Overview

Chicago’s downtown area – The Loop governs the topography and the neighboring districts are named after their directional association with it. The chief districts of the city are:

Downtown:

• Downtown /The Loop
• This area contains the tallest skyscrapers of the city’s skyline, the theatre districts and hosts some of its biggest music festivals.
• Main attractions and landmarks include:
  • Chicago Architecture Foundation: Rated the number one thing to do in Chicago, it offers numerous walking and boat tours across the city.
  • Art Institute of Chicago
  • Millennium Park
  • Cloud Gate: Frequently featured in popular cinema, it is an art installation that reflects Chicago’s magnificent skyline.

The North Side

• Home to one of the biggest LGBT communities in the country, North Side houses Lincoln Park and the sprawling Magnificent Mile.
  • Main attractions and landmarks include:
    • Magnificent Mile: It is a shopping haven starting from North Michigan Avenue to Oak Street alongside the Chicago River.
    • Lakeview: This area includes a cluster of charming little memorabilia shops and sports bars in a middle-class neighborhood.
    • The Gold Coast: Chicago’s history through architecture beside the mesmerizing Lake Shore Drive.
    • Old Town: What used to be a hippie haven boasting the renowned Second City Comedy Club envelops the city’s best preserved historic homes.
    • Lincoln Park: Chicago’s liveliest neighborhood, this enormous park also houses a zoo.

The West Side

• The ghetto of Chicago, West Side has a spate of splendid dive bars and pubs frequented by hipsters and the teenagers from the neighborhood.
  • Main attractions include:
    • West Loop: For the best Greek food in Chicago, look no further than Chicago’s Riverside’s most chic community.
    • Wicker Park: Chicago’s political history is lined across this district.

The South Side

• University of Chicago and the Hyde Park are two of the most iconic spots of the South Side.
  • The main attractions include:
    • Pilsen: Here is where the art scene of Chicago comes alive, one mural at a time.
    • Hyde Park: The Museum of Science and Industry – the largest science museum in the Western Hemisphere is located in this scenic independent village off the South Loop.

General info

The Regional Transportation Authority (RTA) coordinates the operation of the three service boards: CTA, Metra, and Pace for smooth public transportation through Chicago.

As a visitor, the following information will be useful to you:

• With the RTA's new multi-modal trip planner Goroo, you can plan your trip faster, better and more accurately.
  
• You can get travel information from the RTA Travel Information Center by calling (312) 836-7000, which is open from 4:45 am to 1:00 am, every day.
• Train station turnstiles do not accept cash, so you will need to get a transit card. Transit card machines are available at any CTA train station, but not all transit card machines accept credit cards. 
• Children under 7 ride free with a fare-paying customer.
•  CTA Visitor Passes offer you the most economical travel value:
  •     1-Day Visitor Pass for USD 10.00
  •     3-Day Visitor Pass for USD 20.00
  •     7-Day Pass for CTA only is USD 28.00
  •     7-Day Pass for CTA and Pace for USD 33.00
  •     30-Day Pass for CTA and Pace is USD 100.00

Train

• Chicago L Train System
  • Chicago Transit Authority's (CTA's) train system is The 'L' offers services in 8 colored lines namely: Red, Blue, Green, Orange, Brown, Purple, Pink, and Yellow lines.
  • CTA offers rail service 24 hours a day, every day of the year in Chicago
  • Fare information is available here.
  • A detailed schedule is available here.

• Metra
  • Metra provides convenient train service to/from downtown and many suburbs.
  • They offer a USD 7 pass for unlimited rides on the weekends (with up to 3 kids per adult free). 
  • A discounted 10-ride pass may be shared between people.
  • A detailed schedule is available here.

Bus

• CTA Bus Service
  • CTA has 206 routes across which buses run on a regular schedule
  • The detailed schedule is available here.
  • Sunday schedules apply on New Year’s Day, Memorial Day, July 4th, Labor Day, Thanksgiving and Christmas Day.
  • CTA has special “Owl” service which runs from 12:00am to 5:00am. "Owl" service refers to CTA's Night Owl service hours.

• Pace Suburban bus service
  • The detailed schedule is available here.
  • In case of any questions regarding schedules, please call Pace Customer Relations at 847-364-7223, option 3, or the RTA Travel Information Center at 312-836-7000.
  • Fare information is available here.

Taxi

• Private taxi services are available across town.
• The minimum fare for any journey is USD 2.25, then for every 1/9 of a mile travelled it is USD 0.20.
• For the first additional adult passenger there is a USD 1.00 charge and any additional adult is USD 0.50. In addition, for every 30 seconds of time not spent moving the meter adds USD 0.20.
• You are responsible for all tolls.
• Rides originating or terminating at O'Hare or Midway airports are assessed an additional USD 1.00 fee. It is not permitted to charge for baggage.
• Tipping is optional. A rate of 7.5% is considered fair.
• If you have a problem with any Taxi in Chicago demand a receipt which will show the Driver's company, name, number, as well as the date, time, and places of your trip. Then you can call city services by dialing 311 from any land line in the city and file a complaint. 
• You can order a cab on the following numbers:

American-United Taxi: +1 773 248-7600

Checker Cab: +1 312 243-2537

Flash Cab: +1 773 561-1444 [25]

Yellow Cab: +1 312 829-4222

• Water Taxi

• • Chicago Water Taxi

• • • Chicago Water Taxi operates on a closed loop route on the Chicago River, from March to December, shuttling passengers between
      • Chinatown and Madison Street on the south branch.
      • La Salle Street and Michigan Avenue on the main branch.
        
      • North Avenue on the North Branch.
      • During the summer, departures and arrivals are scheduled on:
        • Monday through Friday from 6:45 am to 9:00 pm.
        • Weekends from 10:00 am through 8:30 pm.
        • Saturday nights until 11:00pm for Navy Pier fireworks.
  • Shoreline Sightseeing
    • Shoreline Sightseeing has 11 major touring vessels and eight water taxis.
    • Detailed schedule is available here.
    • It is more expensive (USD 5-7).
    • It serves seven destinations including some on Lake Michigan (Union Station/Sears Tower, Wells & Wacker, Michigan Ave Bridge, Navy Pier-Ogden Slip, Navy Pier-Dock St, Buckingham Fountain, and Museum Campus).
    • It has occasional and less frequent service in the spring and fall.

Chicago in 3 days (Source: Frommers)

Day 1

• Start your day by joining active Lincoln Park singles for biking or jogging.
• Visit Chicago greeter to get into the Chicago feel.
• Spend your afternoon ogling at the universe at the Adler Planeterium.
• Spend the evening at Navy Pier, watching the sunset and riding the 150-foot Ferris wheel in Pier Park.
• Take a Water Taxi tour to feast your eyes with the beautiful shoreline.
• Visit The Green Mill, oldest jazz club in the U.S. opened in 1907.

Day 2

• Start your day with a ride on the Brown Line elevated train and watch the city unfold as the train crosses the Chicago River and screeches past downtown high-rises.
• Explore the swanky shops and restaurants on Wicker Park.
• Spend your afternoon taking a walking tour of the Art Institute of Chicago.
• Watch the sunset from Lake Michigan waterfront.
• Walk to Monroe Harbor for a picture-perfect views of the city.
• Visit The Second City, the world’s premier comedy club for a night full of laughter.

Day 3

• Start your day with a volleyball game on the North Avenue beach.
• Spend your day strolling through the magnificent Millennium Park.
• Watch "Sue," the largest and most complete Tyrannosaurus Rex at Field Museum.
• Watch the last sunset from 103^rd floor of the tallest building of Chicago, Willis Tower.
• Go on a shopping spree to the Magnificent Mile.
• Visit Chicago Theatre, Chicago’s National Landmark Theatre.

• There are two main GSM service providers in the USA - AT&T and T-Mobile.
• Both offer 3G services across the 850 MHz / 1900 MHz bands which supported by most modern quad-band phones.
• If you have an “Unlocked” phone then you can purchase a prepaid / Pay As You Go SIM card for your phone. Check this link for tariff rates.
  
• Prepaid SIM cards are readily available – both at the airport as well as at convenience stores like Walgreens.
• You could consider purchasing a SIM from either of the two bigger players, which might have a broader coverage, or from Mobile Virtual Network Operators (MVNOs) like Ultra Mobile, Black Wireless and H2O, which might have a more flexible pricing.

Local

Chicago is home to several local specialities. For a complete Chicago experience, definitely sample these culinary treasures.

• Deep-Dish Pizza: This pizza is as hearty as pizza can get. Its baked in a deep, round pan filled with cheese and topped with a thick layer of tomato sauce. You get a piping hot, gooey piece of pizza on a buttery, flaky crust. Get a slice of the deep-dish pizza at Original Gino's East of Chicago or Lou Malnati's Pizzeria.
• Chicago-style Hot Dogs: The Chicago-style Hot Dog was created during the Great Depression and since then has become a famous Chicago staple. It is an all beef hot dog on a steamed poppy seed bun, topped with yellow mustard, relish, tomato wedges, chopped onions, pickle, hot peppers and celery salt. You can try a standard or jumbo version at Portillo's or head to Hot Doug's, where you get a Chicago-style hot dog for $2 with all the trimmings. Whatever you do, don't order it with ketchup!
• Italian Beef: This is more than a Chicago speciality, it is a historic icon. The Italian Beef sandwich consists of thin slices of seasoned roast beef bursting out from a long Italian roll, dripping with juices. You can have it hot (with giardiniera peppers) or sweet (with sweet peppers); dipped/wet (the bread is quickly dunked), juicy (wetter) or soaked (even wetter!). You can order the sandwich at Al's Beef, who claim to have invented the Italian beef sandwich, or at Mr Beef on Orleans.
• Local Restaurants
  
  • Gibson's Bar & Steakhouse
  • Foodlife
  • The Italian Village

Gourmet

• Alinea
  • Cuisine: Molecular/Experimental
• Acadia
  • Cuisine: Contemporary take on Classic American Cuisine
• Blackbird
  • Cuisine: Modern

Vegetarian

• Amitabul
  • Cuisine: Asian, Vegan
  • Review: HappyCow
    
• B'Gabs Goodies
  • Cuisine: Vegan, Gluten free, Soy free.
  • Review: HappyCow
    
• Native Foods Café
  • Cuisine: Vegan
  • Review: HappyCow
    
• Urban Vegan
  • Cuisine: Thai/Asian
  • Review: HappyCow
    
• Annapurna
  • Cuisine: Indian
  • Review: HappyCow
    
• Arya Bhavan
  • Cuisine: Indian
  • Review: HappyCow

Refer here for more options.

Drink

• Celtic Crossings
• Miller's Pub
• The Map Room

Dive bars are a norm in Chicago city. Some popular options are:

• Scofflaw
• Big Star
• The Aviary
• Maria’s

Tipping is expected in most places and should always be done unless the service provided was completely unsatisfactory.

• Hotels: Tip your porter USD 1 to 2 per bag depending on the weight. A doorman who helps you hail a cab should be paid USD 1 to 2 as well.
• Restaurants: Tip your server 10 to 15% of the bill for average service. Restaurants will add a service charge for groups of five or more.
• Bars: Tip the bartender USD 1 to 2 per drink.
• Counter Service: Tips are not generally required.
• Taxis: Tip your driver 10 to 15% of the fare; an additional USD 1 to 2 for help with bags.