Do(s):

• See concerts and public art that is of immense importance
• Hop abroad and go on Chicago’s First Lady Cruises
• Get atop the Willis Tower skyscraper for breathtaking 360-degree views of the Chicago skyline and dare to get onto the ledge for an experience of a lifetime
• Watch the stellar plays at the Chicago Theatre
• Experience Jazz music 
• Try the gourmet sausage at Hot ’’G-Dog’’
• Check out the gastronomical delights at Alinea
• Get to know about the impressive buildings from the best point possible, aboard a boat on the Chicago River like that of the Willis Tower, Marina City, Merchandise Mart, to name a few.

Don’t(s):

• Never compare Chicago to New York City
• Never visit during the winter
• Truly remarkable as a tourist activity is to look down on Chicago’s skyline, from the city’s skyscrapers but don’t pay for it
• Wherever possible use public transport as parking can be expensive, confusing, and also a costly affair
• Don’t skip the Art Institute, and don’t expect to see it all in one hour
• Don’t amble along on the lakefront trail and pose a problem for runners and cyclists
• Don’t miss out on the parks
• Don’t miss out on the small, beautiful beaches
• It is good not to waste money on Broadway shows
• Never skip the museums here

The nightlife in Chicago is just perfect for a night owl's nocturnal rendezvous and is not restricted to bars and night clubs. It is also a hub for Jazz clubs, laugh-a-minute comedy shows, swanky speakeasies, sultry Blues, and craft breweries. The clubs are the best place to enjoy music. It is a good idea to invite one's friends to the party as Chicago is all about kicking back and hanging out. There are also sophisticated piano bars here. In the comedy circuit, Chicago is one of the top cities for entertainment and does not fail to disappoint with people like Marlon Wayans having his sold-out shows there. One can also enjoy the Thirsty Ears Festival and the Chicago Drinking Play. It is one of the most popular games revolved around drinking and laughing. Feel like some exciting dance music with the best DJs? Then the smart bars are for you. Check out the Berlin Club, a true gay club for a taste of something unique and out-of-the-ordinary.

• View Chicago's skyline and Lake Michigan from the 360 Chicago Observation Deck.
• Check out the must-see museums.
• Get the all-inclusive Chicago Explorer Pass and save 40% off entrance fees. Get to see 3, 4, or 5 attractions. 
• Helicopter flight at night - a unique and exhilarating thing to do.
• Take the hop-on-hop-off bus tour.
• Visit Lake Meadows Shopping Center, Marshfield Plaza, and Riverview Plaza for shopping.
• One must visit Magnificent Mile, that is a premier commercial district. 
• Skydeck Chicago is also a must-see.
• Lincoln Park Zoo. 

Activities to do:

• Be prepared to get enthralled once you watch the live show of the world-renowned Israeli dance and percussion troop Mayumana.
• It is good to visit Millenium Park at the heart of the city.
• Grant Park with its notable attractions is a happening urban park right in the central business district.
• Chicago Riverwalk is another exhilarating and fun activity involving dining, fishing, kayaking, and wine.
• The lakefront trail is a good thing to enjoy for walking, jogging, and cycling.

• Frank Lloyd Wright Memory Game: Fans of Wright, young and old, will enjoy the Frank Lloyd Wright Designs Memory Game, which features 36 pairs of cards showcasing various shapes and designs Wright used in his art glass windows, carpets, skylights and more.

• The average Chicago winter generates 38 inches of snow, but you can make it snow year-round on the city’s skyscrapers with a snow globe.

•  Tiffany Elsa Peretti Bean Pendant for all those into the extravagant.

• 1930 Al Capone Special Edition Armored Cadillac Model

• Chicago Ties for their quirky designs.

• Garrett Popcorn in a multitude of flavors and packed in very interesting boxes.

• Pick up some Muddy Waters or a compilation album, or sample some Chicago Jazz CDs at local stores.

• Take back some Half Acre Beer Company beer.

• Sue gold-plated ornament for its Hollywood-inspired designs.

• Wild Blossom Mead, a honey wine, which has a very unique taste.

• Sports jerseys of various Chicago-based teams.