Chicago's reputation of Big City meets mid-west friendliness is exemplified with a service by the city- a Chicago Greeter! Enthusiastic city-wise volunteers impart their love and knowledge of Chicago to parties of six or fewer during a free 2-4 hour visits on foot and public transportation. Greeters will even incorporate special interests into your visit whether it be one of the more than 25 neighborhoods, a particular attraction, or Chicago's role in fashion, film, or anything else. To reserve a greeter, call (312)744-8000 or visit their site Chicago Greeter.

There are also several tours highlighting different aspects of Chicago life. There is a Summer Sampler that delves into three ethnic neighborhoods, a public art walk, and several tours of special interest like a tour of historic cemeteries or churches. Prices range from $20- $45, many with student and senior discounts.

If you prefer to guide yourself, the City of Chicago also offers free downloadable tours. You can find out about Chicago's role in the history of blues with a audio tour from legendary Buddy Guy or listen to a audio tour of the architecture of Milenium Park from its creator Frank Gehry. Available in 5 languages (Chinese Mandarian, English, German, Japanese, or Spanish), you can listen and watch from home on your computer, download to your MP3 player, or listen as you explore.

There are two different saver passes that offer admission into multiple attractions for a lower price:
The first option is the Chicago CityPass. The pass saves you nearly 50% off Chicago's five most-visited attractions of the Shedd Aquarium, The Field Museum, Adler Planetarium, Museum of Science and Industry, and an Option Ticket to choose between the skyscraper views from the Hancock Observatory OR the Sears Tower Skydeck. You have nine days from the day of first use to enjoy admission to each attraction once, and will avoid most ticket lines. The pass comes with a booklet which offers attraction information, transportation directions, best times to visit, a map, and special offers. Passes cost $59 for adults and $49 for children 4-11 years old.
The other option is the Go Chicago Card. This pass offers admission to over 25 attractions, activities, and tours. It is up to you tailor your own itinerary. The card is pocket sized, available in 1, 2, 3, 5 & 7 day increments, starting at just $59.99 ($44.99 for kids 12 & under). The card also offers deals and special offers on shopping and dining, special pricing on premium tours and attractions, and a full-color guidebook including maps, points of interest and more to plan your trip.

Chicago is filled with opportunities to have fun. Navy Pier is the Midwest's top tourist destination with a boardwalk, 150-foot Ferries wheel, boat tours, and countless dining and shopping options. Visitor parties of 10 or less can enjoy a free walking tour of Chicago's 24.5-acre, award-winning Millennium Park with a Millennium Park Greeter. Originating at the Millennium Park Welcome Center, located at 201 E. Randolph Street, these daily tours depart at 11:30 a.m. and 1 p.m., from May 25 through October 31. For a birds-eye-view of the city, check out one of the 10 tallest buildings in the world at the Sears Tower Skydeck or the Hancock Observatory. To look even higher in the sky, visit the Adler Planetarium and Astronomy Museum. Or come back to earth with the Brookfield Zoo, Chicago's Botanic Gardens, or Shedd Aquarium which holds the world's largest indoor aquarium- the Oceanarium. In 2003 the aquarium unveiled its Wild Reef shark exhibit.

An attraction that is hard to miss is Chicago's unique and ornate architecture and public artwork that can be found anywhere in the city. Of particular importance is the gift from Pablo Picasso, a 50-foot-tall sculpture of rusted steel at the Civic Center Plaza. This sculpture has become a symbol of the city's modernity. Works by Claes Oldenburg's Batcolumn, Alexander Calder's 53-foot-high red Flamingo stabile, Marc Chagall's Four Seasons mosaic, Louise Nevelson's Dawn Shadow, Joan Miro's Chicago, and Jean Dubuffet's Monument with Standing Beast are other examples of Chicago's deep intellectual connection with public art.

To take a step into the high life while in Chicago, go to Chicago's biggest casino, Hollywood Casino. Simply getting in to another attraction can feel like winning the lottery. The Oprah Winfrey show is notoriously difficult to get into because of the high demand. Reservations are primarily made by phone, although last minute e-mail reservations are occasionally offered. For more information on getting into the show, check Reservation Information for the Oprah Winfrey Show.

For a trip outside the city, take a look at the original town of Pullman, the grand experiment in building a self-contained company town. The founder of the Pullman Company, George Pullman was a titan of Chicago business in the nineteenth century. Known for his innovative sleeper railcars as well as his experiment in social engineering, his company town later became the setting for a seminal moment in American labor history, when the Pullman Strike resulted from his cutting wages without cutting rents. Federal troops put down the strike, but Pullman’s reputation never recovered. Today, many of the structures in this landmark neighborhood are preserved by the Historic Pullman Foundation which operates a visitors center with self-guided walking tours, as well as monthly guided tours. There is also a weekend in October in which residents open their homes to the Historic Pullman House Tour.

To escape the crowds and enjoy some of the lovely summer weather, there is Northerly Island. Past Adler Planetarium and into the remains of Meigs Field there lies an unfinished bit of the Burnham Plan, a 91-acre peninsula filled with tall grass and wildflowers.

For a fun, basic guide of what Chicago has to offer, check out Chicago City Guide. This city guide is available on-line, or you can print it directly from your computer.

Chicago and food are as connected as the Chicago fans are to their beloved Chicago sports teams. Restaurants abound, from the cheap and hearty sandwiches on the street, to the upper echelon of fine dining. If you are looking for recommendations, listen to the locals. New City Chicago guide offers tips on restaurants, bars, and nightclubs right from the people who frequent them. Another option for people who enjoy food as much as many Chicagoans, Chicago Food tours are a treat.

Cafes/Bars/Pubs

It is impossible to mention Chicago and food without mentioning the Chicago "deep-dish" pizza. This type of pizza was invented at Pizzeria Uno, in 1943, reportedly by Uno's founder Ike Sewell. Other Chicago pizza establishments are: Gino's East, Connie's Pizza, and Pizano's.

Another Chicago classic is the Chicago Hot Dog. The all-beef hot dog is steamed or boiled on a poppy seed bun. Topping include: mustard, onion, sweet pickle relish (usually neon green), a dill pickle spear, tomato slices or wedges, sport peppers, and a dash of celery salt; but never ketchup. The complete assembly is sometimes called "dragged through the garden" because of the unique combination of condiments. It is taboo to put ketchup on a Chicago hot dog, many hot dog stands don't even stock the condiment. For a review of the best hot dogs, go to Citysearch's recommendations.

Along with world-class cuisine, Chicago offers cafes that know how to put together a quick meal. Among it's cheap and tasty delicacies, Mr. Beef is a small cafe known only to natives. It is home to a huge italian beef sandwich as well as pizza and other greasy, delicious meals. The Gage has an excellent location in the heart of the city, but why people flock there is because of its unusual, no-nonsense pub grub with dishes like braised rabbit salad, roast elk and beef carpaccio.

The drink of choice in working-class Chicago is beer, but the type of establishment one drinks it in varies widely. Tavern at the Park takes advantage of its proximity to Milenium Park by offering classic Chicago cuisine in a classic Chicago bar. Bars do not get more trendy then those attached to the name of Oprah Winfrey. The Rockit Bar & Grill was designed by Oprah-famed designer Nate Berkus and actually serves a tasty Kobe beef burger. If you are looking for a rowdy place to drink and get to know the locals, try Bar Chicago.

For a complete listing of bars across Chicago, go to Yelp's Chicago Bars. Also note that liquor laws require bars to stop serving at 2AM. Some bars don't close at 2, but they may not serve alcohol for fear of severe fines and closure. Alcohol may also only be bought and consumed by those 21 and older which will be checked frequently.

Restaurants

Chicago's "Loop" used to be the area to eat in, but these boundaries have been extended to north of the Chicago River to Oak Street. North of the bustling Michigan Ave lies upscale restaurants and shops. On the waterfront, Navy Pier offers more than 50 acres of parks, promenades, gardens, shops, restaurants, and entertainment in a renovated warehouse.

If you are looking for a truly Chicago fine dining experience, there are plenty of excellent options: Happy Hour at Andy’s Jazz Club offers live Jazz starting at 5 p.m., followed by dinner at Shaw’s Crabhouse for seafood, Gibsons Steakhouse or Morton's Steakhouse for red meat. Some other note-worthy and expensive restaurants are: Charlie Trotter's, The Dining Room at the Ritz-Carlton Hotel, Aria at the Fairmont Hotel, or Frontera Grill. To get a little closer to Oprah, check out her chef and his restaurant, Table Fifty-Two.

If you want a bite of Chicago without the hefty price tag, there are plenty of areas to search in. The corner of Clark and Diversey up north to Broadway offers cheap and delicious eats. An amazing assortment of shops, bars, and an eclectic group of people line the street. Along with the wonders of architecture and baseball, Chicagoans swear by the Bratwurst and beer while watching a game.