Chicago sightseeing


Why attend Social Connections in Chicago? (above the obvious reason to attend Social Connections 😉 )

The City of Chicago covers an  area of 60,000 hectares and sits 176 meters (578 feet) above sea level on the southwestern shore of Lake Michigan. At 190 km wide and 495 km long, its the 5th largest body of fresh water in the world. The city is traversed by the Chicago and Calumet rivers. Chicago’s extensive parklands, including 3,000 hectares of city parks attract an estimated 86 million visitors annually.

As a multicultural city that thrives on the harmony and diversity of its neighborhoods, Chicago today embodies the values of America’s heartland-integrity, hard work and community and reflects the ideals in the social fabric of  its 77 distinct neighborhoods.

Chicago is recognized across the United States as a very passionate sports town.

Comprehensive Visitor’s Guide

To and from the airport

Chicago is served by two major airports – O’Hare and Midway


O’Hare Airport  is an airport located 17 miles (27 km) northwest of the Chicago Loop. The airport is connected to Chicago by train using the Blue Line of Chicago ‘L’. It runs 24 hours a day.

Blue Line train service operates via elevated and subway from O’Hare (on the northwest side of Chicago) to downtown, then continues through the west side of the city to Oak Park and Forest Park. The normal travel time on the Blue Line from O’Hare to downtown, is 40-45 minutes.

Blue Line trains run 24 hours a day, seven days a week; and all trains leaving the O’Hare station go through downtown.

A free transfer is available to connecting CTA train lines at designated stations. See the Blue Line Route Guide or Maps for connection information.

To make a paid transfer, such as to a bus route, you’ll need a Ventra Card or Ventra Ticket with fare or a pass, or to pay with a personal contactless bankcard (onto which you can load fare or passes at machines).

Getting to the Blue Line from Terminals 1, 2 or 3

If you’re coming from domestic and international flights arriving at Terminals 1, 2 or 3, follow signs in the airport to “CTA Trains” or “Trains to City.” These will lead you to the train station. You can walk from the baggage claim to the train in under ten minutes from any of these three terminals.

Getting to the Blue Line from Terminal 5

If you’re coming from international flights that land in Terminal 5, follow signs to the Airport Transit System (ATS). Ride the next train to Terminal 2 and exit the train at the station. Then, follow signs to “CTA Trains” or “Trains to City.”

(Note: There is no Airline Terminal 4 at O’Hare.)


Chicago Midway International Airport is a commercial airport on the southwest side of Chicago, Illinois, eight miles from the Loop.

The CTA Orange Line provides service directly to Midway Airport.

The fully-accessible Midway station is right next to the airport terminal building, and connected by an enclosed walkway.

About the CTA Orange Line ‘L’

Orange Line train service operates from Midway (on the southwest side of Chicago) to downtown via elevated tracks. (Once reaching downtown, trains travel clockwise around the Loop and then make all stops back to Midway.) The normal travel time to downtown from Midway is 20-25 minutes.

Service operates all day, every day, except during overnight hours (roughly 1 am to 4am) or after 11 pm on Sundays. Alternate overnight (“owl”) service is available via the N62 Archer bus.

A free transfer is available to connecting CTA train lines at designated stations. See the Orange Line Route Guide or Maps for connection information.

To make a paid transfer, such as to a bus route, you’ll need a Ventra Card or Ventra Ticket with fare or a pass, or to pay with a personal contactless bankcard (onto which you can load fare or passes at machines).

Getting to the Orange Line from the Midway Airport Terminal Building

The fully-accessible Midway station is situated just east of the airport terminal building and is connected to the airport via an enclosed walkway.

Follow the signs to “CTA Trains” or “Trains to City” from the airport. An orange line painted on the ground will guide you there.

To find out more information about the two airports that serve Chicago, please visit

Getting around Chicago

Chicago has one of the world’s simplest street patterns and numbering systems. Chicago streets are laid out in a simple grid system. The intersection of State & Madison is essentially Ground Zero in Chicago. In Chicago, there are 8 “standard” city blocks per mile. Although many blocks are further divided in half.

A standard block has 100 address numbers, meaning there are 800 numbers per mile. For example, 800 N. State St is eight blocks north of Madison on State St. 1900 W. Madison is nineteen blocks west of State St on Madison. There are some exceptions to the rule – such as streets that run on an angle – Milwaukee, Elston, Archer to name a few. On Chicago’s south side, the east-west streets are numbered. And those numbers correspond to the address numbers, in hundreds. For example, 87th Street is 8700 south. There actually were “errors” over the first 3 miles south of Madison Street, resulting in 12th Street, 22nd Street, and 31st Street being the first 3 “mile” streets south of Madison Street. South of 31st Street, there are 8 numbered streets per mile. 12th Street eventually became Roosevelt Road, while 22nd Street is now Cermak Road.

Addresses that end in an even number will be on the west or north sides of the street. Odd numbered addresses will be either on the east or south side of the street.

A good source for pdf versions of Chicago streets can be found here.

Many tourist attractions downtown are within walking distance of each other. If not, public transit (CTA) or taxis are an easy option. The CTA website – and click on the trip planner link – is very easy to use. Check out the public transportation section of this site for further details.

Some tourist attractions are simply known for their name – not an address. For example, the John Hancock Center is at 875 N. Michigan Ave. Sears Tower is at 233 S. Wacker Drive. Illinois Center is at 111 E. Wacker. Water Tower Place is at 845 N. Michigan Ave. Navy Pier is at 600 E. Grand Ave.

One way to get to know the city is to have a local show you around, and the City of Chicago Dept. of Cultural Affairs has a service that does just that FOR FREE!

Things to do

Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works. The Chicago Art Institute is known as one of the greatest art museums in the world housing the 2nd largest collection of French Impressionist paintings next to the Louvre.

The Field Museum is a renowned natural history museums. Chicago’s green spaces include Millennium Par, home to the reflective sculpture “Cloud Gate.” The Cubs pro baseball team draws crowds to Wrigley Field. The Magnificent Mile, a 13-block stretch of North Michigan Avenue, offers upscale shopping. To the north, the leafy Gold Coast district has trails along the lake. The food scene includes trendy restaurants and casual spots offering local specialties like deep-dish pizzas and relish-topped hot dogs. Chicago also hosts 2 influential arts groups, the Steppenwolf theater company and Second City improv troupe.

Watching Sport in Chicago

Chicago is one of four U.S. cities to have teams from the five major American professional team sports (baseball, football, basketball, hockey, soccer). Chicago has been named as the Best Sports City by Sporting News three times in 1993, 2006, and 2010.

The Chicago Bears football team plays at the newly renovated Soldier Field. Die-hard fans bundle up in the severest of weather conditions to watch their team play, and over the years, The Chicago Bears have become one of the biggest attractions in Chicago! Be sure to check out the Chicago Bears schedule for your chance to see “The Monsters of the Midway” in action! The Chicago Blackhawks hockey team plays at the United Center, which is the largest arena in the United States. The Chicago Bulls basketball team also plays at the United Center. The Bulls might not be winning championships today, but they still have the best mascot in the league – Benny the Bull – and the Luvabulls dancers.

Chicago is fortunate to have two baseball teams, the north side Chicago Cubs and the south side Chicago White Sox. Locals usually strongly favor one team over the other – talking baseball in some circles is akin to talking politics or religion; the fans take their positions quite seriously! The Cubs play at the historic Wrigley Field and the White Sox play at the modern U.S. Cellular Field. The Chicago Fire soccer team plays at Soldier Field to a diverse crowd of soccer enthusiasts.

Food and Dining

Chicago is regarded as one of the US great cities for restaurants of all varieties (not just the tourist traps of Chicago deep dish pizza and Chicago Style Hot Dogs). Any google search or Yelp searches of restaurants will yield an incredible list of choices. Also, Chicago is a world renowned city for Blues and Jazz, as well as Rock, etc.

Here are some music venues:

Blues Clubs

Jazz Clubs