture out and explore. See the skyline from the top of a skyscraper, from a helicopter, riding a bicycle or while cruising on a luxury vessel. Tours include a fun range of themes from the 1950's gangster culture to spooky ghost trips visiting eerie sites of mass disasters and intimate exclusive dinners with a private chef. Each one is linked to the glimmering lights of the city!

Willis Tower Skydeck Dinner

Willis Tower Skydeck Dinner in Chicago

Willis Tower Skydeck Dinner in Chicago

Enjoy dinner at the top of a skyscraper and delight in the lights of Chicago at night. The Willis Tower Skydeck Dinner is ideal for the whole family. This VIP package takes you up in the high speed elevator to the Skydeck, located 1353 feet in the air on the 103rd floor. Once there, you will be ushered to your exclusive table on the ledge where the views are breathtaking! There are only four tables allocated at any time, after the venue is closed to the public, so you are sure to feel like royalty.

Dinner is a custom-made famous deep-dish pizza with a salad. You can choose your favourite toppings to make the pizza of your dreams. How about BBQ chicken, Canadian bacon, black olives, Jalapeno peppers, mushrooms, garlic or salami? Non-alcoholic beverages are included. After the main course, dessert follows! While you enjoy this scrumptious meal, delight in the views of the lights of the City and start snapping photos.


Ghost Tour by Bus

Ghost Tour by Bus in Chicago

Ghost Tour by Bus in Chicago

A most relaxing way to explore Chicago at night is on a Bus Tour. Throw in a hint of ghosts and spooks and you are set for an evening of fun. The Ghost Tour By Bus turns you into a ghost hunter and explores different parts of the city each night, so you can do this many times and never get bored!

The tour departs from the Congress Plaza Hotel and lasts for about 90 minutes. Your guide is a history expert and will thrill you with tales of the different venues you stop at. Visit the site of the St. Valentine's Day Massacre and the sites of other mass disasters where ghostly spirits still linger. Hold your breathe as you drive through the City Cemetery Grounds, home to over 10000 unmarked graves.

The tour is great for families and groups. As you drive around, don't miss the spectacular scenes of the cityscape at night when the towering skyscrapers are lit up.


Chicago by Night Helicopter Tour - Seasonal

Chicago by Night Helicopter Tour

Chicago by Night Helicopter Tour

Nothing beats seeing the lights of a buzzing metropolis from the sky and you can do just this in the Windy City. See Chicago at night from the comfort of a luxury helicopter. The tour starts at the Vertiport and lasts for 15 minutes. Depending on the time you board, you may see the stunning sunset or the sparkling city lights against a jet black sky. Your pilot will give you a professional talk on the iconic buildings you fly over using a state-of-the-art two-way audio headset.

Fly over Soldier's Field, the Lincoln Park Zoo, Grant Park, the Field Museum and the Shedd Aquarium. Zoom over Lake Michigan and see how the iconic skyscrapers dazzle at night and make a picture-perfect scene. The helicopter is heated, so this tour is ideal for any time of the year. Maximum four people are taken at a time and a minimum of two, making this ideal for a family or a romantic couple.


1950's Nightlife in the Loop Tour

1950's Nightlife in the Loop Tour in Chicago

1950's Nightlife in the Loop Tour in Chicago

Chicago in the 50's was a booming city filled with culture, music, world famous architecture and entertainment. See Chicago at night and be immersed into the 1950's on this exclusive tour. It is designed to thrill those who love learning about old buildings and those who love a vintage vibe. The tour departs from Argo Tea and lasts for two and a half hours. Your very educated guide will take you to the Theatre District where you will learn about stepping out in style in the mid 20th century. Then visit the iconic Berghoff and enjoy a beer before setting off to the Palmer House Hotel where you will sip a classic drink in the grand lobby. Your guide will share videos, music and stories including those of famous entertainers who performed at the iconic Empire Room Nightclub. Soak up the ambiance of vintage Chicago! You must be over 21 to join this tour.


Skydeck Chicago Admission

Skydeck Chicago Admission

Skydeck Chicago Admission

The lights of Chicago at night is a sight that cannot be missed and what better way to view them than from a dizzy height at the top of a skyscraper? Head up to the 103rd floor of the Willis Tower and get exclusive views from the Skydeck.

At a breathe-taking height of 1353 feet you will be awed at the dazzling scene unfolding before your eyes. If you are really brave, step out onto the Ledge, a glass box that extends into space offering a panoramic view as well as one straight down! See the amazing buildings and landmarks like the Navy Pier, Millennium Park and Wrigley Field glittering with lights. If you come in the early evening, the sunsets are stunning too. Then head indoors and learn more about the city using the interactive exhibits. Food, culture, sports, architecture and history are some of the topics that will enthral the whole family.


1960's Nightlife in the Gold Coast Tour

1960's Nightlife in the Gold Coast Tour in Chicago

1960's Nightlife in the Gold Coast Tour in Chicago

Chicago in the 60's was swinging to the beat of music, the rhythms of famous musicians like Frank Sinatra and the bold sexy side of the Playboy Club. See Chicago at night as it was in a by-gone era and get immersed in this fabulous culture. The tour starts at the elegant Drake Hotel where your guide will tell you all about Hugh Hefner. Then set off to Rush Street, where the murky underworld of gangsters mingled with classy entertainers. Spend time exploring the Gold Coast, a magnificent historic neighborhood where you can admire the beautiful mansions of the 7th richest urban area in the USA. The tour ends at the Pump Room, a famous venue for celebrities for over 40 years. Take a peek at Sinatra's private booth before settling down with a drink. This tour caters for small groups, making it intimate and exclusive. You must be over 21!


Chicago Mafia and Blues Night Tour- Seasonal

Chicago Mafia and Blues Night Tour

Chicago Mafia and Blues Night Tour

Step back into the era of the 1920's to 1940's when Chicago was run by gangsters and Mafia, where gun fights were the order of the day and murky characters chilled in smoky speakeasies. Join the Chicago Mafia and Blues Night Tour and explore this fabulous city! Chicago at night is fun and buzzing and your knowledgeable guide will thrill you with stories as you travel along in a luxury vehicle. Visit the spine chilling spot of the St Valentine's Day Massacre. Learn about the Prohibition and the slave trade and then settle down in a bar previously owned by the legendary Al Capone where you can relax to the soft soothing sound of the Blues.

Afterwards, head off to see the lights and the cityscape of hundreds of skyscrapers glimmering against a jet black sky. The sight will remain in your memory for a lifetime! You must be over 21 to join this tour and have photo ID.

Chicago by night cruise - Seasonal

Chicago by night cruise

Chicago by night cruise

See the lights of Chicago at night on a stunning cruise that is ideal for the whole family. Travel by boat from the Riverwalk, just off the Magnificent Mile and relax knowing that you are in capable hands with a professional captain and friendly crew. As the boat cruises down the river you will be awed by the sight of the dazzling lights and the magnificent skyscrapers lit up by floodlights.

On the 90 minute cruise you will learn about the fascinating history of the city and see famous buildings like the Campus Museum, Willis Tower, the John Hancock Building and the corn-cob Marina Building. You will also see the amazing Buckingham Fountain Light display from the water. Each member of the tour gets a complimentary neon light to wave as you sail along. The tour is fully narrated and operates in all weather conditions, dress accordingly!


Chicago Dinner Cruise - Seasonal

Chicago Dinner Cruise

Chicago Dinner Cruise

Put on your best attire and set off for an upmarket dinner cruise to enjoy fine-dining, great wines and see the lights of Chicago at night. Climb aboard a luxury vessel, newly renovated with a stylish interior and ultra posh atmosphere. The celebrity chef will prepare a 3-course meal on board as you cruise along the shores of Lake Michigan and admire the glimmering cityscape.

The cruise departs from Navy Pier, meet your Captain and step aboard. Private tables in a climate controlled dining lounge make the perfect romantic setting. After your meal consisting of an exotic tasting trio, a delectable entr┼Że and a mouth-watering dessert you can stroll around and visit the Captain's bridge. Then dance the night away to the sounds of the live DJ who will play your favorite tunes.

If you take this cruise in the summer months, you will experience the added delight of seeing the spectacular Navy Pier fireworks display from the water.


Chicago Segway Night Tour - Seasonal

Chicago Segway Night Tour

Chicago Segway Night Tour

If you have not yet tried a Segway, now is the time! You don't need to be super fit or experienced and it is safe and suitable for all ages. This two-wheel motorized bike allows you to stand and glide along at a leisurely pace while you are thrilled by the lights of Chicago at night.

The two hour trip is limited to eight people, making this an intimate and exclusive way to learn about the Windy City. Your guide will give you a short briefing and safety lesson and you are off! Follow your guide and see the famous sights. You will pass Buckingham Fountain, Lake Michigan, the Museum campus and the Navy Pier amongst others. Learn about the colorful history of the city and stop to take photos. There is a small amount of space on the Segway to store a bag or holder, don't come overloaded, you need a free hand to wave at passers-by as you glide along!


Haunted Chicago Segway Tour - Seasonal

Haunted Chicago Segway Tour

Haunted Chicago Segway Tour

If you are brave and love spooky adventures then this tour is for you! Take along a group of friends for support! Chicago at night can be an eerie place with ghosts, dark alleys and haunted hotel lobbies. The tour makes use of Segways, fun two-wheel bikes that are easy to drive and suitable for all ages and levels of fitness. Meet your guide at the corner of Monroe Street and Columbus Drive for a short briefing and safety lesson and then set off. Stop in the alley where more than 600 locals perished in 1903. Listen to the creepy sounds of a piano playing in an empty ballroom of the Michigan Avenue Hotel. Feel your spine tingle at the site of the maritime disaster where 800 people drowned and their ghosts drift under the waters. Then lighten up and see the amazing skyline of the city at night as you glide along on your Segway.


City Lights at Night Bicycle Tour - Seasonal

City Lights at Night Bicycle Tour in Chicago

City Lights at Night Bicycle Tour in Chicago

Are you a bike rider? If so, take a unique and fabulous tour with a small group to see the lights of Chicago at night. Cycle around the charming neighborhoods and learn more about this fascinating city. The tour takes 3 hours and is led by a knowledgeable guide. The bicycle and helmets are provided as part of the tour.

Visit the Buckingham Fountain and the Millennium Park. Cycle past the Museum Campus and then head for Downtown where you will be mesmerized by the sparkling city lights. Most of the towering skyscrapers are lit up, creating a wonderland that demands photos!

If you book the tour for a Wednesday or Saturday to see Chicago at night, the tour includes an extra treat -see a stunning fireworks display from the Navy Pier. The tour is suitable for all ages but children must be strong riders.

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